Question

Synthesis of 2 methylpentanoic acid from malonic ester

Answer 1

1) EtO(O)CCH₂C(O)OEt 1. + CH₃ONa, 2. + CH₃CH₂CH₂Br$\implies$ EtO(O)CCH(CH₃CH₂CH₂)C(O)OEt

2) EtO(O)CCH(CH₃CH₂CH₂)C(O)OEt 1. + CH₃ONa, 2. + CH₃J $\implies$ EtO(O)CC(CH₃)(CH₃CH₂CH₂)C(O)OEt

3) EtO(O)CC(CH₃)(CH₃CH₂CH₂)C(O)OEt + H₃O⁺ $\implies$ HO(O)CC(CH₃)(CH₃CH₂CH₂)C(O)OH + 2EtOH

4) HO(O)CC(CH₃)(CH₃CH₂CH₂)C(O)OH + heat $\implies$CH₃CH₂CH₂CH₂(CH₃)C(O)OH + CO₂