STUDY GUIDE AND SOLUTIONS MANUAL
TO ACCOMPANY
ORGANIC CHEMISTRY
TENTH EDITION
, STUDY GUIDE
AND
ORGANIC
SOLUTIONS MANUAL
TO ACCOMPANY
CHEMISTRY
TENTH EDITION
T. W. GRAHAM SOLOMONS
University of South Florida
CRAIG B. FRYHLE
Pacific Lutheran University
ROBERT G. JOHNSON
Xavier University
�
WILEY
JOHN WILEY & SONS, INC.
,BiThinsd-bookRite. The coverset wa10s/pr12inTitemd esby BiRomannd-Ritbye. Aptara Delhi and printed and bound by
was in
Copyr
Copyr ig ht e 201 1 , 2008 J ohn Wi l e y & Sons , I n c. Al l r ig ht s reserv ed.
publby aincyatigmeans
ihton ,2011elbeectr,r2008eoprniocduced,
©
may
John sWitorleeyd aSonsretr,ievaInc.l sAlystlermightorstrraenssemrvied.t edNino aparnytfoofrmthoris
&
, Sectmechaniionsca10�7photor 1oc08opyiof tnhg,e 1r9ecor76 dUniing,tedscStananitensg,Copyror otihgerhtwActise,,
in
excwitheoutpt aseitperhermthiteeprd under
mentDrive,ofDanveapprrs,oMApriait01oerper9wr23,-ictopywebsen perfeeitmetoatisthwww.
ioenCopyroftheightPublCliesarheran,ceorCentautheorr,iIznatc.io, n222thrRosoughewoodpay
to the5Per774,mi(sc2opyrii01ons) 748-Depar
ght.com.tmentReques, JohntsWito ltehye PublSons,isherlnfc.or,
the
permiRisvsieronStrsheoulet,dHoboken, be addresNJed07030-
htEvatp:l/uwatww.ion copiwileey.scaromle progo/vpideredmtios qualionsi.fied academics an6d011,proffeasxi(o2nal01s) f748-orre60view08,pupos website
&
III
onlmayy,notforbeusesolindtorheitrrancoursfesreeds durto iantghtirhdeparnextty.academi c yea r . copi e s a r e l i c ens e d andes
rlaebelturnatrheeaevalvailaublateioatn copy to Wiley. Return insUpontructiocomplnsOutandestaiidofreneofofe oftthhechare UnirevigteeewdreperSttuarintoesd,sh, pliplppieaeanssgee
These
contact your local representative. www.wiley.com/go/returnlabel.
Library of Congress Cataloging-ill-Publication Data
SoloOrmons,ganicT.ChemiGrstarhyalTm. Grabam Solomons.-lOth ed./Craig B. Fryhle.
Main Text
W.
IInSclBp.cmNudes978-in0dex.-470-40141-5 (cloth)
W.
BinChemi
der-readystry,veOrrsgianion clS-TextBN 978-books0-4.70-I5. 5659- Fr y We,7 Craig B. 1 . Title.
547-QD253.-{)c222.S652011
I.
2009032800
Pr10inteI9SdBN8 th978-e7 Uni06-t4e70-d5St4a47839-tes3of4Amer
Study Guide and Solutions Manual
in
2 ic a
, To the Student
Contrary to what you may have heard, organic cannot, then you should go back and study the
chemisty does not have to be a difficult course. It preceding material again. Work all of the prob
will be a rigorous course, and it will offer a chal lems assigned by your instructor from the end of
lenge. But you will learn more in it than in almost the chapter, as well. Do all of your problems in a
any course you will take--and what you learn will notebook and bring this book with you when you
have a special relevance to Iife and the world around go to see your instructor for extra help.
you. However, because organic chemistry can be ap
proached in a logical and systematic way, you will 4. W rite when you study. W rite the reactions,
find that with the right study habits, mastering or mechanisms, structures, and so on, over and
ganic chemistry can be a deeply satisfying experi over again. Organic chemistry is best assimilated
ence. Here, then, are some suggestions about how to through the fingertips by writing, and not through
the eyes by simply looking, or by higWighting
1.
study:
Keep UI' with your work from day to d ay-never
let yourself get behind. Organic chemistry is a
material in the text, or by referring to flash cards.
There is a good reason for this. Organic struc
tures, mechanisms, and reactions are complex. If
course in which one idea almost always builds on
you simply examine them, you may think you un
another that has gone before. It is essential, there derstand them thoroughly, but that will be a mis
fore, that you keep up with, or better yet, be a little
perception. The reaction mechanism may make
abead of your instructor. Ideally, you should try sense to you in a certain way, but you need a
to stay one day ahead of your instructor's lectures
deeper understanding than this. You need to know
in your own class preparations. The lecture, then,
the material so thorougWy that you can explain
will be much more helpful because you will al
it to someone else. This level of understanding
ready have some understanding of the assigned
comes to most of us (those of us without photo
material. Your time in class will clarify and ex
graphic memories) through writing. Only by writ
pand ideas that are already familiar ones.
ing the reaction mechanisms do we pay sufficient
2. Stu d y material in small un its, and be sure that attention to their details, such as which atoms are
you understand each new section before yo u go connected to which atoms, which bonds break in
o n to the next. Again, because of the cumulative a reaction and which bonds form, and the three
nature of organic chemistry, your studying will dimensional aspects of the structures. When we
be much more effective if you take each new idea write reactions and mechanisms, connections are
as it comes and try to understand it completely made in our brains that provide the long-term
before you move on to the next concept. memory needed for success in organic chem
istry. We virtually guarantee that your grade in the
3. Work a l l of the in-chapter and assigned prob course will be directly proportional to the number
lems. One way to check your progress is to work of pages of paper that you fill with your own
each of the in-chapter problems when you come writing in studying during the term.
to it. These problems have been written just for
this purpose and are designed to help you decide S. Learn by teaching and explaining. Study with
whether or not you understand the material that your student peers and practice explaining con
has just been explained. You should also care cepts and mechanisms to each other. Use the
fully study the Solved Problems. If you under Leaming Group Problems and other exercises
stand a Solved Problem and can work the related your instructor may assign as vehicles for teaching
in-chapter problem, then you should go on; if you and learning interactively with your peers.
v
LibraryPirate
TO ACCOMPANY
ORGANIC CHEMISTRY
TENTH EDITION
, STUDY GUIDE
AND
ORGANIC
SOLUTIONS MANUAL
TO ACCOMPANY
CHEMISTRY
TENTH EDITION
T. W. GRAHAM SOLOMONS
University of South Florida
CRAIG B. FRYHLE
Pacific Lutheran University
ROBERT G. JOHNSON
Xavier University
�
WILEY
JOHN WILEY & SONS, INC.
,BiThinsd-bookRite. The coverset wa10s/pr12inTitemd esby BiRomannd-Ritbye. Aptara Delhi and printed and bound by
was in
Copyr
Copyr ig ht e 201 1 , 2008 J ohn Wi l e y & Sons , I n c. Al l r ig ht s reserv ed.
publby aincyatigmeans
ihton ,2011elbeectr,r2008eoprniocduced,
©
may
John sWitorleeyd aSonsretr,ievaInc.l sAlystlermightorstrraenssemrvied.t edNino aparnytfoofrmthoris
&
, Sectmechaniionsca10�7photor 1oc08opyiof tnhg,e 1r9ecor76 dUniing,tedscStananitensg,Copyror otihgerhtwActise,,
in
excwitheoutpt aseitperhermthiteeprd under
mentDrive,ofDanveapprrs,oMApriait01oerper9wr23,-ictopywebsen perfeeitmetoatisthwww.
ioenCopyroftheightPublCliesarheran,ceorCentautheorr,iIznatc.io, n222thrRosoughewoodpay
to the5Per774,mi(sc2opyrii01ons) 748-Depar
ght.com.tmentReques, JohntsWito ltehye PublSons,isherlnfc.or,
the
permiRisvsieronStrsheoulet,dHoboken, be addresNJed07030-
htEvatp:l/uwatww.ion copiwileey.scaromle progo/vpideredmtios qualionsi.fied academics an6d011,proffeasxi(o2nal01s) f748-orre60view08,pupos website
&
III
onlmayy,notforbeusesolindtorheitrrancoursfesreeds durto iantghtirhdeparnextty.academi c yea r . copi e s a r e l i c ens e d andes
rlaebelturnatrheeaevalvailaublateioatn copy to Wiley. Return insUpontructiocomplnsOutandestaiidofreneofofe oftthhechare UnirevigteeewdreperSttuarintoesd,sh, pliplppieaeanssgee
These
contact your local representative. www.wiley.com/go/returnlabel.
Library of Congress Cataloging-ill-Publication Data
SoloOrmons,ganicT.ChemiGrstarhyalTm. Grabam Solomons.-lOth ed./Craig B. Fryhle.
Main Text
W.
IInSclBp.cmNudes978-in0dex.-470-40141-5 (cloth)
W.
BinChemi
der-readystry,veOrrsgianion clS-TextBN 978-books0-4.70-I5. 5659- Fr y We,7 Craig B. 1 . Title.
547-QD253.-{)c222.S652011
I.
2009032800
Pr10inteI9SdBN8 th978-e7 Uni06-t4e70-d5St4a47839-tes3of4Amer
Study Guide and Solutions Manual
in
2 ic a
, To the Student
Contrary to what you may have heard, organic cannot, then you should go back and study the
chemisty does not have to be a difficult course. It preceding material again. Work all of the prob
will be a rigorous course, and it will offer a chal lems assigned by your instructor from the end of
lenge. But you will learn more in it than in almost the chapter, as well. Do all of your problems in a
any course you will take--and what you learn will notebook and bring this book with you when you
have a special relevance to Iife and the world around go to see your instructor for extra help.
you. However, because organic chemistry can be ap
proached in a logical and systematic way, you will 4. W rite when you study. W rite the reactions,
find that with the right study habits, mastering or mechanisms, structures, and so on, over and
ganic chemistry can be a deeply satisfying experi over again. Organic chemistry is best assimilated
ence. Here, then, are some suggestions about how to through the fingertips by writing, and not through
the eyes by simply looking, or by higWighting
1.
study:
Keep UI' with your work from day to d ay-never
let yourself get behind. Organic chemistry is a
material in the text, or by referring to flash cards.
There is a good reason for this. Organic struc
tures, mechanisms, and reactions are complex. If
course in which one idea almost always builds on
you simply examine them, you may think you un
another that has gone before. It is essential, there derstand them thoroughly, but that will be a mis
fore, that you keep up with, or better yet, be a little
perception. The reaction mechanism may make
abead of your instructor. Ideally, you should try sense to you in a certain way, but you need a
to stay one day ahead of your instructor's lectures
deeper understanding than this. You need to know
in your own class preparations. The lecture, then,
the material so thorougWy that you can explain
will be much more helpful because you will al
it to someone else. This level of understanding
ready have some understanding of the assigned
comes to most of us (those of us without photo
material. Your time in class will clarify and ex
graphic memories) through writing. Only by writ
pand ideas that are already familiar ones.
ing the reaction mechanisms do we pay sufficient
2. Stu d y material in small un its, and be sure that attention to their details, such as which atoms are
you understand each new section before yo u go connected to which atoms, which bonds break in
o n to the next. Again, because of the cumulative a reaction and which bonds form, and the three
nature of organic chemistry, your studying will dimensional aspects of the structures. When we
be much more effective if you take each new idea write reactions and mechanisms, connections are
as it comes and try to understand it completely made in our brains that provide the long-term
before you move on to the next concept. memory needed for success in organic chem
istry. We virtually guarantee that your grade in the
3. Work a l l of the in-chapter and assigned prob course will be directly proportional to the number
lems. One way to check your progress is to work of pages of paper that you fill with your own
each of the in-chapter problems when you come writing in studying during the term.
to it. These problems have been written just for
this purpose and are designed to help you decide S. Learn by teaching and explaining. Study with
whether or not you understand the material that your student peers and practice explaining con
has just been explained. You should also care cepts and mechanisms to each other. Use the
fully study the Solved Problems. If you under Leaming Group Problems and other exercises
stand a Solved Problem and can work the related your instructor may assign as vehicles for teaching
in-chapter problem, then you should go on; if you and learning interactively with your peers.
v
LibraryPirate
