Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product [Z] in the following reaction sequence: CH₃- CH₃ | C =CH₂ MCPBA / CH₂Cl₂ [X] [(ii) H₂O^ ] (i) H^ [Y] Conc. H^ [Z] The major product (Z) can be
Correct answer
0
Step-by-step solution
Reaction with MCPBA converts the alkene ( CH ₃)₂ C = CH ₂ into an epoxide, 2,2-dimethyloxirane [X]. The epoxide undergoes acid-catalyzed ring opening with H ₂¹⁸ O . Protonation of the epoxide oxygen is followed by nucleophilic attack of H ₂¹⁸ O at the more substituted tertiary carbon, because the transition state possesses a highly stable tertiary carbocation character. This produces 2-methylpropane-1,2-diol [Y] with the heavy oxygen isotope at the tertiary position: ( CH ₃)₂ C (¹⁸ OH )- CH ₂ OH . Treatment of this