The rate of S_N2 reaction will be negligible | vedclass

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(C) The $S_N2$ mechanism requires a backside attack by the nucleophile on the carbon atom bonded to the leaving group. In $1$-bromobicyclo$[2.2.1]$hep

Vedclass · Accepted Answer

$1-$Bromobicyclo[$2.2$.$1$]heptane

Vedclass · Answer

(C) The $S_N2$ mechanism requires a backside attack by the nucleophile on the carbon atom bonded to the leaving group. In $1$-bromobicyclo$[2.2.1]$heptane (option $C$),the carbon atom attached to the bromine is at the bridgehead position. Due to the rigid bicyclic structure,the backside of the bridgehead carbon is sterically hindered and inaccessible to the nucleophile. Furthermore,the formation of a planar transition state (required for $S_N2$) or a carbocation (required for $S_N1$) at the bridgehead position is geometrically constrained and energetically unfavorable due to Bredt's rule. Therefore,$S_N2$ reactions are negligible at the bridgehead position.

The rate of $S_N2$ reaction will be negligible in:

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