T.W. Graham Solomons', Craig B. Fryhle's, Scott A. Snyder's, Robert G. Johnson's and Jon Antilla's 'Study Guide and Solutions Manual to Accompany 'Organic Chemistry''

730 Pages·2016·9.49 MB·English

by  T.W. Graham Solomons

Study Guide and Solutions Manual to Accompany
T.W. Graham Solomons / Craig B. Fryhle / Scott A. Snyder / Jon Antilla

STUDY GUIDE AND SOLUTIONS MANUAL
TO ACCOMPANY
ORGANIC CHEMISTRY
ELEVENTHEDITION
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STUDY GUIDE
AND
SOLUTIONS MANUAL
TO ACCOMPANY
ORGANIC
CHEMISTRY
ELEVENTH EDITION
T. W. GRAHAM SOLOMONS
UniversityofSouthFlorida
CRAIG B. FRYHLE
PacificLutheranUniversity
SCOTT A. SNYDER
ColumbiaUniversity
ROBERT G. JOHNSON
XavierUniversity
JON ANTILLA
UniversityofSouthFlorida
ProjectEditor JenniferYee
SeniorProductionEditor ElizabethSwain
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ACKNOWLEDGMENTS
Wearegratefultothosepeoplewhohavemademanyhelpfulsuggestionsforvariouseditions
ofthisstudyguide.Theseindividualsinclude:GeorgeR.Jurch,GeorgeR.Wenzinger,andJ.
E.FernandezattheUniversityofSouthFlorida;DarellBerlin,OklahomaStateUniversity;
JohnMangravite,WestChesterStateCollege;J.G.Traynham,LouisianaStateUniversity;
DesmondM.S.Wheeler,UniversityofNebraska;ChrisCallam,TheOhioStateUniversity;
SeanHickey,UniversityofNewOrleans;andNealTonks,CollegeofCharleston.
We are especially grateful to R.G. (Bob) Johnson for his friendship, dedication, and
manycontributionstothisStudyGuideandthemaintextovermanyyears.
T.W.GrahamSolomons
CraigB.Fryhle
ScottA.Snyder
JonAntilla
v
CONTENTS
TotheStudent xi
INTRODUCTION
“SolvingthePuzzle”or“StructureIsEverything(Almost)” xiii
CHAPTER1
THEBASICS:BONDINGANDMOLECULARSTRUCTURE 1
SolutionstoProblems 1
Quiz 15
CHAPTER2
FAMILIESOFCARBONCOMPOUNDS:FUNCTIONAL
GROUPS,INTERMOLECULARFORCES,ANDINFRARED(IR)
SPECTROSCOPY 18
SolutionstoProblems 18
Quiz 30
CHAPTER3
ACIDSANDBASES:ANINTRODUCTIONTOORGANIC
REACTIONSANDTHEIRMECHANISMS 34
SolutionstoProblems 34
Quiz 44
CHAPTER4
NOMENCLATUREANDCONFORMATIONSOF
ALKANESANDCYCLOALKANES 46
SolutionstoProblems 46
Quiz 62
CHAPTER5
STEREOCHEMISTRY:CHIRALMOLECULES 65
SolutionstoProblems 65
Quiz 82
vi
CONTENTS vii
CHAPTER6
IONICREACTIONS–NUCLEOPHILICSUBSTITUTIONAND
ELIMINATIONREACTIONSOFALKYLHALIDES 85
SolutionstoProblems 85
Quiz 103
CHAPTER7
ALKENESANDALKYNESI:PROPERTIESANDSYNTHESIS.
ELIMINATIONREACTIONSOFALKYLHALIDES 106
SolutionstoProblems 106
Quiz 128
CHAPTER8
ALKENESANDALKYNESII:ADDITIONREACTIONS 130
SolutionstoProblems 130
Quiz 153
CHAPTER9
NUCLEARMAGNETICRESONANCEANDMASS
SPECTROMETRY:TOOLSFORSTRUCTURE
DETERMINATION 157
SolutionstoProblems 157
Quiz 180
CHAPTER10
RADICALREACTIONS 182
SolutionstoProblems 182
Quiz 200
CHAPTER11
ALCOHOLSANDETHERS 203
SolutionstoProblems 203
Quiz 225
viii CONTENTS
CHAPTER12
ALCOHOLSFROMCARBONYLCOMPOUNDS:OXIDATION-
REDUCTIONANDORGANOMETALLICCOMPOUNDS 227
SolutionstoProblems 227
Quiz 257
ANSWERSTOFIRSTREVIEWPROBLEMSET 259
(FirstReviewProblemSetisavailableonlyinWileyPlus,
www.wileyplus.com)
CHAPTER13
CONJUGATEDUNSATURATEDSYSTEMS 278
SolutionstoProblems 278
Quiz 299
SUMMARYOFREACTIONSBYTYPE,CHAPTERS1–13 301
METHODSFORFUNCTIONALGROUPPREPARATION,
CHAPTERS1–13 305
CHAPTER14
AROMATICCOMPOUNDS 308
SolutionstoProblems 308
Quiz 323
CHAPTER15
REACTIONSOFAROMATICCOMPOUNDS 325
SolutionstoProblems 325
Quiz 355
CHAPTER16
ALDEHYDESANDKETONES.NUCLEOPHILICADDITIONTO
THECARBONYLGROUP 357
SolutionstoProblems 357
Quiz 386