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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:What starting materials are needed to synthesize each compound by a thermal [4 + 2] cycloaddition?

Question: A solution of 5-methylcyclopenta-1,3-diene rearranges at room temperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products are formed from the starting material by a sigmatropic rearrangement involving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene is not formed directly from 5-methylcyclopenta-1,3-diene by a [1,3] rearrangement.

Question:Using orbital symmetry, explain why a Diels–Alder reaction does not take place under photochemical reaction conditions.

Question:(a) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene?

(b) Does this reaction proceed in a suprafacial or antarafacial manner under

thermal conditions?

(c) Does this reaction proceed in a suprafacial or antarafacial manner under

photochemical conditions?

Question: What product is formed when each compound undergoes thermal electrocyclic ring-opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.
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