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Question

Which one of the following is least reactive in a nucleophilic substitution reaction?

A
CH3CH2Cl
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B
CH2=CHCH2Cl
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C
(CH3)3CCl
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D
CH2=CHCl
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Solution

The correct option is D CH2=CHCl
Due to the +M effect of Cl group, it shows resonance with the double bond in vinyl chloide (CH2=CHCl).
Due to the partial double bond character betwen C and Cl, vinyl chloride (CH2=CHCl) is least reactive towards nucleophilic substitution reaction.

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