Student Study Guide and Student Solutions Manual to accompany Organic Chemistry 11e

Book Preface

We are grateful to those peoplewho have made many helpful suggestions for various editions of this study guide. These individuals include: George R. Jurch, George R.Wenzinger, and J. E. Fernandez at the University of South Florida; Darell Berlin, Oklahoma State University; John Mangravite, West Chester State College; J. G. Traynham, Louisiana State University; Desmond M. S. Wheeler, University of Nebraska; Chris Callam, The Ohio State University; Sean Hickey, University of New Orleans; and Neal Tonks, College of Charleston.

We are especially grateful to R.G. (Bob) Johnson for his friendship, dedication, and many contributions to this Study Guide and the main text over many years.

T. W. Graham Solomons
Craig B. Fryhle
Scott A. Snyder
Jon Antilla

CONTENTS
To the Student xi
INTRODUCTION
“Solving the Puzzle” or “Structure Is Everything (Almost)” xiii
CHAPTER 1 THE BASICS: BONDING AND MOLECULAR STRUCTURE 1
Solutions to Problems 1
Quiz 15
CHAPTER 2 FAMILIES OF CARBON COMPOUNDS: FUNCTIONAL GROUPS, INTERMOLECULAR FORCES, AND INFRARED (IR) SPECTROSCOPY 18
Solutions to Problems 18
Quiz 30
CHAPTER 3 ACIDS AND BASES: AN INTRODUCTION TO ORGANIC REACTIONS AND THEIR MECHANISMS 34
Solutions to Problems 34
Quiz 44
CHAPTER 4 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 46
Solutions to Problems 46
Quiz 62
CHAPTER 5 STEREOCHEMISTRY: CHIRAL MOLECULES 65
Solutions to Problems 65
Quiz 82

CHAPTER 6 IONIC REACTIONS–NUCLEOPHILIC SUBSTITUTION AND ELIMINATION REACTIONS OF ALKYL HALIDES 85
Solutions to Problems 85
Quiz 103
CHAPTER 7 ALKENES AND ALKYNES I: PROPERTIES AND SYNTHESIS. ELIMINATION REACTIONS OF ALKYL HALIDES 106
Solutions to Problems 106
Quiz 128
CHAPTER 8 ALKENES AND ALKYNES II: ADDITION REACTIONS 130
Solutions to Problems 130
Quiz 153
CHAPTER 9 NUCLEAR MAGNETIC RESONANCE AND MASS SPECTROMETRY: TOOLS FOR STRUCTURE DETERMINATION 157
Solutions to Problems 157
Quiz 180
CHAPTER 10 RADICAL REACTIONS 182
Solutions to Problems 182
Quiz 200
CHAPTER 11 ALCOHOLS AND ETHERS 203
Solutions to Problems 203
Quiz 225

CHAPTER 12 ALCOHOLS FROM CARBONYL COMPOUNDS: OXIDATIONREDUCTION AND ORGANOMETALLIC COMPOUNDS 227
Solutions to Problems 227
Quiz 257
ANSWERS TO FIRST REVIEW PROBLEM SET 259
(First Review Problem Set is available only in WileyPlus,
www.wileyplus.com)
CHAPTER 13 CONJUGATED UNSATURATED SYSTEMS 278
Solutions to Problems 278
Quiz 299
SUMMARY OF REACTIONS BY TYPE, CHAPTERS 1–13 301 METHODS FOR FUNCTIONAL GROUP PREPARATION, CHAPTERS 1–13 305
CHAPTER 14
AROMATIC COMPOUNDS 308
Solutions to Problems 308
Quiz 323
CHAPTER 15 REACTIONS OF AROMATIC COMPOUNDS 325
Solutions to Problems 325
Quiz 355
CHAPTER 16 ALDEHYDES AND KETONES. NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 357
Solutions to Problems 357
Quiz 386

CHAPTER 23 LIPIDS 596
Solutions to Problems 596
Quiz 607
CHAPTER 24 AMINO ACIDS AND PROTEINS 610
Solutions to Problems 610
Quiz 625
CHAPTER 25 NUCLEIC ACIDS AND PROTEIN SYNTHESIS 626
Solutions to Problems 626