Q4 B-Damascenone belongs to a family of fragrant natural products called rose ketones tha have þeen used in the perfume industry. In one synthesis of B-damascenone, the reaction o COuiyalent of MCPBA afforded two constitutionally isomeric epoxides JODIerted into diol 4 upon treatment with aqueous nochanism that converts each that
Q4 B-Damascenone belongs to a family of fragrant natural products called rose ketones tha have þeen used in the perfume industry. In one synthesis of B-damascenone, the reaction o COuiyalent of MCPBA afforded two constitutionally isomeric epoxides JODIerted into diol 4 upon treatment with aqueous nochanism that converts each that
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:Q4 B-Damascenone belongs to a family of fragrant natural products called rose ketones that
have been used in the perfume industry. In one synthesis of B-damascenone, the reaction of
compound 1 with one equivalent of MCPBA afforded two constitutionally isomeric epoxides
(compounds 2 and 3), which were then converted into diol 4 upon treatment with aqueous
acid. Identify the structures of epoxides 2 and 3, and propose a mechanism that converts each
of them into compound 4 in the presence of H,O*. (Note: It is reasonable to presume that a
protonated epoxide can open by itself, without the involvement of a nucleophile, if doing so will
give a resonance-stabilized allylic carbocation intermediate.)?
OCH,
OH OCH3
H,O
2+3
MCPBA
(one equiv.)
4
OH
B-Damascenone
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