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Question

What is the correct order of o/p ratio when E+ attacks the following system?

A PhF
B PhCl
C PhBr
D PhI

A
A < B < C < D
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B
A = B = C = D
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C
D < C < B < A
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D
D < B < A < C
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Solution

The correct option is A A < B < C < D
Since halogens show I effect, the o/p ratio depend upon the I effect of the halogens. The order of I effect is:
F>Cl>Br>I
Halogens decrease the electron density on benzene ring by I effect. Since, inductive effect involving delocalisation of sigma bond orbitals, higher the -I effect will decrease the electron density at ortho position more than at the para position. Therefore, if the halogen has higher I effect, the percentage of para product will be higher i.e. in case of fluorine (F) and if the halogen has lower I effect, the percentage of ortho product will be higher i.e. in case of iodine (I).
Hence, the order of o/p ratio is:
A<B<C<D

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