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1. Consider the following sequence of reactions, taken from the early steps in a synthesis of w-fluorooleic acid, a toxic natural compound from an African

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1. Consider the following sequence of reactions, taken from the early steps in a synthesis of w-fluorooleic acid, a toxic natural compound from an African shrub. w-Fluorooleic acid also called "ratsbane," has been used to kill rats and as an arrow poison. Three more steps beyond those below are required to complete its synthesis.) - 1-Bromo-8-fluorooctane + sodium acetylide (the sodium salt of ethyne) compound A(C10H17F) - Compound A+NaNH2 compound B(C10H16FNa) - Compound B + I-(CH CH2)7Cl compound C(C17H30CIF) a) Elucidate the structures of compounds A,B, and C above. b) Write the mechanism for each of the reactions above. 2. Consider the following compound: Develop all reasonable retrosynthetic analyses (working backward from the final target molecule to starting materials usually via one or more intermediates) for this compound (any diastereomer) that, at some point, involve carbon-carbon bond formation by alkylation of an alkynide ion

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