Identify the major product formed in the following reaction sequence: (i) MeOH / H ⁺ (ii) NaOMe / MeOH (iii) aq. NaOH (iv) H ⁺ /

Step-by-step solution

The reaction of butanoic acid with methanol in the presence of an acid catalyst ( H ⁺ ) is an esterification reaction, which yields methyl butanoate. CH₃CH₂CH₂COOH MeOH/H^+ CH₃CH₂CH₂COOMe Treatment of methyl butanoate with sodium methoxide ( NaOMe ) in methanol results in a Claisen condensation. The methoxide ion abstracts an -proton to form an enolate, which then attacks the carbonyl carbon of another methyl butanoate molecule to form a -keto ester (methyl 2-ethyl-3-oxohexanoate). 2 CH₃CH₂CH₂COOMe NaOMe/MeOH CH₃CH