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Ch. 22- Organic Reactions and Biochemistry Saponification Process of making soap Soap is the metallic salt of a fatty acid Reaction: fat + base -> soap + glycerol Reaction How soap works: End of soap molecule w/ a charge (Na ion) is polar and soluble in water Other end (CH3- (CH2)etc) is non-polar and soluble in oil and fat Water= polar, dirt/oil = non polar When using soap, dirt/oil attach to non-polar end of the soap and the polar end of the soap attaches to the water, forms a micelle Micelle (soap bubble) Soap Water Dirt Soap molecule Hydrophyllic end (polar) -likes water Hydrophobic end -non-polar -likes dirt/oil Hard water Hard water has ions in it (Mg, Ca, Fe) Will form an insoluble precipitate with soap and water Makes soap ineffective =soap scum Quality of Soap Depends: on the oils and fats you use On the amount of stirring The temperature Hardness Related to the degree of saturation Saturated fats= harder soaps Unsaturated fats= softer soaps Liquid soaps = soap w/ lots of water Detergent Formed from coal and petroleum Ability not diminished in hard water Have a benzene-sulfonic acid anion instead of carboxylic acid SO3 Breadmaking History 6000-5000 BC Start of bread making/brewing in Egypt 5000-4000 BC Bread ovens found in Babylon 500-200 BC Commercial 100 AD Rome breadmakers in Greece/Rome flour quality standardization Sandwich – John Montague (Earl of Sandwich) Bread Making: Components of Bread Flour- from the wheat berry, is a complex carbohydrate, made of starch and protein, amylase enzyme breaks it down Wheat Berry Endosperm (protein/starch) white flour 1. Bran shell Germ 2. Protein -keeps gas bubbles in bread like spring, kneading organizes it Overkneading breaks chains 3. Gas A. Yeast -sugar + yeast ferment (form CO2 (trapped)) (form alcohol-evaporate-brown edges) -yeast die at 130 º F B. Chemical Agents 1. Baking soda and acid NaHCO3 + vinegar, cream of tarter, buttermilk CO2 + water + salt 2. Baking powder -has baking soda and acid salt (calcium phosphate and NaAl(SO4)2 ) all in one -produces CO2, when mixed with water C. Steam -pita, cream puffs, eclairs - take dough w/out yeast, put in very hot oven, seals outside, moisture inside forms gas pocket, leaves pocket of air when removed Polymers Silly Putty Video Definition Gigantic molecules Mer= unit Monomer = 1 unit Polymer = many units hooked together, covalently Polymerization Joining together of molecules that contain double or triple bonds Cross-linking Bridges formed between chains, gives polymer new properties -C-C-C-C-C-C-C-C-C-C-C-C- -C-C-C-C-C-C-C-C-C-C-C-C- Addition Polymerization Monomer adds to monomer Get chains 1000’s carbons long Ex. Teflon, PVC, polyethylene + Condensation Polymerization Reaction in which you get water and the polymer as products Types: nylon, polyester, cellophane, rayon Types of Polymers 1. Thermoplastic -can be melted and re-melted -soften when heated, can be reshaped and hardens when cooled (long chains lock into place) Recyclable -ex. PVC, nylon, lucite, polystyrene Polystyrene Thermosetting 2. - - - Permanently hardened Not reversible (once set-they are set) Intense heating causing charring (black) Molded into final shape Shape by filing or machining Ex. Bakelite (pot handles, electrical insulation, jewelry) Bakelite 3. Elastomers -polymers with high degree of elasticity -have folded polymer chains, like spring -energy is needed to stretch out -Ex. Rubber- made by vulcanization (rubber w/ sulfur) , by Charles Goodyear (1837), tires PETE Polyethylene Terephthalate Product examples: bottles for soft drink, soy sauce, and cooking oil HDPE High Density Polyethylene -have long chains w/ few side chains (less than 1 per 100 carbons) Product examples: pails; milk jugs, containers for liquid detergent and fruit juice V Polyvinyl Chloride (PVC) Product examples: pipes; bottles for shampoo and mineral water Monomer: vinyl chloride CH2=CHCl LDPE Low Density Polyethylene -have lots of side chains (take up a lot of space) Product examples: shopping bags; housewares, bread bags PP Polypropylene Product examples: household storage containers, yogurt, butter tubs PS Polystyrene Product examples: foam products like drinking cup and food tray, plastic forks Monomer: styrene C=CH2 OTHER Other type of less commonly used plastics Product examples: bottles for ketchup and syrup Ex. Polyester, polytetrafluroethylene (teflon) History of Polymers 1811 – Gay Lussac found cellulose (cotton) and starch have similar chemical structure 1840- Goodyear vulcanized rubber (tires now have 20 different polymers) 1887 – Rayon invented (Chardonnet made from wood cellulose and nitric acid) Early 1900’s – found proteins were polymers 1907 – Bakelite invented (Leo Baekeland-1st synthetic polymer of practical importance) 1935- Nylon invented -invention made it clear that macromolecules could be made in an infinite variety of structures by organic chemistry (found an ever-expanding number of uses for these molecules) History of Nylon DuPont Co. founded to make gunpowder, diversified after WW1, went into silk manufacturing, hired chemist from Harvard to replicate silk process Wallace Carothers (working w/ Elmer Kraemer (UW-Madison) worked unsuccessfully for 2 years DuPont convinced him not to go back to Harvard Discovered adipic acid, mixed it with hexamethylenediamine- in a step-growth condensation reaction Didn’t realize that he had made nylonkilled self (depressed) Another worker stretched the compound, found it orients the molecules so they increase in strength and elasticity 1939- premiered at Worlds Fair 1940- nylon stocking 1946- came back on market after WWII Other forms: velcro, neoprene Nylon Reaction Nylon movie Other Organic Reactions Oxidation Reaction Adding oxygen to organic compounds produces CO2 + water + energy More saturated a hydrocarbon, more energy Oxidation = the reaction takes place through a series of steps (at any step in the sequence unwanted by-products could be formed –like carbon soot or CO.) Important reaction for: energy production in living systems, combustion of hydrocarbons for heating Balancing: balance carbons first, then hydrogens, then oxygens. If it doesn’t balance: start over, double the hydrocarbon Balance: ___ CH3CH2CH2OH + __ O2 __CO2 + ___H2O _2_ CH3CH2CH2OH + _9_ O2 _6_CO2 + _8__H2O Substitution Reaction Reaction in which a hydrogen atom of a hydrocarbon is replaced by a functional group (like oxygen or halogen) Proceed slower than inorganic Are not easily controlled- produce a lot of unwanted byproducts which have to be separated out Hint: all single bonds, 2 reactants, 2 products Alkanes H Br H-C-H + Br2 H-C-H H H + HBr -notice only one Br attaches to hydrocarbon Others: Making an amine: R-X + NH3 R-NH2 CH3-Cl + HX + NH3 CH3 – NH2 + HCl Addition Reactions Starting with a double or triple bond, addition reactions break that bond forming single bonds Forms unwanted by products Hint: 2 reactants (double/triple bond), 1 product (single bond) Examples: Halogen Addition (alkene) H H +Br2 C=C H H (notice: both Br’s attach) H H H -C - C – H Br Br Halogen Addition (alkyne) HH H-C = C – H + 2 Br2 Br-C-C-Br Br Br Hydration Addition Add water, form alcohol, sulfuric acid (catalyst) H H C=C H +H2O H H2SO4> H H H -C - C – H H OH Hydrogenation Addition H Used to make unsaturated oils more solid, less liquidy- to make margarine H H H C=C +H2 Pt> H -C - C – H H H H H (note: double bonds in benzene ring too stable- addition rxn fails) Elimination Reaction Forms a double bond from a single bonded molecule by removing atoms Hint: 1 reactant (single bond), 2 products (with one being a double bond) Example: Dehydration elimination Removing water from alcohols H H OH H2SO4> H H H H- C - C –C- H H2O +H- C – C = C H H H H H (note: make sure you take off the –OH and -H off of neighboring carbons) Biochemistry Biochemistry Study of substances and the chemical reactions involved in life processes A. Proteins Polymers containing long chains of amino acids ½ of non-water mass is protein Makes up muscles & body structure Some used as biological catalysts (enzymes) Proteins differ from each other in the sequence of amino acids and the coiling/twisting of the molecule Amino acids-contain an amine and carboxylic acid group Test for Protein Biuret’s test NaOH and CuSO4 is added to protein, gives pink or blue/violet color change High Protein Foods Meat, nuts, eggs, legumes, fish B. Carbohydrates Made of aldehydes, ketones, and numerous hydroxyl (-OH) groups Have simple sugars and polymers of sugars 1. Sugar Common: glucose, sucrose Monosaccharide = one sugar (glucose) Disaccharide = two sugars (sucrose) Gives you short burst of energy through the oxidation of sugar (forming CO2 and H2O) Test for Sugar Benedict’s Test Contains Copper (II) oxide (blue), when placed w/ sugar it reduces it to copper (I) oxide which gives it a green, red or orange color depending on the amount & type of sugar 2. Polymers of Sugar a. Starches - - polysaccharides, long chains of sugars Medium energy needs Enzymes break them down into simple sugars Test for Starch- Iodine or Lugol’s (turns blue/black) Found in seeds, roots of plants Made of alpha glucose ( ά-glucose) We can digest Cellulose b. - Polymer of ß- glucose (beta-glucose) Can’t digest Made of fibrous structures of plants (oat husk, celery stalk) Gives us roughage, dietary fiber Gives plants structural strength C. Lipids Not soluble in water, like other biochem. Molecules Includes fats, oils, waxes,steroids Made from the triple esters of glycerol Fats 1. - - - used in cell walls formed by glycerol & fatty acids Get unsaturated and saturated fats Gives you stored energy (long term) 1-2% of total calorie intake Test – Sudan IV- floating red droplets or brown bag (see through) Steroids 2. - Type of lipid w/ tetracylic ring nucleus Cholesterol- important steroid (found in bile and cell membrane of brain & spinal cord) Steroid hormones – estrogen, testosterone) How Steroids Work How steroids work Steroids work by imitating the properties of naturally occurring hormones. Muscle tissue is peppered with receptor sites specific to growth. The correct hormonal 'key' can only access these sites or 'locks'. Steroids can activate these receptor sites because their chemical composition is so similar to the hormone testosterone. Once the receptor sites have been stimulated, a domino effect of metabolic reactions takes place as the body is instructed by the drug to increase muscle tissue production. Anabolic Steroid Side effects Damage to the gonads (testicles or ovaries) Liver diseases Malfunctions of the kidneys or heart 'Roid rage', which is characterised by uncontrollable outbursts of psychotic aggression Paranoia Mood swings, including deep depression Severe acne High blood cholesterol levels High blood pressure Injuries to tendons that can't keep up with the increased muscle strength Delusional feelings of being superhuman or invincible Fluid retention Trembling and muscle tremors Stunted bone growth in adolescents. D. Nucleic Acid Found in small quantities Biological polymer found in nuclei of cell Indispensable component of every living thing Determines genetic inheritance, reproduction and growth of cells Monomer units = nucleotide (made of nitrogen base, sugar, and a phosphate group) Sugars- ribose, deoxyribose DNA – deoxyribonucleic acid ( stores & transfers genetic information) RNA – ribonucleic acid (transmission of DNA info, used to make enzymes) E. Enzymes Biological catalyst made of protein molecules Increase the rate of chemical rxns. Over 2000 enzymes have been discovered Each enzyme has a distinctively shaped active site, only molecules w/ complementary shapes can attach to the enzyme Active site- pocket or crevase found in peptide chain, has a distinctive shape (substrate fits into it like a puzzle/induced fit) Important for biochem. Rxns Responsible for energy, repair & growth Enzyme remains unchanged Doesn’t change normal equilibrium position of rxn. (same amount of product formed w/ or w/out the enzyme) F. Vitamins Group of non-protein organic molecules Used to aid enzymatic rxns For growth, digestion, processing of proteins, carboyhydrates & fats Promotes essential biochemical rxns lack of vitamins causes specific diseases Not an energy source Must come from food Classified by solubility Fat soluble vitamins Soluble in non-polar solvents Overdose – stores in liver & becomes toxic (hair loss, nausea, jaundice, death) Examples of Fat soluble vitamins A = antioxidant, vision Source = animal, dark green leafy veggies Deficient –night blind, dry skin D = helps absorb Calcium Source = milk, liver Deficient - rickets E = antioxidant to protect blood cells – grains Deficient – anemia Source K = blood clotting Source- intestinal flora, leafy veggies, liver Deficient – easy bruising, easy bleeding Water soluble vitamins Soluble in polar water Overdose – dissolves in fluids, excrete in urine Example of Water Soluble vitamins Vitamin C and 8 different vitamin B’s Vitamin C Formation of connective tissue, immune system, wound healing Source – orange colored foods (not cheetos) Deficient - scurvy B1( thiamine) – aids rxns in brain Source- grains Deficient- beri beri (nervous disorder) B2 (riboflavin) – converts food into energy, healthy skin and eyes – cereal, green leafy, lean meat Deficient – eye problems Source B3 (niacin) – metabolism Source- lean meat Deficient- irritability, skin eruptions B5 (pantothenic acid) – break down fatty acids and carbohydrate Source –mushrooms, cauliflower, sunflower seeds Deficient- fatigue, tingly limbs B6 (pyridoxine)- converts food-> energy B12 (cobalamin) red blood cells, nervous system Folic Acid – cell production, prevention of birth defects (dna, rna) Source- Biolin raw leafy veggies Also need 15 minerals to help cell function and provide structure The end Oxidation Hydrocarbon + 2 reactants-> oxygen -> carbon 2 products dioxide and water Substitution Alkane + halogen substituted alkane + hydrogen halide Alkene + halogen or water alkyl halide or alcohol Alcohol alkene + water Monomer + monomer polymer Addition Elimination Addition Polymerization 2 reactants 2 products 2 reactants 1 product 1 reactant 2 products