4. When (2E, 4Z, 6E)-octa-2,4,6-triene (right) is heated overnight in a reaction chamber shielded from light, an optically inactive product is formed. If the compound is instead exposed to intense ultraviolet radiation overnight at room temperature, an optically active product is formed (although the mixture is optically inactive). (i) Explain how the reaction occurs, then (ii) explain why two different products form, using whatever diagrams you feel are necessary to clearly support your explanation.

4. When (2E, 4Z, 6E)-octa-2,4,6-triene (right) is heated overnight in a reaction chamber shielded from light, an optically inactive product is formed. If the compound is instead exposed to intense ultraviolet radiation overnight at room temperature, an optically active product is formed (although the mixture is optically inactive). (i) Explain how the reaction occurs, then (ii) explain why two different products form, using whatever diagrams you feel are necessary to clearly support your explanation.

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

Section20.6: Sigmatropic Shifts

Problem 20.12P

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