Answered: OH several steps Hзо* Br brevicomin ОН…

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OH several steps Hзо* Br brevicomin ОН 6-bromohexan-2-one 6,7-dihydroxynonan-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 acidcatalyzed cyclization of 6,7-dihydroxy-nonan-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.

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

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