chemfinal1

chemfinal1 - 2 CH 3 O H 2 N-NH 2 NaOH (excess) HONO N CO 2...

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1 FACULTY OF SCIENCE FINAL EXAMINATION Organic Chemistry 2 CHEM222 and CHEM234 Dec 2007 ANSWERS Question Version 1 Version 2 1 b d 2 d a 3 c d 4 d b 5 b d 6 b a 7 d b 8 b d 9 b a 10 b d 11 c c 12 d c 13 d b 14 b d 15 c b 16 b c 17 c d 18 a b 19 b a 20 c d 21 d c 22 a b 23 a b 24 d b 25 b a 26 c d 27 c d
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2 28- Draw the product for the reaction sequence below. ONLY the molecule in the box will be considered. NO partial points will be given. H+, H 2 O NaH O Ph 3 P=CH-CO 2 CH 3 O O H+, H 2 O O O CO 2 CH 3 29- Draw the product for the reaction sequence below. ONLY the molecule in the box will be considered. NO partial points will be given. 1) CH 2 O 2) NaBH 3 CN NH 2 CO
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Unformatted text preview: 2 CH 3 O H 2 N-NH 2 NaOH (excess) HONO N CO 2 H N O 30-Propose a multistep synthesis to carry out the transformation below (~6 steps): 1- Mg, CO 2 2- DCC, DMAP, (CH 3 ) 2 NH 3- HF (deprotects both at once) 4- CH 3 COCl 5- PhNH 2 followed by NaCNBH 3 Other answers are possible 031-Propose a multistep synthesis to carry out the transformation below (~8 steps): 1-H 2 , Pt 2-HONO 3-NaCN 4-H + or NaOH (CN COOH) 5-PBr 3 (excess, to form acid bromide and alpha-bromo-ketone) 6-PhCH 2 OH (ester formation) 7-H + (elimination of alpha-bromo) 8-CH 3 CH 2 CH 2 ONa to do Michael addition Other answers are possible....
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chemfinal1 - 2 CH 3 O H 2 N-NH 2 NaOH (excess) HONO N CO 2...

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