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Question

Benzyl bromide, on treatment with a nucleophile - triphenylphosphine, is then made to react with n-Butyl lithium - a strong base to give a phosphorus ylid.
Which of the following, on treatment with the said ylid - would yield the hydrocarbon:


A

benzaldehyde

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B

phenylacetaldehyde

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C

hexan-1-one

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D

cyclohexanone

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Solution

The correct option is D

cyclohexanone


The first part - the question statement generates an ylid (phosphorus).
This can olefinate (make an alkene) the carbonyl carbon, replacing the double bond with O
with a double bond with carbon.


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