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Q.

Which of the following statements is not correct?

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a

In electrophilic aromatic substitution reaction, the formation of intermediate arenium cation is the ratedetermining step.

b

The C-H bond in benzene is slightly stronger than the C-D bond in deuterated benzene (C6D6).

c

The overall rate of an electrophilic substitution reaction, except sulphonation in benzene and deuterated benzene, are identical

answer is B.

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Detailed Solution

(a) The formation of intermediate arenium cation is slow while the elimination of H+ from this cation is fast. The former involves the removal of aromaticity while the latter restores aromaticity

(b) The C-D bonds are stronger than C-H bonds. In fact, the bond with the heavier isotope is slightly stronger than that with the lighter isotope.

( c) In electrophilic substitution reactions, the rate-determining step is the formation of arenium cation. Question Image

In this step, E+ bonds to the aromatic ring without cleavage of a C-H bond. The latter is broken in the second step, which is fast as it restores the stable aromatic system. Since C-H or C-D bond is not broken in the rate-determining step, the overall rates of reaction are identical.

 

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