Which one of the products of the following reactions does not react with Hinsberg reagent to form sulphonamide?

Hinsberg reagent is:

$$\mathrm{C_6H_5SO_2Cl}$$

(benzenesulfonyl chloride)

It reacts with:

$$\mathrm{1^\circ\ and\ 2^\circ\ amines}$$

but does not react with:

$$\mathrm{3^\circ\ amines,\ aldehydes,\ ketones}$$

(A)

$$\mathrm{p\text{-}NO_2C_6H_4CN \xrightarrow{Na/Hg,\ C_2H_5OH}}$$

Both:

$$\mathrm{-NO_2 \rightarrow -NH_2}$$

and

$$\mathrm{-CN \rightarrow -CH_2NH_2}$$

Product contains primary amine groups.

Hence, it reacts with Hinsberg reagent.

(B)

$$\mathrm{C_6H_5CN \xrightarrow[\ H_2O\ ]{SnCl_2/HCl} C_6H_5CHO}$$

This is the Stephen reaction.

Product formed is benzaldehyde:

$$\mathrm{C_6H_5CHO}$$

which is an aldehyde.

Hence, it does not react with Hinsberg reagent.

(C)

$$\mathrm{p\text{-}CNC_6H_4CHO \xrightarrow[\ H_3O^+\ ]{LiAlH_4}}$$

$$\mathrm{-CN \rightarrow -CH_2NH_2}$$

$$\mathrm{-CHO \rightarrow -CH_2OH}$$

Product contains a primary amine.

Hence, it reacts with Hinsberg reagent.

(D)

$$\mathrm{m\text{-}CH_3C_6H_4CN \xrightarrow{H_2/Ni}}$$

$$\mathrm{-CN \rightarrow -CH_2NH_2}$$

Product formed is a primary amine.

Hence, it reacts with Hinsberg reagent.

Therefore, the only product that does not react with Hinsberg reagent is:

$$\boxed{\mathrm{Option\ B}}$$