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Chapter 28: Q44P (page 1239)

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

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.

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

Explain why compound A will not undergo a ring-opening reaction under thermal conditions, but compound B will.

a. Name the kind of sigmatropic rearrangement that occurs in each of the following reactions.

b. Using arrows, show the electron rearrangement that takes place in each reaction.

a. Draw the product of the following reaction:


b. If the terminal sp2 carbon of the substituent attached to the benzene ring is labeled with 14C, where will the label be in the product?
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