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Chapter 27: Q 58. (page 1104)

Question: Draw a stepwise, detailed mechanism for the following reaction.

Short Answer

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Answer

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01

[4+2] cycloaddition reaction

The electrocyclic addition reaction between a four-pi system (diene) and a two-pi system (dienophile) is referred to as the [4+2] cycloaddition reaction.

All [4+2] cycloaddition reactions are thermally feasible.

02

Mechanism

The mechanism of the given reaction is shown below.

Mechanism

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Most popular questions from this chapter

Question: Vitamin D3, the most abundant of the D vitamins, is synthesized from 7-dehydrocholesterol, a compound found in milk and fatty fish, such as salmon and mackerel. When the skin is exposed to sunlight, a photochemical electrocyclic ring-opening forms provitamin D3, which is then converted to vitamin D3 by a sigmatropic rearrangement (Section 27.5). Draw the structure of provitamin D3.

Question: What type of pericyclic reaction is illustrated in each reaction?

Question: What type of cycloaddition occurs in Reaction [1]? Draw the product of a similar process in Reaction [2]. Would you predict that these reactions occur under thermal or photochemical conditions?

Question:What product would be formed by the disrotatory cyclization of the given triene? Would this reaction occur under photochemical or thermal conditions?

Question: Draw the product of each Diels鈥揂lder reaction and indicate the stereochemistry at all stereogenic centers
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