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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

Propose a mechanism for the following reaction:

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

b. Are the indicated hydrogens cis or trans?

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.

Problem:a. Under thermal conditions, will ring closure of (2E,4Z,6Z,8E)-2,4,6,8-decatetraene be conrotatory or disrotatory?

b. Will the product have the cis or the trans configuration?

c. Under photochemical conditions, will ring closure be conrotatory or disrotatory?

d. Will the product have the cis or the trans configuration?
See all solutions

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