Answered: ОН several steps Нао* brevicomin Br ОН…

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ОН several steps Нао* brevicomin Br ОН 6,7-dihydroxynonan-2-one 6-bromohexan-2-one

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter10: Oxidation And Reduction

Section: Chapter Questions

Problem 4CTQ

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Question

Brevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan- 2-one.

a. Suggest a structure for brevicomin.

b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.

ОН
several steps
Нао*
brevicomin
Br
ОН
6,7-dihydroxynonan-2-one
6-bromohexan-2-one

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