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Question

Which one of the following compounds is most reactive for aromatic electrophilic substitution reaction?

A
C6H5CN
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B
C6H5F
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C
C6H5I
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D
C6H5NO2
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Solution

The correct option is C C6H5I
Due to -I effect of X-group, it reduces electron density of benzene, so halobenzene is less reactive than benzene for electrophilic substitution reaction.
As electronegativity of F is the highest among halogens, so its -I effect is highest.
So, reactivity of halobenzene compounds towards electrophillic substitution is Ph - I > Ph - F.
-I effect order is as follows:
NO2>CN>F>I
Hence, C6H5CN and C6H5NO2 will be less reactive towards electrophilic substitution than halobenzene.
Hence, the correct answer is option (c).

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