Chem 255 Exam2 Answers

Chem 255 Exam2 Answers - Chemistry 255 Exam 2 Fall 2000...

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Unformatted text preview: Chemistry 255 Exam 2 Fall 2000 **ALL ANSWERS MUST BE IN INK** Nam ID# Please read the following questions very carefully. 1. Please provide IUPAC names for the following compounds. (30 pts) 3 4) Br 3 (@«5~me.¢3-£zum-,_ b) q 3 r 2.“me ~l 3~CzCIOWQAIM C) u c’ H 3 Br \ H3 39135~ l" 3‘Ef2m/w‘ 9(0me d) g '5 \ ’4 g‘/ ‘ W - ~ ~ 3’“an M e) c K n, 61 '5“:S'c\ H”c1 2. State whether the following molecules are enantiomers (E), diastereomers (D), or identical (1). (25 pts) 21) H3 I B’ H /LQ”’CH S $ H Br S3 _/ b) Br \ 9 H Br H c1 Clo”~ S K 1 C 1’ H ""’H 5 Br c1 Br C) {—5 L d) w 6) 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) (9 4. Provide the product(s) for the following reactions. (10 pts) a) 1) Hg(OAc)2 / ————> 2) H20 b) __ HOCl “0 /_\ _____, 5. Provide the reagents needed for the following reactions. (10 pts) W a) m . H M M as M7,)nap9 OH b) J‘. 0/ “L” (K. 6. Provide the starting material needed for the following reaction. (5 pts) c12 7. Provide a detailed mechanism to acount for the formation of the 2 products in the folowing reaction (Hint: think rearrangement). (20 pts) C1 A B l aid/MB 8. During the synthesis of optically pure Prozac (see structure below) at Eli Lilly, the reactor 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 Fae—Q H a "”’CHZCH2NHCH3 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 Pym T’s—w Extra Credit (5 pts) How many stereoisomers would be possible for 1- bromo—Z—chloro—3 -iodocyclopentane? (1% l” r. \/\ ...
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Chem 255 Exam2 Answers - Chemistry 255 Exam 2 Fall 2000...

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