Question

An organic compound containing carbon, hydrogen and oxygen is soluble in dil. H₂SO₄ and does not react with sodium metal or KMnO₄. When it is heated with HI in excess, a single alkyl halide is obtained. The original compound can be ____________.

Options

• CH₃ – CH₂ – CH₂ – OH

• CH₃ – CH₂ – CH₂ – CHO

• CH₃ – CH₂ – O – CH₂ – CH₃

• CH₃ – O – CH₂ – CH₃

Answer 1

An organic compound containing carbon, hydrogen and oxygen is soluble in dil. H₂SO₄ and does not react with sodium metal or KMnO₄. When it is heated with HI in excess, a single alkyl halide is obtained. The original compound can be CH₃ – CH₂ – O – CH₂ – CH₃.

Explanation:

\[\ce{Compound + Na -> No reaction}\]. So, it is not an alcohol.

\[\ce{Compound + KMnO4 -> No reaction}\]. So, it is neither an aldehyde nor a ketone.

As the compound is soluble in dil. H₂SO₄ is ether. Since only a single compound is obtained on heating with excess of HI, therefore the ether is a simple ether.

\[\ce{\underset{Diethyl ether}{C2H5 - O - C2H5} + 2HI ->[\Delta] \underset{Ethyl iodide}{2C2H5I} + H2O}\]