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118BSpr10MT1Key-2 - Reactions(24 pts Draw the structure of...

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Unformatted text preview: . Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct relative stereochemistry, if the reaction is racemic indicate this by either drawing both enantiomers or drawing one and writing - racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. WA / Q x; 3>\ “W Cl W regret no mo ‘ mca <3 012, CH3OH I ____________, Hock (‘9) WM ,1: shaman C 1&9an 2' dtd‘l“ I34 (2) O E H9804, H.2_,O M + /\‘ /L\ H2804 loath at! g L - 1 enolS ’/ l 3“" 1) 03 (we —-—-—-————-——-———-—-> 1) Mg H 0 y\ grim'd =69 ———-————————» ondx=® _ 2) O \ 3) H30+ HI (excess) 327/ :V (2:) CH3SH H §CH3 ROOR /\)r/\ [\J 2. Reactions: (12 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct relative stereochemistry, if the reaction is racemic indicate this by either drawing both enantiomers or drawing one and writing racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. ' Bf > /\ CH CH ON / \ A) O/K ____3__2__a* 0/6; O Q) CH3CHZOH Br ' Br2 (1 GQ) B> _————» M . i /\ LiBr(xs) El“ (9 aha 35: “on: 0) H2804 (cat) d4; \l/ XLCHl—‘f—h CH3 3. Vocabulary: (11 pts) Fill in the blanks with the appropriate vocabulary word. If two words are given circle the correct one. A) Generally an alk’ane I alkene ally] ystem is the most acidic due to Emmet; siuiotillabok B) All®ies with -I less substituents are more stable and are generally(electron ) ich / electron poor. C) Generally a Markovnikov addition adds so the nucleophile is‘ on the @= I less substituted side of the alkene and the two new groups are always I- never anti. D) When both new groups are added to the same face of an alkene the reaction is considered to [email protected] anti. Give an example Hgdm heroine») of oswgk§iw 0' Had E) @/ False Allyl and alkane couplings can be doublets, triplets or quartets. F) True @In 1H NMR an internal alkene is upfield of a terminal alkene. G) A Carbehe. is a six electron carbon that adds to an alkene to form cyclopropane. \ Pit- each ,5 D 4. Mechanism: (12 pts.). Show detailed reaction mechanisms for the following reaction. Include the structure of the expected products and appropriate stereochemistry for all steps. Assume all reagents are in excess. H2, Pd 5. Synthesis: (16 pts) Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. You may use any inorganic reagents you need and organic reagents of five or less carbons. U“ 6. Coupling: (4 pts). In each case indicate which proton is described A, B, C, D or none of the above. Hc‘ Hb Hd Ha R Hd A) A proton has a chemical shift of 8 5.06 ppm with the couplings J= 16 Hz (d), 3 Hz (d), and 2 Hz (t). Which is it? H 5‘ B) A proton has a chemical shift of 8 5.02 ppm with the couplings J= 10 Hz, (d), 3 Hz (d), and 1 Hz (t). Which is it? a 33 4.9% each 7. Nomenclature: (8 pts.) Provide the systematic names or structure of each of the following compounds include E/Z where relevant. Br 5- (pr i5 moAOrlet-g‘ n-9*yn \ ‘0 //‘0‘' ’1 S, d r0 e t A) 3 s 1 w 32 q 5 Br B) a I" 2- (1’- me—bwLZ-Propenyn {VClOIAePl‘G-toi 3- do low — ‘i-iSoPropy l- l-melluil -C\/clopfnl»(n¢ D) ZZ,9E-3—bromo-9—methyl-4-(‘l-methy|propyl)-undec-2,9-dien—7-yn-5-ol /\ B: o 4913 54’“ 8. Spectroscopy: (20 pts.) The unknown compound A (C13H220) gives the following proton and carbon NMR specta. Significant IR peaks were also 6“ observed. What is compound A? 3” 2H 2H 200 150 100 50 0 IR: 3313 (sharp) 3102, 2952, 2210, 165], 1210 and fingerprint cm’]. Ha=1Hk 16Hz(d),9Hz(d),6Hz(d) 111,: 1HJ=9Hz(d),3Hz(d),1Hz(d) Hc=1H,J=16Hz(d),3Hz(d),2Hz(d) Hd=1H,J=8Hz(t), 7Hz(q),6Hz(d),2Hz(d), 1 Hz(d) ...
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