322bs08_e3_key

322bs08_e3_key - Professor T.E. Hogen-Esch April 2nd,...

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Unformatted text preview: Professor T.E. Hogen-Esch April 2nd, Spring 2008 Chem 322b/325b Third Progress Test Initial of Family Name - Name: TA: . Lab Time: 1. (5) 2. (10) 3. (10) 4. (15) 5. (45) 6. (15) Total (1 00) 1. (5) Indicate most (M) and least (L) basic: l-l2N -CH3 H2N —NH2 H2N —NH2 %‘v t it t. A 60 - O ( ) ( ) ( ) (M) (L) 2. (10) Circle and name most accurately the functional groups: L4¢+M¢Ifym’;‘/‘ ‘, flown/e m ~4er (“M fir) 4,". c ‘M O - o NH—COCH c o =<° ll 3 2CH3 0 Q (Ma M4 /6 0J5 u re‘Hq an (e) 3. (10) In strong acid CI-laCN reacts with (CI-l3)300H to give CH:,CONHC(CH3)3 but with CzHSOHJn the presence of a little water the reaction produces Cl-l30020H20H3. Explain these different outcomes with a few chemical equations and less than 30 words. 3458qu! grins 3°Carbocd’,uht‘ck @ 4 (Krfgfis N'- Me-c and? Me; fiMz-CEN-‘é‘gq (§robn (34%!!!) o , l Mc-g-QI- It! C—[fi «£512: elf—L MOD—Dig? _ {has arc-— em; gm argocaé éuf afi‘qaé; ,0er MQC‘I M-c- CE NH Mg— C2Ufi—L l-{to '0 c' u» N, Me~é~oets Ell/0‘” 6,6925%; M a“! (Mf‘ue) 4. (15) Write the mechanism (all intermediates. curved arrows, formal charges): -¥ P5 H kn (CH3)2CO + CH2: NEt2, or H” CH3COCH20H2NEt2 8 x95» / I 0}- ' +. b{o(-/v0“) —-/1 .@+ CHZT—ONCch‘) 6"” J r. , 4- Pro 4 act (————— : CFC” CH2 “\— '\ cu; @ 6:(Oé{~. oz), X” g- Md? b. H «a: EtONa/EtOH CHO + chozEt—> CH=CHC02Et + H20 if 7g \ 10‘ W “256 a) flaunt. 5. (45) Give the structure of the predominant product including stereochemistry where appropriate. If no reaction occurs indicate "no rxn”. a_ OZNON2+,C" + END 0" / \ 1. EtONa/EtOH C CO b- O—CHzcozEt +(Et0)2CO ——> @’ H2 2’4 2. H30+, Heat. / 1L0 @ngf M; -c 2% fig?! 3 my ‘woe’c’ c' CH3 1. CH3! (excess) . c Cpl—CH3 2- A920M203. heat firm "#26 H10) \ M 2 am (K, N i. C 7 M! I ,6 ‘%h¢ " - 0 W ‘1 OZN N2+1C| + QBI‘ —> N 7-3” fldLWé m/J‘?L 1. KOH 3. H2NNH2 ‘ 2_ PhCHZBr ethanol/ A @ 0 w o x ‘ MH +- \ \ r-M O _ g 4 602 @ N EH / I O o _i___, \ c914 ‘. heat 9 H‘ 2H5 H C2145 S-isomer ’1 fl S’CZI‘Q‘I' 0 $’ 5’ / II__ H30+ éflO _.N n. [email protected] N T. #0 o 70? \ o 0 short reaction time o J? 1. Fl NLi i. o __,2 @— CHz 7’5 2. PhCHzBr 1) NH /\‘ ‘ GO —‘_’ O’ N\/ 2) Na BHacN 1) CH2=CHCHZCL base 2) H30+ 6. (15) Outline the synthesis of: a. (5) Q—CHZCHz-?CH3 using the acetoacetic ester method 0 C 0( H; 5/0/Lh C - C C CH 2 "—'—""?' C y C C7 Cflgg zlé Eyck, [IQ/0’ f/ .22in C C- Product A (“C013 b. (10) O—(fHCHa from benz and ethanol as the only carbon sources and any other N needa reagent ‘ ' |H Csz GIL/5019‘ fli- Cz/{s—B'z %) (kl/5 “#2 $46309. macaw 3% Mega +® —~—*’ 6 + (In/J. Nut/2 My Product [I 0 M114 KIMM‘? (1/36. ...
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This note was uploaded on 04/25/2008 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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322bs08_e3_key - Professor T.E. Hogen-Esch April 2nd,...

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