Chapter 14.SE, Problem 58AP

Interpretation Introduction

Interpretation:

Given that myrcene is isomeric with β-ocimene with molecular formula C₁₀H₁₆ has UV absorption maxima 226 nm. On catalytic hydrogenation it gives 2,6-dimethyloctane. Upon ozonolysis followed by treatment with Zn and acetic acid it gives formaldehyde, acetone and 2-oxopentanediol. The structure for myrcene is to be proposed and the reactions are to be given showing the starting materials and products.

Concept introduction:

The UV absorption at 226 nm indicates a conjugated system. The alkenes get reduced when treated with H₂/Pd. During ozonolysis the double bonds in a molecule are cleaved and an oxygen atom gets attached through a double bond with each of the carbon in double bond. By identifying the products of ozonolysis it is possible to locate the position of the double bonds in the molecule.

To propose:

Based on the data the structure for myrcene and to give the reactions showing the starting materials and products.