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Base Catalysed Hydrolysis of Esters

An organic la...

Question

An organic lactum A on acid hydrolysis produces B, an amino acid,.B on treatment with nitrous acid gives C. C on heating with concentrated $H_{2} S O_{4}$ produces a lactone D. A can be synthesized by the reaction of cyclopentanone with hydroxylamine followed by treatment of product with concentrated $H_{2} S O_{4}$ . Deduce structures of A to D.

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Solution

Product A - Formed by Beckmann Rearrangement
Step 1- Hydrolysis will cause the breaking of the bond between $C = O$ and $N H$ ,
Step 2- On reaction with nitrous acid $O H$ will attach at the place of $N H_{2}$ . It is same as reaction with diazonium salt.
Step 3- Heating with concentrated $H_{2} S O 4$ will form the product D.

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