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Chemistry Question on reaction mechanism

The major product X formed in the following reaction sequence is:reaction sequence

A

1

B

2

C

3

D

4

Answer

3

Explanation

Solution

This reaction sequence involves a series of transformations:

  1. Chlorination: Chlorination of the ethylbenzene ring will occur preferentially at the para position due to the activating effect of the ethyl group and the deactivating meta-directing nature of the nitro group.
  2. Reduction: Reduction of the nitro group (-NO2) to an amino group (-NH2) using tin and hydrochloric acid (Sn/HCl).
  3. Diazotization: The amino group is converted into a diazonium group (-N2+) using sodium nitrite and hydrochloric acid (NaNO2/HCl) at a low temperature (273-278 K).
  4. Sandmeyer Reaction : The diazonium group is replaced by an iodide (I) using potassium iodide (KI) via a Sandmeyer reaction. This replacement occurs at the same position as the original amino group (and thus the nitro group).
    Thus, we have 4-iodo-1-ethyl-2-chlorobenzene.