Amines

The product A formed in the following reaction is [figure]

1. [figure]
2. [figure]
3. [figure]
4. [figure]

Answer

(3) [figure]

Solution

Diazotisation, then Sandmeyer reaction:

[figure]

[figure]

∵ NaNO2/HCl at 0–5 °C diazotises –NH2; Cu2Cl2 replaces -N2+ by –Cl.

(1), (4): an extra Cl on the ring ⇒ the ring is not chlorinated here ⇒ (1), (4) are wrong

(2): only the anilinium salt, not the final product ⇒ (2) is wrong

Answer: (3)