IONIC REACTIONS — NUCLEOPHILIC SUBSTITUTION AND ...

P1: PBU/OVYP2: PBU/OVYQC: PBU/OVYT1: PBUP rinter: Bind RiteJWCL234-06 JWCL234-Solomons-v1 December 8, 200921:34 CONFIRMING PAGES6 IONIC REACTIONS NUCLEOPHILICSUBSTITUTION AND ELIMINATIONREACTIONS OF ALKYL HALIDESSOLUTIONS TO (a)cis-1-Bromo-2-methylcyclohexane(b)cis -1-Bromo-3-methylcyclohexane(c) 2,3, (a) 3 (b) vinylic(c) 2 (d) aryl(e) 1 ++ (a)SubstrateNucleophileLeavinggroupIBrBr CH3CH2CH3OH2CH3CH2++I (b)SubstrateNucleophileLeavinggroupClCl( CH3)3CO(CH3)3C2 CH3 OHCH3+++ (c)SubstrateNucleophileLeavinggroupCNBr CN++ (d)(e)SubstrateNucleophileLeavinggroupNH 4+++Br ++NH2 BrBr2 NH385P1: PBU/OVYP2: PBU/OVYQC: PBU/OVYT1: PBUP rinter: Bind RiteJWCL234-06 JWCL234-Solomons-v1 December 8, 200921:34 CONFIRMING PAGES86 IONIC energy of activationProductsReactantsFree- energychangeI +Reaction coordinateFree energy G G Transition stateCH2CH2CH2CH3Cl+ICl ClI (CH3)3 CBrI+(CH3)3 CBr (a) We know that when a secondary alkyl halide reacts with hydroxide ion by SUBSTITUTION ,the reaction occurs withinversion of configurationbecause the reaction is SN2.

Relative Rates of Nucleophilic Substitution 6.20 (a) 1-Bromopropane would react more rapidly because, being a primary halide, it is less hindered. (b) 1-Iodobutane, because iodide ion is a better leaving group than chloride ion. (c) 1-Chlorobutane, because the carbon bearing the leaving group is less hindered than in 1-chloro-2-methylpropane.

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  Reactions, Substitution, Ionic, Nucleophilic, Nucleophilic substitution, Ionic reactions nucleophilic substitution

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