Chapter 28: Q4P (page 1218)
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
Short Answer
a.

b.

c.

d.


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Chapter 28: Q4P (page 1218)
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
a.

b.

c.

d.


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Two products are formed in the following [1,7] sigmatropic rearrangement, one due to hydrogen migration and the other to deuterium migration. Show the configuration of the products by replacing A and B with the appropriate atoms (H or D).

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.
cis-3,4-Dimethylcyclobutene undergoes thermal ring opening to form the two products shown. One of the products is formed in 99% yield, the other in 1% yield. Which is which?

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.

Propose a mechanism for the following reaction:

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