Engineering
Chemistry
Carbocation
Question

Which of the following compounds can give the same carbocation after treatment with HNO3

I and II

I and IV

II and IV

III and IV

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Solution

When treated with HNO3, aromatic compounds undergo nitration. The carbocation intermediate formed is the arenium ion, stabilized by resonance. Compounds that generate the same resonance-stabilized carbocation after electrophilic attack will give the same product distribution.

For the given compounds, focus on the position of the methyl group. Ortho and para directing groups like -CH3 lead to attack at ortho or para positions, generating similar carbocation intermediates if the substitution pattern is symmetric.

Compounds II and IV are symmetric. In II, methyl is meta to itself; attack at any position gives equivalent carbocations. In IV, the two methyl groups are para to each other; ortho attack to one methyl is equivalent. Thus, II and IV produce the same carbocation upon nitration.

Final Answer: II and IV