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Nasiri_118C_MT2_S10

Nasiri_118C_MT2_S10 - Second Examination Chemistry...

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Unformatted text preview: Second Examination Chemistry 118C May 19, 2010 (Closed book, no models) Name (Please print) Last First Middle initial Last 4 digits of Students ID Number: Circle Your Section Section TA Section TA Section TA 1 Patrick Rogers . 7 Devin McNaIly 14 Shengmao Mu 2 HOW DEVISW a Shai|ise Ross 15 Prasad Gawande 3 Jessica Hoch 9 Shengmao Mu 16 Weifeng Lin 4 Devin McNalIy 10 Patrick Roger 17 Justin Culbertson 5 Shailise Ross 12 prasad Gawande 19 Holly Davison ‘ 6 Joseph Badillo 13 Weifeng Lin 20 Justin Culbertson BRO Binh 080 I) 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. 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. II H IIIIIIIIE Li Be B C N F II Na M_ Al Si P S Cl III K Ca Ga Ge As Se Br IIIIIIIII Rb Sr In Sn Sb Te I — EH 4 m— -- e 1 N 18 Ar 35 Kr U1 3 e >< Spring 2010 118C Exam 1 Page 2 of6 4 digits 1D 1. (12 pts) Give the name or draw the structure as appropriate for the following: 1. N-cyclohexylbenzylamine 2. Ethyl 2-isopropyl-3-oxopentanoate 3- V :1 II. (5 pts) Rank the following molecules in decreasing order of basicity. H N A B C D E Most basic Basicity Scale Least basic III. (5 pts) Rank the following molecules in decreasing order of acidity. \io/ M Hi/ \/l?\T/ M A B C D E ? Most Acidic Acidity Scale Least Acidic Spring 2010 118C Exam 1 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, HC1,°C 2. NaCN 3. H3O“, heat I. CH3I (excess) " 0“” 2. ' NH2 @ 2. AgZO, H20, heat 1, < NH HID 3' O 6) 2.NaBH3CN 3.1130+ 1.NaCr0,HSO,HO 4' HO OH 2 2 7 2 4 2 2. C heat 5 CH3(2 Equiv) 1. CH3Li ZEquiv.) - O o 2' \Jko/ 3. H3o+ H300 3. H30+, heat 7 mm 1 . NaCN OzN N02 2. CH3MgBr 3. H3O+ 0 o 1. NaOCHa /\ 8. Womb 2. / c025: 3. Hgo”, heat CH20H 1. Mno2 9' O 2. CH3NH2, A ,HCl Spring 2010 118C Exam 1 Page 4 of6 4 digits ID V. (12 pts) Show detailed mechanism for the following reaction. N"'2 N20: (:1 HNOZ, HCl, °c I VI. (6 Pts) Write the product of the following reaction. Also show the detailed mechanism for the reaction. 0 O O MOH heat A Spring 2010 118C Exam 1 Page 5 ol’6 4 digits ID 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 GM N02 HO Bl’ b. Q _..._.____._... ‘5 Spring 2010 1 18C Exam 1 Page 6 of6 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: C12H1aBr03 ...
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