Question

Analyze the bond disconnections indicated (~~~) in the product below and perform a retrosynthetic analysis. draw the methyl ester starting material and identify the reagents the would construct the indicated c–c bonds.

Answer 1

The final product Methyl pent-4-enoate is synthesized from Methyl Acetate as a starting material.

In step one, Methyl Acetate is reacted with Lithium diisopropylamide (LDA) (1) which acts as a base and abstracts the acidic proton from methyl group next to carbonyl in Methyl Acetate.

In second step, The enolate formed acts as a nucleophile and undergoes SN² reaction with 3-Bromoprop-1-ene (2) and produces Methyl pent-4-enoate.
The reaction is given below,