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The products formed in the following reaction, A and B are A compound containing a cyclohexanone ring with a formyl substituent (–CHO) on the bottom carbon is treated with [Ag(NH3)2]+ / OH− to give A, and then A is treated with NaBH4 to give B.

1. A is cyclohexanone with the –CHO group converted to –CH2OH; B is the corresponding alcohol with the ring carbonyl reduced to –OH and the side chain remaining –CH2OH
2. A is cyclohexanone with the –CHO group converted to –COOH; B is the corresponding alcohol with the ring carbonyl reduced to –OH and the side chain remaining –CH2OH
3. A is cyclohexanone with the –CHO group converted to –COOH; B is the corresponding alcohol with the ring carbonyl reduced to –OH and the side chain remaining –COOH
4. A is cyclohexanone with the –CHO group converted to –COOH; B is the corresponding alcohol with the ring carbonyl reduced to –OH and the side chain remaining –CH2OH

Correct answer: A is cyclohexanone with the –CHO group converted to –CH2OH; B is the corresponding alcohol with the ring carbonyl reduced to –OH and the side chain remaining –CH2OH

Solution

The correct option describes the transformation of the formyl group (–CHO) into a hydroxymethyl group (–CH2OH) in compound A, which is consistent with the reaction conditions involving [Ag(NH3)2]+ that typically oxidize aldehydes to alcohols. Subsequently, the treatment with NaBH4 reduces the carbonyl in A to an alcohol, resulting in compound B, which retains the –CH2OH group from A.

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