Chapter 15.SE, Problem 28AP

Interpretation Introduction

Interpretation:

Ozonolysis of o-xylene yielded three products, glyoxal, 2,3-butanedione and pyruvaldehyde in 3:1:2 ratio. What conclusion can be obtained about the structure of o-xylene from this observation is to be stated.

Concept introduction:

During ozonolysis double bonds present in compounds gets cleaved to give carbonyl compounds. Each carbon in the double bond gets bonded to an oxygen atom. As the benzene ring can be represented by two different resonance forms during ozonolysis, compounds with substituent groups on the benzene ring yield different products. The final ratio in which different products will be formed can be arrived at by considering the products of the ozonolysis of different resonance forms of the reactant.

To state:

What conclusion can be obtained about the structure of o-xylene from the observation that upon ozonolysis it yielded three products, glyoxal, 2,3-butanedione and pyruvaldehyde in 3:1:2 ratio.