CHEM322b - Exam 2 (2005, Fall)

CHEM322b - Exam 2 (2005, Fall) - Organic Chemistry 322 bL 5...

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Unformatted text preview: Organic Chemistry 322 bL 5 % 76h Fall Session 2005 (A, 6 Exam 2 Monday, October10, 2005 0 6 g M L Name Initial of Last Name D 1. Write the product(s) of the following reactions. (32 pts.) a O + /\ __O._> HF CH3 \ C=O O b. 9; \CI AICIa + 0 Zn / Hg c ———-——> HCI A /C H3 d' HN excess 3’2 , CF3 e Br2 FeBr3 OCH3 1‘. Li .___—___> A EtNHQ, EtOH 63 g. A mild H30 0 C. UAH(o+-)3 h. EtQO -78°C OQN O . EtQCuLi I. ___—> O‘C-CI Etgo -78° H3 HCN j. _—_—> 0 cat. base 0 fl H HO C CH Ph-NH-NH CH —CH 2 l- 2 3 weakHe @ 6 m. Ph3P—CH2 O _______——> EtQO O E I —————-> n . o o e 0. Ph— -H+CH3-CH2- H —2H——> o LDA :1 -4o°c stoichiometric 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.) 3. Write the structure of the intermediates involved in these reactions which account for the regiochemistry observed. (10 pts.) 0 II) 4. Given aniline, acetic anhydride, (CHs-C 20 and any inorganic reageants you need, prepare isomerically pure ortho—bromo aniline. (16 pts.) 5_ Given ethyl bromide, ethyl alcohol, and ethylene glycol as well as any inorganic reagents you need. (16 pts.) COgEt Prepare: O OH 6. Given 0/ and any inorganic reagents you need 0 Prepare: ¥;_CH3 (10 pts.) 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 @[email protected] 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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This note was uploaded on 03/15/2012 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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CHEM322b - Exam 2 (2005, Fall) - Organic Chemistry 322 bL 5...

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