MT1Key_Wi03 - N U. Winter 2003 M5 1. (30 pts) Complete the...

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Unformatted text preview: N U. Winter 2003 M5 1. (30 pts) Complete the following reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. /.——— /// 1) ozone excess / 2) M628 excess 0 O __ 3) H O excess H , 2 2 H/LH + 2 first a) O 1) mCPBA + | o 2) EtOH, H30 A 3) PCC \ H b) / OE/c 1) 0504. H202 0 0 2) LAH excess - 3) H104 , flk *HJK c) — H r 1) KOH, hi heat + 660 d) 2) H3O , EtOH ‘NOT WM) 0 limb )1? (K #9540 OH O L) Kotg“ J A e) 5) m l? NQNuL \ 0 2’) fl: ) TCCQ.t 0mm; 0T3 3) TSQ, @A’L—Ho MAJL “OTC LL mt . NC, Winter 2003 a 61; v " 5 2. (15 pts) Fill in the structures of A, B, and C. Propose curved arrow mechanisms for the following (1 "M" .. 3. 3 reaction sequence (no need to draw out the structure of Sia). Show all the proton transfer steps. You can buy the structures of A for 3 pts each and those of B and/or C for 2 pts each. 17¢, 1)Si H 1) gm 2)H:§2.§IaOH . + (‘32 2) O ork up / \ OH, 3) H30+ work up Ll “a N C, Winter 2003 3 $8 3) (15 pts) Fill in the structures of D and E. Propose a curved arrow mechanism for the conversion of D to E. Show all the proton transfer steps. You can @e structures of D and/or E for 3 pts each. MeO 1) LAH / W 2) H3O+ dilute, RT (“l \\ H2804, heat 0 ————" —-—————> o 4W . 4. (20 pts) From methane as the only carbon-containing starting materials, propose a synth is of the following molecule. You may also use NBS, tosyl chloride, pyridine. PCC, Swem’s reagen d any inorganic reagents. Hint: methane can be used to make acetylene. If you do not remember the conditions to do this, just start from acetylene to get partial credits. can MW” CW” W 4+z+4=lo 0' @ienww $0 I Cale‘b lamb NU, Winter 2003 fflis W a.» W‘M‘Qa (16956“ W... VWC p54) i _./————~> (+CECH' +3HL ZC%* bfltfio hub ::69 %2 ::f /'—,L’" w wL£~ULO M 11‘: at Ca 5r: @ W A New A4: 2) m £69 @L (i FE“ 1 Wu @ 19mm, ,A 2’ L l) [4770'( N NL', Winter 2003 5 take 5. (20 pts) Suggest a sequence of reactions for the synthesis of the following molecule from propene as the only carbon-containing starting materials. You may also use NBS, tosyl chloride, pyridine. PC C . Swem’s reagent, and any inorganic reagents. Hint: Remember to count the number of carbons and use the most appropriate building blocks that you can derive from propene. Although non-alkyne solutions do exist for this problem, using alkyne—type reactions (that is reactions which involve alkyne) may help you greatly. \ \OEEJ—fa /\/O(+ /\l/fi\/o:\/\ 2) 2,) Limo), )fir ~ ' FF“) 2M2 2M [00; ‘ , 4r; T (cc N U, Winter 2003 6 6. (20 pts) Starting with l-butyne as the only carbon-containing starting materials. propose a reaction sequence for the synthesis of the following molecule. You may also use NBS, tosyl chloride. pyridine. PCC, Swem’s reagent, and any inorganic reagents. OH ...
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This note was uploaded on 06/12/2008 for the course CHEM 210-2 taught by Professor Coddens during the Winter '08 term at Northwestern.

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MT1Key_Wi03 - N U. Winter 2003 M5 1. (30 pts) Complete the...

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