Chem 255 Exam 2

Chem 255 Exam 2 - heated up and an enantiomeric excess of...

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1 Chemistry 255 Exam 2 Fall 2000 **ALL ANSWERS MUST BE IN INK** Name ID# Please read the following questions very carefully. 1. Please provide IUPAC names for the following compounds. (30 pts) a) b) c) d) e) F Br Br CH 2 CH 3 CH 3 Br H Cl H H Cl
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2 2. State whether the following molecules are enantiomers (E), diastereomers (D), or identical (I). (25 pts) a) b) c) d) e) 3. The following compound is a meso stereoisomer. (a) How many planes of symmetry exist in this molecule? (b) Draw in all planes of symmetry on the structure below. (7 pts) Br Br Cl H H Cl Br Br H Cl H Cl CH 3 I H Br I H Br CH 3 C C H Br H Cl CH 3 CH 3 C C Br H 3 C H Cl H CH 3 Br H H Br Br H Br H O Cl H O H Cl H H
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3 4. Provide the product(s) for the following reactions. (10 pts) a) b) 5. Provide the reagents needed for the following reactions. (10 pts) a) b) 6. Provide the starting material needed for the following reaction. (5 pts) 1) Hg(OAc) 2 2) H 2 O HOCl OH OH Cl 2 Cl H H Cl
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4 7. Provide a detailed mechanism to acount for the formation of the 2 products in the folowing reaction (Hint: think rearrangement). (20 pts) 8. During the synthesis of optically pure Prozac (see structure below) at Eli Lilly, the reactor
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Unformatted text preview: heated up and an enantiomeric excess of 96% was obtained. (15 pts) a) assign the R or S configuration to the stereocenter within Prozac b) determine the percentages of the R and S enantiomers obtained in the synthesis %R = %S = HCl A B Cl Cl + O F 3 C H CH 2 CH 2 NHCH 3 5 9. Draw all of the unique stereoisomers for 1-bromo-2-chlorocyclopentane. (28 pts) a) also provide the R and S designation for each of the stereocenters b) also indicate all of the enantiomeric and diastereomeric pairs Extra Credit (5 pts) How many stereoisomers would be possible for 1- bromo–2–chloro–3-iodocyclopentane? 6 WORK SHEET NO ANSWERS ON THIS PAGE CAN BE USED FOR CREDIT ON A PROBLEM – PUT ALL ANSWERS IN THE APPROPRIATE PLACE 7 WORK SHEET NO ANSWERS ON THIS PAGE CAN BE USED FOR CREDIT ON A PROBLEM – PUT ALL ANSWERS IN THE APPROPRIATE PLACE...
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Chem 255 Exam 2 - heated up and an enantiomeric excess of...

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