10/16/2015 Substitution Reactions

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SKILLBUILDER REVIEW
7.1DRAWINGTHECURVEDARROWSOFASUBSTITUTIONREACTION

CONCERTEDMECHANISMTwocurvedarrowsdrawnin STEPWISEMECHANISMTwocurvedarrowsdrawnintwoseparate
onestep.Nucleophilicattackisaccompaniedby steps.Leavinggroupleavestoformacarbocationintermediate,
simultaneouslossofaleavinggroup. followedbyanucleophilicattack.

TryProblems7.2,7.3,7.4,7.5,7.64a

7.2DRAWINGTHEPRODUCTOFANSN2PROCESS

ReplacetheLGwiththeNuc,anddrawinversionofconfiguration.

TryProblems7.7,7.8,7.45,7.56,7.61

7.3DRAWINGTHETRANSITIONSTATEOFANSN2PROCESS

EXAMPLE STEP1Identifythe STEP2Drawthecarbon STEP3Drawthethreegroupsattachedtothe

Drawthe nucleophileandtheleaving atomwiththeNucandLGon carbonatom.Placebracketsandthesymbol
transitionstate. group. eitherside. indicatingatransitionstate.

TryProblems7.9,7.10,7.11,7.46,7.64e

7.4DRAWINGTHECARBOCATIONINTERMEDIATEOFANSN1PROCESS

STEP1Identifytheleavinggroup. STEP2Drawallthreegroupspointingawayfromeachother.

TryProblems7.14,7.15,7.50,7.51

7.5DRAWINGTHEPRODUCTSOFANSN1PROCESS

EXAMPLEPredictthe STEP1Identifythenucleophileand STEP2ReplaceLG STEP3Ifchiralitycenter,thenSN1will

products. theleavinggroup. withNuc. producepairofenantiomers.

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10/16/2015 Substitution Reactions

TryProblems7.16,7.17,7.54b

7.6DRAWINGTHECOMPLETEMECHANISMOFANSN1PROCESS

Therearetwocoresteps(gray)andthreepossibleadditionalsteps(blue).

TryProblems7.21,7.22,7.23,7.48,7.49,7.52,7.54,7.65

7.7DRAWINGTHECOMPLETEMECHANISMOFANSN2PROCESS

Thereisonecorestep(concerted)andtwopossibleadditionalsteps.

TryProblems7.24,7.25,7.53,7.64,7.66

7.8DETERMININGWHETHERAREACTIONPROCEEDSVIAANSN1MECHANISMORANSN2MECHANISM

RELEVANTFACTORS EXAMPLE

TryProblems7.31,7.32,7.37,7.38,7.40,7.41,7.44,7.55,7.57,7.58

7.9IDENTIFYINGTHEREAGENTSNECESSARYFORASUBSTITUTIONREACTION

EXAMPLE STEP1Analyzethesubstrate STEP2AnalyzetheLG. STEP3Useconditionsthat

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10/16/2015 Substitution Reactions
andthestereochemistry. favorSN2:strongNuc
(NaCN)andapolaraprotic
solvent(DMSO).

TryProblems7.33,7.34,7.59,7.60,7.63

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