CH_3CH_2COCH_3 xrightarrow{NaNO_2/HCl} Major | vedclass

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Question

(C) The reaction of a ketone with $NaNO_2/HCl$ (which generates $HNO_2$ in situ) leads to nitrosation at the $\alpha$-carbon atom.For $CH_3CH_2COCH_3$

Vedclass · Accepted Answer

$CH_3COC(=NOH)CH_3$

Vedclass · Answer

(C) The reaction of a ketone with $NaNO_2/HCl$ (which generates $HNO_2$ in situ) leads to nitrosation at the $\alpha$-carbon atom.For $CH_3CH_2COCH_3$ (butanone),there are two types of $\alpha$-hydrogens: those on the $CH_3$ group and those on the $CH_2$ group.Nitrosation occurs preferentially at the more substituted $\alpha$-carbon (the $CH_2$ group) to form an $\alpha$-nitroso ketone $(CH_3CH(NO)COCH_3)$.This nitroso compound exists in tautomeric equilibrium with its oxime form,$CH_3C(=NOH)COCH_3$ (an $\alpha$-isonitroso ketone).The reaction proceeds as follows:$CH_3CH_2COCH_3 + HNO_2 \rightarrow CH_3CH(NO)COCH_3 \rightleftharpoons CH_3C(=NOH)COCH_3$.Thus,the major product is $CH_3COC(=NOH)CH_3$.

$CH_3CH_2COCH_3 \xrightarrow{NaNO_2/HCl}$ Major product of this reaction is

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