Compound A having molecular formula, `C_(4)H_(10)O` is found to be soluble in concentrated sulphuric acid. It does not react with sodium metal or potassium permanganate. On heating with excess of HI, it gives a single alkyl halide. Deduce the structure of compound A and explain all the reactions.

Explanation

(i) As compound A does not react with sodium metal or potassium permanganate, it cannot be an alcohol.
(ii) As compound A dissolves in conc. `H_(2)SO_(4)`, it may be an ether.
(iii) As compound A on heating with excess of HI gives a single alkyl halide, therefore compound a must be a symmetrical ether.
(iv) The only symmetrical ether molecular formula, `C_(4)H_(10)O` is diethy ether. Thus compound A is diethyl ether, `CH_(3)-CH_(2)-O-CH_(2)-CH_(3)CH_(3)CH_(2)-O-CH_(2)CH_(3)overset("Cone. "H_(2)SO_(4))(to)[underset("Soluble oxonium salt")(CH_(3)-CH_(2)-underset(H)underset(|)overset(+)(O)-CH_(2)-CH_(3))]HSO_(4)^(-)`
`underset("Diethyl ether")underset((A))(CH_(3)CH_(2)OCH_(2)CH_(3))underset(Delta)overset(HI)(to)underset("Ethyl iodide")(2CH_(3)CH_(2)-I)`