Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
A hydrocarbon ( C ₄ H ₈ ) on reaction with m -chloroperbenzoic acid (MCPBA) gives compound (X). Compound (X) on reaction with aqueous KOH gives (Y), which on treatment with concentrated H ₂ SO ₄ forms 2-methylpropanal. The hydrocarbon is:
Options
- ACH ₃ CH ₂ CH = CH ₂
- BCH ₃- CH = CH - CH ₃
Correct answer
3
Step-by-step solution
The reaction of a hydrocarbon with m -chloroperbenzoic acid (MCPBA) indicates the presence of an alkene, which undergoes epoxidation to form an epoxide (X). The epoxide (X) reacts with aqueous KOH to undergo ring opening, forming a vicinal diol (Y). Treatment of the vicinal diol (Y) with concentrated H ₂ SO ₄ results in a pinacol-pinacolone rearrangement to form 2-methylpropanal, CH ₃- CH ( CH ₃)- CHO . In the pinacol rearrangement, the most stable carbocation is formed first. For 2-methylpropane-1,2-diol, protonat