2-Methylpropyl bromide reacts with C_2H_5O^- | vedclass

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Question

(A) Reaction with $C_2H_5O^-$: $C_2H_5O^-$ is a strong nucleophile. $2-$Methylpropyl bromide is a primary alkyl halide. Therefore,it undergoes an $S_N

Vedclass · Accepted Answer

$S_N2$,$A =$ isobutyl ethyl ether; $S_N1$,$B =$ tert-butyl ethyl ether

Vedclass · Answer

(A) Reaction with $C_2H_5O^-$: $C_2H_5O^-$ is a strong nucleophile. $2-$Methylpropyl bromide is a primary alkyl halide. Therefore,it undergoes an $S_N2$ reaction to form isobutyl ethyl ether $(A)$.Reaction with $C_2H_5OH$: $C_2H_5OH$ is a weak nucleophile. The reaction proceeds via an $S_N1$ mechanism. The primary carbocation formed initially undergoes a $1,2-H$ shift to form a more stable tertiary carbocation,which then reacts with the nucleophile to form tert-butyl ethyl ether $(B)$.

$2-$Methylpropyl bromide reacts with $C_2H_5O^-$ to give $A$,whereas on reaction with $C_2H_5OH$ it gives $B$. The mechanism followed in these reactions and the products $A$ and $B$ respectively are:

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