oc2 - Chem 118 C Summer Session I 2006 Second Midterm...

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Unformatted text preview: Chem 118 C Summer Session I / 2006 Second Midterm July 25, 2006 Instructor:Nambiar This exam contains six pages and six problems. Please make sure that your copy contains all the six pages. If there is a problem, please let us know before you start answering. Please answer all questions. I. (40 pts). Draw the structure of the expected organic product (5) formed in the following reactions. Unless mentioned otherwise, you can assume that all reagents are present in excess. If no reaction occurs, write "No Reaction". 1) @NH2 1. NaN02 / HCl / 0°C ___.__——————- 0 2. CuCN / 50°C 0 1. CH3I 2) Q [a «841:3 CH3 2. AgzO / H20 / A p - KMnO4 / NaOH / A - ~— 3) @—CH2CH2CH3 .0 + CH2CH2CH3 l. Br2 / hV 4) ———————-—-—F" 2. NaOCH(CH3)2 / A OH (RCO)2O (1 eq) / A 5) ' . I ' N(CH3)2 CH3Li 6) C2H5NH2 ‘ «5 1. Li OH 2. C02 (\I 3. CH3OH / H+/A s) >/s 1. n-BuLi R 2. R'CHO 3. HgClz, H20 / A 1. NaOCH3 _____————-———. 2. CH2=CH-CO—CH3 v , , 6C(CWC"‘3)} M 9) CH2(COOCH3)2 C3 Ho? ~ 10) CH3CH=CH-O—CH2CH=CH2 H .40 A a” \i J / J II.(20 pts) Show detailed reaction mechanisms for the following, showing the structure of the expected products.. 0 H+ 1. i: + CHzO + NHRz "V “22? W a if 'll\ A 3393 3” gas I; fig}? ? “Va—e 5' v a' (ZN/k} f p . 1+ . 11‘ 7° 01* 4/65. aka/(L " re/flk Iflfl a? lye: ~r H520 J? Mg J t III. (28 pts). Show how you would carry out the following transformations showing the reagents you would use in each step and the structure of the intermediate products formed. OCOC6H5 1. OH H OR 13H COC6H5 % l Kata-‘10? ’ M I I \ ll; / t ,4, .27 it}??? ~37 16;? m A pH garcbté A62qu 65 IL O k\ {L JKaflfio? W a ; e— W 6/. Amt? It 9 0 2 @CHgOH @4H2—CH2—NH~CO—C6H5 \L, 06513 aw, Tawfif at Wig“ MSW @fiéwfl’fi ML 6* 2 O OH l 5‘ OCHz—G A) 9' 6" /' @flHzCHzCHg t l ., IV. (15 pts) Provide a systematic name or draw the structure as appropriate for the following compounds. 2. CH3COCH2COOC6H5 V. O? 3. @CHz-CHz-CHz-N(CH3)2 My {V 23 1‘ W J (PM OH OH NH C OCH 3 NH2 © (Cb @ CH3NH2 (CH3)2NH 1&02 A B C D E F F7)? E> C> «4-) Basicity Scale 6 Low High VI. (16 pts).Compound A (C13H17N02) gave the following proton NMR spectrum. Deduce the structure of compound A. What is the product you expect to get when compound A is heated with sodium hydroxide in water? . ...
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