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Chapter 28: Q15P (page 1231)

Account for the difference in the products obtained under photochemical and thermal conditions:

Short Answer

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a.

b.

Step by step solution

01

Product in photochemical condition 

In the given reaction, the reacting system has three double bonds that are a total of six pie electrons (even number of electrons); thus, under the given photochemical condition, suprafacial rearrangement will take place 1,3 hydrogen shift occurs, which involves four electrons.

A [1,3] sigmatropic migration of deuterium will result in the formation of the product shown as follows:

02

Step 2: Product in thermal condition

In the given reaction, the reacting system has three double bonds that are six pie electrons (even number of electrons); thus, under the given thermal condition, suprafacial rearrangement will take place 1,5 hydrogen shift occurs, which involves six electrons.

A [1,5] sigmatropic migration of deuterium will result in the formation of the product shown as follows:

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Most popular questions from this chapter

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 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.

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

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).

Account for the difference in the products of the following reactions:
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