Exam_3_White - CEM251/Fall 2010/Third Hourly Exam(page 1(12...

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CEM251/Fall 2010/Third Hourly Exam ....... (page 1) (12 points total) 1. Draw the structure of the major organic product of the following reactions: a) 2 pts. Pt show stereochemistry H H D 2 (deuterium) b) 2 pts. H 2 , Pd, , Quinoline CH 3 C CCH 2 CH 3 show stereochemistry Pb(OAc) 2 c) 2 pts. Na, NH 3 C show stereochemistry CH 3 C CH CH 3 CH 3 d) 2 pts. H 2 , Pt (excess) CH 3 CH 2 CH 2 C CH 2. a) (2 pts.) (2 pts.) A B W hich of the above olefins ( A, B or C ) has the highest heat of hydrogenation? b) W hich of the above olefins ( A, B or C ) has the lowest heat of hydrogenation? CH 2 CH 3 CH 2 CH 3 C H CH 2 C
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CEM251/Fall 2010/Third Hourly Exam ....... (page 2) (15 points total) 1. Draw the structure of the major organic product of the following reactions: a) 2 pts. C C CH 3 CH 3 H H show stereochemistry Cl C O O O H Cl C O O H + + b) 2 pts. NaBH 4 2 pts. H 3 O + 1) 2) CCH 3 O CrO 3 , H 2 SO 4 (excess) c) CH 2 CH 2 2 pts. CrO 3 (pcc) OH HCl pyridine d) 2 pts. CrO 3 , H 2 SO 4 OH (excess) e) 2 pts.
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