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Chapter 28: 44 P (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

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.

a. Identify the mode of ring closure for each of the following electrocyclic reactions.

b. Are the indicated hydrogens cis or trans?

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.

If isomer A is heated to about 100 °C, a mixture of isomers A and B is formed. Explain why there is no trace of isomer C or D.

Show how norbornane can be prepared from cyclopentadiene.
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