Solved: Fluoxetine, a heavily prescribed antidepressant marketed under the name Prozac
Chapter 18, Problem 18.56(choose chapter or problem)
Fluoxetine, a heavily prescribed antidepressant marketed under the name Prozac, can be prepared by a route that begins with reaction between a phenol and an alkyl chloride. OH F3C O F3C H Cl + CH3 N CH3 CH3 N CH3 O Fluoxetine F3C H CH3 N H KOH DMSO (a) The rate of the reaction depends on both phenol and alkyl halide. Is this an SN1 or an SN2 reaction? Show the mechanism. (b) The physiologically active enantiomer of fluoxetine has (S) stereochemistry. Based on your answer in part (a), draw the structure of the alkyl chloride you would need, showing the correct stereochemistry
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