BRIEF CONTENTS 1 Structure and Bonding 1 2 Polar Covalent Bonds;Acids and Bases 28 3 Organic Compounds:Alkanes and Their Stereochemistry 9 4 Organic Compounds:Cycloalkanes and Their Stereochemistry 87 5 Stereochemistry at Tetrahedral Centers 113 6 An Overview of Organic Reactions 146 Alkenes and Alkynes 179 8 Reactions of Alkenes and Alkynes 212 9 Aromatic Compounds 265 10 Structure Determination:Mass Spectrometry,Infrared Spectroscopy,and Ultraviolet Spectroscopy 319 Structure Determination:Nuclear Magnetic Resonance Spectroscopy 350 12 Organohalides:Nucleophilic Substitutions and Eliminations 382 13 Alcohols,Phenols,and Thiols;Ethers and Sulfides 435 A Preview of Carbonyl Chemistry 483 4 Aldehydes and Ketones:Nucleophilic Addition Reactions 492 Carboxylic Acids and Nitriles 530 16 Carboxylic Acid Derivatives:Nucleophilic Acyl Substitution Reactions 555 17 Carbonyl Alpha-Substitution and Condensation Reactions 599 18 Amines and Heterocycles 644 19 Biomolecules:Amino Acids,Peptides,and Proteins 678 20 Amino Acid Metabolism 714 21 Biomolecules:Carbohydrates 738 22 Carbohydrate Metabolism 73 23 Biomolecules:Lipids and Their Metabolism 805 24 Biomolecules:Nucleic Acids and Their Metabolism 852 e25 Secondary Metabolites:An Introduction to Natural Products Chemistry 877 e26 Orbitals and Organic Chemistry:Pericyclic Reactions 905 e27 Synthetic Polymers 925B r i e f C o n t e n t s 1 structure and Bonding 1 2 polar covalent Bonds; acids and Bases 28 3 organic compounds: alkanes and their stereochemistry 59 4 organic compounds: cycloalkanes and their stereochemistry 87 5 stereochemistry at tetrahedral centers 113 6 an overview of organic Reactions 146 7 alkenes and alkynes 179 8 Reactions of alkenes and alkynes 212 9 aromatic compounds 265 10 structure Determination: Mass spectrometry, infrared spectroscopy, and Ultraviolet spectroscopy 319 11 structure Determination: nuclear Magnetic Resonance spectroscopy 350 12 organohalides: nucleophilic substitutions and Eliminations 382 13 alcohols, phenols, and thiols; Ethers and sulfides 435 ** a preview of carbonyl chemistry 483 14 aldehydes and Ketones: nucleophilic addition Reactions 492 15 carboxylic acids and nitriles 530 16 carboxylic acid Derivatives: nucleophilic acyl substitution Reactions 555 17 carbonyl alpha-substitution and condensation Reactions 599 18 amines and heterocycles 644 19 Biomolecules: amino acids, peptides, and proteins 678 20 amino acid Metabolism 714 21 Biomolecules: carbohydrates 738 22 carbohydrate Metabolism 773 23 Biomolecules: lipids and their Metabolism 805 24 Biomolecules: nucleic acids and their Metabolism 852 To access the following online-only chapters, enter ISBN: 978-1-285-84291-2 at www.cengagebrain.com and visit this book’s companion website. e25 secondary Metabolites: an introduction to natural products chemistry 877 e26 orbitals and organic chemistry: pericyclic Reactions 905 e27 synthetic polymers 925 v 42912_00_FM_i-xxiv.indd 5 1/16/14 3:00 PM Copyright 2015 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it