Exam_2_Fall_2005_Weber

Exam_2_Fall_2005_Weber - Organic Chemistry 322 bL Fall...

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Unformatted text preview: Organic Chemistry 322 bL Fall Session 2005 Exam 2 Monday, October 10, 2005 Name C Vill‘mg Initial of Last Name [I T.A.’s Name 1. (32 pts) 2. (16 pts) 3 (10 pts) 4 (16 pts) 5 (16 pts) 6. (10 pts) Total (pts) 1. Write the product(s) of the following reactions.. (32 pts.) CH3 \ o C=O b. g I AICI + O —» N0 W o Zn/Hg C. —> ‘\ W “C'A ’ 1/ /CH3 \AN/Qg HN ' d' excess Brz, (A, R EV H20 l / (31/ CF3 e. Br2 ca F eBr3 8/ f. E: LI A \ EtNH2, EtOH \ O 9 g. A mild H30 5 __—’Hzo L c. UAH <o+>3 /\/"\\H h. Eth -78°C ‘ O N 02N L _ O " O—LCI EtZO -730' O'EV i ,7 O N/WPH l~£Q( A /g f“ Ph-NH-NH ' H - H ——————2—> _ V l- C 20 3 weak H99 m e e ’ - Ph3P—CH2 /‘ » . 3 ,_.- 1k . ,._» o ———+Et20 $01; 0 \w‘F‘ MC, l/ flk~C “6&3 fi 0 n. C\/ CF3—COSH 1, “ /o/§;V 01- %‘ E J -o O O O LDA i ———> p. -40°C stoichiometric 1’ 2. A large excess of a 1:1 molar mixture of benzene and hexadeuterio-benzene reacts with a limited amount of HNO3 and H2804. Write the product(s) of this reaction. What is the ratio of these product(s)? Draw a diagram in which free energy is the vertical axis and the progress of this reaction is the horizontal axis. Be certain to label starting material(s), product(s), transition states, intermediate(s) and energy of activation, if appropriate, on this diagram. (16 pts.) Kits, 4 W V @/@D H / ‘D b \ 3 1’13“ 9&3 LC s . / ‘(wke/Heclfzk V~ (CI-flax 19 l jaw/(9 cg} V’Czck‘icv‘ 3. Write the structure of the intermediates involved in these reactions which account for the regiochemistry observed. (10 pts.) 0 || 4. Given aniline, acetic anhydride, (CHa-CZO and any inorganic reageants you need, prepare isomerically pure ortho—bromo aniline.‘ (16 pts.) . O NHL V Nwfiu‘ ii i. /,-\ t kn j. é M530” MI'Q‘UQ » G K/ P C 2(1 C ’———-? gr 4‘ ii U A (0x (S O VeVvaich 5_ Given ethyl bromide, ethyl alcohol, and ethylene glycol as well as any inorganic reagents you need. (16 pts.) 002Et Prepare: O OH 0 , / ' ,_ do ,glk d) 960" é \ r—————-—» 0,, ”. C LCF H8 c 1 Li“; ‘ at, r «dim . ‘ Ll"’Cl «w r. is is i» is all.“ (2 Q, ~/ I: r, «ii/v / if z a” \ ‘ lj/\ QC Ht G 6. Given 0/ and any inorganic reagents you need 0 P . (10 pts.) repare. C_CH3 HG - . / Po” ‘1’ . x (3/ ' :3 H‘OH 0L (Li/L; 3043 j GHQ ck 6 O. A 14g ...
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Exam_2_Fall_2005_Weber - Organic Chemistry 322 bL Fall...

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