Answered: Br NaH NaH H-C=C-H A B H2 + H, Br…

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Br NaH NaH H-C=C-H A B H2 + H, Br addition of H2 (1 equiv) muscalure

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter30: Nutrition

Section: Chapter Questions

Problem 30.69P

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Concept explainers

Aldehydes and Ketones

Aldehydes and ketones are organic compounds that have a carbonyl group, C = O, as their functional group. They both differ in the placement of this carbonyl group in their structures.

Question

Muscalure, the sex pheromone of the common housefly, can be prepared
by a reaction sequence that uses two nucleophilic substitutions. Identify
compounds A–D in the following synthesis of muscalure.

Br
NaH
NaH
H-C=C-H
A
B
H2
+ H,
Br
addition of H2
(1 equiv)
muscalure

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