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spring11sampleexam4key

spring11sampleexam4key - 322b Practice Third Progress Test...

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Unformatted text preview: 322b Practice Third Progress Test Spring 2011, Chapters Solomon 20-22. 1. Write the structure (choose your own example) a”: e: N C? ,H’ a. Esthf 0 b. Lactam c. Oxime A) {:(Cpfid < “f“ d. Sulfonamide e. Thioacetaifi f Osazone H -~ N..- N14 P a N/ i:- N.— Nfi‘ F 6% ‘2 (a f2><i§; g. Imide? h. Carbamate i. Dialkyl carbonate 2 {a 0 ,2 NHL»? \m‘ a «’EENH 0W; a J 2 . Circle the most (M) and leastiL) stronger Brensted acid : RCONH2 RSOgNFig HSOaNHR' Gnu-:2 CNH ( i ( ) ' (M) ( ) (L) 3. Arrange in order of decreasing basicfty: C/ Q Q 900% Q Elie 2> a a g 5;; :2: all: 4. Write ail resonance structures of: _ + 11/ Hscc-NH b HQNC- NH2 0. Ar-N2+ :02 «— Ne‘iN’ gk" “NH 4.. [+HH ‘33sz waif; 1; aye “r” Hm rm ‘f/ .. 3: N“ 5. Write the mechanisms including all intermediates (no resonance structures or transition states please) curved arrows and formal charges if applicable. H a; ..._. ““‘T " m% a...» 1 m .m— 5'? Q” QM g”, (3%; Q“! 4” H“? Q Ma“ T9 Wt?” o. HC(O)(CHOH)30H20H L HC(O)CH20H +HC(O)CHOHCH2OH H20 5 -— 0\ :§ _, M .dn- H...» H "m \ / k" W EH Hwy” §,__:T Z“ M fiH>’C\OH +~ H; OH 6. Give the predominant products if no reaction occurs. Write. ‘no rxn”. 3. CM CW 9 gm QM I, b- QN2+,CI+Ki——+ <6 >""‘m C4“ N"; J W C» ®$o£N/) o. EtNHC—<::>-s——N T3 H02 -"‘“ M \ short reaction time #4:. ’ d©_ICCH3 "I" CH3NH2 --——P- ————r-—H2lNi Oiicjj + m . e. CH3O—@—N2,Cl + @N02 _........ No TQKW Br [OH @0420 _NH2 2 < 55>..CH3N7‘I’2. Q 1) CHsBr Q‘ g. ————> I}! CH3 2) A920,.A 1 0H3 at“: i. 0&0 Na/CH30H Haw any 1" 02"] 8 Br NaOH QaN—w J outed? it)" ‘ " Q 0 002H + >: / x x] 0. 1T @1le a. Starting with benzene and any other needed reagent synthesize : O—CH3 <DM~+ #Nog <— “9%.: HQAfiQNfla-é cofleH3 #35 0:; Ca; a M? o I) 4% watt M 0 cf! “535%“ A.“ €93 Me 669;. '2 Jim 3’ F ng CHon CH200H3 f” b Starting with I} 4WOH Synthesize WORC— 1530 +- wee D Hat-:5“ 3 c HEW OH OH at; 0 H OH OH act/r5- )3 0 agar—as C} W” mats “WW-«e W 0 Starting with QOH and Br130H20H=CH2 synthesize: 0130H20H=CH2 f»- and using any other needed reagent CH20H=130H2 “m w «M<.w.w___] m 9.42;; M” {>— J , a f, 2) ’34:}; ‘1‘”ng G) . 5f W «2 Z ..... I3 J ...
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