EXAM2 - we r _Professor T.E. Hogen-Esch Feb. 23, Spring...

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Unformatted text preview: we r _Professor T.E. Hogen-Esch Feb. 23, Spring 2005 Chem 322D Second Progress Test Initial of Family Name - /( Name: TA: Lab Time: 1. (05) 2. (10) 3. (10) 4. (05) 5. (30) 6. (20) 7. (20) Tetal (100) 1. (05) List the most (M) and least (L) basic: CH30Li LiCHZCOCHa t-BuOK NaCN ( ) (M) ( ) (L) ( ) ffjwrll‘cté, 0 2. (10) Write all of the resonan structures: \ A ML ( M : Z “L M m‘onm(flcm ‘ -- + 4’ /cuz /C+lz 50h CH2 ' . © (3’ «—-—+ <~>+ M + y __ >< X ___.. “We H u :2. l4 + 1 3. (10) Circle and name the functional groups: I O chew V f0“? _ NOH 5&3}; O o o t Z . ) “whiz M 9/ 0 yew ‘7 Z a fru's Ale/61‘ flag/CAM «2 WW” “’1 C 4. (05) Write acceptable structures of: ce a. 2-Chloro—3-pentanone A A X O b.3-Hexenal 0 (26%“ 6’1 M @ (vim 0K) 3%L 5. (30) Give the structure of the predominant product(s). If no reaction occurs write “no rxn". a. CH3—CfH—CH2CH2CH=O H+ (ii-l °“ w Cf’2—\/"Ce b- @— —<i>~s —-s—HN° 01 N CH I 5 x 2 H2304 corvief I’m”), C. H+ CH 3 d. 1)D|BAL-H O—CH: 0 CN 2) H20 e. 1)socr "'>__<‘H:: 0 2 2) Li(t-BuO)3AIH '5’“ i / \ & 14—- /_\ *- HaCQCHfl c «3 / M N‘Kw M mono substitution only 0 g_ _,_ CH CHZCi/s Q—Ci-ECHCHa + HBr ———> bx ~ — ..CH: o - .— c a C14 h' 0mm + CH30H=o—O—H—> \ / H A A 4 pA-{H ‘Cl/L‘Cf/O 0H . __ 4 CN " GOP-i=0 + HON—BE» Q 3H catalyst j. H30+ ’ - QC aqueous 1% M W two products M, 2 %\ i ’fl‘ - 6. (20) Write the mechanisms (include the most important resonance structure of the key intermediate): a) CH30 + Bra -——-> CHSO Br + HBr AiCi3 r» H v~ F' b) / H U CH3 CH3OH o —-————> o + H20 1 ”+ s (#3 (/7! l4 <33 H2 :30? 20;} "I 5) W <’Q€’\ <30, 4’ w? {.4 (+~ H2 0 ) , N’le , loge—a 0g +0 a") (5740”! ’9- éfx W EW’MMSJ ”’ :2C 7. (20) Synthesize: (57!? 61/ ’4 —-—-’ '0 ‘I0 A K r 0 2 (M1 C—frm C; ’9 / a_ (EH3 /CH3 F—Wa/W Q—C=C\ from benzene and saturated monoalcohols _of three carbons or CH3 fewegusing an ylrde as one of the Intermediates. 0 ® Al C, 0 Sec (1, u C#3C"/LO/7/ —————‘t"""v (#3 COO/7’ ‘_""""’ ((715. C'C‘ a: Wraf (Lv P46 p1.co~c#,-—+ M {ll-chi; 0” pr " h“, Mal: 4... pr c—m mow b_ CH 3CH 2(_~,r-1=$—CH20H from saturated monoalcohols of three carbons as the only carbon sourcesJand any other needed reagent. @ CH3 ’0 CC ...
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EXAM2 - we r _Professor T.E. Hogen-Esch Feb. 23, Spring...

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