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(C) The reaction of $1$-bromo$-1-$cyclopentylethane with moist $Ag_2O$ proceeds via an $S_N1$ mechanism.$1$. The leaving group $Br^-$ departs to form

Vedclass · Accepted Answer

$1-$methylcyclohexanol

Vedclass · Answer

(C) The reaction of $1$-bromo$-1-$cyclopentylethane with moist $Ag_2O$ proceeds via an $S_N1$ mechanism.$1$. The leaving group $Br^-$ departs to form a secondary carbocation on the side chain.$2$. This carbocation undergoes ring expansion from a five-membered ring to a more stable six-membered ring carbocation.$3$. $A$ $1,2$-hydride shift occurs to form a more stable tertiary carbocation at the ring carbon.$4$. Finally,the nucleophile $OH^-$ attacks the tertiary carbocation to form $1$-methylcyclohexanol as the major product.

The major product $(A)$ is:

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