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Br NaH н-с-с-н NaH Br + H2 addition of H2 (1 equiv) muscalure

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.9: Heterocyclic Amines

Problem 21P

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

Br
NaH
н-с-с-н
NaH
Br
+ H2
addition of H2
(1 equiv)
muscalure

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