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Chapter 28: 44P (page 1212)

A student found that heating any one of the isomers shown here resulted in scrambling of the deuterium to all three positions on the five-membered ring. Propose a mechanism to account for this observation.

Short Answer

Expert verified

The 1,5 hydrogen shift of the compound forms a non-aromatic intermediate that, on a further 1,5 hydrogen shift, forms an aromatic compound.

Step by step solution

01

1,5 hydrogen shift of D

The 1,5 hydrogen shift of the compound forms a non-aromatic intermediate that, on a further 1,5 hydrogen shift, forms an aromatic compound.

02

1,5 hydrogen shift of H

The same compound is also formed by the 1,5 hydrogen shift of H atom.

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Most popular questions from this chapter

Show how the reactant can be converted to the product in two steps.

Draw the product of each of the following sigmatropic rearrangements:

Problem:Give a molecular orbital description for each of the following:

a. 1,3-pentadiene b. 1,4-pentadiene c. 1,3,5-heptatriene d. 1,3,5,8-nonatetraene

Propose a mechanism for the following reaction:

Explain why maleic anhydride reacts rapidly with 1,3-butadiene but does not react at all with ethene under thermal conditions.
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