Nasiri_118C_MT2_S10_KEY

Nasiri_118C_MT2_S10_KEY - ination Chemistry 118C ‘ models...

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Unformatted text preview: ination Chemistry 118C May 19, 2010 ‘ models) V Name E \ (Please print) Last First Middle initial Last 4 digits of Students ID Number: section «"0" TA Section TA . Section TA 1 Patrick Rogers 7 Devin McNaHy 14 Shengmao Mu 2 Holly Davison 8 Shamse Ross 15 Prasad Gawande 3 Jessica Hoch 9 Shengmao Mu 16 Weifeng Lin 4 Devin McNally 10 patrick Roger 17 Justin Culbertson ' 5 Shai'lse R035 12 Prasad Gawande 19 HOW Dawson 6 Joseph Badillo 13 Weifeng Lin 20 Justin Culbertson BRO 1) This exam consists of 6 pages (including this page) and 8 questions. 2) Do not turn the pages until instructed. 3) Turn in your exam with your ID to your TA after 50 minutes. Binh Dec 4) Put your 4 digits ID in the upper right corner of the next 4 pages. Be sure you have pages 2—6. 5) Please answer clearly in the spaces provided. Back of the pages are only for scratch work. 6) Any request for regrading should be done according to the TA’s instruction. Spring'ZOlO 1 18C Exam Page 2 of6 4 digits ID I. (12 pts) Give the name or draw the structure as appropriate for the following: 1. chyclohexylbenzylamine ©/\ NHO g o o 2. Ethyl 2-lsopropyl-3-oxopentanoate we“ 3 Br OH 3-Bromo—5-ethylphenol 4. WON » 3-Chloro-4-phenylbutanénitrile Cl II. (5 pts) Rank the following molecules in decreasing order of basicity. O H l /\/N O /\/L NH2 \ NH2 U NHZ A B c D E B>E>A>C>D Most basic Basicity Scale Least basic III. (5 pts) Rank the following molecules in decreasing order of acidity. \io/ M Hj\/ \iN/ U A B C D E B>E>C>A>D Most Acidic Acidity Scale Least Acidic Spring 2010 118C Exam Page 3 of6 4 digits ID IV. (36 pts) Provide the structure(s) of the expected major organic product(s). Unless mentioned otherwise, you can assume that all reagents are present in one mole. Show stereochemistry where needed and write NR if there is no reaction. 1. NaNOz, HCI, °c 0002” 2. NaCN 3. H30+, heat 1 . CH3I (excess) - 0”” 2. NH; 2. AgZO, H20, heat 60> - HO—QOH l l.< NH 2. NaBH3CN 3. 1'13'0+ 3. 1. Nazcr207, H2804, H20 2. C heat 5 OCHMZ EquiV-l 1. CH3Li 2 Equiv.) ' O 2' \JLO/ 3. H30+ 1. NaOCH3 2. CH3I"‘—"” 3. H30+, heat 7 gel 1 . NaCN OZN N02- 2- CHzMgBr 3. H30+ 4 OCH3 O H3CO 3. H30+, heat CHZOH 1. Mno2 9' O 2. CH3NH2, )J\ ,HCl Spring 2010 1 18C Exam Page 4 of 6 4 digits ID V. (12 pts) Show detailed mechanism for the following reaction. NHZ NZCI © HNOZ, HC1,°C 1 pt/ ea arrow VI. (6 'Pts) Write the product of the following reaction. Also show the detailed mechanism for the reaction. 0 o O MOH heat )K H\ OH O 53:02 €02 + k ‘17.: A O . 3 pts Spring 2010 118C Exam Page 5 of6 4 digits ID i VII. (14 pts) Show how you would carry out the following transformations in high yield. In addition to the reactants, you may use any organic, and inorganic reagents. You don't need to show the mechanism, just write the steps in order you do the reactions. Only steps productive toward synthesis of the target product would recieve partial credits. OH a. @0013 ©/\/ heat zpts HI 2 t or p 5 H2, PdC 0V 2 t 0H 1)OH‘ p S O 2) WBr (any reasonable halide) 2 pts N02 HO Br b- o ——» U Brz, FeBr3, or PBr3 2 pts 1) Sn, HCl (any reasonable reducing agent) BTUNOZ or H2, 2 pts 2) NaNOz, sto4 (HCl), 0 0C 1 pt 3) H20, H+, heat 1 . Spring 2010 118C Exam Page 6 of 6 4 digits ID VIII. (10 pts) Deduce a reasonable structure using information given below. IR Spectrum: Strong absorption bands at 3100 cm", 2950 cm", 1735 cm" , and 1650 cm“ Chemical Formula: C12H13Br03 260 j, 150 iéo fi 10 10 1o 80 60 4o 20 n PPM Spring 2010 118C Exam Page 6 of 6 4 digits ID VIII. (10 pts) Deduce a reasonable structure using information given below. IR Spectrum: Strong absorption bands at 3100 cm“, 2950 cm", 1735 cm" , and 1650 cm" Chemical Formula: C12H138r03 ,y '2or1é0r1éo r140‘1éor160 rabfi 617' 40 ' 20 PPM Br © 0 10pts @ \69 o o ...
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