Exam_3-2010-Key

Exam_3-2010-Key - l. (8 points) Match the following...

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Unformatted text preview: l. (8 points) Match the following reaction conditions to the proper reaction coordinates. Consider the relative energies within the series in making your assignment. A. An 8N2 reaction in a polar aprotic solvent. B. An 8N2 reaction in a non-polar solvent. C. An 8N2 reaction in a strongly hydrogen-bonding solvent. D. An S N1 reaction in a polar hydrogen-bonding solvent. +2 {or each coma-t an; mafia Reaction Progress 2. (4 pts) Circle the product that would you not expect from the following reaction? +4, {2" cue-Nd Mr (gala 1 pruduH-J H2804, A +0 W 3HW+ an! ——"‘" I or non Ham: 1 GUM? OH 3. (4 pts) Rank order the following in terms of their rate of reaction with EtS‘Na”. ' (l = fastest) + 1 {at Ouch cm Energy ame r NBI‘ WI AVG Me/VI Cs) (5!: 63 @ " ‘er wrwxs vwkc. 4. (30 pts) a) For each compound, indicate in the box whether it will react under SN] conditions (MeOH, A), 5N2 conditions (Na*‘CN, DMF), both, or neither. 1)) Provide the corresponding product or products. . [-1145 b0)! \5 wW-V‘" 24"" SN} [WWW 3gb. Me Me)\/\CI be M o 3"” +~ flmc'5 U H. &r W 3 +3 JPN \OD‘H" -—\ «Cor 5,52. swam; X Me Me No exA beamed CI brand“ A? )5 Mt" Me “+ 3 “NJ ‘ ca“ 35 2“ h QcmgQAJ N Br Na [eye/1‘ 5% 58 C- X 0 Ced’R DO PUHq\ (CW3? 0C. 1 MO : . OTf {30% (6003 EC”) SUK “H + “j + [—— Jr Si 2 E/ Tf—-SOZCF3 “H Migrawocwshjl New” G) Y /\/NH2 9 Una moi—cu Ric: O‘Lm‘l) 7% A“ “Mei—Werwi Are +3 cars—0. 5. (12 pts) Propose a synthesis of 2-butanone using only butane as your starting material and reagents we have covered in 5.12. ‘33 : +7”! / \ _ standard aqueous reaction work-ups where appropriate. 0/7( + 3 /5' 54 OH OH H 403 o b THF OAK + 57’s" 11% + ’8' +1 eq. Na Et +1eq. —- Q H / a“? +3/5' O 335' O 0 0°” Sic/tr ram“ ’ any cvlalmé.¢ a5 OH +SF_ DH ' h + III/ DA 4: + POCls +pyridine _. er’o’m "M 3‘ 5 Oaxx ) X=I; 3" 3/5.. For Kmmh‘; yw new, glimthimw 6. (30 pts) Fill in appropriate starting materials or the products in the boxes given. Assume H 0 Br ¢\‘CH3 Tm: “m 315' + (CH3)300K ——- 1f: *5er 8/ + N- : +5 w U m 0 2. @1300? Na?) DMF )4 q Br isopropanol + N(CH(CH3)2)2Et 50/50 mixture ——_—___—b Heat 7. (12 pts) The following transformation takes place. Give all intermediates (mechanisms welcome but not required). (Hint- CN groups are similar to carbonyls in their ability to support resonance structures that stabilize carbam'ons o. to them) “A OH / /\/J< HO 1. PBr3 N/éC CE) 2. NaCN,DMF _ 5" 3. MCPBA * ‘5' 4- (CH3)3COK, THF T ‘5‘ [ W k 095% P j- ,fi__‘_ } . (fig—h 6‘ WO 9 l #2 WA; mt r7“ 1 Loki 5‘9 £99th £77 NCAf O'Y 4c/\; no (9991‘: a?“ A! I“), 7A3; .r‘s 5.1 r?“- Extra Credit (3pts): Provide a detailed mechanism for the formation of Br2 from the reaction of H-Br with NBS. III N ‘. N 0Y0 —> DVD + . Br-Br + 1 gm each 3+8? +0; *Ecv ghwv\“fl mam" M£L"‘0“”W‘ ...
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This note was uploaded on 02/14/2012 for the course CHEMISTRY 5.12 taught by Professor Saraho'connor during the Fall '09 term at MIT.

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Exam_3-2010-Key - l. (8 points) Match the following...

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