3. The Diels-Alder reaction is quite useful in preparing cyclic or polycylic compounds from dienes. However, the rate that the reaction can occur at, as well as the stereochemistry of the product, can depend on the starting materials used. a) Buta-1,3-diene, A, participates in Diels-Alder reactions, but much more slowly that cyclopentadiene, B, while the compound 3-methylidenecyclohexene, C, does not react at all. Explain the difference in reactivity of these three dienes in Diels- Alder reactions. b) Buta-1,3-diene, A, will react with cyclohexene when heated in a dark container overnight. However, no reaction will occur between buta-1,3-diene and cyclohexene if it is subjected to ultraviolet light during the reaction. Explain this behavior, using whatever molecular orbital (MO) diagrams you feel are necessary.

3. The Diels-Alder reaction is quite useful in preparing cyclic or polycylic compounds from dienes. However, the rate that the reaction can occur at, as well as the stereochemistry of the product, can depend on the starting materials used. a) Buta-1,3-diene, A, participates in Diels-Alder reactions, but much more slowly that cyclopentadiene, B, while the compound 3-methylidenecyclohexene, C, does not react at all. Explain the difference in reactivity of these three dienes in Diels- Alder reactions. b) Buta-1,3-diene, A, will react with cyclohexene when heated in a dark container overnight. However, no reaction will occur between buta-1,3-diene and cyclohexene if it is subjected to ultraviolet light during the reaction. Explain this behavior, using whatever molecular orbital (MO) diagrams you feel are necessary.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.33P

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