homework_5 - first substitution reaction. (a) Draw the...

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Chem624 Organic Chemistry I Spring 2008 Homework 5 (Due Mar 26 Wed) Name__________________ ID ___________________ 1. What product(s) would you expect to obtain from the S N 2 reaction of S -2-iodooctane with sodium cyanide, NaCN (2 pts). Clearly specify stereochemistry where pertinent. I H NaCN 2. What product(s) would you expect to obtain from the S N 1 reaction of R -3-bromo-3- methylhexane with methanol (2 pts). Clearly specify stereochemistry where pertinent. H 3 C Br + CH 3 OH
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3. The antidepressant fluoxetine, sold under the trade name Prozac, can be prepared by a substitution reaction of an alkyl chloride with a phenol using a weak base to generate the phenoxide ion. The final compound has the same stereochemistry as the product of the
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Unformatted text preview: first substitution reaction. (a) Draw the nucleophile structure in the first step (2 pts). (b) Identify the stereogenic (chiral) center in the alkyl chloride starting material. Mark the chiral center with * in the above scheme. (1 point) (c) If the rate of the reaction depends on the concentrations of both the alkyl chloride and phenol, is this an S N 1 or S N 2 reaction? (1 point) (d) If you start with 100% R-alkyl chloride and the substitution proceeds with inversion, draw the chemical structure of Prozac ultimately produced and identify its chiral center as R or S . (3 point) hint: priority O > phenyl > CH 2 Cl N CH 3 CH 3 + CF 3 OH O N CH 3 CH 3 CF 3 O N CH 3 H CF 3 Prozac (fluoxetine)...
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homework_5 - first substitution reaction. (a) Draw the...

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