2-Aminocyclohexane-1-ol on treatment with HNO | vedclass

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Question

(A) The reaction of $2-$aminocyclohexane$-1-$ol with nitrous acid $(HNO_2)$ is a deamination reaction involving the formation of a diazonium salt inte

Vedclass · Accepted Answer

Cyclopentane carboxaldehyde

Vedclass · Answer

(A) The reaction of $2-$aminocyclohexane$-1-$ol with nitrous acid $(HNO_2)$ is a deamination reaction involving the formation of a diazonium salt intermediate.Since the amino group is adjacent to a hydroxyl group,the diazonium ion formed is unstable and undergoes a Tiffeneau-Demjanov rearrangement or ring expansion/contraction depending on the structure.However,for $2-$aminocyclohexane$-1-$ol,the primary product is the ring-contracted product,which is $Cyclopentane 	ext{ } carboxaldehyde$.

$2-$Aminocyclohexane$-1-$ol on treatment with $HNO_2$ produces

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