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Key midterm-2-Fall2005

Key midterm-2-Fall2005 - Student Name Problem 1 Provide a...

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Unformatted text preview: Student Name: Problem 1 Provide a detailed mechanism for the following reactions. Name the final products. A) (10 points) H 9483‘- ‘S-Mew‘j‘ 2?“ m3) Tactile ‘3 —+ CHIC / u H” d 1 /"-~. S‘"“\_',\.) 5% at; L?)\\\/ L: <§>—<~/5\ 5 4, / Hifg“ _ -H __H+ \U / 55¢ 0: / /<: /m Wk M ___.:: / \LM LO/ MM ""— l 0/ [L 3-CjCeOLQ¥j\ -g‘n“-fi*€aj) \‘goqufiic B) (10 oints) .-""\\ p O 3/” \ /\‘—-/ U “I ”\74- U ”7 + 1'] OH ' IK \H/ltzD In?“ \D /’/'\/ I M ~— cu} N __ 0 ¥ \ / u —- ~-” Student Name: Problem 2 Propose a synthetic strategy for the following reaction. Provide all reagents and possible intennediates needed for every step (18 points). Student Name: Problem 3 cu “H Provide the major products for the following reactions (24 points) L“ ¢ NH; N + EN - NaNOz, HCI KCN /O LiAIH4 / a) , —'6;’ [:33 CuCN H03 \ N02 0 /“"N3 heat k0» U01, “Jo H2N 1)©—4,'heatm DCM Q: /—\ <;>—4H _ b) Me0\’2\5H ""————>- H b _ > \H / 2) NaOHIHzo ‘ ‘ j 5 ° 3) H+IH20 J , 0k ob or» CH —- o OHOH 01)):OH , H" O 1 H 0+ 3 [\1/0 c) __.__...OJ\/)< 4) 2) (CH300)20 5 k/é‘ 2) NaOH \ HO OH pyridine and M92504 (1450 [L0 3 / OH H a) (CH300)20 ’4/ 0 x d) 0 pyridine —.._._>. HO OH b) HBrIacetic acid A‘o oA-L 3 OH (cold) 8 f Student Name: Problem 4 a) Draw cyclic Fisher projection, chair conformation and Haworth projection for at —D- Altrose. (12 points) H OH on u o 0 H :‘b u 0 :0 H ”ii on. GM 0H b) Complete the following carbohydrate reaction (8 points). $1) NHOH, HCZCH3)2504 901300” 9009 :3 0 l\€/ o/i/ X \ / “-1 o u cuo ow /‘ 0043 ‘1 5 3 3 0% ¢HZOIH+ 00900“; No OCU3' cu + ' 30 9% 0” Y CH 20H D- Altrose Problem 5 Complete the following reactions (12 points) Br I \ + Na+NH2- Heat / N OCH3 DMSO (>4? , pyridine l \ Cl I .—>.. N NHZ DMF 1) LDAITHF \ 2) CH3-l I , ——> N CH3 Name the following compounds (12 points). Student Name: ...
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