Question

A substance C₄H₁₀O yields on oxidation a compound, C₄H₈O which gives an oxime and a positive iodoform test. The original substance on treatment with a conc. H₂SO₄ gives C₄H₈. The structure of the compound is ______.

Options

• CH₃CH₂CH₂CH₂OH

• CH₃CHOHCH₂CH₃

• (CH₃)₃COH

• CH₃CH₂–O–CH₂CH₃

Answer 1

A substance C₄H₁₀O yields on oxidation a compound, C₄H₈O which gives an oxime and a positive iodoform test. The original substance on treatment with a conc. H₂SO₄ gives C₄H₈. The structure of the compound is CH₃CHOHCH₂CH₃.

Explanation:

\[\ce{C4H8 <-[Conc. H2SO4][(-H2O)] C4H10O ->[Oxidation] C4H8O (R - COCH3)}\]

As a result, C₄H₈O should be CH₃CH₂COCH₃ and C₄H₁₀O should be CH₃CH₂CHOHCH₃.