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Question

The product(s) the following hydrolysis is/are:


A
α,δ di-hydroxy carboxylic acid
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B
a lactone
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C
acetone
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D
acetaldehyde
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Solution

The correct options are
B a lactone
D acetaldehyde

The mechanism is fairly straightforward:

Water attacks the electron-loving carbon of the oxonium shown:

The mechanism goes through a hemi-acetal which then goes onto give acetaldehyde and the other compound which is not isolated:

The compound in square brackets is not isolated as it forms a lactone:


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