Brief Contents Structure and Bonding 1 Polar Covalent Bonds:Acids and Bases 33 3 Organic Compounds:Alkanes and Their Stereochemistry 70 Organic Compounds:Cycloalkanes and Their Stereochemistry 105 Stereochemistry at Tetrahedral Centers 134 6 An Overview of Organic Reactions 17s 7 Alkenes and Alkynes 212 Reactions of Alkenes and Alkynes 251 9 Aromatic Compounds 309 10 Structure Determination: Mass Spectrometry,Infrared Spectroscopy,and Ultraviolet Spectroscopy 367 11 Structure Determination:Nuclear Magnetic Resonance Spectroscopy 404 12 Organohalides:Nucleophilic Substitutions and Eliminations 13 Alcohols,Phenols,and Thiols;Ethers and Sulfides 501 Preview of Carbonyl Chemistry ss5 14 Aldehydes and Ketones:Nucleophilic Addition Reactions 564 15 Carboxylic Acids and Nitriles 610 16 Carboxylic Acid Derivatives:Nucleophilic Acyl Substitution Reactions 64 17 Carbonyl Alpha-Substitution and Condensation Reactions 695 Amines and Heterocycles 749 19 Biomolecules:Amino Acids,Peptides,and Proteins79 20 Amino Acid Metabolism 832 21 Biomolecules:Carbohydrates 862 22 Carbohydrate Metabolism 901 Biomolecules:Lipids and Their Metabolism 936 24 Biomolecules:Nucleic Acids and Their Metabolism 98i Secondary Metabolites:An Introduction to Natural Products Chemistry 1015 Key t eof Topics (chapter as follows) oun ns of organic chemis stry Organic rea ons na th nterparts The organic chemistry of biological molecules and pathwaysBrief Contents 1 Structure and Bonding 1 2 Polar Covalent Bonds; Acids and Bases 33 3 Organic Compounds: Alkanes and Their Stereochemistry 70 4 Organic Compounds: Cycloalkanes and Their Stereochemistry 105 5 Stereochemistry at Tetrahedral Centers 134 6 An Overview of Organic Reactions 175 7 Alkenes and Alkynes 212 8 Reactions of Alkenes and Alkynes 251 9 Aromatic Compounds 309 10 Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectroscopy 367 11 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 404 12 Organohalides: Nucleophilic Substitutions and Eliminations 444 13 Alcohols, Phenols, and Thiols; Ethers and Sulfides 501 Preview of Carbonyl Chemistry 555 14 Aldehydes and Ketones: Nucleophilic Addition Reactions 564 15 Carboxylic Acids and Nitriles 610 16 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 643 17 Carbonyl Alpha-Substitution and Condensation Reactions 695 18 Amines and Heterocycles 749 19 Biomolecules: Amino Acids, Peptides, and Proteins 791 20 Amino Acid Metabolism 832 21 Biomolecules: Carbohydrates 862 22 Carbohydrate Metabolism 901 23 Biomolecules: Lipids and Their Metabolism 936 24 Biomolecules: Nucleic Acids and Their Metabolism 987 25 Secondary Metabolites: An Introduction to Natural Products Chemistry 1015 Key to Sequence of Topics (chapter numbers are color coded as follows): • Traditional foundations of organic chemistry • Organic reactions and their biological counterparts • The organic chemistry of biological molecules and pathways v 39144_ FM_i-xxiv.indd v 8/26/09 10:48:42 AM