mid2 - Chemistry 118 C Fall 2006 Second Midterm Wed....

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Unformatted text preview: Chemistry 118 C Fall 2006 Second Midterm Wed. November 15, 2006 Instructor: Lievens This exam contains seven (7) pages and six (6) problems. Please make sure that your copy contains all seven pages. If there is a problem, please tell the exam administrator prior to beginning. Please answer all questions. Remember that UCDavis Code of Academic Conduct applies to this exam and all other graded work in this class. Name: Last First MI Student ID. # T.A./ Lab Section: l. (40 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. 1) CH3I, A) 2) A920, H20 u REC / \Cfig NaNOz, HCl B) /\N/ /\ N '/ H H20, 0°C A, \U a \1/ Cl hv, CI2 (2 eq) C) . L3,) CI D) N02 0 O O NaOCH3 (cat) A E) 00:3 flow" HOCH3 ' ll Continued. Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. \1 1. o A F) o 1) NH(CH3)2, CH2=O, HCI G) 2) NaHCOS, H20 O 1) NaOCH3, HOCH3 _. , H) 2 eq W/kOCHS N R 2) H30“, H20 C2 0 1“(2003 // , 2) BrCH2CH(CH3)CH20H3 \M’ 4." I) NH 9 3) NH2NH2 r \ H o i l ' . CI 1) KOH, H20, /@\ A/orl J) © 340°C,150atm 4‘ 2) H30+, H2O 2 C I ) UC (ill/(Li « [x W a t . (:1 (I) ngwm 44km guard + Hg-vmzo gt? Haggog 6E2 - ti? H a + N530 /> {r we Z .' V , t??/M»Q, , ./ ‘41 . Mb: nllrusyl u " “"5 7 1‘ f“? ,4) , ‘ W?) l? ' ' A v . v “@xfi @Nzw mow 2s 4K \l / N W 53‘ 2. (10 pts.). Show detailed reaction mechanisms for the following reaction. Include the structure of the expected products. NH2 1) NaNOz, HCl, 0°C 3. (14 pts) Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. 4. (8 pts). Rank the following compounds in decreasing order of acidity. NH OH OH 2 CH3 02N No2 OH OH No2 CH3CH20H CH3CH2NH2 N02 N02 A B C F G D E H E>H>BVF>D7A>é>c Moderately Acidic Poorly Acidic Highly Acidic 5. (8 pts.) Provide the systematic names or structure of each of the following compounds. OH , .. R 7 - L‘l"6\vm\flo ' bromc »P)'I€f\ol A) Br NH 2'. 1° l B) N,N-dimethyI-z-amino-5-phenyI-pentanoic acid H 0/ \/ ’V 3/] , /'7\ H35 CH3 J 'Z-Cl/xl rr M llw/l C) . a“), , 4; N- will anvlti’W/Il’bvl‘anamine O 5» rim—el/lxxfl ~ (2/ ‘Plnmo‘fl/ * lW€Xfifla m: (Le 6. (20 pts.) The unknown compound A (C13H1703N) gives the following proton and carbon NMR spectra. Significant IR peaks were also observed. ‘ IR: 3350 (broad), 3010, 2950, 1810, 1790, and fingerprint. What is compound A? o/d F0 €97 ‘ 6&qu ' Ifiewal CJW EPSF CHfiHB 39* . main 1““in 13?“ wimQ Comyamt’z ZO‘Pt Y OQOfl (i Am hyéihclz; 353’!” N ~H Wei”, 7 ...
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This note was uploaded on 05/08/2008 for the course CHEM 118C taught by Professor Xichen during the Fall '08 term at UC Davis.

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mid2 - Chemistry 118 C Fall 2006 Second Midterm Wed....

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