The structure for compound X is to be determined in the given fragmentation-recombination process of alkenes . Concept introduction: 1,3-dipoles are represented by a Lewis structure such that four electrons (4π) are delocalized over three atoms. One of them is positively charged while the other is negatively charged. The positively charged carbon atom remains unchanged. The alkene is the 2π electron component. This dipole acts as a 4π electron component and can add to an alkene with 2π electron component via the [4+2]-cycloaddition . The second step in the mechanism of ozonolysis of alkenes undergoes a fragmentation-recombination process. The fragmentation step is the reverse of a 1,3-dipolar cycloaddition step. The fragmentation of ozonide yields a carbonyl compound and a 1,3-dipolar compound. The carbonyl compound and 1,3-dipolar compound react again to give a product via 1,3-dipolar cycloaddition. For an unsymmetrical 2π electron component, the two ends of the double bond constitute two possible sites of reaction. In the fragmentation process, the single bond between two carbon atoms attached to the oxygen atoms in the ozonide breaks.

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Chapter 11, Problem 59DSP

Interpretation Introduction

Interpretation:

The structure for compound X is to be determined in the given fragmentation-recombination process of alkenes.

Concept introduction:

1,3-dipoles

are represented by a Lewis structure such that four electrons (4π)

are delocalized over three atoms. One of them is positively charged while the other is negatively charged. The positively charged carbon atom remains unchanged.

The alkene is the 2π

electron component.

This dipole acts as a 4π electron component and can add to an alkene with 2π

electron component via the [4+2]-cycloaddition.

The second step in the mechanism of ozonolysis of alkenes undergoes a fragmentation-recombination process.

The fragmentation step is the reverse of a 1,3-dipolar

cycloaddition step.

The fragmentation of ozonide yields a carbonyl compound and a 1,3-dipolar

compound.

The carbonyl compound and 1,3-dipolar

compound react again to give a product via 1,3-dipolar

cycloaddition.

For an unsymmetrical 2π

electron component, the two ends of the double bond constitute two possible sites of reaction.

In the fragmentation process, the single bond between two carbon atoms attached to the oxygen atoms in the ozonide breaks.

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