Ex2Key - 1) (10 points) Give a reasonable mechanism for the...

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Unformatted text preview: 1) (10 points) Give a reasonable mechanism for the following transformation: ‘rs \ Z} A N NH :01/ 14+ "-—""’ OH , OH )L '. \\1. + H H K "‘ G) ." ’3 0y) 0 . 73’- \ I ’0 I W“ 2'3“ x V cwdaw“ '— ..‘_ i. 2) (10 points) The pKa values of oxaloacetic acid are 2.22 and 3.98; o o in: OH (\qu at) 5“ oxaloacetic acid dog, a) Which carboxyl group is more acidic? . $33 b) The amount of hydrate present in an aqueous solution of oxaloacetic acid is / pH dependent: 95% at pH= 0.1, 81% at pH 1.3, 35% at pH 3.1,13% at pH 4.7, and 6% at pH 12.7. Explain this pH dependence. (Hint: Think about the chloral hydrate and it’s stability) 03??“6‘)‘ 6;: Q \09 'E’l'l #3 g ms, a»: QR 3i...“ a) EVeW @593 (Wt? W‘xPS \b Slag‘ltu I a“ X 5%, r av 4- ' @ go‘x/O’f @. n 3% a“ f .: a O 3 is b . r L -—‘ id -25?) has tVLEV‘D“ “fiéiwfl é ’1 6\ law 4w Ml CDW‘; HE" 3)(15 points) Cardura®, a drug used to treat hypertension is synthesized in the scheme shown below: \‘fi (noncyclic stable intermed.) 2. 3‘3.» Us a Cardura® a) Identify the intermediate A and show the mechanism for it’s formation b) Show the mechanism for conversion from A to B. Which of these steps do you think is faster and why? 4) (10 points) Place the following compounds in order of increasing acidity: 1 being the n t acidic, 5 being the Mgr acidic. /I‘Q{ may? Z-E EN ’ ‘w UQSA/ Br 0 /\/Olk OH O CH30H OH (09 5) (10 points) Give a mechanism for the following transformation: - hi; 3r 2%“? fit "R-‘r gar 365% fig. 01" f‘old f A CD 6) (50 points) Supply the products for each of the reactions below. If there is a major and minor product circle the major product. 21) NHCH3 HCl, trace ____...___._> O b) Br (V 9% NO?— 1)CH3CH2NH2/heat {gag .——————» t‘" 2)OH' m E d) NH2 0 OZN /H\HCI, trace ._————-———-—> 6) + (C6H5)3}: OH NaBH4 Pd(Ph)4 ——-——> (CH3CH2)3N 8) (l 0 points) What carbonyl compound and phosphonium ylide are needed to synthesize the following compounds: Compound < >:CH2 Carbonyl compound Phosphonium ylide W 5?? = as agizggzw g \\ -: Clix; l_.___._ CHCHQCHS 9) (10 points) Determine the structure of the following compound from the spectral data given: (see following page for 13C—NMR) C9H7NO4 MW = 193 é2H E E 1H E ! m E y: 3 1H 3' 15 i l 10 K fi’V t 1 Q V 3500 3000 2500 2000 1500 1000 Wavenumber (Cm'1) IR Data 1H(exchanges) ‘ ,,,,,,,,,,,,,,,,,,,,, ,, unavaiUl -n l. _ .fl- 4 ,1le , a I 1 I uh d d 4 I 0 1H ~ NMR spectrum 1H 010Ié01g'0"'1<i{ll'%0 flit—fl-W‘zb‘ 13‘ 717% “795 7i: 7% 7' 690 H— NMR expanded 13C — NMR spectrum L Structure 10 10) (15 points) Given the following starting materials, synthesize the products shown. You can use carbon sources of no more than 4 carbons in length (excluding the given starting material.) 60 Br CHQCHZOH 11 {@139 ...
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This note was uploaded on 05/13/2010 for the course CHEM 152L taught by Professor Baldwin during the Summer '09 term at Duke.

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Ex2Key - 1) (10 points) Give a reasonable mechanism for the...

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