美国经典的有机化学教材(organic chemistry).pdf
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1、f o u r t h e d i t i o nORGANIC CHEMISTRYFrancis A.CareyUniversity of VirginiaBostonBurr Ridge,ILDubuque,IAMadison,WINew YorkSan FranciscoSt.LouisBangkokBogotCaracasLisbonLondonMadridMexico CityMilanNew DelhiSeoulSingaporeSydneyTaipeiTorontoBackForwardMain MenuTOCStudy Guide TOCStudent OLCMHHE Webs
2、iteORGANIC CHEMISTRY,FOURTH EDITIONCopyright 2000,1996,1992,1987 by The McGraw-Hill Companies,Inc.All rights reserved.Printed in theUnited States of America.Except as permitted under the United States Copyright Act of 1976,no part of thispublication may be reproduced or distributed in any form or by
3、 any means,or stored in a data base or retrievalsystem,without the prior written permission of the publisher.This book is printed on acid-free paper.1 2 3 4 5 7 8 9 0 VNH/VNH 9 0 9 8 7 6 5 4 3 2 1 0 9ISBN 0-07-290501-8Vice president and editorial director:Kevin T.KanePublisher:James M.SmithSponsorin
4、g editor:Kent A.PetersonDevelopmental editor:Terrance StantonEditorial assistant:Jennifer BensinkSenior marketing manager:Martin J.LangeSenior marketing assistant:Tami PetscheSenior project manager:Peggy J.SelleSenior production supervisor:Sandra HahnDesigner:K.Wayne HarmsPhoto research coordinator:
5、John C.LelandSenior supplement coordinator:David A.WelshCompositor:GTS Graphics,Inc.Typeface:10/12 Times RomanPrinter:Von Hoffmann Press,Inc.Cover/interior designer:Jamie ONealPhoto research:Mary Reeg Photo ResearchThe credits section for this book begins on page C-1 and is considered an extension o
6、f the copyright page.Library of Congress Cataloging-in-Publication DataCarey,Francis A.Organic chemistry/Francis A.Carey.4th ed.p.cm.Includes index.ISBN 0-07-290501-8 ISBN 0-07-117499-0(ISE)1.Chemistry,Organic.I.Title.QD251.2.C3642000547dc2199-045791CIPINTERNATIONAL EDITIONISBN 0-07-117499-0Copyrigh
7、t 2000.Exclusive rights by The McGraw-Hill Companies,Inc.for manufacture and export.Thisbook cannot be re-exported from the country to which it is consigned by McGraw-Hill.The InternationalEdition is not available in North AMcGraw-Hill Higher EducationA Division of The McGraw-Hill CompaniesBackForwa
8、rdMain MenuTOCStudy Guide TOCStudent OLCMHHE WebsiteA B O U T T H E A U T H O RFrancis A.Carey is a native of Pennsylvania,educatedin the public schools of Philadelphia,at Drexel Univer-sity(B.S.in chemistry,1959),and at Penn State(Ph.D.1963).Following postdoctoral work at Harvard and mil-itary serv
9、ice,he joined the chemistry faculty of the Uni-versity of Virginia in 1966.With his students,Professor Carey has publishedover 40 research papers in synthetic and mechanisticorganic chemistry.He is coauthor(with Richard J.Sund-berg)of Advanced Organic Chemistry,a two-volumetreatment designed for gra
10、duate students and advancedundergraduates,and(with Robert C.Atkins)of OrganicChemistry:A Brief Course,an introductory text for theone-semester organic course.Since 1993,Professor Carey has been a memberof the Committee of Examiners of the Graduate RecordExamination in Chemistry.Not only does he get
11、to par-ticipate in writing the Chemistry GRE,but the annualworking meetings provide a stimulating environment forsharing ideas about what should(and should not)betaught in college chemistry courses.Professor Careys main interest shifted fromresearch to undergraduate education in the early 1980s.He r
12、egularly teaches both general chemistry and organicchemistry to classes of over 300 students.He enthusi-astically embraces applications of electronic media tochemistry teaching and sees multimedia presentations asthe wave of the present.Frank and his wife Jill,who is a teacher/directorof a preschool
13、 and a church organist,are the parents ofthree grown sons and the grandparents of Riyad andAva.BackForwardMain MenuTOCStudy Guide TOCStudent OLCMHHE WebsiteixB R I E F C O N T E N T SPrefacexxvIntroduction11CHEMICAL BONDING72ALKANES533CONFORMATIONS OF ALKANES AND CYCLOALKANES894ALCOHOLS AND ALKYL HA
14、LIDES1265STRUCTURE AND PREPARATION OF ALKENES:ELIMINATION REACTIONS1676REACTIONS OF ALKENES:ADDITION REACTIONS2087STEREOCHEMISTRY2598NUCLEOPHILIC SUBSTITUTION3029ALKYNES33910CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS36511ARENES AND AROMATICITY39812REACTIONS OF ARENES:ELECTROPHILIC AROMATIC SUBSTI
15、TUTION44313SPECTROSCOPY48714ORGANOMETALLIC COMPOUNDS54615ALCOHOLS,DIOLS,AND THIOLS57916ETHERS,EPOXIDES,AND SULFIDES61917ALDEHYDES AND KETONES:NUCLEOPHILIC ADDITION TO THECARBONYL GROUP65418ENOLS AND ENOLATES70119CARBOXYLIC ACIDS73620CARBOXYLIC ACID DERIVATIVES:NUCLEOPHILIC ACYL SUBSTITUTION77421ESTE
16、R ENOLATES83122AMINES85823ARYL HALIDES91724PHENOLS93925CARBOHYDRATES97226LIPIDS101527AMINO ACIDS,PEPTIDES,AND PROTEINS.NUCLEIC ACIDS1051APPENDIX 1PHYSICAL PROPERTIESA-1APPENDIX 2ANSWERS TO IN-TEXT PROBLEMSA-9APPENDIX 3LEARNING CHEMISTRY WITH MOLECULAR MODELS:Using SpartanBuild and SpartanViewA-64GLO
17、SSARYG-1CREDITSC-1INDEXI-1BackForwardMain MenuTOCStudy Guide TOCStudent OLCMHHE WebsiteP R E F A C ExxvPHILOSOPHYFrom its first edition through this,its fourth,OrganicChemistry has been designed to meet the needs of the“mainstream,”two-semester,undergraduate organicchemistry course.It has evolved as
18、 those needs havechanged,but its philosophy remains the same.The over-arching theme is that organic chemistry is not only aninteresting subject,but also a logical one.It is logicalbecause its topics can be connected in a steady pro-gression from simple to complex.Our approach hasbeen to reveal the l
19、ogic of organic chemistry by beingselective in the topics we cover,as well as thorough andpatient in developing them.Teaching at all levels is undergoing rapid change,especially in applying powerful tools that exploit thegraphics capability of personal computers.Organicchemistry has always been the
20、most graphical of thechemical sciences and is well positioned to benefit sig-nificantly from these tools.Consistent with our philoso-phy,this edition uses computer graphics to enhance thecore material,to make it more visual,and more under-standable,but in a way that increases neither the amountof ma
21、terial nor its level.ORGANIZATIONThe central message of chemistry is that the propertiesof a substance come from its structure.What is lessobvious,but very powerful,is the corollary.Someonewith training in chemistry can look at the structure of asubstance and tell you a lot about its properties.Orga
22、nicchemistry has always been,and continues to be,thebranch of chemistry that best connects structure withproperties.This text has a strong bias toward structure,and this edition benefits from the availability of versa-tile new tools to help us understand that structure.The text is organized to flow
23、logically and step bystep from structure to properties and back again.As thelist of chapter titles reveals,the organization is accord-ing to functional groupsstructural units within a mol-ecule most responsible for a particular propertybecause that is the approach that permits most studentsto grasp
24、the material most readily.Students retain thematerial best,however,if they understand how organicreactions take place.Thus,reaction mechanisms arestressed early and often,but within a functional groupframework.A closer examination of the chapter titlesreveals the close link between a functional grou
25、p class(Chapter 20,Carboxylic Acid Derivatives)and a reactiontype(Nucleophilic Acyl Substitution),for example.It isvery satisfying to see students who entered the coursebelieving they needed to memorize everything progressto the point of thinking and reasoning mechanistically.Some of the important s
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