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118BSpr08MT1Key - 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 stereochemisn’y, 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’. .J" *A’ U ”0‘“ LL w 2) Zn, CHSCOOH W B) Br2 ’u .3 \ED 'CCH3OH Cflgfidi (”mic O l C) \/Hg(OAc)2 H20 JV + /\/u\ HBr 3" _ + 7 E) CHSO Na / szk gr I‘cSDnabIL CI CHSOH on“ “may 1) LDA 2) CHSCHQCH2CI Ms\ 2. Reactions: (12 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemisny, 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’. 0504(cat) A) \ H202 cl cl B) CHCl3 / /\/\ /'°”/C \v’u (uremic) 50H3)3co-K+ l> C) é Lindlars Catalyst q)\ H21pl’X F0? 41/ \H 3. Vocabulary: (10 pts) F111 in the blanks with the appropriate vocabulary word If Mk3 two words are given circle the correct one. A) fight men are large molecules made up of many repeating pieces. Examples are plastics and DNA. B) mCPBA will tend to react fastest witlgctr‘on ri / electron poor alkenes C) In an anti Markovnikov reaction the nucleophile tends to add to the l 936 substituted carbon. D) All a lkene will / v. react in a Birch Reduction. E) A terminal /@m alkene is more stable because of extra \N \l g? VCOO $15ng 1:) or the following an .alkene / alkane is the best acid. G) Dehydration is not preferred for synthesrs of alcohols because it tends to undergo at! “)5 z and does not have defined syn / anti stereochemistry. H) In a Saytzev elimination t e mor / less substituted alkene is formed by using a U K“ {El base. 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. V E r ' C s VIC“ V© \,,c4 44/ \C‘“ H ‘- © q S Pol -'3 ii: Syn add; no"! 511444 and CmefoJlSO. Can‘eof 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. You may use any inorganic reagents you need and organic reagents of four or less carbons. Br ' Wgr BrH sage (It 6. Coupling: (4 pts). In each case indicéte 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 6 1.3 ppm. It forms a doubled tripled triplet with the couplings J: 10 Hz (d), 9 Hz (t), and 8 Hz (t). Which is it? Dong B) A proton has a chemical shift of 6 4.7 ppm. It forms a doubled doubled triplet with the couplings J: 8 Hz, (d), 3 Hz (01), and 2 Hz (t). Which is it? 7. Nomenclature: (8 pts.) Provide the systematic names or structure of each of the following compounds include E/Z Where relevant. OH A) 2 -Z,‘l ml; {SaPn‘h/l-CYCiO purl—2:9. —I~ol Cl Br \ // Z.“ 3-5romr-‘Qflwltchlam elm: «3 -Qn J‘s/K B) Cl C) 1 E,62-1,2-dibromo-7-methyl-nona-1,6—dien-8—3énr-4-ol 4% w “3 OH D ) BrW Br admins; 25,52: ngdhomoc‘m- ZS'DiiCn 4+0! 8. Spectroscopy: (20 pts.) The unknown compound A (Cd-1140) gives the following proton and carbon NMR spectra. Significant IR peaks were also observed. What is compound A? \ H [H 200 p 150 100 50 0 IR: 3300 (sharp), 3100, 2950, 2210, 1630, 1210 and fingerprint cm']. H,=1HJ=3Hz(d),2Hz(t),1Hz(t) Hb=1HJ=3Hz(d),2.5Hz(t),1.5Hz(t) Hc= 2HJ= 7112(t)2Hz(d),1.5Hz(d) =2H,=.] 6Hz(t),25Hz(d),1Hz(d) 02%;: UHSa+= 3 z) \\ Cr. 7. © Mi/VO\CH3 CEC'H 2.+1=)@ H’ ‘H 2091: Q:C. H 2 C:C:H 2+! ?l€ce3 MUS)“ 103M 1 M CHi/c:c\’: 3 +1 © 1" ‘Je. Scored c ”a :4: ”052mm uswriiie OCH‘; 0136 11“} ”51105818490" ’WISQ Maitojflbul-ere My a 0cml ® 0" “2 Speck Can be scared pieces:— IQPIS Ccmreoi~ Siwciwc -7 lé-W ,) 2—113 ...
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