Question

A substance `C_(4)H_(10)O` yields on oxidation a compound `C_(4)H_(8)O` which gives an oxime and a positive iodoform test. The original substance on treatment with conc. `H_(2)SO_(4)` gives `C_(4)H_(8)` . The structure of the compound is
A. `CH_(3)CH_(2)CH_(2)CH_(2)OH`
B. `CH_(3)Ch(OH)CH_(2)CH_(3)`
C. `(CH_(3))_(3)COH`
D. `CH_(3)CH_(2)-O-CH_(2)CH_(3)`

Answer 1

Correct Answer - A
`CH_(3)CH(OH)CH_(2)CH_(3)overset("conc." H_(2)SO_(4))to underset((C_(4)H_(8)))(CH_(3)CH=CHCH_(3) `
`underset(2-"Butanol")(CH_(3)CHOHCH_(2)CH_(3))overset([O])to underset("Butanol")(CH_(3)COCH_(2)CH_(3))`
Butanone gives both an oxime and positive iodoform test, therefore, the original compound is 2-butanol.