Exam_4-2011-Key

Exam_4-2011-Key - Midterm Exam #4 Chem. 5.12, Organic...

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Unformatted text preview: Midterm Exam #4 Chem. 5.12, Organic Chemistry Professor Timothy M. Swager December 7, 2011 100 Points Possible (printed neatly (Signature, required for credit) MIT ID# Name of recitation TA General Instructions Make sure that your exam has 9 numbered pages including this cover and a periodic table. Write all of your answers in the spaces provided. If you run out of room use the back of the page and indicate this for the grader. If in doubt as to the level of detail expected, put down more than you think is necessary. Good Luck! Extra Credit Total l. (4 Pts) Rank-order the following the protons indicated in the following molecule in terms of their acidity (1: most acidic). corn/dang f5 ‘ o o E] o O (2* MA [054' N(CH3)2 :59: 95 L19, Co (QQLHHTZ fS~ H H O O Miflfirflbl Pl". (4 Pts) Rank-order the basicity of the following compounds (1: most basic). H3C—Li /—Li ___'———Li ___'———MgBr E] (4 Pts) Rank-order the carbonyls below in terms of their equilibrium concentration of the hydrates as indicated in the box (1: largest Keg). (CH3)2N (4 Pts) Rank-order the relative acidity of the f0110win g protonated carbonyl compounds ( 1: most acidic). H H..., “I” if \NAN/ ,r/ I k [I] 2. (20 Pts) Fill in the boxes with the appropriate product(s) or starting material for the following reactions. Indicate stereochemistry when relevant. O 1. LiN(CH(CH3)2)2 (1 eq.) THF 2. CH3B1' 0 E10 OEt —D'- 1. soc12 2. Pyridine + EtOH l. LiAlH4 2. Aq. Workup 3. (20 Pts) Fill in the boxes with the appropriate organic product(s) or starting material for the following reactions. Indicate stereochemistry when relevant. O 0 0 ‘4 cars 0 o 1 Br2,KOH “ fl 2 HCUI-IQO 0 AW MMM mm Sf ' " ' Du, 6mm {iv Agr) 0* is: 0 O ———I- +0 41w 1. EtONa,EtOI-I O a 2. Br-(CH2)4-Br Pro (5ow _—I- l. HO-CHZCHZOH Br TsOI-I (cat) 1. CH3Li (excess) 0 0 2. Aq. workup 4. (10 pts) Show detailed mechanism for the following transformation. 0 0 O a??? ———D'- """——""' I /u\/‘\/”\ KOHA/H20 < o (:95 “(@H \9“ L0 . Fwy. \ 4 JP 5 eP‘ \Lgp” < O“ 05 1 u Cf?) \\ (DIM—g :‘ \mfi "Q3 Oh I- 5 3: ‘ L1 J fig? /0 LL91"??? ] S vkxggefig \ IP’ vap / -' amoral-0n efi-pnfe‘zzlxi fl [Wm 64/ , /f0r iépro/vM/mn, * five corn 6/- WWW m 141er “’6’” 1’9"“ / "l for “Mp/We on é/érho/ah/lw karma J'fep z- fiMIMp/u/zo 4/746 (p, Memb ereo’ rm / Mwa’ei a -mémdm: 6f give/fife lmvf wool/07‘0"? q j [3’90 pow/big.) mg (gt/Kalli. W727”, mt a~cflrbon f0 arena!va M 50? ._./ far my— me/nj/Wr/fifly far/aw 564,76 . *QX'h'k Yeang "‘ “0+ 4; 4—l gov r'-M-\id1kéoxiduhm/r Muhm)bvi~ wrong VQAat-fl-l CW 5. (24 Pts) Fi 1 in boxes given with reagents to best carry out the following reactions. 8“ fewvfl‘j,‘ H— was 3WD? flUon'Oln: Ig_ 6. (10 Pts) Propose a synthetic procedure for the following conversion using any reagents or organic fragments (adding C3 or less) we have covered in 5.12. 0 0 OH 0 —h- Mixture of Stereoisomers 0” OH :9 (5 5. ., N F (T IMF ET DNA I 7; - @ BY W V' e1 0 (J, o L) Extra Credit (4 Pts) Give a detailed mechanism for the following transformation. .r O ‘. _ O u ————h JEJQH $0012 Cl V Cr“ 8:6 / u /\ Cl 1; +1 «gar (mu-g" o a‘Hackl’nj a” ‘12.»; +1— ?0" deproiomhm and Ole (em/Fnfi. +1 90* 363mm ‘bemaiim. +1. "i‘Or ale aHocHhfl eifler CFO Dr (.5069. ...
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Exam_4-2011-Key - Midterm Exam #4 Chem. 5.12, Organic...

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