Questions: c) Propose a synthesis placing the appropriate substrate/reagent in the boxes below. The synthesis should produce the product as the major product. substrate

c) Propose a synthesis placing the appropriate substrate/reagent in the boxes below. The synthesis should produce the product as the major product.
substrate

Transcript text: c) Propose a synthesis placing the appropriate substrate/reagent in the boxes below. The synthesis should produce the product as the major product. substrate

Solution

Solution Steps

Step 1: Identify the Product

The product is 1-methylbicyclo[2.2.1]hept-2-ene. It is a bridged bicyclic alkene.

Step 2: Retrosynthetic Analysis

The product can be formed via a Diels-Alder reaction. The methyl group on the bridge suggests a cyclopentadiene with a methyl substituent on one of the sp3 carbons. The dienophile would then be ethylene (ethene).

Step 3: Forward Synthesis

1-methylcyclopentadiene + ethene → 1-methylbicyclo[2.2.1]hept-2-ene