Muscalure, the sex pheromone of the common housefl y, can be prepared by a reaction

Chapter 7, Problem 7.83

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Muscalure, the sex pheromone of the common housefl y, can be prepared by a reaction sequence that uses two nucleophilic substitutions. Identify compounds AD in the following synthesis of muscalure. CH3(CH2)7CH2Br CH3(CH2)11CH2Br NaH NaH HCCH A B C D + H2 + H2 addition of H2 (1 equiv) H H C C CH3(CH2)7CH2 CH2(CH2)11CH3 muscalure

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