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он several steps H30* brevicomin Br ÓH 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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Concept explainers

Organomagnesium compounds

The interaction of alkyl halide with Mg metal in a suitable ether solvent is the common method for the synthesis of the Grignard reagent.

Hydrolysis Grignard Reactions and Reduction

Organomagnesium halides are Grignard reagents. Francois Auguste Victor Grignard, a French chemist who received the Nobel Prize in Chemistry in 1912, created these highly useful reagents.

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.

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
H30*
brevicomin
Br
ÓH
6-bromohexan-2-one
6,7-dihydroxynonan-2-one

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