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Organic Chemistry and Biochemistry The study of carbon-containing compounds and their properties. The vast majority of organic compounds contain chains of rings of carbon atoms. The study of the chemistry of living things. Copyright©2000 by Houghton Mifflin Company. All rights reserved. 1 Hydrocarbons . . . compounds composed of carbon and hydrogen. Saturated: carbon-carbon bonds are all single alkanes [CnH2n+2] H H H C C H H H Copyright©2000 by Houghton Mifflin Company. All rights reserved. 2 Hydrocarbons (continued) Unsaturated: contains carbon-carbon multiple bonds. H H H C H C H C H Copyright©2000 by Houghton Mifflin Company. All rights reserved. 3 Rules for Naming Alkanes 1. For alkanes beyond butane, add -ane to the Greek root for the number of carbons. C-C-C-C-C-C = hexane 2. Alkyl substituents: drop the -ane and add -yl. -C2H5 is ethyl Copyright©2000 by Houghton Mifflin Company. All rights reserved. 4 Rules for Naming Alkanes 3. Positions of substituent groups are specified by numbering the longest chain sequentially. C C-C-C-C-C-C 3-methylhexane 4. Location and name are followed by root alkane name. Substituents in alphabetical order and use di-, tri-, etc. Copyright©2000 by Houghton Mifflin Company. All rights reserved. 5 Substitution Reactions Primarily where halogen atoms replace hydrogen atoms. CHCl 3 Cl 2 h CCl 4 HCl Copyright©2000 by Houghton Mifflin Company. All rights reserved. 6 Cyclic Alkanes Carbon atoms can form rings containing only carbon-carbon single bonds. C3H6, C4H8, C6H12 Copyright©2000 by Houghton Mifflin Company. All rights reserved. 7 Alkenes and Alkynes Alkenes: hydrocarbons that contain a carboncarbon double bond. [CnH2n] CC=C propene Alkynes: hydrocarbons containing a carboncarbon triple bond. CCCCC 2-pentyne Copyright©2000 by Houghton Mifflin Company. All rights reserved. 8 Nomenclature for Alkenes 1. Root hydrocarbon name ends in -ene C2H4 is ethene 2. With more than 3 carbons, double bond is indicated by the lowest numbered carbon atom in the bond. C=CCC is 1-butene Copyright©2000 by Houghton Mifflin Company. All rights reserved. 9 Addition Reactions . . . in which (weaker) bonds are broken and new (stronger) bonds are formed to atoms being added. catalyst CH2 CHCH3 H2 CH3CH2CH3 Copyright©2000 by Houghton Mifflin Company. All rights reserved. 10 Aromatic Hydrocarbons A special class of cyclic unsaturated hydrocarbons. Cl FeCl3 + Cl2 benzene + HCl Chlorobenzene Copyright©2000 by Houghton Mifflin Company. All rights reserved. 11 The Common Functional Groups Class Halohydrocarbons Alcohols Ethers Aldehydes General Formula RX ROH ROR O R C H Copyright©2000 by Houghton Mifflin Company. All rights reserved. 12 The Common Functional Groups Class Ketones General Formula O R C R' Carboxylic Acids Esters Amines Copyright©2000 by Houghton Mifflin Company. All rights reserved. O R C OH O R C O R' RNH2 13 Polymers . . . are large, usually chainlike molecules that are built from small molecules called monomers. Monomer Polymer Ethylene Polyethylene Vinyl chloride Polyvinyl chloride Tetrafluoroethylene Teflon Copyright©2000 by Houghton Mifflin Company. All rights reserved. 14 Types of Polymerization Addition Polymerization: monomers “add together” to form the polymer, with no other products. (Teflon) Condensation Polymerization: A small molecule, such as water, is formed for each extension of the polymer chain. (Nylon) Copyright©2000 by Houghton Mifflin Company. All rights reserved. 15 Proteins •Natural polymers made up of -amino acids (molecular weight from 6000 to >1,000,000 g/mol). •Fibrous Proteins: provide structural integrity and strength to muscle, hair and cartilage. Copyright©2000 by Houghton Mifflin Company. All rights reserved. 16 Proteins (continued) • Globular Proteins: roughly spherical shape transport and store oxygen and nutrients act as catalysts fight invasion by foreign objects participate in the body’s regulatory system transport electrons in metabolism Copyright©2000 by Houghton Mifflin Company. All rights reserved. 17 -Amino Acids NH2 always attached to the -carbon (the carbon attached to COOH) H H2N C •C = -carbon COOH R Copyright©2000 by Houghton Mifflin Company. All rights reserved. 18 Bonding in -Amino Acids • H H O H H N C H R C N C R' O + H2O C OH • A peptide linkage •There are 20 amino acids commonly found in proteins. Copyright©2000 by Houghton Mifflin Company. All rights reserved. 19 Levels of Structure •Primary: Sequence of amino acids in the protein chain. •Secondary: The arrangement of the protein chain in the long molecule (hydrogen bonding determines this). •Tertiary: The overall shape of the protein (determined by hydrogen-bonding, dipole-dipole interactions, ionic bonds, covalent bonds and London forces). Copyright©2000 by Houghton Mifflin Company. All rights reserved. 20 Carbohydrates •Food source for most organisms and structural material for plants. •Empirical formula = CH2O •Monosaccharides (simple sugars) pentoses - ribose, arabinose hexoses - fructose, glucose Copyright©2000 by Houghton Mifflin Company. All rights reserved. 21 Carbohydrates (continued) •Disaccharides (formed from 2 monosaccharides joined by a glycoside linkage) sucrose (glucose + fructose) •Polysaccharides (many monosaccharide units) starch, cellulose Copyright©2000 by Houghton Mifflin Company. All rights reserved. 22 Nucleic Acids •DNA (deoxyribonucleic acids): stores and transmits genetic information, responsible (with RNA) for protein synthesis. (Molar mass = several billion) •RNA (ribonucleic acid): helps in protein synthesis. (Molecular weight = 20,000 to 40,000) messenger RNA transfer RNA Copyright©2000 by Houghton Mifflin Company. All rights reserved. 23
