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.