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Which sequence of reactions can be used to synthesize 3-chloroaniline starting from benzene?

1. Chlorination followed by nitration and then reduction
2. Nitration followed by chlorination and then reduction
3. Nitration followed by reduction and then chlorination
4. Nitration, reduction, acetylation, chlorination, and finally hydrolysis

Correct answer: Nitration followed by chlorination and then reduction

Solution

To place Cl and NH2 in a meta relationship, the deactivating meta-director must be introduced before the second group. Nitrate benzene to nitrobenzene (NO2 directs meta), chlorinate to give m-chloronitrobenzene, then reduce the NO2 to NH2, giving 3-chloroaniline. Reducing first would give an amine (an o,p-director), leading to ortho/para products.

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