CHEM322b - Exam 2 (2009, Spring)b

CHEM322b - Exam 2 (2009, Spring)b - Professor T.E....

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Unformatted text preview: Professor T.E. Hogen-Esch Chem 322b Initial of Family Name Feb. 25, Spring 2009 Second Progress Test .a \-f O {-2 1. (10) Indicate the strongest g3) and weakest (W) acid: a); " ‘ 1““ HZCO CHagH=O (CH3)ZC=O CH3000H20HQCOCH3 CHaCOCl-lgCOCHa (CHaCO)3CH (W) l ) ( > ( ) (:3) (fl) 2. (10) Indicate the strongest (S) and weakest (W) base: {(9 7"» H9 10 35'? 30 3f; LiOH LiCHgCH=O CHaOLi Q—ou LiH NH2Li BuLi BuC acu () () () (w’) (l() (5) (l 3. (15) Write the appropriate labels in each of the boxes. Choose from: Bronsted base (BB), Bronsted acid (BA), Electrophile (E), Nucleophlle (N) and leaving group (LG). Example: + H3O+ 4. (15) Write the mechanisms including stereochemistry if appropriate. Include only the most important resonance structure of any intermediates. HCI ,OCHa + _——> + H20 I \ OH ' fl 0““P‘w /' No” i + HLO r \" 0/ / X0“. 4- HCA «3: .al _ T ...___ / W w—m 61%..95/ \f’ i- + / M / "H253 V‘ / 0% has =mToFl‘mi vasoan KWOLUF‘K carp—Q + H3C-g'3-CI 591—» CHao—Q—ECHs + HCI o Q) 0 o + Hui I “- 4AiLl§ / 0/ + i éWlo‘S’r" imf’opt‘mt mfiwfimnm “$6, / S {WUL L VA...- 5. (30) Give the structure of the predominant products. If no reaction occurs write “no rxn”. a (F32, 020 CH—C —-——-> ' " NaOD b an H... ‘0»?! - O c —» cwx ;« m “a . aqueous (“t-T, / k LC} (one: eqlf'v') work up ‘if . O J/ H d' QCHO + H2N~NHCONH2 Eli-i» a.“ \ fed NHL u N Y ‘ \‘5/ 0 wir—iE—p 8- H+ 0E1— H + ——————-> T 5L} ff ‘LI'I': f' Br 1. Ph3P A ,1“, ' 2 BuLi’ U ' W H Nikki r \H Brz/FeBra (H, E. + I" 9. H3C ———————-> my £5301; No2 TW 0 Pr 0d acts Kw L k. 'I :P 0 K ' "L h- 0 1)(i-Bu)2AIH Mk V CN -—-—-—-—-—> H 2) H20 ) ID _ O OMe HO+ l H ,/ o I. .3 , Z MLDH + H/fo‘f’ J. MGM H O OMe dilute o f} “w three products ,4 NH2 ' CH3COCIIAICI3 6'“ j ——-> m r 2‘“ L" ' aqueous work up “K I O O OH uh 6. (20) Synthesize: a. from ethylbenzene and alcohols of two carbons or fewer as the only carbon sources and using the Wittig synthesis. ’3.— ‘Pha “LL _ I L (T «Vb» ~:: " MO“ 35337 Hi“ WW PowldchYJ-J- WW; 0 l N - "r" HXH ——\=v + Pth=~o b. 0 from o and a one carbon compound as the only Mot carbon sources. HZN - . up ' _. . - . I z'" "- ...
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CHEM322b - Exam 2 (2009, Spring)b - Professor T.E....

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