118bwin08prfinalkey

118bwin08prfinalkey - l. (24 pts). Draw the structure of...

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Unformatted text preview: l. (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. Clz Cl A) / ‘ A . /\‘/\ H20 m («mural c) ' o 1) BH K“ B) O/\ 2 \\ H 2) H202, H20, NaOH n HBr (1 eq) 7 \ c) N 0°C ‘ //\/ Br . 0 OH ' 1)/\HLC' ,AICI3(1.Seq) 0H D) Cl 2) H30+ \ 3) Pd/C, H2 ‘ o E) CF3C03H (0Y0 2. (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. d- H0013 G) / W (CH3)SCO'K+ \ Na, NH3 M H) \ / l H Br c: ’ 15\r l3.- )\/ 7 / \ I) —‘_—’ x \ + \ J AIC|3 (cat) , \A\ /\/lCJ)\ CH3CH20H (2 eq) OCHZCH3 J) H o /\/\\ ZS 4 Oculctt3 NH2NH2, NaOH K) W W 0 heat 0 O 1 ) (CH30H2)QCUU “v L) ‘ \/ 2) (CH3)ZCHCHZBr . . r OLC 21m C 3 L2‘ eat/L1 3. (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless othewvise noted. If no reaction occurs, state ‘No Reaction’. w M M ROOR 3" z u NC heat " E N) + —" gm 5 NC / ._. .= = cu / N02 : “Hz 8 1) Zn(Hg) HCI Var n “ \ O) 2) Br2, FeBrS / Pat H P) /Y\ ————+ , ‘ O - o o \ 6 fi/ CH30H20'Na+ + I Q) CH3CH20H \ heat [5 4 \ / O N N R) H/U\(\ L, \ 4. (30 pts). Show the detailed reaction mechanism for each of the following reactions. Include the structure of the expected products and all relevant resonance structures. O 1)NaOH(cat.) H o A) 2) \/u\ _ H added slowly ® 3) heat 0 u a, \5 06 \ - MK H 3:9 I \Hé—a» \'//‘~H +HZO 9%“ H 9“ Q) i: Ox 0 ‘\ __, E ‘(L9 “'5’ g ‘ H e H o H OH L‘?‘ o o {3) l *1, 39H 03 to” Cpl/w "e Qua/“Lye {-1120 B) \K\ “2 Pd/C “‘44 H H Mn:CL=—:)c.fi’ .2 I M a PA 25’ -—a Pd e‘ Vé\ €ng Mfi\ ‘3 /CH3 ‘ gchfl a—a (1)21, c :c-H: Cu: w l *4 IA 5. (20 pts). Show how you would carry out the following synthesis. Include the reagents you would need for each step and the intermediate products formed in each step. ‘ I\/\/\OH ' H 1) /\$9 209 73 H30+ /’\\ \\ \/\/\°H l l’cc. maul /\\ ' o :3 LDA \\\/\J‘ N A\ ° \ H 2) cHscnlu ‘5’ kn 6. (12 pts.). Circle the aromatic compounds below. Uni) ES O \ 313VS {ac/L3 «1 Fe! {YR 7. (12 pts.) For each of the following compounds indicate the primary site for electrophilic aromatic substitution with an arrow. is each 3? no Br ORA-1'}— OZN N (:1 F30 3 0“ H2N W 0 CN T 0“ A B C D 8. (18 pts.). Give the proper (IUPAC) chemical name or draw the structure of each of the following compounds. WH - (0,611”. -g I‘me‘h‘V’ nbnt’3’7. A) \ \ - dien—I-ywz. Cl OH QE‘ S-cHoro-2-mefkq|octu-(o-en-3'o\ B) M 0H 1' \ j S / C) 4-ethenyl-3-ethynyI-2-methylphenoI D) \ I” zE-‘T-bromooc‘t'Z’en'V‘Oflfi o B H 0 CI z—cmm , 4-mew benzamhyuh E) or Z'CHoro — ‘I-mehwl benzm “#94qu o o Z-eh‘ytfl-meikql ~§-o><o ’ocfinql 39% eack q, (36 pts.) The unknown compoumi A (C15H2902) gives the following proton and carbon NMR specta. Significant IR peaks were also observed. Compound B forms after reacting compound A with an excess of CllgCHzLi followed by H30+. What are compounds A and B? / 3“ R5 1m 2” 2,“ 2H 200 150 100 50 0 IR: v 3100, 3059, 2950, 1730, 1210, 800, 700 6111'}. HA=IHJ=3Hz(d),2I—rz(q) HB=1HJ=3Hz(d),1Hz(q) Hc=3HJ=2Hz(d),1Hz(d) °\ '3“ \ \ Com Pouncl A * -\\/ Ell; We) 0 CH3 0‘4 ComPOUNX B ...
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This note was uploaded on 08/18/2008 for the course CHEM 118b taught by Professor Lievens during the Winter '08 term at UC Davis.

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118bwin08prfinalkey - l. (24 pts). Draw the structure of...

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