Question

An alkene 'A' on ozonolysis yields acetone and an aldehyde. The aldehyde is easily oxidised to an acid 'B'. When 'B' is treated with bromine in presence of phosphorus it yields a compound 'C' which on hydrolysis gives a hydroxy acid 'D'. This acid can also be obtained from acetone by the reaction with hydrogen cyanide followed by hydrolysis. Identify the compounds A, B, C and D.

Answer 1

The hydroxy acid 'D' is also obtained from acetone by the reaction with HCN followed by hydrolysis, so the structure of hydroxy acid 'D' is

Since, hydroxy acid 'D' is obtained by the hydrolysis of 'C' with aqueous alkali, therefore the compound 'C' has a bromo group at that place where the compound 'D' has a hydroxy group. Hence, the structure of 'C' is

Compound'C' is formed try the bromination of compound 'B', so the structure of compound 'B' is

Compound 'B' is obtained by the oxidation of aldehyde which is the ozonolysis product of alkene 'A'. Thus, the structure of aldehyde is

Hence, the compound A, B, C and D are, respectively