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ORGANIC CHEMISTRY AS A SECOND LANGUAGE, 4e ORGANIC CHEMISTRY AS A SECOND LANGUAGE, 4e First Semester Topics DAVID KLEIN JohnsHopkinsUniversity VICEPRESIDENT&DIRECTOR PetraRecter DEVELOPMENTEDITOR JoanKalkut ASSISTANTDEVELOPMENTEDITOR MalloryFryc SENIORDIRECTOR DonFowley PROJECTMANAGER GladysSoto PROJECTSPECIALIST NicholeUrban PROJECTASSISTANT AnnaMelhorn SENIORMARKETINGMANAGER KristineRuff DIRECTOR LisaWojcik SENIORCONTENTSPECIALIST NicoleRepasky PRODUCTIONEDITOR BharathySuryaPrakash COVERPHOTOCREDITS AbstractPouringCoffeeisolated:©VasinLee/Shutterstock Coffeebeanspouringfromscoop:©Fuse/GettyImages,Inc. Espressocoffeeinaglasscuponwhitebackground:©RobStark/Shutterstock Flask:©NormChristiansen Largepinkpapaver(poppy):©MargaretRowe/GardenPictureLibrary/GettyImages,Inc. Poppies:©KuttelvaserovaStuchelova/Shutterstock StudioShotofCherryTomatoesinpaperbag:©JessicaPeterson/TetraImages/CorbisImages CherryTomatoes:©NatalieErhova(summerky)/Shutterstock Evolutionofredtomatoisolatedonwhitebackground:©AlenaBrozova/Shutterstock Curlofsmoke:©stavklem/Shutterstock Thisbookwassetin9/11TimesLTStdRomanbySPiGlobalandprintedandboundbyDonnelleyHarrisonburg. Thisbookisprintedonacid-freepaper.∞ Foundedin1807,JohnWiley&Sons,Inc.hasbeenavaluedsourceofknowledgeandunderstandingformorethan 200years,helpingpeoplearoundtheworldmeettheirneedsandfulfilltheiraspirations.Ourcompanyisbuiltona foundationofprinciplesthatincluderesponsibilitytothecommunitiesweserveandwhereweliveandwork. 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Uponcompletionofthereviewperiod,pleasereturntheevaluationcopytoWiley.Returninstructionsandafreeof chargereturnshippinglabelareavailableat:www.wiley.com/go/returnlabel.Ifyouhavechosentoadoptthistextbook foruseinyourcourse,pleaseacceptthisbookasyourcomplimentarydeskcopy.OutsideoftheUnitedStates,please contactyourlocalsalesrepresentative. ISBN:978-1-119-11066-8(PBK) LibraryofCongressCataloging-in-PublicationData: Names:Klein,DavidR.,author. Title:Organicchemistryasasecondlanguage:firstsemestertopics/David Klein,JohnsHopkinsUniversity. Description:4thedition.|Hoboken:JohnWiley&Sons,Inc.,[2017]| Includesindex. Identifiers:LCCN2016003041(print)|LCCN2016006248(ebook)|ISBN 9781119110668(pbk.)|ISBN9781119234524(pdf)|ISBN9781119234517(epub) Subjects:LCSH:Chemistry,Organic—Studyandteaching.|Chemistry, Organic—Problems,exercises,etc. Classification:LCCQD256.K541452017(print)|LCCQD256(ebook)|DDC 547.0071/1—dc23 LCrecordavailableathttp://lccn.loc.gov/2016003041 Printingidentificationandcountryoforiginwilleitherbeincludedonthispageand/ortheendofthebook.Inaddition, iftheISBNonthispageandthebackcoverdonotmatch,theISBNonthebackcovershouldbeconsideredthecorrect ISBN. PrintedintheUnitedStatesofAmerica 10987654321 INTRODUCTION IS ORGANIC CHEMISTRY REALLY ALL ABOUT MEMORIZATION? Isorganicchemistryreallyastoughaseveryonesaysitis?Theanswerisyesandno.Yes,becauseyou willspendmoretimeonorganicchemistrythanyouwouldspendinacourseonunderwaterbasket weaving.Andno,becausethosewhosayit’ssotoughhavestudiedinefficiently.Askaround,and youwillfindthatmoststudentsthinkoforganicchemistryasamemorizationgame.Thisisnottrue! Formerorganicchemistrystudentsperpetuatethefalserumorthatorganicchemistryisthetoughest classoncampus,becauseitmakesthemfeelbetteraboutthepoorgradesthattheyreceived. Ifit’snotaboutmemorizing,thenwhatisit?Toanswerthisquestion,let’scompareorganicchem- istrytoamovie.Pictureinyourmindamoviewheretheplotchangeseverysecond.Ifyou’reina movietheatrewatchingamovielikethat,youcan’tleaveevenforasecondbecauseyouwouldmiss somethingimportanttotheplot.Soyoutryyourhardesttowaituntilthemovieisoverbeforegoing tothebathroom.Soundsfamiliar? Organicchemistryisverymuchthesame.Itisonelongstory,andthestoryactuallymakessense ifyoupayattention.Theplotconstantlydevelops,andeverythingtiesintotheplot.Ifyourattention wandersfortoolong,youcouldeasilygetlost. Youprobablyknowatleastonepersonwhohasseenonemoviemorethanfivetimesandcan quoteeverylinebyheart.Howcanthispersondothat?It’snotbecauseheorshetriedtomemorize themovie.Thefirsttimeyouwatchamovie,youlearntheplot.Afterthesecondtime,youunderstand whyindividualscenesarenecessarytodeveloptheplot.Afterthethirdtime,youunderstandwhythe dialoguewasnecessarytodevelopeachscene.Afterthefourthtime,youarequotingmanyofthelines byheart.Neveratanytimedidyoumakeanefforttomemorizethelines.Youknowthembecause theymakesenseinthegrandschemeoftheplot.IfIweretogiveyouascreenplayforamovieand askyoutomemorizeasmuchasyoucanin10hours,youwouldprobablynotgetveryfarintoit.If, instead,Iputyouinaroomfor10hoursandplayedthesamemovieoveragainfivetimes,youwould knowmostofthemoviebyheart,withouteventrying.Youwouldknoweveryone’snames,theorder ofthescenes,muchofthedialogue,andsoon. Organicchemistryisexactlythesame.It’snotaboutmemorization.It’sallaboutmakingsense oftheplot,thescenes,andtheindividualconceptsthatmakeupourstory.Ofcourseyouwillneed torememberalloftheterminology,butwithenoughpractice,theterminologywillbecomesecond naturetoyou.Sohere’sabriefpreviewoftheplot. THE PLOT Thefirsthalfofourstorybuildsuptoreactions,andwelearnaboutthecharacteristicsofmolecules thathelpusunderstandreactions.Webeginbylookingatatoms,thebuildingblocksofmolecules, andwhathappenswhentheycombinetoformbonds.Wefocusonspecialbondsbetweencertain v vi INTRODUCTION atoms,andweseehowthenatureofbondscanaffecttheshapeandstabilityofmolecules.Then,we needavocabularytostarttalkingaboutmolecules,sowelearnhowtodrawandnamemolecules.We seehowmoleculesmovearoundinspace,andweexploretherelationshipsbetweensimilartypesof molecules.Atthispoint,weknowtheimportantcharacteristicsofmolecules,andwearereadytouse ourknowledgetoexplorereactions. Reactionstakeuptherestofthecourse,andtheyaretypicallybrokendownintochaptersbased oncategories.Withineachofthesechapters,thereisactuallyasubplotthatfitsintothegrandstory. HOW TO USE THIS BOOK Thisbookwillhelpyoustudymoreefficientlysothatyoucanavoidwastingcountlesshours.Itwill pointoutthemajorscenesintheplotoforganicchemistry.Thebookwillreviewthecriticalprinciples andexplainwhytheyarerelevanttotherestofthecourse.Ineachsection,youwillbegiventhetools tobetterunderstandyourtextbookandlectures,aswellasplentyofopportunitiestopracticethekey skillsthatyouwillneedtosolveproblemsonexams.Inotherwords,youwilllearnthelanguageof organicchemistry.Thisbookcannotreplaceyourtextbook,yourlectures,orotherformsofstudying. This book is not the Cliff Notes of Organic Chemistry. It focuses on the basic concepts that will empoweryoutodowellifyougotolecturesandstudyinadditiontousingthisbook.Tobestusethis book,youneedtoknowhowtostudyinthiscourse. HOW TO STUDY Therearetwoseparateaspectstothiscourse: 1. Understandingprinciples 2. Solvingproblems Althoughthesetwoaspectsarecompletelydifferent,instructorswilltypicallygaugeyourunderstand- ingoftheprinciplesbytestingyourabilitytosolveproblems.Soyoumustmasterbothaspectsofthe course.Theprinciplesareinyourlecturenotes,butyoumustdiscoverhowtosolveproblems.Most studentshaveadifficulttimewiththistask.Inthisbook,weexploresomestep-by-stepprocessesfor analyzingproblems.Thereisaverysimplehabitthatyoumustformimmediately:learntoaskthe rightquestions. Ifyougotoadoctorwithapaininyourstomach,youwillgetaseriesofquestions:Howlong haveyouhadthepain?Whereisthepain?Doesitcomeandgo,orisitconstant?Whatwasthelast thingyouate?andsoon.Thedoctorisdoingtwoveryimportantandverydifferentthings:1)asking therightquestions,and2)arrivingatadiagnosisbasedontheanswerstothosequestions. Let’simaginethatyouwanttosueMcDonald’sbecauseyouspilledhotcoffeeinyourlap.Yougo toanattorneywhoasksyouaseriesofquestions.Onceagain,thelawyerisdoingtwoveryimportant andverydifferentthings:1)askingtherightquestions,and2)formulatinganopinionbaseonthe answerstothosequestions.Onceagain,thefirststepisaskingquestions. Infact,inanyprofessionortrade,thefirststepofdiagnosingaproblemisalwaystoaskquestions. Thesameistruewithsolvingproblemsinthiscourse.Unfortunately,youareexpectedtolearnhow todothisonyourown.Inthisbook,wewilllookatsomecommontypesofproblemsandwewill seewhatquestionsyoushouldbeaskinginthosecircumstances.Moreimportantly,wewillalsobe developingskillsthatwillallowyoutofigureoutwhatquestionsyoushouldbeaskingforaproblem thatyouhaveneverseenbefore. INTRODUCTION vii Manystudentsfreakoutonexamswhentheyseeaproblemthattheycan’tdo.Ifyoucouldhear whatwasgoingonintheirminds,itwouldsoundsomethinglikethis:“Ican’tdoit … I’mgonna flunk.”Thesethoughtsarecounterproductiveandawasteofprecioustime.Rememberthatwhenall elsefails,thereisalwaysonequestionthatyoucanaskyourself:“WhatquestionsshouldIbeasking rightnow?” Theonlywaytotrulymasterproblem-solvingistopracticeproblemseveryday,consistently.You willneverlearnhowtosolveproblemsbyjustreadingabook.Youmusttry,andfail,andtryagain. Youmustlearnfromyourmistakes.Youmustgetfrustratedwhenyoucan’tsolveaproblem.That’s thelearningprocess.Wheneveryouencounteranexerciseinthisbook,pickupapencilandworkon it.Don’tskipovertheproblems!Theyaredesignedtofosterskillsnecessaryforproblem-solving. Theworstthingyoucandoistoreadthesolutionsandthinkthatyounowknowhowtosolve problems.Itdoesn’tworkthatway.IfyouwantanA,youwillneedtosweatalittle(nopain,no gain).Andthatdoesn’tmeanthatyoushouldspenddayandnightmemorizing.Studentswhofocus onmemorizingwillexperiencethepain,butfewofthemwillgetanA. Thesimpleformula:Reviewtheprinciplesuntilyouunderstandhoweachofthemfitsintothe plot;thenfocusallofyourremainingtimeonsolvingproblems.Don’tworry.Thecourseisnotthat bad if you approach it with the rightattitude. This book will act as a road map for yourstudying efforts.