An organic compound `'A'` having molecular formula `C_(4)H_(10)O` does not react with sodium metal. On hydrolysis with dilute `H_(2)SO_(4)` It gives only one organic compound `'B'` . The compound B on heating with red phosphours and iodine gives compound 'C'. The compound C can also be obtained from compound 'A' on heating with excess HI. Identify the compounds A, B and C.

Explanation

(1) The organic compound'A' with molecular formula `C_(4)H_(10)O` may be an alcohol or ether.
(2) Since 'A' does not react with sodium (Na), It is not react with sodium (Na), it is not an alcohol . Hence 'A' may be an ether.
(3) Since an ether 'A' on hydrolysis with dilute `H_(2)SO_(4)` gives only one compound 'B', the compound 'A" must be a symmetrical (simple) ether. Hence compound 'A' may be, `C_(2)H_(5) - O - C_(2)H_(5)`.
`underset((A))underset("diethyl ether")(C_(2)H_(5)-O-C_(2)H_(5))+H_(2)Ooverset("dil." H_(2)SO_(4))underset("heat, pressure")rarrunderset((B))underset("ethyl alcohol")(2C_(2)H_(5)-OH)`
(4) `underset((B))underset("ethyl alcohol")(3C_(2)H_(5)-OH+PI_(3))overset("red" P + I_(3))underset(Delta)rarrunderset((C))underset("ethyl iodide")(3C_(2)H_(5)-I)+underset("phosphorus acid")(H_(3)PO_(3))`