Chem%20118C%20SSI%202011%20Mid%201%20key

Chem%20118C%20SSI%202011%20Mid%201%20key - Mtg/mm 1 I. (30...

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Unformatted text preview: Mtg/mm 1 I. (30 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Unless mentiOnecl otherwise, you can assume that all reagents are present in excess. If no reaction occurs, write "No Reaction". 1.C6H5MgBl‘ _+ 1) CH3COOH _ CW + y 0+! l.CH3MgBr(1 equivalent) £5 H 0 C3 2) RCHgCOOCI—h IQ “0”; '0 mell 2. Hungom deg 4' cl 0 KOI-l 3) { \o WWI? H20l250C 4) C(jHfi-CO-NHZ A. 1.KCN _ / 5) R-CHgl _ Q—C “fag; qu/H 2.LiAll—I_t w 6)CH3CH2CH3CN l.H+Il-[20KA d, 9 H 2.1mm ‘63’ o 1. LiAlH4 9H 7) L‘NH ! , \ H 2. H+f H30 _ p H 0 NaOHngOXA M 3) —-—o- 9/4. H RLi C: H _. —-tl/l-l + R 9)CH3—CO-NH2 ______.._ a 1. [(CH3)2CH-CH2I2A1H pf! 10) R-COOCH3 R*W 4’ 0% 2.H+!H20 [I.(20 pts) Show detailed mechanisms for the following reactions, showing the structure of the expected products. 1. 1. KCN e) R-CHgBr g$3.0 2. KOHIHQOXA __ C9 3/ f— H (V _ A" elk-33" 4? 4*6151-335“: A” 6&4 H ‘17? 90+! GD __-.~ :2.— 2W” - _ ._ fi-A-CH 4412*“ 51 <1 ’0‘ we glwaf" 5L 5 Hit-5x” “‘“figfl (k-@fi§h__ lfifiik r47 fl’efifi“ g '1‘ W6]; — 67 \> 19+ij 7 —--' éfiHjCOCH3 + CHgO + RzNH may $63110 c“ a- III. (18 pts). Show how you would carry out the following transformations showing the reagents you would use in each step and the structure of the intermediate products formed. 1. RCOBr RCHgCONHCHgCI-h agglqu u) - wt” (fl 3‘ PM '1 5‘ r—v ‘3 a) Gide. she: 2. CH3CH20H FCH3CH2NHCOC6H5 toes egcw l 9W0/ l 0/an; t _. v M Mu CH’W Wa— glfiwiflé a) #40 3. CHg-COOH ,_ CH3~§H-CH3 151$ " :7 g—MO/ elseth 01%un /0 ' I 05050 t) 3 IV (8 pts) Rank the following compounds in the decreasing order of acidity. COOH COOH COOH NHCI—I3 KNHg CHgOI-I NH; KOH £3 5 6] C7 Br N02 A B C D E F G H A>C> G>F>5z>3>>lw E: ngh Acidity Low V. (10 pts) Provide a systematic name or draw the structure as appropriate for the following compounds. 1 ‘ ’46“ l. CH3EHCHQCH2COOH if -C'>/w°M0 W"? 4 f N02 a Dario MIWMJR 4. CH3-CH(OH)—CH2~CH2-CN A " :7 wt] 0 H M—ngf 4W3) Ex) 3. CH3-CHI-CO-NHCH3 {V‘— 3. Methanoic (E) 2 butenoic anhydride VI. (22 pts). An unknown compound A (C6H702N) gave the proton NMR spectrum shown below. IR spectrum showed sharp peaks at 1700 cm"1 and lfiSOcm'i. Determine the structure of compound A. What would you expect to get when 1) compound A is reacted with LiAlH4 and 2) compound A is heated with acidic water? .r-C’H 5cm“- ,waj’cflj l VII. (12 pts) Show the structure of the products formed under each of the reaction conditions shown. ...
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This note was uploaded on 10/18/2011 for the course OCHEM 118A taught by Professor Schore during the Spring '08 term at UC Davis.

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Chem%20118C%20SSI%202011%20Mid%201%20key - Mtg/mm 1 I. (30...

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