322bs08_e4_key

322bs08_e4_key - Chem 322bl325b Fourth Progress Test April...

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Unformatted text preview: Chem 322bl325b Fourth Progress Test April 23, Spring 2008 Initial of Family Name - Name: k TA: Lab Time: 1. (5) 2. (5) 3.(10) 4.(15) 5.(45) 6. (5) 7.(15) Total (100) 1. (5) Identify the functional groups. Choose the most accurate description: 0 OCH 0 0H HC=NNHPh 0 do 03 <3. . fl 1 I . CHZOH . _ / {item 674% (15am flar/ 0L 1; 5 {-2 P 2. (5) Indicate the most (M) and least (L) reactive towards EtONa: OCH3 02N N02 3. (10) A D-aldopentose, upon treatment with HNOa, prod s an optically inactive aldaric acid. The Ruff degradation (1) Bra/H20, (2) ctatco3 and heat, (3) Hzole *oi the tgent: ose gives a D-aldotetrose that is e Fisher structure of the aldopentose. oxidized with HN03 to give an optically active tartarlc acid. Write Show your reasoning. ~30 IJO 4. (15) Write the mechanisms (all intermediates, formal charges, curved arrows): a. -. QB.) + 3CH3 HK+——> OiNHCHa + Q13 + CH3NH2 (I / NHCH3 @ \> C - fl Q 1/ HZ/uo/J @ i b. H=O OH— §H=o H H C'ZHOH ———§ CHZOH CHon (D) (D) + (L) @ "3 0 ~ CL I 0 LI H ’ ,t/ 0 (420/4 C. f3! ——#* \3’9 - o C, _ + @ (\va ©3233 L 95”) @ (M f “v ‘ f‘o’hflé 1 flag M jflf/oriwy{t~éw‘&/E A r 0 0 H30“ 0 Cw H 43/12 H Lit—«(Jo ch‘z/‘é 5. (45) Write the structure of the predominant product. If no reaction occurs write “no rxn”: o) (I, c 3- NaOH/A - QOH + C02 .——> @0’1 W high pressure Ca: A/tc Pd.“ 0 K fl-f’ Mr, '3' 0c 02N Br + CH30K ——A——> 0.2 N Al” L Br 32, c. QOCH2C“=“C“2 —hr 70” ea &//2C f/ : Cf/Z afl/J‘Z W d. J. “ V HOzC—Q—OH + Ncho3 M: 020—— 0 —0// 1 crle H f B-D-Glucose 1) CHSOH/HCI “20 ‘ P1 ' 2) CH3IINaOH m0 / mu : 19 6¢( excess 011‘l 00; 0‘ a C (12,0 H w” co 0" two products OMe m'0 I CH20Me C o H30+ / ht OH 0 H _’ HZ + H two products 9‘ a A KOH _ ’ OH j- Br—@—CH2802‘©‘3r heat (Hz 502 \/ Mt, L ,«f 4/43/4460 Aw. W M” I o Ci 2 7 2.) 3 1) 03 7" L 6] 7 + Biz/Clo 3‘ y 2) Zn/CHSCOZH I a 5 l—/ i ‘ 3’ c.“ z: 0 ' Two products 2 I , H 7 Q 6. (5) The critical micelle concentration (crnc) depends on the temperature due to the hydrophobic effect, which is said to be “entropy driven”. Should the cmc decrease or increase with temperature? Explain your reasoning. Hint: answers should include no more than three or four sentences and one well known equation. K za/‘ig'mq ,1“; /7 5 .197 S”, j: J: a/ 4‘5 M /£e /éo/»Wc .c/fax/Akr Jfi—c‘oé 4 //4 [W ‘ My? (Afsfoxdfiw) @ Mdc'cazh #a/ A 6(213 #d 7—45) Wmcwa '40 4270114417147 ’6. #Mu M CMC Alf [’4’6’7/244421/ W44) M flaw fl [3 7 (15). a. Synthesize OZN—Q—O—Q from Q—Br as the only carbon source and any other needed reagent. 3.53 C q /\ 32 LEV—05L, 02m. ' V 14/2507 ...
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322bs08_e4_key - Chem 322bl325b Fourth Progress Test April...

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