The reaction of 1-(text{aminomethyl})cyclohex | vedclass

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Question

(D) The reaction of a primary aliphatic amine with nitrous acid $(NaNO_2 + HCl)$ produces a highly unstable diazonium salt.This diazonium salt rapidly

Vedclass · Accepted Answer

cyclohexanone

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(D) The reaction of a primary aliphatic amine with nitrous acid $(NaNO_2 + HCl)$ produces a highly unstable diazonium salt.This diazonium salt rapidly undergoes decomposition to form a carbocation,which then undergoes rearrangement or elimination to form a stable product.In this specific case,the $1-(	ext{aminomethyl})cyclohexan-1-ol$ reacts with $NaNO_2/HCl$ to form a diazonium salt at the $-	ext{CH}_2	ext{NH}_2$ group.The resulting carbocation undergoes a ring expansion (Tiffeneau-Demjanov rearrangement) to form a seven-membered ring ketone,which is cycloheptanone.

The reaction of $1-(\text{aminomethyl})cyclohexan-1-ol$ with $NaNO_2/HCl$ gives $A$. Identify $A$.

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