An alcohol of unknown structure gave a positive Lucas test in about five minutes. When alcohol was heated with concentrated `H_(2)SO_(4)` an alkene was formed with the formula `C_(4)H_(8)`. Ozonolysis of this alkene gave a single product, `C_(2)H_(4)O`. What was the structure of the alcohol ?

Explanation

[Hint]
`C_(4)H_(8)` on ozonolysis gave only a single product `C_(2)H_(4)O`ie., `CH_(3)CHO`, hence `C_(4)H_(8)` has the structure `CH_(3)CH=CHCH_(3)`. This can be obtained froma secondary alcohol. Hence, the unknown was Butan-2-ol `(CH_(3)CHOHCH_(2)CH_(3))`.
`CH_(3)-overset(OH)overset(|)(C)H-CH_(2)CH_(3)overset(H_(2)SO_(4))(rarr)CH_(3)CH=CHCH_(3)underset(Zn//H_(2)O)overset(O_(3))(rarr)2CH_(3)CHO`