SOLUTIONS MANUAL TO ACCOMPANY ORGANIC CHEMISTRY ELEVENTH EDITION T. W. GRAHAM SOLOMONS

This page is intentionally left blank

, STUDY GUIDE
AND
SOLUTIONS MANUAL
TO ACCOMPANY

ORGANIC
CHEMISTRY
ELEVENTH EDITION



T. W. GRAHAM SOLOMONS
University of South Florida


CRAIG B. FRYHLE
Pacific Lutheran University


SCOTT A. SNYDER
Columbia University


ROBERT G. JOHNSON
Xavier University


JON ANTILLA
University of South Florida

,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


vi

, CONTENTS vii


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