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Index Index page numbers in boldface refer to boldface terms in the text. Page numbers in italics refer to figures. Tables are indicated by a t following the page number. Boxed material is indicated by a b following the page number. A AARS (aminoacyl-tRNA synthetase), 714 ABO blood group system, 532b–533b antigens and, 815 Absolute temperature entropy, 143b Absolute zero, 12, 143b Abzymes, 631, 633 Acesulfame-K, 796b Acetal(s), 466, 466–68, 470 formation of glycoside, 527–28, 540–41 Acetaldehyde, 317, 460, 751 Acetamide, 499, 507 Acetanilide, 505 Acetate buffers and ion of, 261, 262 in citric acid cycle, 733–37 Acetic acid (CH3COOH), 195, 243b, 460, 478, 488, 504, 507, 616b ammonia and, reaction between, 244, 247–48 boiling point, 162t buffers and, 261, 262 ethanamine and, reaction between, 502 ethanol and, reaction between, 229–30, 231, 501 water and, reaction between, 247 Acetic anhydride, 499, 503, 507 Acetoacetate as component of ketone bodies, 759 Acetoacetic acid, 492b Acetone (C3H6O), 317, 458 boiling point, 154 keto and enol forms of, 468 in ketone bodies, 759 Acetyl (CH3CO2) transporting molecule, 732 Acetylcholine, 616b, 644–48 Alzheimer’s disease and, 647b–648b botulism and, 647b, 648 calcium signaling to release, 645b effects of nerve gases on, 646b regulation of, 648 removal of, from receptor site, 646 storage and action of, as chemical messengers, 644 Acetylcholinesterase, 616b, 646 nerve gas effects on, 646b Acetylcholine transferase, 647b Acetyl-CoA carboxylase, 779b Acetyl coenzyme A (Acetyl CoA), 647b biosynthesis (anabolism) of fatty acids and, 777, 778, 780 in common catabolic pathway, 733, 733, 735 b-oxidation of fatty acids and formation of, 755, 756 oxidative decarboxylation of pyruvate and formation of, 752 structure, 733, 734 N-Acetyl-D-galactosamine, 532b N-Acetyl-D-glucosamine, 521–22, 532b, 538 Acetylene (C2H2), 324, 353, 356 molecular shape of, 95, 95 structural formula, 311t Acetyl groups, 732, 733 Acetylsalicyclic acid, 502b, 507 Achiral objects, 424, 437 Acid(s), 241. See also Acidity (pKa) amino acids as, 585, 620 buffers, 261–65, 267, 269t carboxylic. See Carboxylic acids conjugate acid–base pairs, 244–46 conjugate bases of, 245t defined, 240–42 esterification catabolism and, 488–89, 492 fatty, 479–82 hydration reaction catabolism and, 366–68, 403–5 ionization constant (Ka), 249–50, 270 monoprotic, and diprotic, 244 pH, pOH, and, 256–58 pH of buffers, calculating, 265–67 position of equilibrium in acid–base reactions, 247–49 properties of, 250–53 as proton donor, 244 reaction between amines and, 448, 453 strength of, 242–44, 248 titration used to calculate concentrations of, 259–61 triprotic, 244 types of, 243b Acid–base indicators, 258, 258, 259 Acid–base reaction, 244 Acidic polysaccharides, 538–39, 540 Acid ionization constant (Ka), 249, 249–50, 270 Acidity (pKa), 249 of alcohols, 402–3 of amino acids, 585 of carboxylic acids, 485, 492 of phenols, 390 of thiols, 412, 415 of water, 253–56 Acidosis, human respiratory and metabolic, 268b Acid rain, 88b, 180b, 231 Aconitate, 733 Acquired immunity, 810. See also Adaptive immunity Acquired immunodeficiency syndrome (AIDS), 614, 624b. See also Human immunodeficiency virus (HIV) Actinium-225, 296 Activating receptor, 827, 837 Activation, enzyme, 618 Activation energy, 213, 235, 634 chemical reaction rates and, 214–16 Activation stage of protein synthesis, 702–3 Active sites, enzyme, 618, 622b, 633 Active transport, 554b Actual yield of product mass in chemical reactions, 123, 134 Acyl carrier protein (ACP), 778, 784 Acyl CoA, 778 Acyl groups, 499 Adaptive immunity, 810, 810–11, 836 cells of. See B cell(s); T cell(s) Addition reactions of alkenes, 363t Adenine (A), 666, 667, 672, 673, 673 Adenosine, 702 Adenosine deaminase (ADA) deficiency, 721 Adenosine diphosphate (ADP), 622b, 668, 730, 742 Adenosine monophosphate (AMP), 668, 730 Adenosine triphosphate (ATP), 668, 742 chemiosmotic pump and production of, 739–40 consumption of, in anabolic pathways, 773, 774, 777 energy storage and release by, in catabolism, 728, 730 glucose catabolism and yield of, 753, 754t, 755 in protein synthesis activation, 702 Adenylate cyclase, 650–51 Adhesion molecules, 823 ADP. See Adenosine diphosphate (ADP) Adrenalin, 586. See also Epinephrine Adrenergic chemical messengers, 643, 650–55, 661 control of neurotransmission, 652 histamines, 654–55 monomine, 649–50, 650 removal of neurotransmitters, 652 removal of signals, 651–52 secondary messengers, 650–51 Adrenocorticoid hormones, 564, 564–65, 573 Affinity maturation, antigen-antibody binding, 820 Agonist drugs, 641, 661 AIDS. See Acquired immunodeficiency syndrome (AIDS) Air pollution acid rain, 88b, 180b, 231 caused by hydrates, 194b caused by incomplete fuel combustion, 130 nitric oxide, 88b radon, 292b Alanine, 581, 587, 649, 783 catabolism of, 765 formation of, 704 stereochemistry of, 583 Alanine aminotransferase (ALT), 629 Alanyglycine, 589, 618 Albuterol, 311, 451b Alcohol(s), 397–419, 398, 414 acetal formation by adding of, 466–68, 470 anhydrides and, reaction between, 507, 513 breath-alcohol screening, 407b characteristic reactions of, 402–7 commercially important, 413–14 functional group (—OH hydroxyl group), 313, 313t, 313–14, 398 hemiacetal formation by adding of, 465–66, 470 nomenclature for, 398–400 physical properties of, 400–402, 412t primary, secondary, and tertiary, 314, 400 structure of, 398 I1 91123_33_Index_pI2-I22 pp3.indd 2 11/21/08 6:38:17 PM Index Aldehydes, 457–74, 458 characteristic reactions of, 462–68 functional group, 313t, 316, 316–17, 458 naming, 458–61 naturally occurring, 461b oxidizing monoamines to, 652 physical properties of, 461–62 unsaturated, 458 Alditols, 528, 528–29, 541, 541 Aldohexoses, 518, 520t Aldonic acids, 529, 541, 541 Aldopentoses as cyclic hemiacetals, 524 D- forms of, 520t Aldoses, 518 oxidation of, 529 Aldosterone, 564, 564 Aldotetroses, 518, 520t Aliphatic amines, 442, 452 base strength of, 447, 448t, 453 Aliphatic carboxylic acids, 476, 477t Aliphatic hydrocarbons, 324 Alkali metals, 47 melting and boiling points of, 48t noble gas notation and Lewis dot structures for, 57t Alkaloids, 443b Alkalosis, 269b Alkanes, 323, 323–48, 346 boiling points of, 340, 340t characteristic reactions of, 342–44 constitutional isomers and, 326–28 cycloalkanes. See Cycloalkane(s) density of, 341 ethane as. See Ethane first ten, with unbranched chains, 325t haloalkanes, 344–45 melting points of, 340, 340t naming, 328–31 physical properties of, 340–42, 402t shapes of, 334 solubility of, 341, 402t sources of, 332 writing structural formulas of, 323–25 Alkenes, 324, 352, 352–81 alcohol conversion to, by dehydration, 403–5 characteristic reactions of, 363–70 ethylene as. See Ethylene (C2H4) naming, 355–61 physical properties of, 361–62 polymerization of, 370–73 structure of, 354 terpenes and, 362–63 Alkyl group, 329, 346 eight most common, 329t Alkynes, 324, 352–53, 352–81 acetylene as. See Acetylene (C2H2) naming, 355–61 physical properties of, 361–62 structure of, 354 Allergies, 829 Allosteric enzymes, 626 binding activators’ and inhibitors’ effect on, 627 regulator and regulatory site of, 626–27 Allosteric proteins, quaternary structure and, 605b Allosterism, enzyme regulation by, 626, 634 Alloys, 179 Alpha (a) amino acids, 579–80, 580 Alpha emission, 281–82, 300 Alpha (a) particles, 278, 281–82, 300 electricity and, 277 energy level of, 289, 289 ALT (alanine aminotransferase), 629 Alternative splicing, 713, 714 Aluminum, 3 91123_33_Index_pI2-I22 pp3.indd 3 Alzheimer’s disease, 600b acetylcholine and, 647b–648b acetylcholine transferase and, 647b Amides, 499, 499–500, 512 hydrolysis of, 505–7, 513 preparation of, 502–3, 513 protein synthesis and, 587 reactions of esters with ammonia and amines to form, 508–9 Amines, 442, 442–56 acids and, reaction between, 252–53 aliphatic, and aromatic, 442 alkaloids and, 443b ammonia, anhydrides and, reaction between, 508–9, 513 basicity of, 447–49, 448, 448t, 453 characteristic reactions of, 449–52, 453 classification of, 441–43 esters, ammonia and, reaction between, 507–9, 513 functional group, 313t, 315, 315–16 heterocyclic, 442 hydrogen bonding between molecules of secondary, 446 naming, 444–46 physical properties of, 446–47 primary, secondary, and tertiary, 315, 441, 452 separation and purification of, 452 -amine (suffix), 444, 445, 446, 452, 499 Amino acid(s), 579, 579–83, 608 alpha, 579–80, 580 biosynthesis (anabolism) of, 782–84 carboxyl group in, 585, 587–88 catabolism of nitrogen in, 760–65 characteristics of, 584–86 common types, 580t, 581–582 C-terminus of, 589, 593 essential, 782, 782b, 795 as neurotransmitters, 643, 649, 661 N-terminus of, 589, 593 peptide bonds between, 587–90 protein formation by, 587–90. See also Protein synthesis sequence of, in N-terminal decapeptides of b-globin in select species, 715b specificity of tRNA for unique, 714 structure, 579 uncommon, 586–87 as zwitterions, 583–84 Amino acid pool, 748 Amino acid sequence, 666 enzyme action on, 615 protein function linked to, 594 Aminoacyl-tRNA synthetase (AARS), 700, 703, 714 4-Aminobenzoic acid, 388, 476 Amino group, 587–90 functional group, 315, 315–16 transamination and exchange of, 761 Amino- (prefix), 460, 476 Amino sugars, 521–22 Ammonia (NH3), 243b acetic acid and, reaction between, 244, 247–48 acids and, reaction between, 252–53 anhydrides, amines, and, reaction between, 508–9, 513 base strength of, 448t conversion of nitrogen to, by Haber process, 234b esters, amines, and, reaction between, 507–9, 513 as fertilizer, 93, 234b molecular polarity of, 98 molecular shape of, 93, 94 urea formation from carbon dioxide and, 762–64 ■ I2 water and, reaction between, 227 as weak base, 242 -ammonium (suffix), 446 Ammonium acetate, 507 Ammonium benzoate, 486 Ammonium chloride, 308 Amorphous solids, 165 Amoxicillin, 501b AMP. See Adenosine monophosphate (AMP) Amphetamines, 442b Amphiprotic substance, 245, 270 amino acids as, 584 a-Amylase, 792 b-Amylase, 792 Amyloid plaques and fibril formation, 600b, 647b Amylopectin, 536, 536, 540 Amylose, 536, 540 Anabolic Steroid Act of 1990, 567b Anabolic steroids, 566b–567b Anabolism, 727, 743 of amino acids, 782–84 biosynthetic pathways of, 772–73 of carbohydrates, 773–77 in central metabolic pathway, 784 of lipids, 777–81 summary of, 784 Anaerobic pathway, 749 Analgesics, 502b, 631b. See also Aspirin; Ibuprofen Androstenedione, 566b -ane (suffix), 329, 329, 346 Anesthesia, ethers and, 410b Aneuploid cells, 834b Angina, 401b, 624b Anhydrides, 499, 512 hydrolysis of, 503, 513 phosphoric, 509 reaction between alcohols and, 507, 513 reactions between ammonia, amines, and, 508, 509, 513 Anhydrous substance, 192 Aniline (C6H5NH2), 384, 444, 505 Animal(s) fatty acids in fats of, 479t structural proteins in, 578 typical cell of, 729, 729 Anion, 69, 99 naming monatomic, 72 solvated, 191, 192 Anion transporter, 554b Anisole, 384 Anode, 131b, 192 Anomeric carbon, 523, 539 Anomers, 523, 539 Antacids, 253b Antagonist drugs, 641, 648, 661 Anthracene, 386 Antibiotics, 295, 828b chiral, 424b b-lactam (penicillins, cephalosporins), 501b problems associated with using, 828b Antibodies, 579, 811 affinity maturation in binding, with antigens, 820 antigen recognition by, 815, 818 b12, 835 B cells and, 814, 818–19, 819 binding of, to antigen epitope, 816 catalytic, 630–31, 632b future research about, 835–36 2G12, 837 IgG-type, 818 monoclonal, 821b, 822 neutralizing, 835 V(J)D gene’s role in diversification of, 819, 820, 822 11/21/08 6:38:17 PM I3 ■ Index Anticoagulants, 539 Anticodon, 700, 723 Anticodon loops in tRNA, 677 Antigen(s), 579, 811, 815, 836 affinity maturation in binding with antibodies, 820 antibody recognition of, 815, 818 characteristics of, 815 diversification of immunoglobulin response to, 819–20, 820 epitope of, 815. See also Epitope major histocompatibility complexes and, 815 Antigen-antibody complex, 818 Antigen presenting cells (APCs), 814 Antihistamines, 655 Anti-inflammatory drugs, 570, 571b, 572. See also Aspirin Antilogarithms (antilogs), 255–56 Antioxidants, phenols as, 390–93 Antisense strand, 697 Antiseptics, 132b Antithrombin III, 539 Antiviral therapy, 709b, 832 APCs (antigen-presenting cells), 814 apoB-100 protein, 561 Apoenzyme, 618, 633 Appetite, role of peptides in, 655 AP site (apurinic/apyrimidinic site), 689 Aqueous solution(s) carboxylic acids in, 485 defined, 124 ionization of water and, 254–56 ion reactivity with, 124–27 micelles in, 483, 483 pH of, 258 Arachidonic acid, 572, 794 Archeological objects, radioactive dating of, 285b Arenes, 324, 383, 393. See also Benzene (C6H6) Arginine, 582, 615, 655, 763 Argininosuccinate, 763 Aristotle (384–322 BCE), 3 Aromatic amines, 442, 452 base strength of, 448t, 449, 453 Aromatic compounds, 382 benzene structures as, 382–83, 383 naming, 384–87 Aromatic sextet, 384 Aromatic substitutions, 387, 393 Arrhenius, Svante (1859–1927), 241, 270 Artificial fats, 796b–797b Artificial sweeteners, 793, 796b–797b Aryl group, 383 Ascorbic acid (Vitamin C), 526b A site (acceptor site), ribosome, 703 binding to, 703–4 Asparagine, 581 Aspartame, 589b, 796b Aspartate, 585, 763 Aspartate aminotransferase (AST), 629 Aspartic acid, 581, 585 Aspirin, 211, 311, 502b, 507 action of, 570, 571b, 631b Asthma, 451b, 572 Astrochemistry, isotopic abundances and, 43b -ate (suffix), 499 Atherosclerosis, 561, 563 Athletes foods to enhance performance by, 803b respiratory and metabolic acidosis in, 268b Atkins Diet, 793–94 Atmosphere pollution in. See Air pollution pressure of air in, 143 Atmosphere (atm), 143 Atom(s), 31–61 atomic number, 39, 39–40 atomic weight, 41, 41–42 91123_33_Index_pI2-I22 pp3.indd 4 configuration of, in stereocenter, 338 Dalton’s theoretical postulates on, 35–37 defined, 35 electron configuration, 49–57 ionization energy of, 58–60 ions of. See Ion(s) isotopes of, 40–41 mass number of, 39 mass of, 42–43 matter and, 31–35 periodicity in electron configuration and chemical properties, 57–60 Periodic Table of elements and, 43–49 size of, 42–43, 57–58, 61 subatomic particles, 38, 38t, 39 Atomic energy, 298, 298–300. See also Nuclear energy Atomic mass, 42–43 Atomic mass unit (amu), 38 Atomic number, 39, 39–40, 61 ionization energy versus, 60 Atomic weight, 41, 41–42, 61, 109 ATP. See Adenosine triphosphate (ATP) Attractive forces between molecules, 171 gases and, 153–54 states of matter and, 141–42 types of, 153–57 Autoimmune disease, 829 Automobile, liquid behavior and hydraulic brakes of, 157 Autoxidation, 390 Avery, Oswald (1877–1955), 666 Avogadro, Amadeo (1776–1856), 110 Avogadro’s law, 148, 148, 171 Avogadro’s number, 110 Axial bonds, 335, 346 Axon, nerve, 640, 642 myelin sheath around, 558b B b12 antibody, 835 Background radiation, 291 Bacteria, 388 fixation of nitrogen by, 234b macrophage ingestion of, 812 recombinant DNA techniques using, 718, 718–19 Baeyer, Adolph Von (1835–1917), 508b Baking soda, 252 Balances, measuring mass using, 10, 10 Balloon models, predicting bond angles using, 93 Barbiturates, 508b Barbituric acid, 508b Barometer, mercury, 143 Basal caloric requirements, 791, 805 Base(s), 241 amines as, 447–49, 448 amino acids as, 585 buffers, 261–65, 267, 269t. See also Buffer(s) carboxylic acids reaction with, 486–88, 493 conjugate, 245t conjugate acid–base pairs, 244–46 defined, 240–42 determining strength of, 242–44 important types of, 243b pH, pOH, and, 256–58 pH of buffers, calculating, 265–67 position of equilibrium in acid–base reactions, 247–49 properties of, 250–53 as proton acceptor, 244 titration used to calculate concentrations of, 259–61 water, 253–56 Base(s), nucleic acid, 666, 666–67 complementary pairing of, 672, 673 composition and ratio of, in two species, 671t damage to DNA, and repair, 687–89 pairing of, 672, 673 primary structure of DNA and, 670–71 principal types of, 667 sequence of, 679 triplets of (codons), 700, 701t Base excision repair (BER), 687, 688 Batteries, 131b, 132, 132–33 B cell(s), 811, 812, 814–15, 836 self/nonself determination, and, 826 B-DNA, 674 Beadle, George (1903–1989), 666 Becquerel, Henri (1852–1908), 276–77 Becquerel (Bq), 287 “Bends,” nitrogen bubbles in blood as cause of, 183b Bentley, Robert, 817b Benzaldehyde, 384, 461b, 462 Benzene (C6H6), 182, 324, 382–84, 393 characteristic reactions of, 387–89 discovery of, 382 naming derivatives of (aromatic compounds), 384–87 phenols and, 389–93 structure of, 382–84 1,4-Benzenediamine, 510 1,4-Benzenedicarboxylic acid (terephthalic acid), 510 Benzenediol, 389 Benzenesulfonic acid, 388 Benzo[a]pyrene, 387b Benzodiazepine, 446 Benzoic acid (C6H5COOH), 195, 384, 462, 486 separation of, from benzyl alcohol, 487, 487 Benzyl alcohol, separation of benzoic acid from, 487, 487 Beta emission, 280, 300 Beta (b) particles, 278, 280 electricity and, 277 energy level of, 288–89, 289 BHA (butylated hydroxyanisole), 393 BHT (butylated hydroxyltoluene), 393 Bicarbonate ion (HCO32) reactions between acids and, 251–52 reactivity with hydrogen chloride to form carbon dioxide, 125 Bile salts, 569, 573, 794 Binary compound, 77 Binary covalent compound, 87, 100 Binary ionic compound, 77, 77–78, 100 Binding proteins, 697 Binding site, enzyme, 436 Biochemical pathway, 728. See also Biosynthetic pathways; Common catabolic pathway Biochemistry, 308–9 Bioenergetics. See Metabolism Biological membranes. See Membrane(s) Biological messengers. See Chemical messengers Biological pollutants, 660b Biomolecules, chirality in, 436. See also Enzyme(s) Biosynthetic pathways, 772, 772–86. See also Anabolism amino acids and, 782–84 carbohydrates and, 773–77 flexibility of, 772–73 Le Chatelier’s principle in, 773 lipids and, 777–80 Bisphenol A, 660b Bleaching as an oxidation reaction, 133 Blood, human. See also Red blood cells (erythrocytes); White blood cells (leukocytes) acidosis of, 286b alcohol content of, 407b alkalosis of, 269b anticoagulants, 539 “bends” caused by nitrogen bubbles in, 183b buffers in, 265 11/21/08 6:38:18 PM Index cholesterol levels in, 481b, 560, 563 clotting of, 570, 579, 615 coagulated, 188 filtration of, 203, 203b glucose in, 518, 520, 530b, 659b, 792 hemodialysis of, 203, 203b in isotonic solution, 178 as mixture, 34 NADPH and defense against oxidative damage in, 753 pH of, 257, 265, 269b, 286b, 448 proteins in, as colloidal dispersion, 197 serum, 188 sickle cell disease affecting, 596b, 716 transfusions of, 532b–533b types, 532b–533b, 815 whole, 188 Blood alcohol content (BAC), 407b Blood pressure control of, 654b high, 624b measurement of, 159b Blood vessels, 624b, 654b Blow molding of high-density polyethylene, 373 Body mass, drug dosage and, 11b Body mass index, 779b, 791 Boiling point, 142, 161, 161–63, 171 of alcohols, 402t, 412t of alkali metals, 48t of alkanes, 340, 340t, 402t of carboxylic acids, 478, 479t of compounds of comparable weight, 462t, 479t dipole-dipole interactions and, 154, 154–55 elevation of, 198–99 of ethers, 409–10 of ethylene glycol, 199 factors affecting, 161–63 of halogens, 48t of noble gases, 49t normal, 161 of thiols, 412t Bond(s). See Chemical bonds Bond angles, 92 in carbon compounds, 311t predicting, in covalent molecules, 92–96 Bonding electrons in Lewis dot structures, 83 Bone grafts, 73b Boric acid (H3BO3), 243b Botox, 647b Botulism, 647b, 648 Boyle’s law, 144, 144, 146, 146t, 170 human lungs, breathing, and, 145b Brain, human, 640 Alzheimer’s disease effects on, 600b, 647b glucose and ketone bodies as energy source for, 758–59, 793b medical imaging of, 294, 294 peptides in, and chemical communication, 655–57 Breathing, 145b Brwnsted, Johannes, 244, 270 Bromination reactions in alkenes, 363t, 368–69 Bromine, 44 addition of, to alkenes, 368–69, 375 aluminum and, reaction between, 3 three states of matter for, 17 4-Bromobenzoic acid, 385 Bronchodilators, 451b Brown, Michael, 561 Brown fat, 738b Brownian motion, 196, 204 “Buckyballs” (buckminsterfullerene), 164 Buffer(s), 261, 261–65 capacity of, 264–65 common useful synthetic biochemical, 267, 269t defined, 261 functioning of, 262–63 91123_33_Index_pI2-I22 pp3.indd 5 in human blood, 265, 592, 592 pH of, 263–67 proteins as, 592, 592 Buffer capacity, 264, 264–65, 270 Butanamide, 505 Butane (C4H10), 115, 331 boiling point, 154 condensed structural formula, model, and lineangle formula, 325 conformations of, 334, 334 constitutional isomers, 326 1,4-Butanediamine (putrescine), 446 Butanedioic acid (succinic acid), 476 Butanoic acid, 479, 505 1-Butanol, 398 2-Butanol, 398, 403, 421 2-Butanone (methyl ethyl ketone (MEK)), 461 Butene, 403 cis-trans isomers of, 354, 369, 421 Butylamine, 445 C Caffeine, 803b Calcium (Ca21) drugs affecting messenger function of, 641t as secondary chemical messenger, 645b strontium-90 and, 45b Calmodulin, 645b Calorie, 21, 21–22 Calvin, Melvin (1911–1997), 776b Calvin cycle, 776b cAMP. See cyclic AMP (cAMP) Cancer carcinogens, 387b, 717, 723 colon, 791 drugs for treatment of, 670b, 817b metastatic, 295 monoclonal antibodies and treatment for, 821b oncogenes and, 717b potential vaccine for, 825b radiation as cause of, 291 radiation therapy for, 295–96 skin, 506b smoking and, 387b taxol for, 310b Capsaicin, 392b Captopril, 424b Carbocation, 365, 375 Carbohydrate(s), 517–45 bandages made from, 537b biosynthesis. See Carbohydrate anabolism blood types and, 532b catabolism of. See Carbohydrate catabolism defined, 518 disaccharides, 533–35 monosaccharides. See Monosaccharides oligosaccharides, 533–35 polysaccharides, 536–38 processing of, 792–94 Carbohydrate anabolism, 773–77 conversion of atmospheric CO2 to glucose in plants, 773–74, 775b–776b conversion of glucose to other carbohydrates in animals, 775–77 synthesis of glucose in animals, 774–75 Carbohydrate catabolism, 733, 748 energy yield from glucose catabolism, 753–55 glycolysis reactions and, 748–53 Carbon-14, 285b Carbonate(s) as blood buffer, 265 reactions with acids, 251–52 solubility of, 127t Carbonate ion (CO322), 89, 90 Carbon (C) a-, 468 ■ I4 anomeric, 523 atomic size of, 58 compounds containing. See Organic chemistry crystalline forms of, 164 geometries of compounds with, 311t orbital box diagram for, 53 single, double, and triple bonds in compounds of, 311t Carbon dioxide (CO2), 36 bicarbonate ion reaction with hydrogen chloride to form, 125 conversion of, to glucose in plants, 773–74, 775b–776b molecular shapes of, 95 as product of acid-carbonate/bicarbonate reactions, 252 supercritical, 169b urea formation from ammonia and, 762–64 vapor of gaseous, 166 Carbonic acid (H2CO3), 180b, 511 Carbon monoxide, 36 Carbon skeleton of amino acids, 764–65 Carbon tetrachloride (CCl4), 18, 182, 344 Carbonyl group, 316, 319, 457, 475 monosaccharides and, 522 polarity of, 461 Carboxyl group, 317, 317–18, 319, 475, 499 in amino acids, 585, 587–88 loss of CO2 from, 490–91 polarity of, 478 Carboxylic acids, 475, 475–97 aldehyde oxidation to, 462–63, 469 characteristic reactions of, 485–91 derivative compounds of. See Amides; Anhydrides; Esters functional group, 313t, 317, 317–18, 475 naming, 475–78 physical properties of, 478–79 primary alcohol oxidation, 406 soaps, detergents, and, 479–84 trans fatty acids, 481b–482b Carboxylic amide, 499, 512 Carboxylic anhydride, 499, 512 Carboxylic ester, 318, 499, 512 Carboxypeptidase, 615, 795 Carcinogens, 387b, 717, 723 Cardiac stimulants, 451b Carnitine, 755 Carnitine acyltransferase, 755 Catabolism, 727, 743 of carbohydrates. See Carbohydrate catabolism chemiosmotic pump and ATP production in, 739–40 citric acid cycle’s role in, 733–37 common catabolic pathway of, 728, 747–48, 749 common pathway of, 728 conversion of chemical energy produced by, 742–46 electron and H1 transport in, 737–39 energy yield resulting from, 741 of lipids. See Lipid catabolism mitochondria’s role in, 728–29 principal compounds of, 730–33 of proteins. See Protein catabolism summary of, 767 Catalyst(s) chemical reaction rates and presence of, 220, 220–21, 235 effects of, on chemical equilibrium, 235 energy diagram for, 220 enzymes as, 579, 623, 625 heterogeneous, and homogeneous catalyst, 220 polymerases, in transcription process, 696 Catalytic antibodies, 630–31 against cocaine effects, 632b Catalytic hydrogenation, 369 11/21/08 6:38:18 PM I5 ■ Index Catalytic reduction, 369 Catecholamines, 586 Cathode, 131b, 192 Cation, 69 from metals forming one positive ion, 72t from metals forming two different positive ions, 72t naming monatomic, 71–72 solvated, 191, 192 Cech, Thomas, 678 Cefalexin, 501b Cell(s) common metabolic pathway in, 727, 728–29 components of, 729 fat storage in, 748 structure of, 729 Cell communication. See Chemical communications Cell membranes. See Membrane(s) Cell reprogramming, stem cells and technique of, 835b Cellulose, 536–38, 540, 578, 791 structure, 537 Celsius scale, 11 Central dogma of molecular biology, 696, 696 Cephalins, 553 Cephalosporins, 501b Ceramide, 556, 780 Cerebrosides, 556 Chain, Ernst, 501b Chain-growth polymers, 370 Chain length, formation of radicals, 393 Chain reaction, nuclear, 298 Chair conformation, 335, 335, 346, 525, 540 of monosaccharides, 525–27 Chaperone proteins, 600, 608, 609 gene regulation at post-translation stage and role of, 714, 723 Chargaff, Erwin (1905–2002), 670 Chargaff’s rules on DNA base pairing, 672, 673 Charles’s law, 145, 146, 146t, 170 Chemical bonds, 68–107 anabolic steroids, 566b anions and cations, 69, 71–73 anti-inflammatory drugs, 571b, 572 axial, 335 classification of, 81t covalent, 68, 73–74, 79–87, 92–96 determining polarity of, 97–99 electronegativity and, 74–75, 81t equatorial, 335 ionic, 68, 73–74, 75–77 octet rule governing eight valence electrons of, 69–71 predicting angles of covalent, 92–96 resonance in (contributing structures), 89–92 Chemical change, 2, 26. See also Chemical reaction(s) Chemical communications, 640–64 acetylcholine as messenger in, 644–48 adrenergic messengers in, 650–55 amino acids and, 649 hormones as, 641–42, 642t, 643, 657–58, 660–61 immune system and, 812. See also Immune system molecules involved in, 640–41. See also Chemical messengers; Receptors of chemical messages neurotransmitters as, 641–43, 649. See also Neurotransmitters peptides and, 655–57 steroid hormones as, 657–58, 660–61 Chemical connections acetylcholine release, 646b acid rain, 180b, 231 acids, 243b air pollution, 194b 91123_33_Index_pI2-I22 pp3.indd 6 aldehydes, 461b alkaloids, 443b alkalosis, 269b Alzheimer’s disease and acetylcholine transferase, 647b amino acids, 766b, 782b amphetamines, 442b analgesics, 502b anesthesia, 410b antacids, 253b antibiotics, 501b, 828b anticancer drugs, 670b antiseptics, 132b artificial sweeteners, 796b–797b ascorbic acid, 526b astrochemistry, 43b athletic performance enhancement, 803b barbiturates, 508b bases, 243b “bends” (gas bubbles in blood), 183b blood glucose levels, 530b blood pressure, 159b blood types, 532b–533b body temperature, 221b botulism, 646b Boyle’s law, 145b breath alcohol screening, 407b breathing, 145b calcium as secondary chemical messenger, 645b capsaicin in chilies, 392b carcinogens, 387b catalytic antibodies against cocaine, 632b cell membranes, transport across, 554b chemotherapy agents in cancer treatment, 817b cis-trans isomerism, 361b coral chemistry and human bones, 73b desalinization of water, 201b diabetes, 659b diabetes mellitus, 492b diabetic ketoacidosis, 760b dieting, 796b–797b dissolving surgical stitches, 512b DNA fingerprinting, 684b dopamine, 653b drug dosage and body mass, 11b drug solubility, 450b Earth’s crust, elements in, 37b elements, 33b, 37b emulsions and emulsifying agents, 197b entropy, 143b enzyme inhibitors, 624b enzymes, 591b, 622b, 630b, 631b epinephrine, 451b esters as food-flavoring agents, 489b ethers, 410b ethylene, 353b ethylene oxide as chemical sterilant, 409b fertilizers, 234b fever, 219b food dyes, 391b food guide pyramid, 790b freons, 345b galactosemia, 522b gasoline octane rating, 343b glucose blood levels, 530b goiter, 388b Haber process, 234b hemodialysis, 203b hydrates, 194b hyperbaric medicine, 151b hypothermia and hyperthermia, 22b ice density, 162b immunizations, 825b indoor radon, 292b insulin, 595b iodine ion, 388b ionic compounds, 80b isotopic abundances, 43b ketoacidosis, 760b ketone bodies, 492b ketones, 461b lactate accumulation in muscles, 752b laser surgery and protein denaturation, 607b Le Chatelier’s principle, 233b metabolic acidosis, 286b metals as historic landmarks, 47b monoclonal antibody therapy, 821b multiple sclerosis, 558b muscle relaxants, 616b mutations and biochemical evolution, 715b myelin sheath around axons, 558b nerve gases, 646b nitric oxide, 88b, 654b nitroglycerin, 401b nitro group in explosives, 389b nuclear power plant accidents, 286, 300b obesity, 738b oncogenes, 717b p53, 717b Parkinson’s disease, 653b pharmacogenomics, 687b photosynthesis, 775b–776b plastics recycling, 374b poisonous puffer fish, 337b protein/peptide conformation-dependent diseases in humans, 600b protein quaternary structure and allosteric proteins, 605b–606b proteomics, 632b pyrethrins, 500b radioactive dating, 285b rancidity of oils and fats, 550b recycling, 374b respiratory acidosis, 286b reverse osmosis, 201b sex pheromones in two species of corn borer, 358b sickle cell disease and, 595, 596b signal transduction effects on metabolism, 757b smoking, 387b specific heat of water, 23b stem cells, 834b–835b strontium-90, 45b sunscreens and sunblocks, 506b supercritical carbon dioxide, 169b taxol, 310b telomeres, telomerase, and life span of organisms, 681b time-released medications, 222b tissue damage caused by radiation free radicals, 293b tooth enamel solubility, 127b tranquilizers, 446b trans fatty acids, 481b–482b UV radiation protection, 506b vaccinations, 825b viruses, 709b vision, 361b voltaic cells, 131b water density, 162b waxes, 550b weight-reducing drugs, 738b weight reduction, 793b Chemical energy, 20–21. See also Energy ATP production, 739–40 bioenergetics and. See Metabolism conversion of, to other energy forms, 741–42 Chemical equation(s), 114, 134 balancing, 114, 114b, 115 net ionic, 125 Chemical kinetics, 211. See also Chemical reaction rates 11/21/08 6:38:18 PM Index Chemical messengers, 640, 661 acetylcholine as, 644–48 adrenergic, 650–55 classes of, 643 hormones as, 640–43 lipids as, 547 neurotransmitters, 640–43 nitric oxide as, 88b role of peptides, 655–57 secondary. See Secondary messengers sex pheromones as, 358b steroid hormones as, 657–58, 660–61 Chemical properties, 2. See also Chemical reaction(s) of acids and bases, 250–53 of amino acids, 585 of organic and inorganic compounds, 309t of proteins, 590–93 of water, 253–56 Chemical reactant(s), 109 concentration of, and reaction rate, 217–18 Le Chatelier’s principle and addition or removal of, 229–32 limiting reagents and, 121–22 nature of, 217 presence of catalyst and reaction rate, 220, 220–21 temperature of, and reaction rate, 218–20 Chemical reaction(s), 2, 26, 109, 109–40. See also Chemical reactant(s) acid–base, 244, 247–49 activation energy of, 213 agents for electron transfer in biological oxidation-reduction, 731 of alcohols, 402–7, 415 of aldehydes and ketones, 462–68, 469–70 of alkanes, 342–44, 346 of alkenes, 363–70, 375–76, 403 of amides, 502–3, 505, 509, 513 of amines, 449–52, 453 of anhydrides, 503, 507, 513 balancing chemical equations, 114–17 of benzenes and derivatives, 387–89, 394 of bromine and aluminum, 3 of carbohydrate catabolism, 748–53 of carboxylic acids, 485–91, 492–93 definition and terms related to, 108–9 endothermic, 133, 216, 232 equilibrium in. See Equilibrium, chemical of ethers, 410, 488–89, 501, 503–4, 508–9, 513 exothermic, 133, 215, 216, 232 of glycolysis, 748–53 heat of, 133 of lipid catabolism, 755–59 of lipids, 549 mass relationships in, calculation of, 118–24 molecular weights and formula weights related to, 109–10 moles, and calculating mass relationships in, 110–14 of monosaccharides, 527–33, 540–41 in nuclear chemistry, 301 oxidative, reductive, and redox, 128–33 of photosynthesis, 775b–776b polymerization, of ethylenes, 370–73 predicting reactivity of ions in aqueous solutions, 124–27 of protein catabolism, 760–65 rates of. See Chemical reaction rates regioselective, 364 side reactions, 123 of thiols, 412–13, 415 of water (hydrolysis), 503–7 Chemical reaction rates, 210–39 activation energy and, 213, 214–16 changing, 217–21 91123_33_Index_pI2-I22 pp3.indd 7 of enzymes, 615 equilibrium and. See Equilibrium, chemical initial, 211, 218 measuring, 210–13 molecular collisions and, 213–14, 219 relationship of activation energy and reaction rate, 214–16 Chemiosmotic pump, ATP production and role of, 739–40 Chemiosmotic theory, 739 Chemistry defined, 2, 26 matter and, 1–3 organic. See Organic chemistry Chemokines, 824, 829, 836 Chemotherapy agents, 817b Chernobyl nuclear accident, 300b Chirality, 420–40 enantiomerism and, 420–26 medicinal drugs and, 424b optical activity, and laboratory detection of, 434–35 significance of, 436–37 stereocenter configuration, 427–30 stereoisomer numbers for molecules with two or more stereocenters, 430–34 Chiral objects, 423, 437 Chitin, 522, 537b Chitosan, 537b Chlorine (Cl2), 44 addition of, to alkenes, 368–69, 375 atomic size of, 57–58 atomic weight of, 41 as oxidizing agent, 132b reaction between methane and, 343 3-Chloroaniline, 385 Chlorobenzene, 387 Chlorodiazepoxide (Librium), 446b Chloroethane, 311t 1-Chloro-4-ethylbenzene, 385 Chlorofluorocarbons (CFCs), 344, 345b Chloroform (CHCl3) boiling point, 162t density, 19 Chloromethane (CH3Cl), 195, 343 reaction between iodide ion and, 216 4-Chloro-2-nitrotoluene, 386 Chlorophyll, photosynthetic reactions and, 775b–776b Chloroplasts, 775b Cholera (Vibrio cholerae), 652 Cholesterol, 560, 573 bile salts as oxidation products of, 569 biosynthesis (anabolism) of, 780, 781 blood levels of, 481b, 560, 563 drugs for lowering, 781 gallstones composed of, 561 high-density lipoprotein and, 481b lipoproteins as carriers of, 561–63 low-density lipoprotein and, 481b, 561, 563 stereocenters of, 424 structure, 560 transport of, 561–63 Choline, 555, 616b, 648 Cholinergic chemical messengers, 641, 641–48, 643, 661 Chromatin, 683 Chromosomes, 666 DNA replication and opening of, 683 DNA structure in. See Deoxyribonucleic acid (DNA) superstructure of, 675 telomeres at end of, 681b Chylomicrons, 561 composition and properties of human, 562t Chymotrypsin, 794 Cinnamaldehyde (oil of cinnamon), 461b, 464 ■ I6 Cinnamyl alcohol, 464 Cis (prefix), 338, 346 Cis-trans isomers, 337–39, 346, 375, 421 of alkenes, 354, 357, 359 in human vision, 361b Citric acid cycle, 727, 729, 733–37, 743, 749, 792 carbon balance in, 733 diagram of, 733 effect of glucose shortages on, 758 energy production by, 736 enzymes of, 729, 737–39 glycolysis and, 752 steps of, 733–36 Citronellal (citronella oil), 461b Citrulline, 654b, 762, 763 Class switch recombination (CSR), 820 Clavulanic acid, 501b Cloning of DNA, 689 using viruses, 719, 720 Clostridium botulinum, 646b Cluster determinants, 823, 836 Coal, 413 Coated pits, 561 Cocaine, 443b catalytic antibodies against, 632b dopamine neurotransmitter and, 653b Coding strand, 696 Codon, 700, 716b, 723 genetic code and, 701t stop, 701, 714 Codon recognition site, 700 Coefficients, 115 Coenzyme(s), 618, 633 NAD1 and FAD, 731 vitamins as, 798t Coenzyme A (CoA), 648, 732, 752 Coenzyme Q, 737–39 Cofactors, enzyme, 618, 633, 798t Cold compresses, specific heat of water and, 23b Collagen, 578, 598, 601, 603 Colligative properties, 197–203 dialysis, 202–3 freezing point depression, 197–98 osmotic pressure, 199–203 Collins, Robert John, 410b Collision theory. See Kinetic molecular theory Colloids, 195–203 Brownian motion in, 196 colligative properties of, 197–203 properties of, 196t types of, 195t Combined gas law, 146, 170 Combustion, 114 alkane-oxygen reaction and, 342 heat of, 134 of methane, 129 of propane, 114, 114, 115 as redox reaction, 130 Common catabolic pathway, 727, 728, 747–48 ATP (energy) production and, 739–40 carbohydrate, lipid, and protein catabolism in, 749 citric acid cycle in, 733–37 compounds of, 730–33 electron and H1 transport, 737–39 energy yield, 741 summary, 767 Common names aldehydes and ketones, 460–61 alkenes and alkynes, 356 amines, 445–46 carboxylic acids, 476–78 ethers, 408–9 Common nomenclature, 331, 331–32 Competitive inhibitors of enzymes, 618, 620, 621, 623, 624b, 633, 648 11/21/08 6:38:18 PM I7 ■ Index Complementary base pairs, 672, 673, 691 Complement pathway, 818 Complete protein, 795 Complex lipids hydrolysis of, 748 structure of, 551, 572 Compound(s), 30, 30–32, 34, 61 binary, 77 binary ionic, 77, 77–78 bonds. See Chemical bonds of common catabolic pathway, 730–33 covalent, 82–86 formulas for, 33, 34 inorganic, 309t ionic, 75–77 organic, 309t, 309–11 properties of, 309t rotation of plane-polarized light by, 434–35 zwitterions, 583, 583–84 Concentration of solutions, 184–91 dilution as expression of, 188–89 molarity as expression of, 185–88 parts per million as expression of, 190–91 percent concentration as expression of, 184–85 pH and pOH as expressions of acid–base, 256–58 titration and calculation of, 259–61 Condensation, 153 Condensed structural formula, 314 Configuration of atoms in stereocenters, 338 Conformations, molecular, 334, 334, 346 of cycloalkanes, 335–37 Coniine, 443b Conjugate acid, 244, 270 Conjugate acid–base pairs, 244–46 Conjugate base, 244, 270 Conjugated proteins, 601 Connective tissues, 538 Consensus sequences, 697 Conservation of energy, law of, 21 Conservation of mass, law of, 36, 60 Constant composition, law of, 36, 60 Constitutional isomers, 326–28, 346, 421 carbon atoms and formation of, 329t Contributing structures, 89, 100, 383 writing, 91–92 Conversion factor(s), 12–13, 13 choosing correct, 13b mass relationships in chemical reactions calculated using, 118 metric system and English system, 10t molar mass as, 111 Conversion of measurement units, 12–17 Cooking oils, 390 Copper, reduction of zinc by, 128 Copper(II) nitrate (Cu(NO3)2), 125 Coral, 73b Corey, Robert, 596 Cori, Gerty and Carl, 777 Cori cycle, 774, 777 Corn borer, sex pheromones in, 358b Cortisol, 564, 564–65, 829 Cortisone, 564, 565 Cosmic rays, 278, 291 Coulomb, 289 Covalent bonds, 68, 73–74, 74, 79–87, 92–96, 100, 153t formation of, 79–80 Lewis structures for, 82–86 nonpolar and polar, 80–81 octet rule exceptions applied to, 86–87 tertiary protein structure stabilized by, 598 Covalent compounds binary, 87 boiling points of, factors that affect, 163 bond angles in, 92–96 91123_33_Index_pI2-I22 pp3.indd 8 formula weights for two, 109t Lewis structures of, 82–86 water as solvent for, 194–95 COX enzyme, anti-inflammatory drugs and inhibition of, 569–70, 571b, 572 Creatine, 803b Creatine phosphokinase (CPK), 629 Crenation, 202, 204 Creutzfeldt-Jakob disease, 600b Crick, Francis, 672, 673 Cristae, mitochondria, 729 Cro-Magnon cave paintings, dating of, 285b Cross-linking structure of collagen, 603 Crutzen, Paul, 345b Crystallization, 164, 164, 171 Crystals anhydrous, and hygroscopic, 192 carbon, 164 hydrated, 192 sodium chloride, 76 C-terminus (C-terminal amino acid), 589 Curie, Marie and Pierre, 277 Curie (Ci), 287 Curved arrow, 365 drawing, 90 Cyclic alkane. See Cycloalkane(s) Cyclic AMP (cAMP) as secondary messenger, 650–51 Cyclic ether, 409, 415 Cyclic GMP (cGMP), 624b Cycloalkane(s), 332, 332–33, 346 cis-trans isomerism in, 337–39 examples, 333 naming, 311 shapes of, 335–37 Cycloalkenes, 358–59 Cyclobutane, 333 Cyclohexanamine, 444 Cyclohexane, 333, 335–37, 369 Cyclohexanol, 398, 464 Cyclohexanone, 464 Cyclohexene, 369, 403 Cyclohexylamine, 445 Cyclooxygenase (COX), 569, 631b 1,3-Cyclopentadiene, 359 Cyclopentane, 333, 335, 335 Cyclopentanol, 464 Cyclopentanone, 464 3-Cyclopentenecarboxylic acid, 488 Cysteine, 582, 783 cystine as dimer of, 584–85 Cysteine protease, 623, 625 Cystine, 585 Cystinuria, 766b Cytochrome c, 594, 739 Cytochrome oxidase, 739 Cytokines, 812, 824, 829, 836 action mode of, 826 classes of, 824, 826 Cytoplasm, anabolic reactions in, 773 Cytosine (C), 667, 667, 672, 673, 689 deamination of, and uracil formation, 687, 688 Cytotoxic (killer) T cells (Tc cells), 814 D D, L system amino acid configuration, 580 carbohydrate configuration, 519–21 Dacron polyester, 511 Daily Value, food labels listing, 788, 789, 791 Dalton, John (1766–1844), 35–37 Dalton’s law of partial pressure, 150, 150–52, 171 Dark reactions, photosynthesis, 775b–776b Debranching enzymes, 792 Decamethonium bromide, competitive inhibition by, 648 Decarboxylation reactions, 490–91, 493, 734 Dehydration, converting alcohols to alkenes by acid-catalyzed, 403–5, 415 Democritus (460–370 BCE), 31–32 Denaturation of proteins, 605–8 human laser eye surgery and, 607b Dendrites, 640, 642 Dendritic cells, 811, 814 interaction of, with T cell, 814 Density, 18, 18–19, 26 of alkanes, 341 of ice and water, 162b b-2-Deoxy-D-ribose, 667 Deoxyribonucleic acid (DNA), 666, 691 amplification of, 689–91 circular (plasmids), 718 double helix of. See Double helix, DNA gene expression and, 696 higher-order structures of, 674–76 looping of, 712 nucleic acid structure and, 666–69 nucleotide sequence in, 675. See also Nucleotide sequences in DNA primary structure of, 670–72, 671 recombinant manipulation of, 718–20 repair of, 687–89 replication. See Replication, DNA RNA and, comparisons between, 674–75 secondary structure of, 672–74 Desalinization of water, 201b Designer enzymes, 629–31 Detergents bile salts as, 569 soaps and, 479–84 synthetic, 388–89, 484 Dextrorotatory rotation, 435, 437 Diabetes mellitus, 659b, 792 blood glucose testing, 530b insulin-dependent, 829 insulin for, 594, 595b. See also Insulin ketoacidosis, 760b ketone bodies and, 492b Dialysis, 202–3 Diastereomers, 421, 431 Diastolic blood pressure, 159b Diatomic elements, 37 Diazepam (Valium), 446b Dichloroacetic acid, 485 Dichloromethane, 343, 344 Diclofenac, 572 Diet, human. See also Nutrients; Nutrition, human calories in, 791–92 carbohydrates, 792–94 essential amino acids in, 782, 782b, 795 fats, 794 food additives and flavorings in, 489b food dyes in, 391b performance-enhancing, 803b protein, 794–95 puffer fish in, 337b reduced cholesterol and saturated fatty acids in, 563 serving sizes, 789 sports drinks, 569 trans fatty acids in, 481b–482b vitamins, minerals, and water in, 797–805 weight reduction through, 788, 792, 796b–797b Dietary Reference Intakes (DRI), 788 Diet faddism, 788 Diethyl carbonate, 511 Diethyl ether (CH3CH2OCH2CH3), 397, 408, 412, 414 density, 18 in solution with water, 181 Diethylmethylamine, 445 11/21/08 6:38:19 PM Index Diethyl pentanedioate (diethyl glutarate), 499 Diethyl propanedioate (diethyl malonate), 508b Digestion, 788, 792 Diglycerides, 548 Dihydroxyacetone, 518 Dihydroxyacetone phosphate, 509, 749, 755 Dilution of concentrated solutions, 188–89 1,2-Dimenthylcyclohexane, cis-trans forms of, 421 Dimethylacetylene, 356 Dimethylamine, 316, 441 1,3-Dimethylbenzene, 385 1,4-Dimethylcyclohexane, cis-trans forms of, 339 N,N-Dimethylcyclopentanamine, 444 1,2-Dimethylcyclopentane, cis-trans forms of, 338 Dimethyl ether (CH3OCH3), 408 N,N-Dimethylformamide, 499 6,6-Dimethyl-3-heptyne, 355 Dimethylphospate, 509 2,2-Dimethylpropane (C5H12), 163 Dimethyl sulfide (CH3SCH3), 412 -dioic acid, 476 Diol, 400 Diol epoxide, 387b Dioxin, 191 Dipeptide, 587, 593 translocation of, in protein synthesis, 705 Diphosphate ion, 509 Diphosphoric acid, 509 Dipole, 81, 100 Dipole-dipole interactions, 153t, 154, 154–55, 171 Dipropyl ether (C6H14), 195 Diprotic acids, 244 Disaccharides, 533, 533–36 Discriminatory curtailment diets, 788 Diseases and conditions AIDS. See Acquired immunodeficiency syndrome (AIDS); Human immunodeficiency virus (HIV) Alzheimer’s disease, 600b, 647b atherosclerosis, 561, 563 autoimmune, 829 botulism, 646b cancer. See Cancer caused by protein and peptide conformation changes, 600b cholera, 652 Creutzfeldt-Jakobs disease, 600b cystinuria, 766b diabetes. See Diabetes mellitus ear infections, 828b familial hypercholesterolemia, 563 fetal alcohol syndrome, 751 galactosemia, 522b goiter, 388b gonorrhea, 828b gout, 192, 193 Guillain-Barré syndrome, 558b kwashiorkor (protein deficiency), 782b, 795 lipid storage, 559b–560b marasmus, 791 multiple sclerosis, 556, 558b nutritional, 782b, 791, 795, 796b–797b, 797 Parkinson’s disease, 586, 653b phenylketonuria (PKU), 766b prion-related, 600b rheumatic fever, 828b rheumatoid arthritis, 538 rickets, 797 SARS (severe acute respiratory syndrome), 830 severe combined immune deficiency (SCID), 721 sickle cell, 595, 596b, 679, 716 smallpox, 825b strep throat, 828b viruses as cause of, 709b Dissociation, 124 Disulfide, oxidation of thiol to, 413, 413, 415 91123_33_Index_pI2-I22 pp3.indd 9 Disulfide bond, 585 DNA. See Deoxyribonucleic acid (DNA) DNA ligase, 686 DNA polymerase, 681b, 689, 691 DNA strands, (2) and (1), 696 Docosahexenoic acid (C22H32O2), 482b, 779–80 Dodecylbenzene, 389, 484 Donepezil, 648b Dopamine, 447, 632b, 649 depletion of, in Parkinson’s disease, 653b drugs affecting messenger function of, 641t Double bond, 83 Double-headed arrows, 89 Double helix, DNA, 672 leading and lagging strands of, 681, 682 origin of replication in, 680–81 relaxation of, 683 replication fork in, 680–81 unwinding of, 683, 686 Dressings, 537b Drugs. See also Pharmaceutical drugs agonist, and antagonist, 641 amphetamines, 442b “angel dust” (PCP), 649 antacids, 253b antibiotics, 295, 424b, 501b anticancer, 670b anti-inflammatory, 570, 571b, 572. See also Aspirin barbiturates, 508b catalytic, 632b chemical communications and nerve transmissions affected by, 640–41, 641t chiral, 424b cocaine, 443b, 632b dosage of, and body mass, 11b genetic influences on metabolism of, 687b ibuprofen, 311, 427, 430, 437, 502b ionic compounds, 80b macrolide, 829 morphine, 626, 655 naproxen, 437 nicotine, 443b oral contraceptives, 568b Photofrin, 607b solubility of, 450b taxol, 310b time-released, 222b tranquilizers, 446b Viagra, 624b D-Sorbitol, reduction of D-glucose to, 528 Dust particles, 195 Dyes, food, 391b Dynamic equilibrium, 223 E Earth, elements in crust of, 37b, 308, 308 Effective collision (molecules), 213, 235 Eggs, denatured proteins in, 605, 608 Eicosapentaenoic acid (C20H30O2), 482b Electrical energy, 20 conversion of chemical energy to, 741–42 Electrically charged ions. See Anion; Cation Electricity ion solutions as conductors of, 192–93 radioactive waves and, 278 Electrolytes, 192, 192–93, 193, 204 Electromagnetic radiation, 278–79 Electromagnetic spectrum, 278 Electron(s), 38, 61 agents for transfer of, in biological oxidationreduction reactions, 731 configuration of, in atoms, 49–56 distribution of, in shells, 50t ground state, 49 pairing electron spins, 52 ■ I8 transport of, citric acid cycle and, 737–39 valence, 55 Electron capture (E.C.), 283, 301 Electron configuration, 51 Lewis dot structures, 55–56 noble gas notations, 54–55 octet rule, elements of Group 1A–7A, 69–71 orbital box diagrams of, 52–54 relationship of, to position in Periodic Table, 56–57 rules governing, 51–52 Electronegativity carboxyl acids and, 485 chemical bonds and, 74–75, 81t, 100 Electron pushing, 90 Electron transport chain, 727, 737–39, 743 energy yield, 741 proton gradient and, 739 uncouplers of, 738b Electron transporting molecules, FAD and NAD1 as, 731 Electron-volt (eV), 279 Electrophoresis, 684b Element(s), 30, 61 classification of, 44–46 in Earth’s crust, 37b, 308, 308 electronegativity values, 74t ground-state electron configurations of first, 19, 53t in human body, 37b inner transition, 44 Lewis dot structures for first 18, 55t main-group, 44, 57, 58 monatomic, diatomic, and polyatomic, 36–37, 37 octet rule for valence electrons of Groups 1A-7A, 69–71 periodicity in properties of, 47–49 transition, 44 transmutation of, 280 transuranium, 297 Elongation, transcription and, 698 Elongation factors, 704, 705 Elongation stage in protein synthesis, 703–6 Embryonal carcinoma cells (EC), 834b Embryonic stem cells, 834b Emulsions, 197 Enantiomerism, 339, 420–26 Enantiomers, 421, 423, 437 action of enzymes and, 436–37 drawing, 426 of glyceraldehydes, 518, 519 mirror images and, 420–22 optically active, 434, 434–35 Endothermic reactions, 133, 134 chemical equilibrium and, 232 energy diagram for, 216 End point of titration, 260 Energy, 20–21 agents for storage of, in common catabolic pathway, 730–31 bioenergetics. See Metabolism chemical reaction rates and, 213, 216, 221 conversion of, 21 entropy as measurement of dispersal of, 143b extraction of, from food, 748–55 forms of, 20–21 ionization, 58–60 kinetic (KE), 20 law of conservation of, 21 levels of, for electron orbitals, 52 of molecular collisions, 213 phases changes in matter states and role of, 166–70 potential, 20 storage of, in lipids, 547 Energy of ionizing radiation, 287, 288–89 -ene (suffix), 355 11/21/08 6:38:19 PM I9 ■ Index English system of measurements, 8 conversion factors between metric system and, 10t temperature measurement in, 11–12 time measurement in, 11 Enhancers (DNA sequences), 698, 710, 710, 723 Enkephalins, 655 drugs affecting messenger function of, 641t similarities between morphine and, 626 Enol, 468 Entropy, 143b Envelope conformation, 335, 346 Environmental problems acid rain, 88b, 180b, 231 air pollution. See Air pollution atmospheric ozone depletion, 345b nuclear accidents, 287, 300b nuclear waste, 299 ocean oil spills, 18 thermal pollution, 182 Enzyme(s), 614, 614–38, 633 action of, and molecule and molecule’s enantiomer, 436–37 active sites of, 618, 622b allosteric, 626, 627 binding site, 436–37 carbohydrate hydrolysis by, 792 as catalysts, 579, 614–15, 623 catalytic antibodies to treat drug addiction, 632b chirality in, 436–37 citric acid cycle, 729, 737–39 classification of, 616, 617t designer, 629–31 digestive, 748 factors influencing activity of, 618–19 in gluconeogenesis, 774 inhibition of, 624b mechanisms of action, 619–24 medical uses of, 624b, 628–29 models of, 620–23 naming, 616, 617t in protein digestion, 794–95 regulation of, 625–28, 630b substrate specificity of, 615, 616b terminology related to, 618 transition-state analogs of, 629–31, 632b Enzyme activity, 618–19 inhibition of, 618, 620, 621, 623, 624b mechanisms of, 619–24 pH and, 619 substrate concentration and, 618–19 temperature and, 619 Enzyme assays, medical diagnosis and use, 629t Enzyme–substrate complex, 620 Epidermal growth factor (EGF), 824 Epigenic mechanism, 835b Epinephrine, 451b, 649, 757b drugs affecting messenger function of, 641t oxidation of, to aldehyde, 652 Epitope, 815, 836 binding of antibody to, 816, 826 Equatorial bonds, 335, 346 Equilibrium, 158 evaporation/condensation, 158 Equilibrium, chemical, 221–24, 235 in acid-base reactions, 247–49 defined, 223 equilibrium constant and, 224–29 Le Chatelier’s principle and, 229–35 time necessary to reach, 229 Equilibrium constant (K), 224–29, 235 Equivalence point, 259 Ergogenic aid, 803b Erythritol, 529 Erythrose, 431 Essential amino acids, 782, 782b, 795 91123_33_Index_pI2-I22 pp3.indd 10 Essential fatty acids, 548, 794 Essential oils, plant, 362 Esterase, degradation of cocaine by, 632b Esters, 499, 512 Fischer esterification of carboxylic acid and formation of, 488–90, 493, 501, 513 as flavoring agents in human food, 489b functional group, 313t, 318, 319 hydrolysis of, 503–4, 513 phosphoric, 509, 531 of polyunsaturated fatty acids, 390 reactions between ammonia, amines, and, 509 waxes as simple, 550b Estradiol, 564, 568 Ethanal, 458 Ethanamine (Ethylamine), reaction between acetic acid and, 502 Ethane structural formula, 311t, 324 thermal cracking of, 353 Ethanedioic acid (oxalic acid), 476 Ethanethiol (CH3CH2SH) (ethyl mercaptan), 397, 398, 400, 411 Ethanoic acid, 488. See also Acetic acid Ethanolamine, 555 Ethanol (CH3CH2OH), 195, 397, 398, 413, 466, 488, 504, 507 boiling point, 162t, 409–10 dehydration of, to alkene, 403, 415 hydrogen bonding in liquid state, 401–2 percent concentration of, in water, 185 production of, by acid-catalyzed hydration of ethylene, 366 reaction between acetic acid and, 229–30, 231, 501 structural formula for, 311 water and, in solution, 181 Ether(s), 408–11, 414 anesthesia and, 410b cyclic, 409 nomenclature, 408–9 physical properties, 409–10 reactions of, 410–11 structure, 408 Ethics, stem cell research and, 835b Ethyl, 330 Ethylbenzene, 384 Ethylene (C2H4), 324, 356, 413 acid-catalyzed hydration of, 366 dehydration of ethanol to, 403, 415 molecular shape of, 94 as plant growth regulator, 353b polymerization reactions of, 370–71, 376 structural formula, 311t structure, 354 thermal cracking of ethane to produce, 353 Ethylene glycol, 199, 400, 414 Ethylene oxide, 409, 414 Ethyl ethanoate (ethyl acetate), 499, 501, 504, 507 Ethylnodiol diacetate, 568b Etoposide, 817b Eukaryotes gene expression in, 696, 697–98, 702–8 gene regulation in, 710–14 properties of mRNA in prokaryotes and, during transcription and translation, 680 Evaporation, 158, 160 Evolution Darwin’s theory of, universality of genetic code as support for, 700 mutations and biochemical, 715b Excitatory neurotransmitters, 649 Exercise lactate accumulation in muscles during, 752b respiratory and metabolic acidosis in, 286b weight loss and, 793b Exons, 679, 680, 691, 698, 698 Exothermic reactions, 133, 134 chemical equilibrium and, 232 energy diagram for, 215 Explosives, 389b, 401b Exponential notation, defined, 5, 6–7, 26 Expression cassette, 721 Extended helix, protein secondary structure, 598, 609 Extensive metabolism (EM) of drugs, 687b External innate immunity, 811 Ex vivo gene therapy, 721, 723 Eye, human laser surgery on, and role of denatured proteins, 607b role of cis-trans isomerism in human vision, 361b F Fabricius (1537–1619), 4 Fabry’s disease, 559t Facilitated transport, 554b Fact, defined, 3 Factor-label method of converting measurements, 12–15, 26 examples, 13–17 FAD (flavin adenine dinucleotide), 743 biological oxidation reduction reactions and, 731 reduction of, to FADH2, 731, 736 structure, 732 FADH2, 739 Fahrenheit scale, 12 reduction of FAD to, 731, 736 Familial hypercholesterolemia, 563 Faraday, Michael (1791–1867), 383 Farnesol, 362–63 Farnesyl pyrophosphate, 781 Fats, 548, 572. See also Lipid(s) artificial, 796b–797b body processing of dietary, 794 dietary, 789, 796b–797b percentage of fatty acids in select common, 549t rancidity of, 550b saponification of, 550–51 storage of, in fat cell, 748 Fat storage depots, 748 Fatty acids, 479–82, 547 biosynthesis (anabolism) of, 777–80 catabolism of, by b-oxidation, 748, 755–57 energy yield from catabolism of stearic acid, 757, 758t essential, 548, 794 formation of, 748 most abundant, 479t omega-3, 481b percentage of, in common fats and oils, 549t physical state of, 548–49 saturated and unsaturated, 479t, 480, 563 trans, 481b–482b, 549 FDG (18-fluorodeoxyglucose), 294 Feedback control, enzyme regulation by, 625, 625–26, 634 Fe(III), 798b Fermi, Enrico (1901–1954), 298 Fertilizers ammonia as, 93 Haber process and fixation of atmospheric nitrogen by bacteria as, 234b Fetal alcohol syndrome, 751 Fever, danger of high human body, 219b Fiber, dietary, 791 Fibers, synthetic, 509–11 Fiberscope, 607b Fibrinogen, 579 Fibrous proteins, 579 Fischer, Emil (1852–1919), 488, 518 11/21/08 6:38:19 PM Index Fischer esterification of carboxylic acids, 488–90, 493, 501, 513 Fischer projections, 518, 518–19, 539 formulas, 518–19 Fleming, Alexander, 501b Florey, Howard, 501b Fluid mosaic model of membranes, 552, 553 Fluoride in drinking water, 71 Fluorine, 44 electronegativity of, 74 Fluorouracil, 670b Food. See also Diet, human body processing of, 792–94 counting calories in, 791–92 nutrition in. See Nutrients; Nutrition, human performance-enhancing, 803b Food additives, 489b Food dyes, 391b Food Guide Pyramid, 789, 790b Food labels, 788 Food metabolism. See Catabolism Formaldehyde (CH2O), 460 Lewis structure and ball-and-stick model of, 83 molecular shape of, 94 reaction between hydrogen and, to produce methanol, 221 Formic acid, 460, 476 Formula, 33, 34 line-angle, 324 predicting, for ionic compounds, 76–77 structural, 83. See also Structural formulas Formula weight (FW), 109, 109–10, 133 for two ionic, and two covalent compounds, 109t Franklin, Rosalind (1920–1958), 672, 673 Free radicals, 293b Freezing-point depression, 197–98, 204 Freons, 345, 345b Frequency (n), electromagnetic radiation, 278 Fructofuranose, 525 Fructose catabolism and, 754 cyclic hemiacetals of, 525 D- form of, 519, 520t Fructose 1,6-bisphosphate, 749, 750 Fruits, ethylene and ripening of, 353b FTO, 779b Fuller, Buckminster (1895–1983), 164 Fumarate, 735, 763 Functional groups, 313–18 alcohols, 313, 313–14, 398 aldehydes and ketones, 316, 316–17 amines/amino groups, 315, 315–16 carboxylic acids, 317, 317–18 carboxylic esters, 318 common types of, 313t defined, 313, 319 ethers, 408 thiols, 411, 412 Fungus (fungi), growth inhibitors of, 486 -furan-, 523 Furanose, 523, 539 Furchgott, Robert, 654b Fusion, nuclear, 296, 296–97 G GABA (g -Aminobutyric acid), 477, 649 gag gene, 831 Galactosamine, 521 Galactose catabolism and, 754 D- form of, 519, 520t, 532b inability to metabolize, 522b Galactosemia, 522b Galantamine, 648b Galen (200–130 BCE), 3 91123_33_Index_pI2-I22 pp3.indd 11 Gallstones, 561 Gamma emission, 283, 301 Gamma (g) rays, 278, 278–79, 301 Gangliosides, 556 Gap junctions, 554b Gaseous state, 142 Gas(es), 17, 26, 142 Avogadro’s law, idea gas law and, 148–50 Boyle’s law, Charles’s law, and Gay-Lussac’s law governing behavior of, 144–48 condensation of, 153 Dalton’s law of partial pressure and, 150–52 Henry’s law and solubility of, 182–83 ideal, 148 kinetic molecular theory on behavior of, 152–53, 219 noble, 48, 49t phase change from solid to, 166–70 pressure and reaction rates between, 217 pressure change and chemical equilibrium between, 233–35 solubility of select, in water, 180t Gasoline, octane rating of, 343b Gaucher’s disease, 559t Gauze, 537b Gay-Lussac’s law, 146, 146t, 170 GC box, 710 Geiger-Müller counter, 287, 301 Gene(s), 666, 679, 691. See also Human Genome Project coding and noncoding sequences in (exons, introns), 679, 680, 698, 698 CYP2D6, and drug metabolism, 687b mutations in, 291, 715–17, 820 structural, 697, 698 transcription of. See Transcription Gene conversion (GC) mutation, 820 Gene expression, 696, 696–725 defined, 696 DNA manipulation and, 718–20 DNA transcription into RNA, 697–99 gene regulation and, 708–14 genetic code and, 700–702 mutations, 715–17 proteins’ role in, 579 stages of protein synthesis as, 702–8 translation and protein synthesis facilitated by RNA in, 700 General transcription factor (GTF), 710 Gene regulation, 708–14 of post-transcriptional level, 713, 714 on transcriptional level, 710–12 on translational level, 714 Gene therapy, 686b, 721–22 Genetic code, 700, 701t, 723 second, 703 Genomics, 602b personal, 685b response to drugs based on individual, 687b Geometries of carbon compounds, 311t Geraniol (rose, other flowers), 362 Geranyl pyrophosphate, 781 GILT (gamma-interferon inducible lysosomal thiol reductase), 816 Globin gene, exons and introns of, 679 Globular proteins, 579 Glucagon, 656 Glucocerebrosides, 559b Glucocorticoids, 829 Glucogenic amino acids, 764, 768 Gluconate, 529 Gluconeogenesis, 774, 784 Glucophage (Metformin), 659b Glucopyranose, 528, 529, 534 chair conformations of, 525 b-D-glucopyranose, 528 ■ I10 Haworth projections of, 523, 524 mutarotation of, 527, 540 Glucosamine, 521 Glucose (C6H12O6), 518 blood levels of, 518, 520, 530b, 659b, 792 breakdown of glycogen to, 630b, 748–49, 755 carbohydrate conversion of, 775–77 catabolism of, 748–53 CO2 conversion to, in plants, 773, 775b–776b D- form of, 519, 520t glycolysis of, 748–53 ketone bodies formed in response to shortages of, 758–59 medical imaging of uptake and metabolism of, 294 oxidation of, enzymes and, 615 reaction rate of, with oxygen, 211 reduction of D-, to D-sorbitol, 528 synthesis of, 774–75 Glucose oxidase, 527 Glucose 6-phosphate, 748, 752 Glucuronic acid, 531, 538 Glutamate, 585, 764 biosynthesis (anabolism) of amino acids and, 782, 783 oxidative deamination of, 761, 761–62, 764 transamination and formation of, 761 Glutamic acid, 581, 585 drugs affecting messenger function of, 641t reuptake of, 649 Glutamine, 581, 764 Glutathione protection against oxidative damage and role of, 753 Glyceraldehyde, 518 amino acid configuration in, 580, 583 enzyme surface and interaction with R and S, 436 stereocenter and enantiomers of, 518, 519 Glyceraldehyde 3-phosphate, 749, 755 Glycerin, 400, 401b, 414 Glycerol, 400, 547, 748, 780 catabolism of, 755 Glycerol 1-phosphate, 780 Glycerol 3-phosphate, 753 Glycerophospholipids, 551, 553–55, 573 Glycine, 581, 583, 594 Glycocholate, 569 Glycogen, 536, 540 breakdown of, to form glucose, 630b, 748–49, 755 depletion of, in athletes, 803b enzyme actions on, 792 role of glycogen phosphorylase in breakdown or synthesis of, 630b, 757b, 773 Glycogenesis, 777 Glycogenolysis, 754 Glycogen phosphorylase, 627 effects of signal transduction on, 757b as enzyme regulation model, 630b Glycogen synthase, 757b Glycol, 400, 414 Glycolic acid, 512b Glycolipids, 551, 556–57, 573, 780 Glycolysis, 622b, 748–53, 768 citric acid cycle and, 752 energy yield from glucose catabolism, 753–55 of glucose, 748–51, 750, 751, 752 glycerol catabolism and, 755 overview, and entrances/exits from, 751 pentose phosphate pathway and, 752–53, 753 phosphoric esters in, 509 pyruvate as end product of, 465 Glycoproteins cytokines as, 824 immunoglobulins as, 816 11/21/08 6:38:20 PM I11 ■ Index Glycosides (acetals), formation of, 527, 527–28, 540–41 Glycosidic bonds, 527, 534, 536, 538 in DNA and RNA nucleosides, 667–68, 668 hydrolysis of, which link monosaccharides, 792 Goldstein, Joseph, 561 Golgi bodies, 729 Gonorrhea, drug resistant strains of, 828b Good, N. E., 267 Gout, 192, 193 G-protein, 650 cascade of adenylate cyclase and, 650, 651, 652 effect of cholera toxin on, 652 Gram (g), defined, 10 Graphite, surface of, 42 Gravity, 10–11 specific, 19, 19–20 Ground-state electron, 49 configurations for, of first 18 elements, 53t GTP. See Guanosine triphosphate (GTP) Guanine (G), 666, 667, 668, 672, 673 Guanosine, 668 Guanosine diphosphate (GDP), 650, 651 Guanosine triphosphate (GTP) formation of, in citric acid cycle, 735 signal transduction cascade and, 650, 651 Guillain-Barré syndrome, 558b H Haber process, 234b Hahn, Otto (1879–1968), 298 Hair, reversible denaturation of proteins in, 607–8 Half-life t1/2, 284–86, 300 radioactive dating of archeological objects based on, 285b of select radioactive nuclei, 286t Haloalkanes, 344–45 chlorofluorocarbons, 344–45 as solvents, 345 Halogenation of alkanes, 343–44, 346, 368–69, 375 of benzene and derivatives, 387, 394 Halogens, 44, 44 alkane reactions with, 343–44, 346 melting and boiling points of, 48t Harvey, William (1578–1657), 4–5 Haworth, Walter N., 523 Haworth projection, 523, 523–25, 540 Heart, human angina, 401b, 624b atherosclerosis and, 561, 563 conversion of lactate to pyruvate in, 628 lactate accumulation in, 752b myocardial infarction in, 563, 629 Heat, 20–25, 26 measurement of, 21–22 produced by chemical reactions, 133 specific. See Specific heat (SH) temperature and, 21–22 Heat energy, 20 conversion of chemical energy to, 742 Heating curve for phase change from ice to water vapor, 166, 166, 167 Heat of combustion, 134 Heat of fusion, 166, 171 Heat of reaction, 133, 133 Heat of vaporization, 166, 171 Helicases, 686, 691, 697 Helicobacter pylori bacterium, 655 Helium (He), orbital box diagram for, 52 a-Helix, protein secondary structure, 596, 609 Helix-turn-helix transcription factor, 712 Helper T cells (TH cells), 814 development of, 815 HIV infection and, 824, 830 Heme protein 91123_33_Index_pI2-I22 pp3.indd 12 as coenzyme, 618 in myoglobin and hemoglobin, 606b reactions of catabolizing, 766–67 structure of, 604 Hemiacetal, 465, 465–66 formation of monosaccharide cyclic, 522–27, 540 Hemodialysis, 203b Hemoglobin, 579, 592, 601 amino-acid sequence of N-terminal decapeptides of b-globins, in select species, 715b comparison of, with myoglobin, 606b sickle cell disease and, 595, 596b, 679, 716 structure of, 601, 604 transport of oxygen by, 606b Hemolysis, 202, 204 Henderson-Hasselbalch equation, 265, 265–67 Henry’s law, 182, 183 Heparin, 539, 539 HEPES buffer, 269t Heptane, 343b Herbicides, 191 Herceptin (drug), 821b Heredity, 665–94 DNA amplification, 689–91 DNA repair, 687–89 DNA replication, 679–86 DNA structure, 666, 670–76 genes, 666, 679 information flow in, 676 molecules of, 665–66 nucleic acid structure and, 666–69 RNA, 666, 670–78 Heroin, 632b Herpes virus, 709b Heterocyclic aliphatic amine, 442 Heterocyclic amine, 442, 452 Heterocyclic aromatic amine, 442 Heterogeneous catalyst, 220 Hexanal, 462 Hexanediamine (hexamethylenediamine), 510 1,6-Hexanediamine (hexamethylenediamine), 444 Hexanedioic acid (adipic acid), 476, 510 Hexanoic acid (caproic acid), 462, 476 Hexanol, 458 Hexene, 355, 357 High-density lipoproteins (HDL), 481b, 561, 573 blood serum levels of, 563 composition and properties of human, 562t transport of cholesterol by, 562–63 High-density polyethylene (HDPE), 372–73, 373 Highly active antiretroviral therapy (HAART), 832 Histamine, 654–55 drugs affecting messenger function of, 641t Histidine, 582, 585, 623, 625, 654 Histone(s), 666, 673, 675, 691 acetylation and deacetylation of key, 683 Histone deacetylase, 683 HIV. See Human immunodeficiency virus (HIV) HIV-1 protease, 614, 624b HMG-CoA reductase, 563 Homogeneous catalyst, 220 Homogeneous mixture, 179. See also Solution(s) Homosalate, 506b Hormones chemical messenger functions of, 640, 641–43, 661 pituitary, 643 principal, 642t proteins as, 579 sex hormones, 565–68 steroid. See Steroid hormones Hot-air balloons, 146 Household substances, 257 Human body anesthesia and effect of ethers on, 410b blood. See Blood, human blood pressure, 159b bone grafts, 73b brain. See Brain, human breath-alcohol screening, 407b breathing, and Boyle’s law on gases, 145b calcium in, and strontium-90 hazards to, 45b cis-trans isomerism in human vision, 361b diet. See Diet, human diseases and conditions affecting. See Diseases and conditions drugs and. See Drugs drug solubility in, 450b electrolyte maintenance, sports drinks for, 194 elements in, 37b elements required by, 33b eye, and vision. See Eye, human fever, 219b goiter, and iodide ion, 388b gout caused by sodium urate monohydrate in joints of, 192, 193 heart. See Heart, human hypothermia/hyperthermia in, 22b immune system. See Immune system; Immunity kidneys, 203b lowering temperature of, 221b mass of, and drug dosage, 11b medical care of. See Medicine muscles. See Muscle(s) nuclear radiation effects on, 286, 289–91 nutrition. See Nutrition, human obesity, 481b, 738b oral contraception for, 568b pH of fluids in, 257 poisons that affect, 337b polynuclear aromatics effects on, 387b radon effects on, 292b smoking effects on, 387b sun protection for, 506b tissue damage caused by radiation free radicals, 293b tooth decay, 127b toxins that affect or toxins affecting, 337b water in, 195 Human Genome Project, 602b, 685b–686b, 713 Human immunodeficiency virus (HIV), 829–36 CD4 molecule, helper T cells and, 824, 830 infection process, 830 methods of attacking immune system, 832 search for vaccine against, 832, 833, 833 structure of, 830 treatment for infection by, 614, 624b, 832 Hyaluronic acid, 538 Hybridization of nucleic acids, 689 Hybridoma, 822 Hydrated ions, 191 Hydrates, 191 air pollution caused by, 194b Hydration, 366 acid-catalyzed, 366–68, 375 alkenes reactions of, 363t, 366–68 Hydrocarbons, 323, 346 aliphatic, 324 alkanes, 324. See also Alkanes alkenes, 324. See also Alkenes alkynes, 324. See also Alkynes arenes, 324. See also Benzene (C6H6) cyclic, 332. See also Cycloalkane(s) saturated, 324 thermal cracking of, 353 unsaturated, 324 Hydrochloric acid (HCl), 243b addition of, to 2-butene, to alkenes, 365 hydrolysis of proteins by, 748 11/21/08 6:38:20 PM Index magnesium and, reaction between, 251 methylamine and, reaction between, 253 norepinephrine and, reaction between, 449 polar covalent bond, 80, 81 potassium hydroxide and, reaction between, 251 reaction between bicarbonate ion and, to form carbon dioxide, 125 reaction between water and, 214, 241, 247 solubility in water, 195 in stomach acid, 794. See also Stomach acid Hydrochlorination reactions in alkenes, 363t, 363–66 Hydrochlorofluorocarbons (HCFCs), 345b Hydrofluorocarbons (HFCs), 345b a-Hydrogen, 468 Hydrogenation in alkenes, 363t, 369–70, 376 catalytic, 369 of lipids, 549–50 Hydrogen bond(s), 79, 153t, 155, 155–56, 171 intermolecular, 597 intramolecular, 597 nucleic acid base pairs and, 673 Hydrogen bonding, 401, 414 between secondary amine molecules, 446 tertiary protein structure stabilized by, 599, 609 Hydrogen cyanide, structural formula, 311t Hydrogen (H) addition of, to alkenes, 369–70 covalent bonds, 79–80 electron configuration in, 49 orbital box diagram of, 52 reaction between formaldehyde and, to produce methanol, 221 transport of H1, 731, 737–39, 741 Hydrogen halides, addition of, to alkenes, 363–66 Hydrogen sulfide, 87 Hydrohalogenation, 363–66 Hydrolases, 616, 617t Hydrolysis, 503–7 acetals, 467 amides, 505 anhydrides, 503 esters, 503–4 glycosidic bonds, 792 triglycerides, 550b Hydrometer, 20 Hydronium ion, 195, 241 expressed as pH and pOH, 256–58 Hydroperoxides, 393 Hydrophobic interactions, tertiary protein structure stabilized by, 598, 599, 609 Hydroxides, 127t Hydroxy-, 460, 476 3-Hydroxybutanoic acid, 492b b-Hydroxybutyrate as component of ketone bodies, 759 5-Hydroxyhexanoic acid, 476 Hydroxyl group, 314, 319, 414 alcohol and, 398 monosaccharides and, 522 phenols and, 389 Hydroxylysine, 586, 587 4-Hydroxy-3-methoxybenzaldehyde (vanillin), 390 4-Hydroxymethylcyclopentene, 488 Hydroxymethylglutaryl CoA, 781 4-Hydroxypentanal, 522 Hydroxyproline, 586, 587 2-Hydroxypropanoic acid. See Lactic acid Hydroxyurea, 596b Hygroscopic substance, 192 Hyperbaric chamber, 151b Hyperbolic curve, 606b Hyperglycemia, 530b 91123_33_Index_pI2-I22 pp3.indd 13 Hypertension, 624b Hyperthermia, 22b Hypertonic solutions, 202, 204 Hyperventilation, 269b Hypoglycemia awareness, 595b Hypothalamus, 655 Hypothermia, 22b Hypothesis, 3, 26 Hypotonic solutions, 202, 204 Hypoxia, 151b I Ibuprofen, 311, 502b, 572 enantiomerism in, 427, 437 -ic acid (suffix), 499 Ice density of water and, 162b phase change from, to water vapor, 166–70 Ideal gas, 148, 153 Ideal gas constant, 148 Ideal gas law, 148 -ide (suffix), 528 Ignaro, Louis, 654b Immune response. See also Immune system regulation of, 824, 826 speed of, 811–12 Immune system, 809–39 adaptive immunity and, 810, 810–11 antigen simulation of, 815 cells of, 812–15, 813t components of, 811 HIV, AIDS, and, 829–36 immunoglobulins, 816–22 introduction to, 809–12 organs of, 812–15 overview, 810 proteins’ role in, 579 regulation of, 824, 826 self versus nonself, determination by, 826–29 specificity, and memory of, as key features, 810–11 T cells and T-cell receptors of, 822–24 Immunity, 809 adaptive, 810, 810–11 innate, 810, 814 vaccinations and, 825b Immunizations, 825b Immunogen, 630 Immunoglobulin(s), 811, 816, 836, 836. See also Antibodies; Major histocompatibility complexes (MHC); T-cell receptor(s) B cell synthesis of, and function, 818, 819 classes of, 816–17, 817t constant, and variable domains on molecules of, 811, 836 IgA, 817 IgE, 818 IgG, 816, 818 IgM, 816 monoclonal antibodies and, 822 structure, 817–18 T-cell receptors and, differences between, 823 V(J)D gene and diversification of responses in, 819, 820, 820 Imprinting, genetic information, 835b Indomethacin, 572 Induced-fit model of enzyme activity, 620, 620–23, 634 Inflammatory response, 824 Influenza virus, 709b Infrared light, 278 Inhibition, enzyme, 618, 620, 621, 623, 633 medical uses of, 624b Inhibitory neurotransmitters, 649 Inhibitory receptor, 827, 837 Initial rate of reaction, 211, 218 ■ I12 Initiation factors, 703, 704 Initiation signal, 698 Initiation stage of protein synthesis, 703, 704 Innate immunity, 810, 836 cells of, 814 self/nonself discriminate in cells of, 826–27 Inner transition elements, 44 Inorganic compounds, 309t Insect pests, corn borers as, 358b Insulin, 656–57, 665 A and B chains of, 594 diabetes and production of, 530b, 659b polypeptide structure of, 594 production of, by recombinant DNA techniques, 719 use of, 595b Integral membrane proteins, 604 Intensity of ionizing radiation, 287–88 Interleukins (ILs), 824 Intermolecular forces. See Attractive forces between molecules Intermolecular hydrogen bonds, 597 International System of Units (SI), 8 International Union of Pure and Applied Chemistry (IUPAC), 328–29, 346. See also IUPAC naming system Intramolecular hydrogen bonds, 597 Introns, 679, 680, 691, 698, 698 In vivo gene therapy, 721–22, 723 Iodide, reaction between chloromethane and, 216 Iodine, 44 Iodine-125, 296 Iodine-131, 293, 296 decay curve of, 284 Ion(s), 59, 61. See also Anion; Cation electricity conducted by solutions of, 192–93 forces of attraction between molecules and, 153t, 153–56 hydrated, 191 naming polyatomic, 72 predicting reactivity of, in aqueous solutions, 124–27 spectator, 125 Ion channel, chemical messengers and opening of, 646, 648, 651 Ionic bonds, 68, 73–74, 74, 75–77, 100, 153t formation of, 75–76 Ionic compound(s), 75 containing polyatomic ions, 79 formula weights for two, 109t in medicinal drugs, 80b from metals forming more than one positive ion, 78–79 from metals forming one positive ion, 77–78 molar mass as conversion factor for, 111 predicting formulas of, 76–77 water as solvent of, 191, 192 Ionization energy, 59, 60, 61 atomic number versus, 60 Ionization of water, 254 Ionizing radiation, 286–89 energy of, 288–89 intensity of, 286–89 as mutagens, 716 b-Ionone, 461b Ion product of Kw (water constant), 254, 270 Iron daily requirements for, 798b in food, 798b mixture of sulfur and, 35 Isobutane, 331 Isobutylene, 356 Isocitrate, oxidation and, decarboxylation of, 734–35 Isoelectric point (pI), 584, 591–92, 592, 608 Isoleucine, 582 11/21/08 6:38:20 PM I13 ■ Index Isomer(s), 421 constitutional, 326–28 stereoisomers, 339. See also Stereoisomers Isomerases, 616, 617t Isopentane, 331 Isopentenyl pyrophosphate, 781 Iso- (prefix), 331 Isoprene, 359, 362, 781 Isoprene unit, 362, 375 Isopropyl alcohol, 414 2-Isopropyl-5-methylcyclohexanol, 433 2-Isopropyl-5-methylphenol (Thymol), 390 Isoproterenol, 451b Isotonic solutions, 201 Isotopes, 40–41, 61 radioactive, 279–80, 294t Isotopic abundance, 43b Isozymes (isoenzymes), 628, 628, 634 -itol (suffix), 528 IUPAC naming system, 328–29, 346 alcohols, 398–400 aldehydes and ketones, 458–61 alkanes, 328–31 alkenes and alkynes, 355–56 amines, 444–45 carboxylic acids, 475–76 prefixes used in, to show carbon presence, 329t J Jackson, Charles, 410b Jencks, William, 630 Jenner, Edward, 825b Joule (J), 22 K Ka, acid ionization constant, 249, 270 for weak acids, 249t Kekulé, August (1829–1896), 308 Kekulé’s structure of benzene, 383 Kelvin (K) temperature scale, 12, 143b gas laws and, 146 Keratin, 579, 597, 607 a-Ketoacid, 761 Ketoacidosis, 760b b-Ketocarboxylic acid, decarboxylation of, 491 Keto-enol tautomerism, 468–69, 470, 491 Ketogenic amino acids, 765, 768 a-Ketoglutarate, 491, 735, 761, 782, 783 a-Ketoglutaric acid, 491, 765 Keto group, 761 2-Ketohexoses, D-forms of, 521t Ketone(s), 457–74, 458 characteristic reactions of, 462–68 functional group, 313t, 316, 316–17, 458 keto-enol tautomerism, 468–69 naming, 458–61 naturally occurring, 461b oxidation of secondary alcohol to, 406, 415 physical properties of, 461–62 Ketone bodies, 758–59, 759, 765, 768, 794 diabetes and, 492b, 760b 2-Ketopentoses, D-forms, 521t Ketoses, 518 as reducing sugars, 529 Ketosis, 794 Kevlar, 510 Kidneys, hemodialysis of human, 203b, 204 Killer (cytotoxic) T cells (Tc cells), 814 Kinases, 621b Kinetic energy (KE), 20, 26 conversion of potential energy to, 20 temperature and increase in, 142, 219 Kinetic molecular theory, 152, 152–53, 171 chemical reactions and, 213–14, 219 Knoop, Franz, 755 Köhler, Georges, 822 91123_33_Index_pI2-I22 pp3.indd 14 Koshland, Daniel, 620 Krabbe’s leukodystrophy, 559t Krebs, Hans (1900–1981), 734, 764 Krebs cycle. See Citric acid cycle Kwashiorkor, 782b, 795 L Laboratory tools. See Tools Lactams, 500 b-lactam antibiotics, 501b b-Lactams, 501b Lactate accumulation of, in muscles, 752b glucose conversion of, 774, 774 glycolysis, glucose catabolism, and, 750, 751, 752 pyruvate conversion of, 628 Lactate dehydrogenase (LDH), 629 isozymes of, 628, 628 Lactic acid, 479, 510 muscle tissue and production of, 435 rotations for enantiomers of, 435 Lactones, 499 Lactose, 534, 540 Lagging strand, DNA replication, 681, 682, 691 Lakes, specific heat of water and temperature of, 23b Landsteiner, Karl (1868–1943), 532b Laser surgery, human eye, 607b Lavoisier, Antoine Laurent (1743–1794), 36 Law of conservation of energy, 21 Law of conservation of mass, 36, 60, 114 Law of constant composition, 36, 60 L-dopa (L-Dihydroxyphenylalanine), 586, 653b Lead, 36, 43 Leading strand, DNA replication, 681, 682, 691 Le Chatelier, Henri (1850–1936), 229 Le Chatelier’s principle, chemical reactions and, 229, 229–35, 235 addition of reaction component and, 229–31 change in pressure and, 233–35 change in temperature and, 232–33 effects of catalyst and, 235 overcoming effects of, in biosynthetic pathways, 773 removal of reaction component in, 231–32 sunglasses and application of, 233b Lecithin, 553 Length, measurement of, 8–9 Leptin, 656 Lerner, Richard, 630 Leucine, 581, 701, 765 Leucine zipper, 712 Leukocytes. See White blood cells (leukocytes) Leukotriene receptors (LTRs), 572 Leukotrienes, 572, 573 Levorotatory rotation, 435, 437 Lewis, Gilbert N. (1875–1946), 55, 69 Lewis dot structures, 55–56, 61, 83, 100 for alkali metals, 57t for covalent compounds, 82–86 for elements 1-18, 55t for select small molecules, 84t Ligand-gated ion channels, 648 Ligands. See Chemical messengers Ligases, 616, 617t Ligation process in DNA replication, 686 Light as energy, 20 IR (infrared), 278 plane-polarized, 434–35 reaction between silver chloride on sunglasses and sun, 233b Tyndall effect of colloid-sized particles on, 195–96 UV (ultraviolet), 278 visible, 278 Light reactions, photosynthesis, 775b–776b Limiting reagent, 121, 121–22, 134 Limonene, 362 Line-angle formula, 324 Linear alkylbenzenesulfonates (LAS), 484 Linoleic acid, 549, 553, 794 Linolenic acid, 794 Lipases, 615, 748, 794 Lipid(s), 546–77, 572 cell membrane transport, 554b classification of, 546–47 complex, 551, 551 function-based classification of, 546–47 glycerophospholipids, 553–55 glycolipids, 556–57 membrane structure and role of, 552–53 metabolism of. See Lipid catabolism myelin sheath around nerve axons and, 558b oxidation and rancidity of, 550b processing of, 794 prostaglandins, thromboxanes, and leukotrienes, 569–72 simple, 551 sphingolipids, 555, 555–56 steroids, 558, 558–63. See also Steroid(s) storage disease of, in humans, 559b–560b structure-based classification of, 547 triglycerides, 547–51 waxes, 550b Lipid bilayers, 552, 573 space-filling molecular model of, 553 transport across, 554b Lipid biosynthesis, 777–80 Lipid catabolism, 733, 748 energy yield from, 757–58, 758t glycerol catabolism, 755 b-oxidation of fatty acids, 755–57 Lipoproteins, 561 cholesterol transport by, 561–63 composition and properties of human, 562t high-density (HDL). See High-density lipoproteins (HDL) low-density. See Low-density lipoproteins (LDL) Liquid(s), 17, 26, 142 behavior of, at molecular level, 157–63 boiling point of, 161–63 density of water versus ice, 162b solidification of, 153 surface tension on, 158 vapor pressure of, 158–61, 161 Liquid state, 142 Liter (L), defined, 9 Lithium aluminum hydride (LiAlH4), 488, 493 Lithium (drug), 71 Lithium (Li), orbital box diagram for, 52 Lock-and-key model of enzyme activity, 620, 634 Logarithms (logs), using antilogs and, 255–56 London, Fritz (1900–1954), 154 London dispersion forces, 153t, 154, 171 Low-density lipoproteins (LDL), 481b, 561, 573, 780 blood serum levels of, 563 composition and properties of human, 562t structure of, 562 transport of cholesterol in, 561–62 Low-density polyethylene (LDPE), 372 fabrication of, 372 Lowry, Thomas, 244, 270 Luteinizing hormone (LH), 565 Lyases, 616, 617t Lymph, 812, 813 Lymphatic system, 813, 814–15, 836 Lymph nodes, 813, 814–15 Lymphocytes, 812, 836. See also B cell(s); T cell(s) development of, 815 effect of vaccines on, 825b monoclonal antibody production from, 822 Lymphoid organs, 812, 836 Lysine, 582, 586, 615 11/21/08 6:38:20 PM Index Lysosomes, 615, 729 antigen processing in, 816 Lysozyme, 615 M Macrolide drugs, 829 Macrophages, 810, 812, 814, 815, 836 self/nonself determination and, 826–27 Mad cow disease, 600b Magnesium hydroxide (Mg(OH)2), 243b Magnesium metal, reaction with hydrochloric acid, 251 Main-group elements, 44 atomic radii of, 57, 59 Major groove, B-DNA, 674 Major histocompatibility complexes (MHC), 811, 814, 815–16 classes of (MHC I, MHC II), 815–16, 816 Malate, 736 Maloney murine leukemia virus (MMLV), 721, 722 Malonyl-CoA, 779b Malpighi, Marcelo (1628–1694), 4 Maltose, 534, 540 Mannitol, 529 Mannosamine, 521 Manometer, mercury, 144, 144 MAO inhibitors, 652 Marasmus, 791 Markovnikov, Vladimir (1838–1904), 364 Markovnikov’s rule, 364, 366 Mass defined, 10 law of conservation of, 36, 61, 114 measurement of, 10–11 Mass number, 39, 61 Mass per unit volume. See Density Mass relationship calculations chemical reactions, 118–24 using moles, 110–14 Matrix, mitochondria, 729 Matter, 1–3 atoms as basic component of, 31–32 classification of, 32–35. See also Compound(s); Element(s); Mixture(s) defined, 2 energies involved in phase changes in, 166–70 states of, 2, 17–18, 141–42. See also Gas(es); Liquid(s); Solid(s) Mayapple (Podophyllum peltatum), antitumor effects of extract from, 817b MDR1, 716b Measurement, 8–12 of blood pressure, 159b of chemical reaction rates, 210–13 converting units of, 12–17 of energy dispersal (entropy), 143b of nuclear radiation, 286–89 of pressure, 143–44 Mechanical energy, 20 chemical energy conversion to, 742 Medical imaging, 292–95 positron emission tomography (PET), 295 radioactive isotopes useful for, 294t Medications. See Pharmaceutical drugs Medicine, 1–2. See also Drugs; Human body; Pharmaceutical drugs anesthesia, 410b bone grafts, 73b dissolving surgical sutures, 512b enzymes and enzyme inhibition used in, 624b, 628–29 gene therapy, 721–22 hyperbaric oxygen chamber, 151b medical imaging of. See Medical imaging nuclear, 292–96 91123_33_Index_pI2-I22 pp3.indd 15 Meitner, Lise (1878–1968), 298 Melting point, 142, 171 of alkali metals, 48t of alkanes, 340, 340t of halogens, 48t of noble gases, 49t Membrane(s), 552, 573 biosynthesis of lipids of, 780–81 fatty acids in, 479t role of lipids in structure, 547, 552–53 transport across, 552, 554b Memory, 621b Memory cells, 814 Mendeleev, Dmitri (1834–1907), 4, 43–44 Menstrual cycle, hormones and, 565 Mental disorders, 71, 585 Menthol oxidation product, 406 peppermint flavor, 362, 406 Menthone, 406 Mercaptan, 411, 415 2-Mercaptoethanol (HOCH2CH2SH), 607 Mercury(II) oxide, decomposition of, as endothermic reaction, 133 Messenger RNA (mRNA), 676, 691 properties of, during transcription and translation, 680 protein synthesis and role of, 703 transcription of, 697, 698 translation and role of, 700 Metabolic acidosis, 268b Metabolism, 726, 726–46, 743 anabolic pathway of, 728. See also Anabolism catabolic pathways of, 727, 728. See also Catabolism chemical energy (ATP) conversion into other energy forms in, 742–46 chemiosmotic pump and ATP production in, 739–40 citric acid cycle’s role in, 733–37 electron transport in, 737–39 H1 transport in, 737–39 mitochondria’s role in, 728–29 principal compounds of common catabolic pathway, 730–33 signal transduction effects on, 757b Metal(s), 44, 44–45, 46, 61 alkali, 47. See also Alkali metals binary ionic compounds named from, 77–78 cations named from, 72t reaction of acids, 251 use of, as historic landmarks, 47b Metal-binding fingers of transcription factors, 712 Metal hydroxides, 251 Metal ion coordination, 598–99, 609 Metalloids, 46, 46, 61 Metal oxides, acid reactions with, 251 Meta (m) locator, 385, 393 Meteorites, 47b, 285b Meter (m), 9 Methadone, 450b Methamphetamines, 442b Methanal, 458 Methandienone, 566b Methane chlorine and, reaction between, 343 oxygen and, reaction between, 342–43 structure of, 94, 324 Methanethiol (CH3SH), 411 Methanol (CH3OH), 195, 413 COH bonds polarity in, 401–2 model of, 398 reaction of formaldehyde and hydrogen to produce, 221 structural formula, 311t Methenolone, 566b ■ I14 Methionine, 582, 701, 714 Methionine enkephalin, 626 Methoxycyclohexane, 408 Methyl, 330 Methylacetylene, 356 Methylamine, 316, 441, 447 hydrochloric acid and, reaction between, 253 structural formula, 311t Methylammonium hydroxide, 447 3-Methylaniline, 444 2-Methyl-1,3-butadiene (isoprene), 359 3-Methylbutanal, 458 3-Methylbutanoic acid (Isovaleric acid), 476 3-Methyl-1-butyne, 355 Methylcyclohexane, 337, 458 Methyleneimine, 311t Methyl ethyl ketone (MEK), 461 1-Methylguanosine, 677 5-Methyl-3-hexanone, 458 4-Methyl-1-hexene, 355 4-Methyloctane, 329 Methyl orange as pH indicator, 258 3-Methylphenol, 389 2-Methylpropane, 326 2-Methyl-1-propanethiol, 411 2-Methyl-1-propanol, 398 2-Methyl-2-propanol, 398, 403 2-Methylpropene, 403 Metric system, 8, 26 basic units in, 9t conversion factors between English system and, 10t heat measurement in, 22 length measurement in, 8–9 mass measurement in, 10–11 prefixes in, 9t temperature measurement in, 11–12 time measurement in, 11 volume measurement in, 9–10 Mevalonate, 781 Micelles, 483, 483 Micro RNA (miRNA), 678, 691 Mifepristone (RU 486), 565, 568 Millimeters of mercury (mmHg), 143 Millirem, 290 Milstein, César, 822 Mineralocorticoids, 564 Mineral oil, 340 Minerals, 795, 798t–802t. See also specific mineral Mini-satellites, DNA, 679 Minor groove, B-DNA, 674 Mirror images of molecules, 421, 421, 423, 437 Miscible solutions, 181 Mitchell, Peter (1920–1992), 739 Mitochondria, role in cell catabolism, 728, 729, 743 Mixture(s), 34, 35, 61, 196t. See also Colloids; Solution(s); Suspensions Molarity (M), 185–88, 204 Molar mass, 110–11, 133 Molecular collisions chemical reactions resulting from, 213–14 energy of, 213 kinetic molecular theory on, 152–53, 171, 219 Molecular weights (MW), 109, 109–10, 133 Molecule(s), 34, 35. See also Attractive forces between molecules; Compound(s) biological. See Biomolecule(s) conformations of, 334, 335 functional groups in. See Functional groups gases, and kinetic molecular theory, 152–53 handedness of. See Chirality liquids, behavior of, 157–63 mirror images of, 421, 421 polarity of, 97–99, 100 11/21/08 6:38:21 PM I15 ■ Index predicting bond angles in covalent, 92–96 superposable, and nonsuperposable, 422 with two or more stereocenters, 430–34 Mole (mol), 110, 133 calculating mass relationships using, 110–14 defined, 110 one-mole quantities of select metals and compounds, 111 Molina, Mario, 345b Mollusks, shell construction in, 127 Monatomic anions, 72, 99 Monatomic cations, naming, 71–72 Monatomic elements, 36 Monoamine chemical messengers, 649–50. See also Dopamine; Epinephrine; Histamine; Norepinephrine (noradrenaline); Serotonin action of, 650 inactivation of, 652 Monoamine oxidases (MAOs), 652 Monoclonal antibodies, 822 cancer therapy using, 821b production of, 822 Monoglycerides, 548 Monomers, 370, 375 Monoprotic acids, 244 Monosaccharides, 517–33, 518, 539 amino sugars, 521–22 blood types and, 532b–533b carbohydrate breakdown to form, 748 characteristic reactions of, 527–33, 540–41 cyclic structures of, 522–27 D and L forms of, 519–21 defined, 518 D-Monosaccharide, 519, 520t, 539 extraction of energy from. See Glycolysis Fischer projection formulas for, 518–19 galactosemia as inability to utilize, 522b L-ascorbic acid to, 526b nomenclature for, 518 physical properties of, 522 processing of, 792 structure for, 518 Montreal Protocol, 345b MOPS buffer, 267, 269t Morphine, 626, 655 Morton, W. T. G., 410b Movement, role of proteins in muscle, 579 Mullins, Kary B. (1945–), 689 Multiple sclerosis, 556, 558b, 829 Multipotent stem cells, 834b Murad, Ferid, 654b Muscle(s), 435 contraction of, 742 enantiomer of lactic acid in, 435 enzymes and relaxation of, 616b lactate accumulation in, 752b proteins and, 579 storage of oxygen in, by myoglobin, 606b Muscone, 461b Mutagens, 716, 723 Mutarotation, 527, 540 Mutations, 715, 715–17, 723 biochemical evolution and gene, 715b silent, 716b in V(J)D gene, 820 Myelin sheath, multiple sclerosis and other diseases affecting, 558b Mylar polyester, 511 Myocardial infarction, 563, 629 Myoglobin, 606b Myrcene (bay oil), 362 N NADH glucose catabolism and, 753–54 NAD1 reduction to, 731, 735, 736, 755 91123_33_Index_pI2-I22 pp3.indd 16 NAD1 (nicotinamide adenine dinucleotide), 491, 743 in biological oxidation-reduction reactions, 731 reduction to NADH, 731, 735, 736, 755 structure of, 732 NADPH, pentose phosphate pathway, 752–53 NADP1 (nicotinamide adenine dinucleotide phosphate), 753 Naming. See Nomenclature Nandrolone decanoate, 566b Nanotubes, 164, 195 Naphthalene, 386 Naproxen, 437 Natural gas, 332, 346 Natural killer (NK) cells, 809, 810, 814, 836 Negative modulation, 626 Neon (Ne), orbital box diagram for, 54 NER (nucleotide excision repair), 689, 717 Nerve cell anatomy, 640, 642 myelination of axons of, 558b Nerve gases, 641t Nerve transmission, drugs affecting, 641t Net ionic equation, 125, 134 Network solids, 165 Neurofibrillar tangles, 600b, 647b Neuron, 640, 642. See also Nerve cell Neuropeptide Y, 655 Neurotransmitters, 640, 661 amino acids as, 649 cholinergic, 641, 641–48 classification of, 641–43 effects of cocaine on, 632b excitatory, and inhibitory, 649 regulation of, 648, 652 removal of, 652 signal transduction and, 650, 651 Neutralization as property of acids and bases, 251 Neutralizing antibody, 835 Neutral solution, 256, 270 Neutron, 38, 39, 61 in isotopes, 280 Nicotine, 443b, 644, 648 Nicotinic receptor, 644 Niemann-Pick disease, 560t Nirenberg, Marshall (1927–), 700 Nitration of benzene and derivatives, 387–88, 394 Nitric acid (HNO3), 243b Nitric oxide (NO) as air pollutant, 88b macrophage function and, 814 as secondary chemical messenger, 88b, 654b 4-Nitroaniline, 444 Nitrobenzene, 388 4-Nitrobenzoic acid, 388 Nitrogen catabolism of amino acid, 760–64 Haber process and conversation of, to ammonia, 234b Nitroglycerine (trinitroglycerin), 389b, 401b Nitrous oxide, 410b N-Methylacetamide, 499 N-Methyl-D-aspartate (NMDA) receptor, 649 Nobel, Alfred (1833–1896), 401b Noble gases, 48 melting and boiling points of, 49t notations, 54–55, 57t octet rule for electron configuration, 69t Nomenclature. See also IUPAC naming system alcohols, 398–400 aldehydes and ketones, 458–61 alkanes, 328–31 alkenes and alkynes, 355–61 amines, 444–46 aromatic compounds, 384–87 binary ionic compounds, 77–78 carboxylic acids, 475–78 common, 331, 331–32. See also Common names enzymes, 616 ethers, 408–9 glycosides, 528 ionic compounds containing polyatomic ions, 79 monatomic cations, 71–72 monoatomic anions, 72 polyatomic ions, 72 thiols, 411–12 Nonbonding electrons in Lewis dot structures, 83 Noncompetitive inhibitors of enzymes, 618, 620, 621, 623, 633 Nonelectrolytes, 192 Nonmetals, 46, 46, 61 Nonpolar covalent bonds, 80, 80–81, 100 Nonspecific immune-system cellular interactions, 813t Nonsteroidal anti-inflammatory drugs (NSAIDs), 502b, 570, 571b, 572. See also Aspirin Nonsuperposable molecules, 422 Norepinephrine (noradrenaline), 449 absorption of, into receptor site, 650, 651 drugs affecting messenger function of, 641t oxidation of, to aldehyde, 652 reaction between hydrochloric acid and, 449 Norethindrone, 568b Norethynodrel, 568b Normal boiling point, 161 Novocain, 450b N-terminus (N-terminal amino acid), 589, 593 Nuclear chemistry, 276–306 detection and measurement of nuclear radiation, 286–89 emission of radioactivity by atom nucleus, 279–83 nuclear fission and atomic energy, 298, 298–99 nuclear fusion, 296, 296–97 nuclear half-life, 284–86 nuclear medicine, 292–96 radioactive dating, 285b radioactivity, 276–79 relationship of radiation dosimetry to human health, 289–91 Nuclear energy, 20 accidents involving, 286, 300b fission, 298, 298–99 fusion, 296, 296–97 Nuclear equation, balancing, 280–81 Nuclear fission, 298, 298–99, 301, 301 Nuclear fusion, 296, 296–97, 301 Nuclear medicine, 292–96 medical imaging, 292–95 radiation therapy, 295–96 Nuclear power plant accidents, 286, 300b Nuclear reaction, 280 Nuclear weapons testing, health hazard of, 45b Nucleic acids. See also Deoxyribonucleic acid (DNA); Ribonucleic acid (RNA) structure of, 666–69, 670–72. See also Nucleotide(s) of viruses, 709b Nucleophilic attack DNA replication and, 683 enzyme mechanisms and, 623 peptide bond formation and, 706 Nucleosides, 667, 669, 669t Nucleosomes, 674, 691 Nucleotide(s), 668, 669, 671 bases of, 666, 666–67 DNA replication, and addition of, 683 eight, in DNA and RNA, 669t excision repair of, 687–89 Okazaki fragments of, 686 phosphate of, 668–69 sequences of, in DNA, 675. See also Nucleotide sequences in DNA sugars of, 667–68 11/21/08 6:38:21 PM Index Nucleotide excision repair (NER), 689, 717 Nucleotide sequences in DNA, 675 coding and noncoding (exons, introns), 679, 680, 698, 698 satellite, 679 Nucleus (atom), 38, 39 half-life of radioactive decay, 284–86 radioactivity emission by, 279–83 Nucleus (cell), 729 Numbers, notation of, 5–7 Nutrients, 787 classification of, 788 disease caused by insufficient, 782b, 791, 795 essential amino acids, 782, 782b, 795 essential fatty acids, 548, 794 food guides on, 789, 790b food labels listing, 788 minerals as, 795, 798t proteins, 795 recommended daily allowances of, 788, 791 requirements for, 799t–802t structure of, 799t–802t vitamins, 795, 798t water as, 805 Nutrition, human, 787–808. See also Diet, human athletic performance enhancement and, 803b calorie count and, 791–92 carbohydrate processing, 792–94 dietary protein processing and, 794–97 fats processing, 481b–482b, 794 measurement of, 787–91 minerals, 797–805 protein complementation, 795 vitamins, 797–805 water, 797–805 Nylon-66, 510 O Obesity biological basis of, 779b dietary fats and, 481b health dangers of, 791–92 weight-reduction drugs, 738b Octanal, 406 Octane rating, 343b Octanoic acid, 406 1-Octanol, 406 Octet rule, 69, 70, 99 exceptions to, 86–87 Octyl p-methoxycinnamate, 506b Odors. See Scents and odors —OH (hydroxyl) group, 314, 389, 398, 414 -oic acid (suffix), 476, 499 Oils, 548, 572 percentage of fatty acids in select common, 549t rancidity of, 550b Oil spills, 18 Okazaki fragments, 686, 691 Oleic acid, 549 Olestra, 796b–797b Oligosaccharides, 533 -ol (suffix), 398, 414 Omega-3 fatty acids, 481b Oncogenes, 717b Open complex, 710 Optically active compounds, 434, 434–35, 437 Oral contraception, 568b Orbital(s), 50, 61 distribution of, within shells, 50t energy levels for, 51 rules governing, 51–52 1s, 2s and 2p, 51 shapes and spatial orientation of, 51 Orbital box diagrams, 52–54, 53t Organelles, 729, 743 91123_33_Index_pI2-I22 pp3.indd 17 Organic chemistry, 308–22 functional groups, 313–18 introduction to, 308–9 obtaining organic compounds for, 309–11 writing structural formulas, 311–13 Organic compound(s) isolation of, from nature, 309 properties of inorganic and, compared, 309t structural formulas for, 311–13 synthesis of, in laboratory, 309–11 Origin of replication, 680 Orinase (Tolbutamide), 659b Ornithine, 615, 762, 763 Ortho (o) locator, 385, 393 -ose (suffix), 518, 528 Osmolarity, 200, 204 Osmosis, 199–200, 201b Osmotic membrane, 199 Osmotic pressure, 199, 199–203, 204 Ovulation, 565 Oxalic acid, 476 Oxaloacetate, 736 from malate, 736 from PEP, 758 Oxalosuccinate, 734–35 Oxalosuccinic acid, 491 Oxidation, 128–33, 134. See also Redox reactions b-, 748, 755–57, 768 of aldehydes and ketones, 462–63, 469 of alkanes, 342, 346 bile salts as product of cholesterol, 569 defined, 128 of fats and oils, and resulting rancidity, 550b of monosaccharides, 529–31, 541 obtaining energy from fatty acids by b-oxidation, 748, 755–57, 768 of primary and secondary alcohols, 405–6, 415 of thiols, 413, 415 Oxidation–reduction reaction, 128, 731. See also Redox reactions Oxidative damage, protection against, 753 Oxidative deamination, 761, 761–62, 764, 768 Oxidative phosphorylation pathway, 730, 741, 743, 749, 754 uncouplers of, 738b Oxidizing agents, 128, 133 antiseptics as, 132b Oxidoreductases, 616, 617t 3-Oxobutanoic acid, 492b Oxonium ion, 367 Oxygen (O2) alkanes and, reaction between, 342–43 hemoglobin and myoglobin behavior when binding, 605b–606b hyperbaric chambers for deprivation of, 151b orbital box diagram for, 54 steel wool and, chemical reaction between, 217 Oxytocin, 655 function, 594–95 structure, 595 Ozone (O3) chlorofluorocarbons effects on, 345b as oxidizing agent, 132b P p53, 717b Paclitaxel (Taxol), 310b Padimate A, 506b Pain signals, transmission of, 655–56 Papain, 623, 625 Paraffin wax, 340, 340 Para (p) locator, 385, 393 Parkinson’s disease, 586, 653b Partial pressures, Dalton’s law of, 150–52 Parts per billion (ppb), 190 ■ I16 Parts per million (ppm), 190–91 Pascal, 143 Passive transport, 554b Pasteur, Louis, 825b Pauling, Linus, 74, 596 structure of benzene by, 383 theory of resonance by, 89, 383 Pauling scale, 74t Penicillins, 501b enzyme inhibition by, 623 1,4-Pentadiene, 359 Pentanal, 464 Pentane (C5H12), 163, 325, 331 1,5-Pentanediamine (cadaverine), 446 Pentanedioic acid (glutaric acid), 476 Pentanoic acid, 479 1-Pentanol, 464 Pentobarbital, 508b Pentose phosphate pathway, 752, 752–53, 753, 768 Pent- (prefix), 518 Peppers, capsaicin in, 392b PEP (phosphoenolpyruvate), 758 Pepsin, 618, 794 Peptide(s), 590 as chemical messengers, 643, 655–57 human disease caused by conformation changes in, 600b protein synthesis from. See Protein synthesis side chains of, 590 Peptide bond, 587–90, 608 formation of, in protein synthesis, 704, 706 Peptide linkage, 587 Peptidergic chemical messengers, 643, 655–57, 661 Peptidyl transferase, 704, 705 Percent concentration (%w/v) of solutions, 184–85, 204 Percent yield of product mass in chemical reactions, 123, 134 Periodic properties, 57–60 atomic size, 57–58 ionization energy, 58–60 Periodic Table, 4, 43–49, 61 classification of elements in, 46 inner transition elements in, 44 main-group elements in, 44 origin of, 43–44 periodicity in, 47–49, 57–60 relationship of electron configuration, to position in, 56–57 transition elements in, 44 Peroxidase, 631b Peroxide, 372 Personal genomics, 685b Pesticides, 500b PETN (pentaerythritol tetranitrate), 389b Petroleum, 332, 346 fractional distillation of, 332, 332 ocean spills of, 18 pH (hydronium ion concentrations), 256–58, 270 of buffers, 263–64, 265–67 enzyme activity and, 619 of human blood, 257, 265 indicators of, 258, 258t, 259 isoelectric point (pI), 584, 591–92, 592 values of, for select common materials, 258t Phagocytes, 816 Phagocytosis, 816 Pharmaceutical drugs. See also Drugs analgesics, 502b antibiotics, 295, 424b, 501b, 828b antihistamines, 655 antiviral, 709b, 832 body mass effects on dosage of, 11b bronchodilators, 451b 11/21/08 6:38:21 PM I17 ■ Index chemical communications and nerve transmissions affected by, 640–41, 641t chemotherapy, 817b diabetes mellitus, 659b enantiomer, 421, 424b genetic variation in responses to, 687b ionic compounds in, 80b lithium, for depression, 71 MAO inhibitors, 652 monoclonal antibodies, 821b nitroglycerin, 401b statin drugs, 781 time-released, 222b tranquilizers, 446b weight-reducing, 738b Pharmacogenomics, 687b Phase, 166, 171 Phase change, 166, 171 Phase diagram, 168, 170 for water, 168 Phenanthrene, 386 Phencyclidine (PCP), 649 Phenobarbital, 508b Phenol(s), 384, 389–93, 402 acidity of, and reaction with bases, 390, 394 as antioxidants, 390–93 structure and nomenclature, 389–90 Phentermine, 442b 2-Phenylacetamide, 508 Phenylalanine, 582, 586, 765, 795 faulty catabolism of, in humans, 766b genetic code and, 700 Phenyl group C6H5, 384 Phenylketonuria (PKU), 766b pH indicator, 258, 258t, 259 Phosgene, 511 Phosphate as buffer, 265 nucleic acids, 668–69 solubility of, 127t transfer of phosphate groups, in common catabolic pathway, 730–31 Phosphatidylcholine, 553, 554b, 780 Phosphatidylethanolamine, 553 Phosphatidylinositol 4,5-bisphosphates (PIP2), 555 Phosphatidylinositol (PI), 555, 555 Phosphatidylserine, 553 Phosphine, 86 Phosphoenol pyruvate (PEP), 622b Phospholipids, 551, 572. See also Glycerophospholipids; Sphingolipids Phosphoric acid (H3PO4), 86, 243b Phosphoric anhydrides, 510 Phosphoric esters, 510, 531 Phosphorus (P), 54 Phosphorus pentachloride, 86 Phosphorylated protein kinase, 712 Phosphorylation, 730 of enzymes, 627 in glycolysis process, 748–52 Photofrin (drug), 607b Photons, 278 Photorefractive keratectomy (PRK), 607b Photosynthesis, 773, 775b–776b, 784 Physical changes, 2, 26 Physical properties, 2 of alcohols, 400–402 of aldehydes and ketones, 461–62 of alkanes, 340–42 of alkenes and alkynes, 361–62 of amines, 446–47 of carboxylic acids, 478–79 of colloids, 196t, 197–203 of ethers, 409–10 of monosaccharides, 522 91123_33_Index_pI2-I22 pp3.indd 18 of solutions, 179–81, 196t of suspensions, 196, 196t of thiols, 412 of triglycerides, 548–49 Picropodophyllin, 817b Piperidine, 442 PIPES buffer, 269t Pituitary hormones, 643 pKa (acid strength). See Acidity Plane-polarized light, 434–35, 437 Plant(s) anabolism in, 775b–776b cellulose in, 536–38, 578 ethylene as regulator of growth in, 353b photosynthesis and carbohydrate biosynthesis in, 773 terpenes in essential oils of, 362 Plasma, 201 Plasma cells, 814, 819 Plasmids, 718, 719 Plastics polyethelene, 370–73 recycling of, 374b a-Pleated sheet, 597 b-Pleated sheet, 596, 597, 609 Pluripotent stem cells, 834b PM (poor metabolism) of drugs, 687b pOH (OH2 concentrations), 256–58, 270 Point mutations, 820, 822 Poison(s) disrupted chemical messaging by, 648 puffer fish, 337b Poison ivy, 390 Polar compounds in solutions, 182 solvation of, by water, 195 Polar covalent bonds, 80, 80–81, 100 Polarimeter, 435, 437 Polar molecules, 97–99, 100 Pol II transcription factor, 710, 711 Poliomyelitis virus, 709b Polyamides, 510 Polyatomic elements, 37, 37 Polyatomic ions, 72, 99 ionic compounds containing, 79 names of common, 72t Polycarbonates, 511 Polyenes, 359–60 Polyesters, 510–11 Polyethylene, 370–73, 371t low-density, and high-density, 372–73 recycling, 374b Poly(ethylene terephthalate) (PET), 510–11 Polymer(s), 370, 375 chain-growth, 370 important, derived from ethylenes, 371t Polymerase chain reaction (PCR), 689, 690, 691 Polymerases, 697 Polymerization, step-growth, 509, 509–11 Polymerization reactions of ethylenes, 370–73, 376 Polynuclear aromatic hydrocarbons (PAHs), 386–87, 387b, 393 Polypeptides, 590, 609 Poly- (prefix), 371 Polysaccharides, 533, 536–38 acidic, 538–39 cellulose as, 536–38 glycogen as, 536 starch (amylase, amylopectin) as, 536 Polyunsaturated oils, 549 Polyvinyl chloride (PVC), 371 Positive cooperativity, oxygen binding by hemoglobin and, 605b Positive modulation, 626 Positron emission, 282–83, 300 Positron emission tomography (PET), 294, 295 Postsynaptic membranes, 640, 642, 661 Post-transcription stage, 699, 713 Post-translational modification, 586 Post-translation stage of gene regulation, 713 Potassium bicarbonate, 252 Potassium hydroxide (KOH), 251 Potassium permanganate solution, 188 Potassium sulfate (K2SO4), 125 Potential energy, 20, 26 kinetic energy, conversion of to, 20 Pre-initiation complex, 703, 710 Prenylation, 780 of ras protein, 781b Pressure, 143 effect of change in, on chemical equilibrium in gases, 233–35 partial, Dalton’s law and, 150–52 solubility of gases and, 182 standard temperature and, 148–49 temperature and, in gases, 146 vapor, of liquids, 158–61, 161 volume and, in gases, 144, 144 Presynaptic nerve ends, 642, 661 Priestley, Joseph, 410b Primary (1°) alcohol, 314, 399, 414 oxidation of, 405–6, 415 Primary (1°) amine, 315, 441, 452, 476 Primary structure of protein, 593, 593–95, 603, 609 Primases, 686 Primer(s), nucleic acid hybridization of DNA, 691 RNA, 683, 686 Principal energy levels, 51, 61 Prion proteins, 600b Products in chemical reactions, 109 Proenzymes (zymogens), enzyme regulation by, 626, 634 Progenitor cells, 834b Progesterone, 564, 661 biosynthesis of hormones from, 564 female reproductive cycle and, 565 Prokaryotes gene expression in, 696 properties of mRNA molecules in, during transcription and translation, 680 ribosome structure in, 678 Proline, 581, 587 Proline racemase, 629–30, 631 Promoters, 698, 710, 723 Pro Osteon, 73b 2-Propanamine, 444 Propane (CH3CH2CH3) balancing equation for, 115 combustion of, 114, 114 condensed structural formula, model, and line-angle form, 325 reaction of oxygen with, 343 Propanedioic acid (malonic acid), 476 1,2-Propanediol (propylene glycol), 400 1,2,3-Propanetriol (glycerin), 400, 401b, 482 2-Propanol (isopropyl alcohol), 315, 398 Propanone (acetone), 458. See also Acetone (C3H6O) 2-Propenal (acrolein), 458 Propene acid-catalyzed hydration of, 367 polymerization of, 371 structure of, 354 Propofol, 531 Proportional counter, 287 Propylamine, 445 Propylene, 356 Propylene glycol, 400 11/21/08 6:38:22 PM Index Prostaglandin(s), 569, 569–72, 573 Prostaglandin enderoperoxide synthase (PGHS), 631b Prosthetic group, 601 Proteasomes, post-translational gene regulation and, 713 Protein(s), 578–611 allosteric, 605b amino acids, 579–83. See also Amino acid(s) binding, 697 chaperone, 601, 608 combined amino acids to form, 587–90 complement of, expressed by genomes, 602b complete, 795 conjugated, 601 denatured, 605–8 enzymes as, 4, 579. See also Enzyme(s) fibrous, 579 functions of, 578–79 gap junctions constructed of subunits of, 554b globular, 579 human body processing of, 794–97 human disease caused by conformation changes in, 600b integral membrane, 604 isoelectric point, 584, 591–92, 592 metabolism of. See Protein catabolism modification of, and enzyme regulation, 627 prenylation of, 781 primary structure of, 593, 593–95, 603 properties of, 590–93 protective function of, 579 quaternary structure of, 601–4, 605b–606b secondary structure of, 596, 596–97, 603 synthesis of. See Protein synthesis tertiary structure of, 598–600, 603 zwitterions, 583, 583–84, 592 Protein anabolism, 782–84. See also Protein synthesis Protein catabolism, 748, 760–65 amino acid carbon skeleton processing in, 764–65 heme catabolism, 766–67 nitrogen processing in, 760–64 overview, 760 Protein–cofactor complexes, 773 Protein complementation, 795 Protein kinase M, 621b Protein microarrays, 602b Protein modification, enzyme regulation and, 627, 634 Protein synthesis, 702–8. See also Gene expression activation stage, 702–3 biosynthesis of amino acids and, 782–84 elongation stage, 703–6 genes and, in prokaryotes versus in eukaryotes, 679, 680 hereditary information in DNA for direction of, 666, 670, 696 initiation stage, 703, 704 molecular components of reactions at four stages of, 702t role of different RNAs in, 677–78, 678t termination stage, 706, 707 Proteome, 602b Proton(s), 38, 39, 61 in isotopes, 280 properties of, and location in atoms, 38t Proton channel, 737, 740 Proton gradient, 739 Proton-translocating ATPase, 740, 743 Proust, Joseph (1754–1826), 36 Prusiner, Stanley, 600b P site, ribosome, 703 Psoriasis, 829 91123_33_Index_pI2-I22 pp3.indd 19 Puffer fish, tetrodotoxin and poisonous, 337b Purines, 442, 721 in DNA and RNA nucleotides, 666–67, 672–73, 673 Pyramidal molecular shape, 93 -pyran-, 523 Pyranose, 523, 539 Pyrethrins as natural insecticide, 500b Pyridine, 442 Pyridoxal phosphate, 510 Pyrimidine, 442 in DNA and RNA nucleotides, 667, 673, 673 Pyrrolidine, 442 Pyruvate, 465, 622b, 628, 783 amino acid carbon skeleton catabolism and production of, 764–65 glycolysis and production of, 749, 750 oxidative decarboxylation of, and production of acetyl CoA, 752 Pyruvate dehydrogenase, 752 Pyruvate kinase active site and substrates of, 622b model of, 622b phosphorylation, 627 regulation of glycolysis by, 749 Q Quaternary structure of proteins, 601, 601–4, 609 allosteric proteins and, 605b–606b hemoglobin, 601, 604 R R, S system, 427, 427–30, 437 applied to ibuprofen, 430 meaning of R and S in, 427 priorities for some common groups, 427t Racemic mixture, 424, 424b, 437 Radiation dosimetry, human health and, 289–91, 290t, 291, 291t Radiation therapy, 295–96 Radical (free radical), 390 formation of, from nonradical, 391 reaction of, to form new radical, 392–93 tissue damage caused by, 293b Radioactive dating of archeological objects based on, 285b Radioactive isotopes, 279, 280 Radioactive materials, 279 Radioactivity average exposure to, from common sources, 291t detecting and measuring nuclear, 286–89 discovery of, 276–77 electricity and, 277–78 half-life of, 284–86 human health and, 289–91, 293b particles and rays encountered in, 279t three types of, 277–79 Radon, health hazard from indoor pollution caused by, 292b Rads, 289–90, 290t, 301 Rain, acid, 180b R— (alkyl group), 329, 329t, 346 Rancidity of fats and oils, 550b Random coils, protein, 596, 597, 609 Rate constant, 218 Rate of reaction, 222, 235. See also Chemical reaction rates RDX (cyclonite), 389b Reactants. See Chemical reactant(s) Reaction mechanism, 365, 375 Receptors of chemical messages, 640, 661 amino acid, 649 cholinergic (acetylcholine), 644 Recombinant DNA techniques, 718–20, 723 Recommended Daily Allowances (RDA) of nutrients, 788, 789, 799t–802t ■ I18 Recycling plastics, 374b Red blood cells (erythrocytes) destruction of aged, 766 sickle cell anemia and, 595, 596b, 679, 716 Redox reactions, 128–33 important categories of, 130–33 Reducing agent, 128 Reducing sugars, 529, 540 Reduction, 128–33, 134. See also Redox reactions of aldehydes and ketones, 463–65, 470 of alkenes, 370, 376 of carboxylic acids, 488, 493 defined, 128 of monosaccharides to alditols, 529, 541 Regioselective reactions, 364 Regulator of allosteric enzyme, 626 Regulatory portion of eukaryotic gene, 698 Regulatory site, enzyme, 626 Rems, 290, 301 Replication, DNA, 676, 679–86, 696 general features of, 683, 686 leading and lagging strands in bidirectional, 681, 686 origin of, 680 replication fork, 680, 686 replisomes in, 683 semiconservative nature of, 681 steps of, 683, 686 Replication, RNA, 696 Replication fork, 680, 686 Replisomes, 683 components of, and functions, 683b Residues, amino acid, 590 Resonance, 89–92, 100 theory of, 89–91 writing acceptable contributing structures, 91–92 Resonance hybrids, 89, 90, 383 Resonance structure (resonance contributors), 89, 383–84. See also Contributing structures Respiration as oxidation reaction, 130, 130–31 Respiratory acidosis, 268b Response elements, 710 Restriction endonucleases, 719 Retinol, human vision and, 361b Retrovaccination, 836 Retroviruses, 830 Reuptake, 649, 661 Reverse denaturation, 608 Reverse desalinization, 201b Reverse osmosis, 201b Reverse transcriptase, 831, 831 Reversible chemical reactions, 221, 221–22 Rheumatic fever, 828b Rheumatoid arthritis, 538, 829 Rhodopsin, 780 Ribofuranose, 524 b-D-ribofuranose (b-D-Ribose), 528, 667 Ribonucleic acid (RNA), 666, 691 bases of, 666–67 classes of, 676–78 nucleotides and nucleosides of, 669t phosphate of, 668–69 primer, in DNA replication, 683, 686 roles of different kinds of, 678t splicing of, 678, 680, 713, 713 structure of DNA and, 670–76 sugars of, 667–68 transcription of DNA information to. See Transcription translation and role of, 699–700 Ribose, 527, 667 pentose phosphate pathway and production of, 752–53 11/21/08 6:38:22 PM I19 ■ Index Ribosomal RNA (rRNA), 677–78, 678t, 691, 696. See also Ribosomes post-transcription methylation of, 699 translation and role of, 699–700 Ribosomes, 677, 677–78 protein synthesis in, 699–700, 703–6 role as ribozyme, 706 40S ribosome, 700 60S ribosome, 700 structure of prokaryotic, 678 Ribozymes, 614, 678, 691, 706 Rivastigmine, 648b RNA. See Ribonucleic acid (RNA) RNA polymerases, 697, 699 Rodbell, Martin (1925–1998), 650 Roentgens (R), 289, 290t Röntgen, William, 277 Rowland, Sherwood, 345b R (relaxed) form of enzyme, 626, 627 RU 486 (Mifepristone), 565, 568 Rusting as redox reaction, 131, 131–32 S Saccharides, 518 disaccharides, 533–35 monosaccharides. See Monosaccharides oligosaccharides, 533 polysaccharides, 536–38 Saccharin, 796b Salicin, 502b Salicylic acid, 502b, 507 Salmeterol, 451b Salt bridges, tertiary protein structure stabilized by, 598, 599, 609 Salts as product of reactions between acids and ammonia/amines, 253, 270 soaps and formation of, 483 Saponification, 482, 504 of fats, 550–51 Sarcoplasmic reticulum, 554b SARS (severe acute respiratory syndrome), 830 Satellites, DNA, 679 Saturated fats, 479t, 480, 548, 549t, 563 Saturated hydrocarbons, 324, 346 Saturated solution, 181 Scents and odors, 412, 446 aromatic compounds. See Aromatic compounds carboxylic acids, 479 Schultz, Peter, 630 Schwann cells, 558b Scientific method, 3–5, 26 Scintillation counters, 287 Screening for alcohol on human breath, 407b Seaborg, Glenn (1912–1999), 297, 297 Second (s), measurement of, 11 Secondary (2°) alcohol, 314, 399, 414 oxidation of, 406 Secondary (2°) amine, 315, 441, 452 Secondary messengers, 640, 643, 650–51, 661. See also Prostaglandin(s); Thromboxanes action of peptidergic messengers, hormones, and neurotransmitters and role of, 656–57 calcium as, 645b cyclic AMP (cAMP) as, 650–51 nitric oxide as, 654b steroid hormones as, 642–43 Secondary structure of proteins, 596, 597–98, 603, 609 extended helix of collagen, 598 a-helix, and b-pleated sheet, 596, 597, 597, 609 Second genetic code, 703 Seeding, 182 Selenocysteine, 708b Semiconservative replication of DNA, 681 Semipermeable membrane, 199 91123_33_Index_pI2-I22 pp3.indd 20 Sense strand, 697 Serendipity, defined, 4 Serine, 555, 581 Serotonin, 585, 650, 653b drugs affecting messenger function of, 641t Severe combined immune deficiency (SCID), 721, 811 Sex hormones, 565–68, 573 Sex pheromones, 358b Shells (atom), 51, 61 distribution of electrons in, 50t distribution of orbitals within, 50t valence, 55 Shine-Dalgarno (RNA) sequence, 703, 704 Shroud of Turin, dating of, 285b SH (sulfhydryl) group, 411 SI. See International System of Units (SI) Sickle cell anemia, 595, 596b, 679, 716 Side chains, peptide, 590 Side reactions, 123 Sievert, 290 Sieving portions of enzyme, 714 Sigmoidal curve, 606b Signal transduction, 650, 651, 661 in DNA replication, 683 effects of, on metabolism, 757b removal of signal amplification and, 651–52 Significant figures (numbers), 6, 6–7, 26 Silencers (DNA sequences), 710 Silent mutations, 716b Silicon in microprocessor chips, 120 Silk, 597b Silver acetate, 230 Silver chloride (AgCl), 125 reaction with sunlight, 233b Silver cyanate, urea produced from reaction between ammonium chloride and, 308 Silver-mirror test, 463 Single bond, 79, 83 Skunk, scent of, 412 Small interfering RNA (siRNA), 678, 691 Small nuclear ribonucleoprotein particles (snRNPs), 678, 691 Small nuclear RNA (snRNA), 678 Smallpox, 825b Smelting of ores, 180b Smoking, carcinogenic polynuclear aromatics and, 387b Snake venom, 648 Soaps, 479–84, 551, 572. See also Detergents cleaning function of, 483–84 fatty acids and, 479–82 micelles and, 483 saponification of fats and production of, 551 structure and preparation of, 482–83 Sobrero, Ascanio (1812–1888), 401b Sodium acetate, 505 Sodium benzoate, 486 Sodium bicarbonate, 245 Sodium borohydride (NaBH4), 464 Sodium carbonate, reactions between acids and, 251 Sodium chloride (NaCl), 68, 70, 71, 75 crystal structure, 76 solution of, 181 Sodium 4-dodecylbenzenesulfonate, 390, 484 Sodium ethanethiolate (CH3CH2S2Na1), 412 Sodium hydroxide (NaOH) (lye), 243b, 504 titration of sulfuric acid (H2SO4) with, 259 Sodium (Na), 46 atomic size, 57 orbital box diagram for, 54 Sodium pentobarbital (Nembutal), 508b Sodium phenoxide, 402 Sodium urate monohydrate in human joints as cause of gout, 193 Solenoid, 674, 675 Solid(s), 17, 26, 142, 142, 142 amorphous, 165 characteristics of various, 164–65 network, 165 phase change from, to gas, 166–70 solubility of, as function of temperature, 182 types of, 165t water of hydration in, 191 Solid hydrates, 191 Solidification, 153 Solid state, 142. See also Solid(s) Solubility, 181, 204 of alcohols, 402t of alkanes, 341, 402t of drugs in human body fluids, 450b as function of temperature, 182 of hydrochloric acid, 195 of sulfur trioxide, 195 Solute, 179, 204 nature of solvent and, 182 Solution(s), 178–95, 204 aqueous. See Aqueous solution(s) characteristics and properties of, 179–81 concentration of. See Concentration of solutions factors affecting solubility, 181–83 introduction to, 178–79 isotonic, hypertonic, and hypotonic, 202 most common types of, 179t properties of colloids, suspensions, and, 196t units for expressing concentration of, 184–91 water as superior solvent, 191–95 Solvated anions and cations, 191 Solvent(s), 179, 204 haloalkanes as, 345 nature of solute and, 182 water as, 191–95 Somatic cells, 681b gene therapy in, 721 telomeres in chromosomes of, 681b Somatic hypermutation (SHM), 820 Specific gravity, 19, 19–20, 26 Specific heat (SH), 22–25, 26, 166 for common substances, 22t of water, 23b, 166 Specific immune-system cellular interactions, 813t Specificity of enzymes, 615 Specific rotation, 435 Spectator ions, 125, 134 Sphingolipids, 551, 555, 555–56, 573 Sphingomyelin, 554b, 556, 780 Sphingosine, 555 Sphygmomanometer, 159b Spider silk, 578, 597b Splicing of RNA molecules, 678, 680 alternative, 713 Sports drinks, 569 Standard temperature and pressure (STP), 148 Starch, 536, 540 action of enzymes on, 792 States of matter, 2, 17–18, 141–42. See also Gas(es); Liquid(s); Solid(s) energies involved in phases changes in, 166–70 Stearic acid, 549, 757–58, 758t Steel wool, 217 Stem cells, 834b–835b development of lymphocytes from, 815 history of research on, 835b promises and potential of research on, 834b–835b Step-growth polymers, 509, 509–11 polyamides, 510 polycarbonates, 511 polyesters, 510–11 11/21/08 6:38:22 PM Index Stereocenters, 338, 424, 437 specifying configuration of, 427–30 stereoisomers, 430–34 Stereoisomers, 339, 421 of alkenes, 354, 359, 375 of amino acids in proteins, 580, 583 cis-trans, 337–39. See also Cis-trans isomers diastereomers, 421, 431 enantiomerism and, 339, 420–26 for molecules with two or more stereocenters, 430–34 Steroid(s), 558, 558–63, 573, 643 cholesterol, 561. See also Cholesterol lipoproteins and cholesterol transport, 561–63 physiological roles of, 564–68 structure, 560 Steroid hormones, 564–68, 657 adrenocorticoid, 564, 564–65 anabolic steroids, 566b–567b oral contraception, 568b as secondary messengers, 642–43, 657–58, 660–61 Sticky ends, DNA, 719 Stitches, dissolving surgical, 512b Stoichiometry, 118, 118–21, 134 limiting reagents and, 121, 121–22 percent yield calculations, 123–24 Stomach acid food catabolism and role of, 792, 795 human, use to antacids to relieve, 253b Storage proteins, 579 Strassman, Fritz (1902–1980), 298 Strep throat, 828b Strong acid, 242t, 245t Strong base, 242, 245t Strong electrolytes, 193 Strontium-90, 284 calcium, human bones, and, 45b Structural formulas, 83 of alkanes, 323–25 condensed, 314 for organic compounds, 311–13 Structural gene, 698, 698 Structural isomers. See Constitutional isomers Structural proteins, 578 Styrene, 384 Subatomic particles, 38 Sublimation, 167, 171 Subshells, 50, 61 Substance P, 656 Substrate, 618–19, 633 concentration of, and enzyme activity, 618–19 Substrate specificity, 615 Succinate, 491, 736 Succinic acid, 476 Succinylcholine, 616b as competitive inhibitor, 648 Sucralose, 796b Sucrose (C12H22O11), 182, 195, 518, 533–34, 540 Sugars amino, 521–22 as component of nucleic acids, 667–68 glucose. See Glucose reducing, 529, 540 table. See Sucrose (C12H22O11) Sulfhydryl (SH) group, 411, 415 Sulfides, 127t Sulfonation of aromatic compounds, 388–89, 394 Sulfur mixture of iron and, 35 nucleophilic attack by, 623, 625 Sulfur dioxide (SO2), 87, 180b, 194b Sulfuric acid (H2SO4), 87, 180b, 243b Fischer esterification and, 501 titration of, with sodium hydroxide, 259 Sulfur trioxide (SO3), 180b, 194b 91123_33_Index_pI2-I22 pp3.indd 21 Sumner, James, 4 Sunglasses, 233b Sunscreens and sunblocks, 506b Supercritical carbon dioxide (CO2), 169b Superposable molecules, 422 Supersaturated solution, 181 temperature and, 182 Surface tension, liquids, 158, 171 Suspensions, 196 properties of colloids, solutions, and, 196t Sweeteners, artificial, 589b, 794, 796b–797b Sweetness, 535t Synapse, 640, 642, 661 Systolic blood pressure, 159b T Table salt. See Sodium chloride (NaCl) Table sugar. See Sucrose (C12H22O11) TATA box, 698, 710 Tatum, Edward (1909–1975), 666 Tau proteins, 647b Taurine, 569, 649 Taurocholate, 569 Tautomers, 468 Taxol, search for, and discovery of, 310b Tay-Sachs disease, 560t T cell(s), 811, 812, 836. See also T-cell receptor(s) cytotoxic (Tc cells), 814 growth and differentiation of, 827 helper, 814. See also Helper T cells (TH cells) interaction of, with dendritic cell, 814 memory, 814 self/nonself determination, and selection of, 826 T-cell receptor complex, 823, 824 T-cell receptor(s) (TcR), 811, 822–23 adhesion molecules of, 823 CD4 molecule and HIV infection, 824, 831 differences between immunoglobulins and, 823 peptide antigen recognition by, 815 structure of, 823, 823 Telomerase, 681b Telomeres, 681b Temperature body, 221b chemical equilibrium affected by, 232–33 chemical reaction rates affected by, 218–20 density and, 19 entropy and, 143b enzyme activity and, 619 fever, 219b heat and, 21–22 kinetic energy and, 142, 219 measurement of, 11–12 pressure and, in gases, 146 solubility of solids as function of, 182 standard pressure and, 148 vapor pressure and, 161 volume and, in gases, 146 Temperature scales, 11–12 Template strand, 697 Terbutaline, 451b Termination sequence, transcription process, 699 Termination stage of protein synthesis, 706, 707 Terpenes, 362–63, 375 Tertiary (3°) alcohol, 399, 414 oxidation of, 406 Tertiary (3°) amine, 315, 441, 452 Tertiary structure of proteins, 598, 598–600, 603 forces leading to formation of, 601 forces stabilizing, 598–600 TES buffer, 269t Testosterone, 565, 568 anabolic steroids and, 566b Tetracycline, effects of, 295 Tetrahydrofuran (THF), 409 ■ I20 Tetrodotoxin in puffer fish, 337b Tetr- (prefix), 518 Theoretical yield of product mass in chemical reactions, 123, 134 Theory, defined, 4, 26 Thermal cracking, 353 Thermal decarboxylation, 490–91 Thermal pollution, 182 Thermogenin, 738b Thiols, 411–13 functional group of SH (sulfhydryl) group, 411 nomenclature of, 411–12 physical properties of, 412 reactions of, 412–13, 415 structure of, 411 Threonine, 582 Threose, 431 Thromboxanes, 570, 573 Thudichum, Johann, 556 Thymine (T), 667, 667, 672, 673 Thyroid goiter in, 388b medical imaging of, 293 Thyroxine, 293, 388b, 586, 587 Time equilibrium in chemical reactions and, 229 measurement of, 11 Tincture, 397 Titration, calculating solution concentrations using, 259, 259–61, 270 acid-base titration, 260 TNT (2,4,6-trinitrotoluene), 389b Tollens’ reagent, 463 Toluene, 384 nitration of, to TNT explosive, 389b Toluidine, 444 Tools balances, 10 barometer, 143 Geiger-Müller counter, 287 hydrometer and urinometer, 20 manometer, 143, 144 pH meter, 258 polarimeter, 435 Tooth enamel solubility and decay, 127b Topoisomerases (gyrases), 683, 691 Torricelli, Evangelista (1608-1647), 143 Toxins cholera, 652 tetrodotoxin, in puffer fish, 337b Trace elements, 798t Tranquilizers, 446b Trans (prefix), 338, 346. See also Cis-trans isomers Transamination, 761 Transcription, 676, 696, 697–99 properties of mRNA during, 680 Transcriptional-level gene regulation, 710–12 at post-transcription level, 713 at transcriptional level, 710–12 Transcription factor, 658 Transcription factors, 698, 723 gene expression and role of, 710, 711, 712, 713 helix-turn-helix, and leucine zipper, 712 metal-binding fingers of transcription factors, 712 Trans fatty acids, 481b–482b Transferases, 616, 617t Transfer RNA (tRNA), 677, 678t, 691, 696 initiation of protein synthesis and role of, 703 specificity of, for unique amino acid, 714 structure of, 677 translation and role of, 700 Transition elements, 44 Transition state, 215, 216, 235 enzyme catalysts and, 623, 634 11/21/08 6:38:22 PM I21 ■ Index Transition-state analogs, 629, 631, 632b, 634 Translation, 676, 696–97, 723 properties of mRNA during, 680 Translational-level gene regulation, 708, 714 Translocation, elongation stage of protein synthesis, 705 Translocator inner membrane (TIM), 727 Translocator outer membrane (TOM), 727 Transmembrane channels, 554b Transmembrane protein, 644 Transmutation, 280 Transport across membranes, 552, 554b anion, 554b cholesterol, 561–63 facilitated, 554b of oxygen by hemoglobin, 606b passive transport, 554b removal of neurotransmitters by, 649 role of proteins in, 579 Transporter molecules, 649 Transuranium elements, 297 Triacylglycerols, 548. See also Triglycerides 2,4,6-Tribromophenol, 386 Tricarboxylic acid (TCA) cycle, 491. See also Citric acid cycle Trichloroacetic acid, 485 Triglycerides, 483, 547, 548 physical and chemical properties of, 548–51 structure of, 547–48 Trigonal planar, 95 2,3,4-Trihydroxybutanal, 430, 431 Trimethylamine, 315, 441, 446 Trimethylpentane, 343b Trinitrotoluene, 738b Triol, 400 Trioses, 518 Tripeptide, 589, 593 Triphosphate ion, 509 Triphosphoric acid, 509 Triple bond, 83 Triple point, 168 Tri- (prefix), 518 Triprotic acid, 244 Trisaccharides, 533 TRIS buffer, 268, 269t tRNAfMet, 703, 704 Trypsin, 615, 618, 795 regulation of, 626 Tryptophan, 582, 615, 795 T (taut) form of enzyme, 627, 627 Tumor necrosis factor (TNF), 824 Tumor suppressor genes, 717b 2G12 antibody, 836 Tyndall effect, 195, 195–96 Tyrosine, 582, 586, 587, 795 U Ubiquinone. See Coenzyme Q Ulcers, 655 Ultra-extensive metabolism (UEM) of drugs, 687b Ultraviolet (UV) light, 278, 506b Universal gas constant (R), 148 Unsaturated aldehydes, 458 Unsaturated fats, 479t, 480, 548, 549t, 757 Unsaturated hydrocarbon, 324 Unsaturated solution, 181 Uracil (U), 667, 667, 687, 688 Uranium-235, 298 Urea, 508b, 615 formation of, 308, 762–64 Urea cycle, 762–64, 768 Urease, 615 91123_33_Index_pI2-I22 pp3.indd 22 Uridine, 668 Uridine diphosphate (UDP)-glucose, 776, 777 Uridine triphosphate (UTP), glucose conversation to other carbohydrates and role of, 776, 777 Urine glucose in, 530b ketone bodies in, 759 pH of, 257 Urinometer, 20 Uronic acids, oxidation of monosaccharides to, 530–31 Urushiol, 390 U.S. Department of Agriculture (USDA), 789, 789 V Vaccines, 825b against HIV infection, 832, 833 Valence electrons, 55, 61 octet rule, 69–71 Valence shell, 55, 61 Valence-shell electron-pair repulsion (VSEPR) model, 92–96, 100 of alkenes, 354 of carbon compounds, 311t predicted molecular shapes based on, 96t Valine, 581 Vanillin (vanilla bean), 461b Vapor, 159 phase change from ice to water, 166–70 Vaporization, heat of, 166, 171 Vapor pressure of liquids, 158–61, 159, 171 temperature and change in, 161 Vasoconstrictors, 451b Vasopressin function, 594–95 structure, 595 Vegetable oils, fatty acids in, 479t Very-low-density lipoprotein (VLDL), 561 composition and properties of human, 562t Vesicles, neurotransmitters stored in, 642, 661 Viagra (drug), 624b, 654b Vidarabine (Vira-A) (drug), 709b Vinyl chloride, 371 Viruses, 709b antiviral therapy, 709b, 832 gene therapy using, 721–22, 722 HIV. See Human immunodeficiency virus (HIV) recombinant DNA using, 719 Vision, role of cis-trans isomerism in human, 361b Vitamin(s) nutritional importance of, 797, 798t, 804–5 sources, functions, deficiencies and daily requirements of, 799t–802t Vitamin A (retinol), 361b, 363 Vitamin B, 618, 804 Vitamin C, 311, 526b, 797 Vitamin D, 797, 805 Vitamin E, 393, 797 V(J)D gene, diversity of immune response due to recombination and mutation of, 819 Voltaic cells, 131b Volume, 9–10 measurement of, 9–10 pressure and, for gases, 144, 144, 146 temperature and, for gases, 146 Von Euler, Ulf, 569 VSEPR. See Valence-shell electron-pair repulsion (VSEPR) model W Water constant (Kw), 254 Water (H2O) acetic acid and, reaction between, 247 acid–base properties of, 253–56 ammonia and, reaction between, 227 boiling point, 162t density of, 18, 162b energies involved in phase change from ice to vapor, 166–70 formulas, 34 gas solubility in, 180t hydrochloric acid and, reaction between, 214, 247 hydrogen bonds joining molecules of, 155 hydrolysis reactions involving, 503–7 ion product of, Kw (water constant), 254 ion reactivity with, 126 Lewis structure and ball-and-stick molecules, 94 models of, 34 molecular polarity of, 98 as nutrient, 805 phase diagram for, 168 reverse osmosis and production of drinkable, 201b solubility of alcohols and alkanes in, 402t solutions with, as solvent. See Aqueous solution(s) as solvent, 191–95 specific heat of, 23b Water of hydration, 191 Water-strider (insect), 158 Watson, James (1928–), 672, 673 Wavelength (l), electromagnetic radiation, 278 Waxes, 550b paraffin, 340, 340 Weak acids, 242, 245t Ka and pKa values for select, 249t Weak bases, 242t, 243, 245t Weak electrolytes, 193 Weight, defined, 10 Weight reduction in humans artificial sweeteners and, 796b–797b diets for, 788, 792, 794, 796b–797b drugs for, 738b reasons for difficulty of, 793b Wells, Horace, 410b White blood cells (leukocytes), 811, 812, 826, 836 lymphocytes as type of. See Lymphocytes Wilkins, Maurice (1916–2004), 672 Wine grapes, fermentation of, 397 Wöhler, Friedrich (1800–1882), 308 X X as symbol for halogen, 44 X-rays, 278 Xylene, 385 Xylitol, 529 Y Yeast, 252 Yew, Pacific (Taxis brevifolia), production of taxol from bark of, 310b -yne (suffix), 355, 375 Z Zeno of Elea (b. 450 BCE), 31–32 Zinc fingers, transcription factors, 712, 713 Zinc oxidation, 128 Zwitterions, 269t, 583, 583–84, 592, 608 Zymogens. See Proenzymes (zymogens) Warren, John, 410b Waterbeds and specific heat of water, 23b 11/21/08 6:38:23 PM
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