JEE Main · 2022 · 26 Jun 2022 · Shift 2 · Hydrocarbons

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Halogenation of which one of the following will yield m-substituted product with respect to methyl group as a major product?

(A)(see structure)
(B)(see structure)
(C)(see structure)
✓ Correct
(D)(see structure)

Answer: (C)

Solution

In electrophilic aromatic substitution, the electrophile attacks at positions ortho and para to the stronger electron-releasing group (ERG). The ERG strength order is -OH > -CH₃. In option (C) (o-cresol), the -OH group directs the electrophile to its ortho and para positions. The para position with respect to -OH is meta with respect to -CH₃. Hence, halogenation gives the m-substituted product relative to the methyl group.

JEE Main · 2022 · 26 Jun 2022 · Shift 2 · Single correct option

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