Fluoxetine, a heavily prescribed antidepressant marketed under the name Prozac, can be prepared by a route that

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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.

(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 enantiomers of Fluoxetine has (S) stereochemistry. Based on your answer in part (a), draw the structure of the alkyl chloride you would need, showing the correctstereochemistry.

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