Fall 2009 Test #1 key

Fall 2009 Test #1 key - Chemistry 322a Please Print Exam...

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Unformatted text preview: Chemistry 322a Please Print Exam No. 1 September 16, 2009 Key Last name KEY First four digits of USC ID First letter of last name p 0 S r Name ofTA (1MB) —— -——— (2) (20) (3) (12) —-—-— --—— (4) (10) -——- —-—- (5) (10) ——-—-— -—- Total (125) (6) (15) -—— -—-- (7) (34) —-——- —— (3) (15) —- ~— Show your answers In the exam clearly. Any other comments or even scribbles may be subject to grading and consequent loss of points. Please note that there is a scratch paper for your use in the back. Detach and use it. Do not submit. - page 2 - Last name (C) (d — _ — . . . _ . . - . — u c — - — _ _ _ _ . _ — . . . . — _ . . . . _ . . . _ . _ . . _ . . _ — . - - u — - . - — u — - - - — — - . - c - - - - . . . . _ _ . . _ . _ . . . . . . . _ . . . . . -- 2. Draw all the other reasonable resonance structures of the given molecule. If there is no possible resonance structure, say "None". Use the boxes given next to each molecule. Wrong structures will be subject to loss of points. (20 pts) 9 Am” None O (9 V©/\ ._. None ’Vs O - Page 3 - Last name 3. For the following possible acid-base reaction, answer the questions. (12 pts) (a) What are the formal charges of the marked carbon and nitrogen atoms? Circle one. o A/H CH3NH2 .40". . . _ . . . _ . c - - — — — u - - - . u . - — . c - - . . — — - . _ . _ . . . . . _ . . . . _ . - _ _ . - . . - - . . . . . c u . . - c . - - . - - . . . _ . . _ . _ _ _ - . n . . . _ . . . _ . . . -- 4. Draw the most stable conformation of 2-methyI-3-phenylbutane using a Newman projection. You can consider phenyl is bigger than methyl. (10 pts) {for 7 G “‘ l [4% Jtéa, - CH3 M" CL“ 7 30 7% H H :. “‘6 H “VJ/AL H CH3 _ «Mt/TL WM’ Ph H ’0‘“ 66‘” - page 4 - Last name 5. Draw two possible chair conformations of the following compound. Circle the more stable one. (10 pts) Me "\Me Cl NE; >r0‘0' 1 q e WEI . . . _ - . . . _ . . . . _ _ _ . . - -—---——-------——--—---—-- --——-----------—--_——-_--------—-—--—-—-----——-_--—_---- 6. Give the systematic name for the structure, or the structure for name. When applicable, use isobutyl, sec-butyl, tert-butyl, and isopropyl. (15 pts) 3—sec-butyl—2-(1—chloropropyl)-5-fluoro-5-hexene-1 ,4—diol “'1th $‘ (0 f 4-cycloheptyl~6-isobutyl-2-cyclohexen-1 -ol HO I W— 1. 3 ’1 “‘3 W 3 . . _ . - - — - . . u - - c u - . - - — - o o o ~ - — u - - . . - - _ - - - - c — - o — - — u . u . . a - - . - - . . _ . u - - . - - - . . - _ — - . . . . o — - . . _ - u — - . . - — — - . .- 7. Draw the most reasonable structure in the box given. If you think there are two possible structures, please draw only the better one. (34 pts total) a. The compound A has the molecular formula of CaHso. . The IR spectrum shows a significant peak at 3100 - 3600 cm". A This compound doesn't react under hydrogenation conditions. OH’ 7pts - Page 5 - Last name (3 O (lw~c:c~c‘ht 9r HC:C-.N ‘ 6* flz‘a b. The compound B has the molecular formula of C3H30N. The lR spectrum shows a sharp peak at 2200 cm'1 and O a significant peak at 3100 - 3600 cm“. The most notable /LNH2 peak is a very strong peak at about 1700 cm". 1% CSCLlfl C20 iopts 2%» NH c. The compound C has the molecular formula of 05H8_ The lR spectrum shows a sharp peak at 2200 cm“. /\ This compound doesn't react with a base, NaNHz. ‘i‘fiv‘ M7 Ciel-lg call-(pug 7 pts d. The compound D is an aromatic compound with the 0 molecular formula of CBHBO. This compound doesn't undergo acid-base reaction with NaOEt. however it reacts readily with another base, 9: 10 pts 8. Outline 3 synthesis of F from E, G, and H as carbon sources. You may utilize other reagents such as acids, bases, and other reagents. (16 pts) F E H 9 NH2 '\/\/\3, NH 9 I _ 2 z ¢ P“ CCU Br Br Br Br ...
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Fall 2009 Test #1 key - Chemistry 322a Please Print Exam...

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