Question

The major product (X) of the reaction is :

$\xrightarrow[\text{dil. HCl}]{\text{NaNO}_2}$ X

Answer 1

1-oxaspiro[2.5]octane

Answer 2

The primary amine undergoes diazotization with NaNO2/dil. HCl to form an unstable aliphatic diazonium salt. This salt decomposes by releasing N2 gas, generating a tertiary carbocation at the carbon previously bearing the amino group. The adjacent hydroxyl group (-CH2OH) then acts as an intramolecular nucleophile, with its oxygen atom attacking the carbocation center. This leads to the formation of a protonated epoxide, which subsequently deprotonates to yield 1-oxaspiro[2.5]octane as the major product. This is a common rearrangement in the diazotization of primary amines with appropriately placed hydroxyl groups.