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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ap200

1-(Aminomethyl)cyclopentan-1-ol is treated with $NaNO X_{2}$ /dilute $HCl$ at 273 K. Which statements are correct?

AThe primary amine is converted into a diazonium ion
BNitrogen gas is evolved
CThe main carbonyl product is cyclohexanone
DThe main carbonyl product keeps a five-membered ring

Answer: A, B, C

The primary amine with

HNO X_{2}

gives

R - CH X_{2} - N X_{2} X^{+}

. Loss of

N X_{2}

is accompanied by migration of a ring carbon to the

CH X_{2}

, expanding the ring by one carbon to give cyclohexanone. So the five-membered ring statement is wrong.

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