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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

Will a concerted reaction take place between 1,3-butadiene and 2-cyclohexenone in the presence of ultraviolet light?

Problem:a. For conjugated systems with two, three, four, five, six, and seven conjugated蟺 bonds, construct quick MOs (just draw the lobes at the ends of the conjugated system as they are drawn on pages 1220 and 1221) to show whether the HOMO is symmetric or antisymmetric.

b. Using these drawings, convince yourself that the Woodward鈥揌offmann rules in Table 28.1 are valid.

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

Explain why maleic anhydride reacts rapidly with 1,3-butadiene but does not react at all with ethene under thermal conditions.

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.
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