JEE Advanced · 2014 · 25 May 2014 · Paper 2 · Alcohols Phenols and Ethers

The acidic hydrolysis of ether (X) shown below is fastest when

(A)one phenyl group is replaced by a methyl group.
(B)one phenyl group is replaced by a para-methoxyphenyl group.
(C)two phenyl groups are replaced by two para-methoxyphenyl groups.✓ Correct
(D)no structural change is made to X.

Answer: (C)

Solution

The acidic hydrolysis of ethers proceeds via carbocation formation. Para-methoxyphenyl groups are electron-donating (due to the +M effect of the methoxy group), which stabilizes the carbocation intermediate formed during hydrolysis. Replacing both phenyl groups with para-methoxyphenyl groups provides maximum stabilization of the carbocation, making the reaction fastest.

JEE Advanced · 2014 · 25 May 2014 · Paper 2 · Single correct option

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