What is the major product "P" of the following reaction? (i) $\mathrm{NaNO}_{2}, \mathrm{HCl}, 278 \mathrm{~K}$ (ii) $\mathrm{H}_{2} \mathrm{O}$ (major product) P

JEE Main · 2021 · 25 Jul 2021 · Shift 2 · Compounds Containing Nitrogen

What is the major product "P" of the following reaction?
(i)

NaNO_{2}, HCl, 278 K

(ii)

H_{2} O

(major product)
P

(A)(see structure)
(B)(see structure)
(C)(see structure)
(D)(see structure)
✓ Correct

Answer: (D)

Solution

Nitrous acid, generated in the cold from

NaN O_{2}

and HCl, converts a primary aliphatic amine into an alkanediazonium ion. Unlike an aryl diazonium ion, this one has no ring to delocalise the positive charge, so it loses

N_{2}

as soon as it is formed, even at 278 K, and water attacks the electron-deficient carbon left behind. The amino group is thereby replaced by a hydroxyl group on the same carbon skeleton, so P is (1-methylcycloheptyl)methanol.

JEE Main · 2021 · 25 Jul 2021 · Shift 2 · Single correct option

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