practicemt4_key - Practice Exam#4 5.13 Organic Chemistry II...

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Unformatted text preview: Practice Exam #4 5.13: Organic Chemistry II Fall 2003 ° Midterm exam #4 will be held on Friday, December 5, from 12—1pm. ° Ten points will be subtracted from your exam if you take it in the wrong room. ° Notes, books, and calculators will not be allowed in the exam. ° You will be free to use molecular models during the exam. ° You will be given a periodic table. ° The exam will cover reading (Ch. 22) and lecture material through Unit VII (Monday, December lst). Knowledge of prior material (5.12 82: 5.13) is also assumed. ' For best results, take this test as if it were your exam (without a key in 50 minutes!). That way, you'll know what areas to work on before you get to the real exam. Practice, Practice, Practice!!! 1. a) Rank the following carbonyl compounds based on the acidity of the indicated a—proton. (1 = most acidic, 5 = least acidic) o o o o o o o o HacO/AKHKCHg, HSCJKI HfiOMOCHs HaCOJJ\I H3,C/u\l/U\CH3 H H H H H b) Rank the following carbocations based on stability. (1 = most stable, 5 = least stable) NH2 CH3 OH A A HCA HCA A H30 9 H H3069 CH3 $CH3 eacH3 H30 EB CH3 2. In the boxes, please provide the reagents for the illustrated transformations. Include work-up steps and be specific about quantities of reagents where relevant. More than one step may be required. a) l. MaoEt (lequAV-3 2- 10g (stmwem O 3. “’69 (00ka b) /U\ /t-Bu Me Me t-Bu IZ 3. Please provide the products of the following reactions. If no reaction is expected, write "NR". a) 0 Me cm.NaOEt :3 a) -———> Me EtOH Eta WH/ o b) O MCPBA Mekt-Bu N jkO ”+3“ c) (—D 0 c /U\ Base M '—'——-—-> Me SMe (1 equiv) N SM (2 equiv) d) O H+ _-—_> Me Me e) C) u\ k 030%)“ ___.HZSO4 \: PL Ph Ph f) O MgBr2 PM —+ w A/t 4. Please provide the reagents for the following transformations. Be specific about quantities of reagents where relevant. a) N A N 0 1 HO 7,—NH2 l} QQ O l b) ' "M ‘ "emu“! MWWW o o PhJLMe Pth/Me without over-alkylation wt. Hack: COzMe COO 0 Me020 Mes + I) | o d) 'BrL (tequb A Q20 H 0 Br without over-bromination e) “'5 06B 65 o o A o MewOMe MeJVMe Me 5. Please provide a detailed mechanism for the following transformation. Show all arrow pushing. O O O O tM 06 H + M _°a.;e_, \ OMe t) MeO OMe OH \+ 16:69 a“ 9 ll \\ UAW CK (%-b)§o \H o /\ 41‘? ca \ 9\ 00%‘K ON 0}»? 0 o 9‘60” ll. M K 3% ON (-3. l /00 M l .. \ ’ /t/\‘4 / .5 E l ,l M/kje " E7l\o/\\\3 6. Please provide a detailed mechanism for the following transformation. Show all arrow pushing. O we] MGAWOYMQ IV'eMe/I\LO/I A H 0 ll @ h/\N/\ O a < 0‘ N/l\\p/\/o\/ N 'tfi u '39” “k M.- “ ‘9 o 0‘ n Mk5) #T N ®k“/\ 7. Please provide a detailed mechanism for the following transformation. Show all arrow pushing. O O cat.eOH Me WM bsde-CM. . Me Me 8. Please provide a detailed mechanism for the following transformation. Show all arrow pushing. m "0 ‘. Cl 0 0,94 0 é o” o P} W 0k \ (9% ®/\'l 0 9,0001% N O( 9. Please provide a synthesis of the indicated compound. All of the carbon atoms should be derived from methyl acetate. 0 Jk Me OMe methyl acetate o 0 [equiv if 0 MJKOH t (He/[KW 7:33 wo/\/‘ MV‘ 0 o Heafi 0‘ (l , “cm V0 49L M} \w fig: MR at? f FROG) A ox (5 o 65 \ [Lo/“\(BN F399 (Lakotl + MH Him LLM Mar3 NAOH QVBF (—9 \NlHQ) c5 (‘40 Ag 10. Please provide a synthesis of the indicated compound. All of the carbon atoms should be derived from isopropanol. ...
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