Organic Chemistry As a Second Language: First Semester Topics

397 Pages·2016·36.724 MB·

by  David R. Klein

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
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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
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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.