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118BWin08MT1Key - 1 Reactions(20 pts Draw the structure of...

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Unformatted text preview: 1. Reactions: (20 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemishy, 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’. Br (Cl'lsksoo'K+ /\ A) Y\ (CH3)3COH j \ B) * * i1)mCPBA(1eq) 0” fl“ 2) H3O+ (excess) CH2N2 CH! C) W chemig hv 1 H 0A ,HO ’4 2) NaBH4, NaOH, H20 5 CH3 H mum} c Pd/C ' \/ E) CtlsC/HZCHZCHZClg 2 LifilS EON/i4 2. Reactions: (12 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistiy, 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’. fl A) /J\/ HCI ' M HBr, ROOR W3 B I“ ' H / 1)Na NH *2 / ’ 3 Ar 2) H20 ,l L! (3)3 eat all 3. Vocabulary: (8 pts) Fill in the blanks with the appropriate vocabulary word. If two words are given circle the correct one. + \ A) A cis [@kene is more stable. .\. \ B) A Markovnikov addition adds the nucleophile to the m0 l Q substituted carbon. 4- Z C) There are three pieces of information we can get from mass spectrometry, list two of them: »%m\ul0\ &O~%m9n\fl\lm ' {Soirng + l D) If we add H+ to an alkene with no extra nucleophile present we’ll get a fish; m e r . ‘l' l E) A carbocation is most stable on a primary / secondary / @carbon. + 3 F) The pKa ofan alkyne is [email protected] / 44 / so. + \ G) A major problem with mechanisms that involve a carbocation is TQQMH¥ mgnl of the cation. Mrs 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. ' Wk Bra CH3OH ® CH 6H \)\ {gr-[Er 2::1’ “U “M (D Rte x anh': (D D , 1 67h Sttfeockem=© reca.locl+ma-Palltclc=® (Lays 5. Synthesis: (12 pts) Show how you would cany out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. 6. Coupling: (4 pts). In each case indicate which proton is described A, B, C, D or none of the above. Hc Hb Hd72h_< Ha RHd A) A proton has a chemical shift of 6 5.7 ppm. It forms a doubled tripled doublet with the\3 couplings J= 16Hz (d), 7 Hz (t), and 6 Hz (d). Which is it? C 2, P B) A proton has a chemical shift of 5 4.9 ppm. It forms a doubled doubled triplet with the couplings J= 16 Hz, (d), 2 Hz (d), and 1 Hz (t). Which is it? A Z ho Pol filial. NCAA"- 7. Nomenclature: (8 pts.) Provide the systematic names or structure of each of the following compounds include E/Z Where relevant. Br OH l A) 1W (312-) ~8browoiem'7-eh-I’Yn'q—di Cl Cl .. (waif \ni I .. - .. - B) MQE) q, C o auntie“ z en 9 ym ‘ 3 s 7 \w ” Br C) \(L H-iommovi—ei‘kyi'Z'meikyicx/ciohex-ivtm D) 2E,52—6-bromo—4-ethyl-3,5-dimethylocta-2,5-diene \ \ unis @3ch -\ ~¥or may” 8‘“ wbi‘ht“ 6 8. Spectroscopy: (20 pts.) The unknown compound A (CwHMOz) gives the following proton and carbon NMR spectra. Significant IR peaks were also observed. What is compound A? 2H 3H , 1H 1H 6 HA “8 5 4 I 3 Hz, 2 1 200 150 100 50 0 IR: 3100,2950, 2210,1730,1630 and fingerprint cm"; HA: m 5: q Hz (A) ’ W: (q) DEE“ H Zpts HQ : m 3': 00,03,701“) AWQN = 7. {a}: ' Hc : 3H: 757%“) .IHzloU Co‘s aflkew : 3,3‘3 (2+0 - - ’r /\ 0 CH3 uH [P $\/\o/“\é\ 1J3” [email protected]@HH+I) or ZOEA3 M K/‘f/VO‘DA 0000: @ 0 how vMASMch/u ’Pieces = Wfls 15‘9"- Camacho” “News (we. _ , ‘ Nuchflto‘mwn Wan" C:C -' Pk \iiomd‘ 3‘; no shudzre PmP‘A’7 Ia PM L83 SCQWCL ...
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