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Question


Consider the above compounds and choose the correct option(s) regarding nucleophilic aromatic substitution?

A
(I) is more reactive than (II)
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B
(III) is less reactive than (II)
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C
CX bond does not break in the rate determinig step
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D
CX bond is broken in the rate determinig step
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Solution

The correct options are
A (I) is more reactive than (II)
B (III) is less reactive than (II)
C CX bond does not break in the rate determinig step
(a) More electrongative F atom increases the electrophilicity of the carbon to which it is attached hence 1-fluoro-4-nitrobenzene is more reactive.

(b) Reactivity will be more when NO2 is attached at ortho and para position to the leaving group and activates the ring towards nucleophilic substitution..

(c) In RDS, attack of nucleophile happens and CX bond breaks in fast step.

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