Question 31.39 - Organic Chemistry

Question

Draw a stepwise mechanism for the following conversion, which forms camphene. Camphene is a component of camphor and citronella oils.

Step-by-Step Solution

Answer

Answer

Mechanism of the reaction

Step 1: About camphene

The organic compound that is bicyclic and common monoterpene is camphene. This compound is present as minor constituents in mango, cypress oil, camphor oil, etc. The food additives use camphene in major quantities.

Step 2: About the camphene structure

The camphene structure is comprised of two cyclic rings known as bicycles. There are two methyl groups at the second carbon atom, and there is a methylidene group at the third carbon atom.

Step 3: About the mechanism

The single bond at the OPP group of the starting material gets shifted, resulting in the formation of a cation. The cation is made cyclic ring by some rearrangements. The obtained product is subjected to 1,2-shift twice and is treated with a base.

This will give camphene. 

Mechanism of the reaction