Sample_Exam_3-1 - CEM251/Fall 2009/Third Exam(page 1 I(2...

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CEM251/Fall 2009/ Third Exam ..... (page 1) I. (2 pts. each box, 16 points total ) 1. Draw the structure of the major organic product of the following reactions: a) 2 pts. H 2 , Pt CH 3 CH 2 CH 3 show stereochemistry b) 2 pts. H 2 , Lindlar Catalyst show stereochemistry CH 3 C CCH 2 CH 3 c) 2 pts. Na show stereochemistry CH 3 C CCH CH 3 CH 3 NH 3 d) 2 pts. H 2 (excess) CH 3 C CCH 2 CH 3 Pt e) 2 pts. C C H CH H CH 2 CH 3 show stereochemistry Cl C O O O H Cl C O O H + f) 2 pts. OsO 4 NaHSO 3 show stereochemistry 1) 2) g) 2 pts. CrO 3 H 2 SO 4 , H 2 O CH 2 CH 2 OH 2 pts. CrO 3 , pyridine, HCI (PCC)
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CEM251/Fall 2009/ Third Exam ..... (page 2) II. (10 points total ) 2. (4 pts.) Draw the structure of X (C 9 H 14 ) in the box: H 2 (excess) 4 pts. O 3 CH 3 CH 2 CH 3 X (C 9 H 14 ) 1) 2) Pt Zn, H 2 O H CCH 2 CCH 2 CH 3 O O CH 3 C CH 2 O C H O + 3. (4 pts.) Outline the steps in a synthesis of pure trans -2-hexene starting from acetylene and any other desired reagents: 2 pts. 4) A B C Rank alkenes A, B and C in order of i n c r e a s i n g heat of hydrogenation.
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Sample_Exam_3-1 - CEM251/Fall 2009/Third Exam(page 1 I(2...

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