The sex pheromone of the common house fly has the molecular formula C23H46.   It can be synthesized in the lab using the following synthetic sequence.    Give the structures of the pheromone and the intermediates A and B.   n-C13H27C≡CH     +      n-butyl lithium      →      A (C15H27Li)    A    +     n-C8H17Br    →     B (C23H44) B     +     H2 with Lindlar catalyst     →      the pheromone

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
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The sex pheromone of the common house fly has the molecular formula C23H46.   It can be synthesized in the lab using the following synthetic sequence.    Give the structures of the pheromone and the intermediates A and B.  

n-C13H27C≡CH     +      n-butyl lithium      →      A (C15H27Li)   

A    +     n-C8H17Br    →     B (C23H44)

B     +     H2 with Lindlar catalyst     →      the pheromone   

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