The bromides formed by the cleavage of ethers | vedclass

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Question

(D) For ether $A$ (phenyl $n$-propyl ether): The $C-O$ bond between the phenyl group and oxygen cannot be cleaved because the $C-O$ bond has partial d

Vedclass · Accepted Answer

$n$-propyl bromide and $tert$-butyl bromide

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(D) For ether $A$ (phenyl $n$-propyl ether): The $C-O$ bond between the phenyl group and oxygen cannot be cleaved because the $C-O$ bond has partial double bond character due to resonance. Therefore,cleavage occurs at the alkyl side,yielding phenol and $n$-propyl bromide.For ether $B$ ($tert$-butyl $n$-propyl ether): The cleavage occurs to form the more stable carbocation. The $tert$-butyl group forms a $3^{\circ}$ carbocation,which is much more stable than the $n$-propyl carbocation. Thus,the $C-O$ bond between the $tert$-butyl group and oxygen is cleaved,yielding $tert$-butyl bromide and $n$-propanol.Therefore,the bromides formed are $n$-propyl bromide and $tert$-butyl bromide.

The bromides formed by the cleavage of ethers $A$ and $B$ with $HBr$ respectively are:

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