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Q.

Which of the following will give alkyne on reaction of phosphorous-penta -chloride followed by dehydrohalogenation with Sodamide ?

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a

Benzoic acid

b

Acetophenone

c

Benzaldehyde

d

Benzyl alcohol

answer is B.

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Detailed Solution

aldehydes or ketones can form gem dihalides on reaction with PCl5 . The gem dihalides having  hydrogens will undergo double dehydrohalogenation to form Alkynes.          Only acetophenone will form gem dihalide with PCl5 . Further, it will undergo dehydrohalogenation with  NaNH2 and forms phenyl-Acetylene.          Other compounds will form halogen derivative but will not participate in dehydrohalogenation due to lack of alpha hydrogens.
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