STUDY GUIDE
AND
SOLUTIONS MANUAL
TO ACCOMPANY
ORGANIC
CHEMISTRY
ELEVENTH EDITION
T. W. GRAHAM SOLOMONS
University of South Florida
This page is intentionally left blank CRAIG B. FRYHLE
Pacific Lutheran University
SCOTT A. SNYDER
Columbia University
ROBERT G. JOHNSON
Xavier University
JON ANTILLA
University of South Florida
, CONTENTS vii
CHAPTER 6
CONTENTS IONIC REACTIONS–NUCLEOPHILIC SUBSTITUTION AND
ELIMINATION REACTIONS OF ALKYL HALIDES 85
Solutions to Problems 85
Quiz 103
To the Student xi
INTRODUCTION
CHAPTER 7
“Solving the Puzzle” or “Structure Is Everything (Almost)” xiii
ALKENES AND ALKYNES I: PROPERTIES AND SYNTHESIS.
ELIMINATION REACTIONS OF ALKYL HALIDES 106
CHAPTER 1 Solutions to Problems 106
THE BASICS: BONDING AND MOLECULAR STRUCTURE 1 Quiz 128
Solutions to Problems 1
Quiz 15
CHAPTER 8
ALKENES AND ALKYNES II: ADDITION REACTIONS 130
CHAPTER 2 Solutions to Problems 130
FAMILIES OF CARBON COMPOUNDS: FUNCTIONAL Quiz 153
GROUPS, INTERMOLECULAR FORCES, AND INFRARED (IR)
SPECTROSCOPY 18
Solutions to Problems 18 CHAPTER 9
Quiz 30 NUCLEAR MAGNETIC RESONANCE AND MASS
SPECTROMETRY: TOOLS FOR STRUCTURE
CHAPTER 3 DETERMINATION 157
ACIDS AND BASES: AN INTRODUCTION TO ORGANIC Solutions to Problems 157
REACTIONS AND THEIR MECHANISMS 34 Quiz 180
Solutions to Problems 34
Quiz 44
CHAPTER 10
RADICAL REACTIONS 182
CHAPTER 4
Solutions to Problems 182
NOMENCLATURE AND CONFORMATIONS OF Quiz 200
ALKANES AND CYCLOALKANES 46
Solutions to Problems 46
Quiz 62 CHAPTER 11
ALCOHOLS AND ETHERS 203
CHAPTER 5 Solutions to Problems 203
STEREOCHEMISTRY: CHIRAL MOLECULES 65 Quiz 225
Solutions to Problems 65
Quiz 82
vi
,viii CONTENTS CONTENTS ix
CHAPTER 12 CHAPTER 17
ALCOHOLS FROM CARBONYL COMPOUNDS: OXIDATION- CARBOXYLIC ACIDS AND THEIR DERIVATIVES:
REDUCTION AND ORGANOMETALLIC COMPOUNDS 227 NUCLEOPHILIC ADDITION-ELIMINATION AT
Solutions to Problems 227 THE ACYL CARBON 389
Quiz 257 Solutions to Problems 389
Quiz 418
ANSWERS TO FIRST REVIEW PROBLEM SET 259 CHAPTER 18
(First Review Problem Set is available only in WileyPlus, REACTIONS AT THE α CARBON OF CARBONYL
www.wileyplus.com)
COMPOUNDS: ENOLS AND ENOLATES 421
Solutions to Problems 421
CHAPTER 13 Quiz 446
CONJUGATED UNSATURATED SYSTEMS 278
Solutions to Problems 278
Quiz 299 CHAPTER 19
CONDENSATION AND CONJUGATE ADDITION REACTIONS
OF CARBONYL COMPOUNDS: MORE CHEMISTRY OF
SUMMARY OF REACTIONS BY TYPE, CHAPTERS 1–13 301 ENOLATES 448
Solutions to Problems 448
Quiz 482
METHODS FOR FUNCTIONAL GROUP PREPARATION,
CHAPTERS 1–13 305 CHAPTER 20
AMINES 488
CHAPTER 14 Solutions to Problems 488
Quiz 526
AROMATIC COMPOUNDS 308
Solutions to Problems 308
Quiz 323 CHAPTER 21
PHENOLS AND ARYL HALIDES: NUCLEOPHILIC AROMATIC
SUBSTITUTION 530
CHAPTER 15 Solutions to Problems 530
REACTIONS OF AROMATIC COMPOUNDS 325 Quiz 547
Solutions to Problems 325
Quiz 355
ANSWERS TO SECOND REVIEW PROBLEM SET 550
(Second Review Problem Set is available only in WileyPlus,
CHAPTER 16
www.wileyplus.com)
ALDEHYDES AND KETONES. NUCLEOPHILIC ADDITION TO CHAPTER 22
THE CARBONYL GROUP 357 CARBOHYDRATES 566
Solutions to Problems 357 Solutions to Problems 567
Quiz 386 Quiz 592
, x CONTENTS
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
Special Topics A–F and H are available only in WileyPlus,
www.wileyplus.com. Solutions to problems in the Special Topics
are found on the following pages:
13
Special Topic A C NMR Spectroscopy 634
Special Topic B Chain-Growth Polymers 636
Special Topic C Step-Growth Polymers 637
Special Topic D Thiols, Sulfur Ylides, and Disulfides 643
Special Topic E Thiol Esters and Lipid Biosynthesis 645
Special Topic F Alkaloids 646
Special Topic G Carbon Carbon Bond-Forming and
Other Reactions of Transition Metal
Organometallic Compounds 651
Special Topic H Electrocyclic and Cycloaddition Reactions 654
APPENDIX A EMPIRICAL AND MOLECULAR FORMULAS 659
Problems 661
Additional Problems 662
Solutions to Problems of Appendix A 663
APPENDIX B ANSWERS TO QUIZZES 667
APPENDIX C MOLECULAR MODEL SET EXERCISES 682
AND
SOLUTIONS MANUAL
TO ACCOMPANY
ORGANIC
CHEMISTRY
ELEVENTH EDITION
T. W. GRAHAM SOLOMONS
University of South Florida
This page is intentionally left blank CRAIG B. FRYHLE
Pacific Lutheran University
SCOTT A. SNYDER
Columbia University
ROBERT G. JOHNSON
Xavier University
JON ANTILLA
University of South Florida
, CONTENTS vii
CHAPTER 6
CONTENTS IONIC REACTIONS–NUCLEOPHILIC SUBSTITUTION AND
ELIMINATION REACTIONS OF ALKYL HALIDES 85
Solutions to Problems 85
Quiz 103
To the Student xi
INTRODUCTION
CHAPTER 7
“Solving the Puzzle” or “Structure Is Everything (Almost)” xiii
ALKENES AND ALKYNES I: PROPERTIES AND SYNTHESIS.
ELIMINATION REACTIONS OF ALKYL HALIDES 106
CHAPTER 1 Solutions to Problems 106
THE BASICS: BONDING AND MOLECULAR STRUCTURE 1 Quiz 128
Solutions to Problems 1
Quiz 15
CHAPTER 8
ALKENES AND ALKYNES II: ADDITION REACTIONS 130
CHAPTER 2 Solutions to Problems 130
FAMILIES OF CARBON COMPOUNDS: FUNCTIONAL Quiz 153
GROUPS, INTERMOLECULAR FORCES, AND INFRARED (IR)
SPECTROSCOPY 18
Solutions to Problems 18 CHAPTER 9
Quiz 30 NUCLEAR MAGNETIC RESONANCE AND MASS
SPECTROMETRY: TOOLS FOR STRUCTURE
CHAPTER 3 DETERMINATION 157
ACIDS AND BASES: AN INTRODUCTION TO ORGANIC Solutions to Problems 157
REACTIONS AND THEIR MECHANISMS 34 Quiz 180
Solutions to Problems 34
Quiz 44
CHAPTER 10
RADICAL REACTIONS 182
CHAPTER 4
Solutions to Problems 182
NOMENCLATURE AND CONFORMATIONS OF Quiz 200
ALKANES AND CYCLOALKANES 46
Solutions to Problems 46
Quiz 62 CHAPTER 11
ALCOHOLS AND ETHERS 203
CHAPTER 5 Solutions to Problems 203
STEREOCHEMISTRY: CHIRAL MOLECULES 65 Quiz 225
Solutions to Problems 65
Quiz 82
vi
,viii CONTENTS CONTENTS ix
CHAPTER 12 CHAPTER 17
ALCOHOLS FROM CARBONYL COMPOUNDS: OXIDATION- CARBOXYLIC ACIDS AND THEIR DERIVATIVES:
REDUCTION AND ORGANOMETALLIC COMPOUNDS 227 NUCLEOPHILIC ADDITION-ELIMINATION AT
Solutions to Problems 227 THE ACYL CARBON 389
Quiz 257 Solutions to Problems 389
Quiz 418
ANSWERS TO FIRST REVIEW PROBLEM SET 259 CHAPTER 18
(First Review Problem Set is available only in WileyPlus, REACTIONS AT THE α CARBON OF CARBONYL
www.wileyplus.com)
COMPOUNDS: ENOLS AND ENOLATES 421
Solutions to Problems 421
CHAPTER 13 Quiz 446
CONJUGATED UNSATURATED SYSTEMS 278
Solutions to Problems 278
Quiz 299 CHAPTER 19
CONDENSATION AND CONJUGATE ADDITION REACTIONS
OF CARBONYL COMPOUNDS: MORE CHEMISTRY OF
SUMMARY OF REACTIONS BY TYPE, CHAPTERS 1–13 301 ENOLATES 448
Solutions to Problems 448
Quiz 482
METHODS FOR FUNCTIONAL GROUP PREPARATION,
CHAPTERS 1–13 305 CHAPTER 20
AMINES 488
CHAPTER 14 Solutions to Problems 488
Quiz 526
AROMATIC COMPOUNDS 308
Solutions to Problems 308
Quiz 323 CHAPTER 21
PHENOLS AND ARYL HALIDES: NUCLEOPHILIC AROMATIC
SUBSTITUTION 530
CHAPTER 15 Solutions to Problems 530
REACTIONS OF AROMATIC COMPOUNDS 325 Quiz 547
Solutions to Problems 325
Quiz 355
ANSWERS TO SECOND REVIEW PROBLEM SET 550
(Second Review Problem Set is available only in WileyPlus,
CHAPTER 16
www.wileyplus.com)
ALDEHYDES AND KETONES. NUCLEOPHILIC ADDITION TO CHAPTER 22
THE CARBONYL GROUP 357 CARBOHYDRATES 566
Solutions to Problems 357 Solutions to Problems 567
Quiz 386 Quiz 592
, x CONTENTS
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
Special Topics A–F and H are available only in WileyPlus,
www.wileyplus.com. Solutions to problems in the Special Topics
are found on the following pages:
13
Special Topic A C NMR Spectroscopy 634
Special Topic B Chain-Growth Polymers 636
Special Topic C Step-Growth Polymers 637
Special Topic D Thiols, Sulfur Ylides, and Disulfides 643
Special Topic E Thiol Esters and Lipid Biosynthesis 645
Special Topic F Alkaloids 646
Special Topic G Carbon Carbon Bond-Forming and
Other Reactions of Transition Metal
Organometallic Compounds 651
Special Topic H Electrocyclic and Cycloaddition Reactions 654
APPENDIX A EMPIRICAL AND MOLECULAR FORMULAS 659
Problems 661
Additional Problems 662
Solutions to Problems of Appendix A 663
APPENDIX B ANSWERS TO QUIZZES 667
APPENDIX C MOLECULAR MODEL SET EXERCISES 682
