CONTENTS Preface v To the Student vii CHAPTER 1 CHEMICAL BONDING 1 CHAPTER 2 ALKANES 25 CHAPTER 3 CONFORMATIONS OF ALKANES AND CYCLOALKANES 46 CHAPTER 4 ALCOHOLS AND ALKYL HALIDES 67 CHAPTER 5 STRUCTURE AND PREPARATION OF ALKENES: ELIMINATION REACTIONS 90 CHAPTER 6 REACTIONS OF ALKENES: ADDITION REACTIONS 124 CHAPTER 7 STEREOCHEMISTRY 156 CHAPTER 8 NUCLEOPHILIC SUBSTITUTION 184 CHAPTER 9 ALKYNES 209 CHAPTER 10 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS 230 CHAPTER 11 ARENES AND AROMATICITY 253 CHAPTER 12 REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION 279 iii iv CONTENTS CHAPTER 13 SPECTROSCOPY 320 CHAPTER POUNDS 342 CHAPTER 15 ALCOHOLS, DIOLS, AND THIOLS 364 CHAPTER 16 ETHERS, EPOXIDES, AND SULFIDES 401 CHAPTER 17 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 426 CHAPTER 18 ENOLS AND ENOLATES 470 CHAPTER 19 CARBOXYLIC ACIDS 502 CHAPTER 20 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION 536 CHAPTER 21 ESTER ENOLATES 576 CHAPTER 22 AMINES 604 CHAPTER 23 ARYL HALIDES 656 CHAPTER 24 PHENOLS 676 CHAPTER 25 CARBOHYDRATES 701 CHAPTER 26 LIPIDS 731 CHAPTER 27 AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS 752 APPENDIX A ANSWERS TO THE SELF-TESTS 775 APPENDIX B TABLES 821 B-1 Bond Dissociation Energies of Some pounds 821 B-2 Acid Dissociation Constants 822 B-3 Chemical Shifts of Representative Types of Protons 822 B-4 Chemical Shifts of Representative Carbons 823 B-5 Infrared Absorption Frequencies of mon Structural Units 823 PREFACE t is our hope that in writing this Study Guide and Solutions Manual we will make the study of or- ganic chemistry more meaningful and worthwhile. To be effective, a study guide should be more Ithan just an answer book. What we present here was designed with that larger goal in mind. The Study Guide and Solutions Manual contains detailed solutions to all the problems in the text. Learning how to solve a p