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Arrange the following compounds in order of increasing reactivity toward electrophilic substitution on the aromatic ring: A: chlorobenzene B: anisole (–OMe) C: toluene (–Me) D: benzonitrile (–CN)

1. D < A < B < C
2. B < C < A < D
3. A < B < C < D
4. D < B < A < C

Correct answer: D < A < B < C

Solution

The order of reactivity toward electrophilic substitution is influenced by the substituents on the aromatic ring. Electron-withdrawing groups like –CN in benzonitrile decrease reactivity, while electron-donating groups like –OMe in anisole and –Me in toluene increase it. Thus, the correct order reflects the decreasing influence of these groups on reactivity.

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