322bs06_sample_e3_key

322bs06_sample_e3_key - 322D Practice Third Prog Test...

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Unformatted text preview: 322D Practice Third Prog. Test Spring 2006, Chapters Solomon 18-20 + topic B. 1. Circle and give the most accurate names of the functional groups. €57Lt/L fm/fl/e .- %ocyafiaé 2. in each of the following pairs, circle the stronger Bronsted acid CHaCHZCOaH or r H200 r CHscOZEt Cw or Q?) 3. Arrange in order of decreasing basicity: O/> C a a l <3H(cozEt)2 éHzcozEt 6H2000H3 (EHZCOMCHa)2 5H(COCH3)2 (a) (b) (C) a (d) (e) Ow (a) (b) (C) (d 4. Write all resonance structures of: - a 6- H30 C-NH— b. HZNC-NHZ c. Air-NZ”? : <7,_.\>—— F55 N‘ g R ~ NH +C”)H N it” ‘ Q! H3C-__ ’ ' Hw’g” Z </ \ is m 5. Write the mechanisms including all intermediates (no resonance structures ofiansition states® please) curved arrows and formal charges if applicable. a. I;NH HCI/NaNOa < Db. NO 0'; Et NH :C CO (if d. [email protected]=O+CH2(Coga)—2—Effl——> Q—<:o>'cex C 2 )2 2 e. Cl— + N02 -—-> A 1)BuLi H30+ Cf/ZCf/S O f- 'S\/'5 2)PhCH28( CH“ (w.- -————> - .06 IN “ IW+CHSNH2——'H2' <E>’ 12 O i. HgC-@-—(“3—NH + ’Nazcog ————> Cris-“Q’soz ~"@ . < .— o ' 2. BtCH 261mm2 ~ 1. _ OH -HZO QT c m_ ——————> ———-> 2. CHQCOCI O 6/ 3 s n- w @—< > 4.H=O. +.HS(CH2)3SH ————> ’ 5» +120 0. 1)BuLi 3) HgCl2lH20 <3>.Cg2CH= O s 7. Give equations describing the synthesis of: (Hi I C HL C 02 El ' x 25% 0 Iva» ; a. \(O using , the—acetowacetic- ester. method. 2) 1 O D 0” g N &(C¥/z}4 5‘. ng- Cl? 9 5+0 ace/é (Free 002 £1 9 b. 02N= NH from NH2 as the only carbon source and any other needed reagent. 0% / Z; #L ._ 4’ "520 x ' 0 A; N JQ _. Nfl/ '19c-—---"" 2 o 2.. @”“*‘°—m 02“ (EV emf/Cf; a $439222, c. O . H2002Et from and CH3002H and any other needed reagent or compound using enamine chemistry 0" HZCHZCOZH using CF|2(COZEt)2 and any other needed reagents 3 o " x9 H0 Na, J )6” 257‘ r Ore-C” 2a ...
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322bs06_sample_e3_key - 322D Practice Third Prog Test...

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