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.
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Account for the difference in the products obtained under photochemical and thermal conditions:
Problem:Which of the following are correct? Correct any false statements.
a. A conjugated diene with an even number of double bonds undergoes conrotatory ring closure under thermal conditions.
b. A conjugated diene with an antisymmetric HOMO undergoes conrotatory ring closure under thermal conditions.
c. A conjugated diene with an odd number of double bonds has a symmetric HOMO.
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.
Propose a mechanism for the following reaction:
Why was a deuterated compound used in the last reaction on the preceding page?
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