Q1(h). Organolithium and Baeyer–Villiger sequence

Answer in brief

As printed, ethanol quenches MeLi; under the likely intended dry-ether conditions P is the methyl ketone, Q the decalinyl acetate and R the corresponding alcohol.

Key points

• In dry ether, excess MeLi first deprotonates DCO₂H and then adds to its lithium carboxylate; hydrolysis gives DCOCH₃.
• Perbenzoic acid forms a Criegee intermediate; the secondary decalinyl group migrates rather than methyl, yielding D–OCOCH₃ with retention of configuration.
• Base hydrolysis cleaves the acetate at its acyl centre, releasing D–OH after work-up.
• Literal ethanol gives MeLi + EtOH → CH₄ + LiOEt, so the sequence requires correcting EtOH to a dry ethereal solvent.