322B Exam 1 Fall 2006

322B Exam 1 Fall 2006 - _ Professor T.E. Hogen-Esch Sept....

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Unformatted text preview: _ Professor T.E. Hogen-Esch Sept. 11, Fall 2006 Chem 322b First Progress Test Initial of Family Name / Name: [I\ TA: Lab Time: 1. (10) 2. (10) 3. (10) 4. (20) 5. (30) 6. (20) Total (100) ' 1. (10) Name the following: 3 ‘7‘ 3 >—/OK__ 00H Br N02 Memm..&-g§% .. na‘éa/flW-é fimm 2. (10) Indicate which of the following is aromatic (A), anti-aromatic (AA) or non—aromatic (N): Q Q U C3 Q £35 (1%) (N) (NH) (:4) (H) 3. (10) Write all reasonable resonance structures of: l w A [70571 (2 _ '5 . a- we» b- Q's-@7902 co 6 .3 c. , <i>—CH2 NON£ 4. (20) Write the reaction mechanisms (all intermediates, including formal charges, curved arrows): fi’ 3 ‘4 t I + I; UV or Br 2 ——> i ROOR + + HBr “844.61% / Br b + ‘ —6rf'6r~ ' @B‘Lr + (CH3)2CO—> H3O » (CH3)3COH (7“ W‘s/C”? / Ln“ 0? \3 Cd; WVJ CH3 \ / t—r- /C\ CH3 We _ H\+ 0% 3 “(he 5. (30) Give the predominant reaction products, including stereochemistry where appropriate. If no reaction occurs write “no rxn”. a. CH30HZMgBr + HcECCH3 C2 H5- b. Ho+ ' _ - 2CH3Ci-12MgBr + 0002043 _, 3 , Oiglllleb O M .{ . _ -i 0+ 1% 04”“ M‘ “f” CI CH30H2'VlgBr + CI-gCHO —>2)H3—> Cflgch’zi CH3 0“ 3) P00 0 d. + ’ ‘ CH30H2MgBr + W __>2)_H3O, C143 CHZCfiZCOz/f O 3)HZCrO4 M 8' Q + CHsCHQMgBr —> <\ 27 17C; cage/3) i. WN—Ba 03$; Q< A tWO products 1 Z N fl “4/, 1)Mg,EtO . ~ , j. Hzc=CHCHZBr m—02> Hzcz<yCH2D 2 6. (20) £QA CECCH from a. Synthesize <:>< 3 <:>—OH and propyne (HCECCHS) OH as the only carbon sources and any other needed reagents. 0, OH jig”; w o 4. (43 CECH f7" 34:5 CH3 CECWQ’; b. Synthesize and any needed dienoph‘ile as the only carbon sources. H / from D ...
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322B Exam 1 Fall 2006 - _ Professor T.E. Hogen-Esch Sept....

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