The preparation of the sex pheromone of the bollworm moth, (E)-9,11-dodecadien-1-yl

Chapter 19, Problem 19.41

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The preparation of the sex pheromone of the bollworm moth, (E)-9,11-dodecadien-1-yl acetate, from compound A has been described. Suggest suitable reagents for each step in this sequence. (a) Compound A (E isomer) HOCH2CH CH(CH2)7CO2CH3 Compound B HCCH CH(CH2)7CO2CH3 O (b) Compound B Compound C CHCH CH(CH2) H2C 7CO2CH3 (c) Compound C Compound D CHCH CH(CH2) H2C 7CH2OH (d) Compound D (E)-9,11-Dodecadien-1-yl acetate CHCH CH(CH2)7CH2OCCH3

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