An alkane A on ozobolysis yields acetone and an aldeyde. The aldehyde is easily oxidised to an acid B. When B is treated with bromine in presence of yields a compound C which on hydrolysis gives a hydroxyle acid D. This acid can also be obatined from acetone by the reaction with hydrogen cyanide followed by hydrolysis. Identify the compounds A, B C and D.

Explanation

(i) The structure of hydroxy acid [D] can be established from acetone as follows :

(ii) As the hydroxy acid [D] has been obtained from a bromo compound [C] by hydrolysis, the compound [C] is `(CH_(3))_(2)C(Br)COOH` and the correponding acid [B] is `(CH_(3))_(2)CHCOOH`.
(iii) As [B] has been formed by the oxidation of the an aldehyde therefore, the structure of aldehyde is `(CH_(3))_(2)CHCHO`.
(iv) Since the alkene [A] on ozonolysis gives acetone and the aldehyde indicated as above, the structure of alkene can be established as follows :

The sequence of reactions is shows as follows :