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Diastereomers

From analysis...

Question

From analysis and molecular weight determination, the molecular formula of (A) is $C_{3} H_{7} N O$ . The compound gave following reactions.
(i) On hydrolysis it gives an amine (B) and a carboxylic acid (C)
(ii) Amine (B) reacts with benzene sulphonyl chloride and gives a product which is insoluble in aqueous sodium hydroxide solution.
(iii) Acid (C) on reaction with Tollen's reagent gives a silver mirror what are A, B and C.
Explain the reactions.

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Solution

On hydrolysis of $A$ having formula $C_{3} H_{7} N O$ gives amine $(B)$ and a carboxylic acid. $A$ should be acid amide. Amine $(B)$ reacts with benzene sulphonyl chloride and gives a product which is insoluble in aqueous $N a O H$ solution. So amine $(B)$ should be secondary amine. Acid $(C)$ reacts with Tollen's reagent to give silver $(A g)$ mirror. So, acid should be $H C O O H$ because it has aldehydic hydrogen which can be oxidized by Tollen's reagent.
(Refer to Image)
$∴$ So $A$ will be $N, N - d i m e t h y l f o r m a m i d e$

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