Question

An organic compound (A) of molecular formula CH₄O on mild oxidation gives (B) of formula CH₂O that reduces tollen’s reagent. (B) on reaction with methyl magnesium bromide followed by acid hydrolysis will give (C) of molecular formula C₂H₆O which liberates H₂ gas with metallic sodium. Identify A, B, C and explain the reactions involved.

Answer 1

1. (A) is identified from the molecular formula as methanol (CH₃OH).

2. CH₃OH – methanol on mild oxidation will give formaldehyde as (B). Aldehydes reduce Tollen’s reagent to silver mirror. So, (B) is HCHO (methanal)

3. Formaldehyde reacts with CH₃ MgBr, followed by acid hydrolysis produces primary alcohol and (C) is identified from the formula as CH₃ – CH₂OH – Ethanol. Ethanol liberates H₂ gas with metallic sodium.