Treatment of 1-(aminomethyl)cyclohexan-1-ol with NaNO2/dilute HCl at 273 K gives mainly

JEE Main levelSingle correct optionDifficulty 2 of 3ap079

Treatment of 1-(aminomethyl)cyclohexan-1-ol with $NaNO X_{2}$ /dilute $HCl$ at 273 K gives mainly

The primary amine forms a diazonium ion, which loses

N X_{2}

as the

CH X_{2}

becomes electron deficient. A ring carbon migrates from the carbinol carbon to the

CH X_{2}

(Tiffeneau-Demjanov ring expansion), expanding the ring by one carbon, and loss of

H X^{+}

from the oxonium gives a seven-membered ketone, cycloheptanone.