Worksheet15.

2
Halogenoalkanes
1 2chlorobutane,1chloropropaneand2chloro2methylpropanearehalogenoalkanes.
a Foreachone,give:
i itsmolecularformula
ii itsstructuralformula
iii itsdisplayedformula
iv itsskeletalformula.
b Twoofthesehalogenoalkanesareisomersofeachother.Identifywhichtwoand
identifythetypeofisomerismtheyshow.
c Usingtermsfrompart a ofthisquestion,definetheterm isomers.
d NamethehalogenoalkanewhosestructuralformulaisCH3CHBrCH3.
2 Bromoethanereactswithhotaqueoussodiumhydroxidetoformethanol.Themechanism
forthereactioniscallednucleophilicsubstitution.Innucleophilicsubstitutionreactions,
iodoethanereactsfasterthanbromoethane,whichreactsfasterthanchloroethane,which
reactsfasterthanfluoroethane.
a Whatisthenameofthemechanismbywhichbromoethanereactswithhotaqueous
sodiumhydroxide?
b Whichothersingleworddescribesthisparticularreaction?
c Whatisthenucleophilein thisreaction?
d Whatismeantbytheterm nucleophile?
e Writeabalancedchemicalequationforthisreaction.
f Drawdiagramstoillustratethismechanism,usingdisplayedformulaeandcurlyarrows.
g Explainwhytherelativeratesofhydrolysisofthehalogenoalkanesshowthetrend
described.
h Howcouldtherelativeratesofhydrolysisofiodoethane,bromoethaneandchloroethane
bedemonstratedbysimpletesttubereactions?
3 a Give threeusesofCFCsbeforetheywerebanned.
b NamethemonomersusedtomaketheplasticsknownasPVCandPTFE.

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4 Inasimilarreactiontotheoneinquestion 2,10.9gofbromoethanewasreactedwithhot
aqueoussodiumhydroxidetoform3.45gofethanol.
[Ar values:H=1.0,C=12.0,O=16.0,Br=79.9]
a
b
c
d

Calculatethenumberofmolesofbromoethanethatwereused.
Calculatethenumberofmolesofethanolthatwereformed.
Calculatethepercentageyield.
Calculatethenumberofgramsofethanolthatwouldhavebeenformedifthepercentage
yieldhadbeen65.0%.

CambridgeInternationalASandALevelChemistry

OriginalmaterialCambridgeUniversityPress2011

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