Identify the starting compound from the following data: C ₆ H ₁₄ O ( X ) on reaction with HI yields a haloalkane (A) and an alcohol (B). Compound (A) on reaction with aqueous NaOH gives an alcohol (C). Compounds (B) and (C) on reaction with CrO ₃ in anhydrous medium yields Butanone and Ethanal respectively.

Step-by-step solution

The molecular formula of compound (X) is C ₆ H ₁₄ O , which corresponds to an ether. The reaction of ether (X) with HI produces a haloalkane (A) and an alcohol (B). Compound (B) on oxidation with CrO ₃ yields Butanone. Since Butanone is a ketone, (B) must be a secondary alcohol, specifically Butan-2-ol ( CH ₃ CH ₂ CH(OH)CH ₃ ). Compound (A) is a haloalkane derived from the other part of the ether. Reaction of (A) with aqueous NaOH yields alcohol (C). Alcohol (C) on oxidation with CrO ₃ yields Ethanal. Since Ethanal