322bs08_e2_key

322bs08_e2_key - Professor T.E. Hogen-Esch M a r C A 5:...

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Unformatted text preview: Professor T.E. Hogen-Esch M a r C A 5: Spring 2008 Chem 322b 2 00 g Second Progress Test Initial of Family Name - Name: ’6‘? TA: Lab Time: 1. (05) 2. (10) 3. (05) 4. (20) 5. (40) 6. (20) Total (100) 1.(5) In each of the following series indicate the most (M) and least (L) basic: @ou Oou Cw 02N—QOU Q0 ( ) ( ) (M) (L) ( )OLi 1%“ 0M Wf§% 40%. ‘ M M m 4:321‘ 9‘ "L’f'j if “Mg/fir L. 2. (10) In each case write ano'tiher tautomer and circle me dominant form. d: 001 °c>=o 11 11 1 10 w ©=a {$0114 ® @EJQé @4914 3. (5) Circle and name 1119 functional groups: ‘ j OR. C‘W e watfifddlf’ndl 5,“: WW; flag/be ygd’o/z O XEM I a(L,0 /% .(Ufimx W (#7 /e/. (EC C1'rc[€. «Mm/x44, 4. (20) Write the mechanisms (curved arrows, all intermediates including formal charges): a. CHzc'z OOH + ~02+ —> OaN—O-OH Include the electronic structure at the n'rtronium ion and glve only the most important resonance structure of the key intermediate. _ '5 "‘ —— tag“? ———v Ho /; N02 HOW “4—9 Ho_<’_ H + 0 3 + 8H (taboo! 0K 4 Pin “ C” Di _ H j / \ -—9- WI C ~—9 -—([./ j COJ L‘EO \O 5. (40) Write the predominant product including stereochemistry where : - - ropriate. If no reaction occurs Write “no rxn": 1 fr: 082 a. + ___... Ho._@& CH3 monobromlnatlon C [/3 FeBr ‘2 b. QO_C.© “3,2 _3__... a: 05:. u . . 0 monobromlnatlon 0 _._-—D _ an ' Bra/ROOF! 0H ( T d c CH20I2 heat /@ (“FF NOT \ N1 firch m “mm pm CH \0 H30+ H 0+ 9. MgBr + (CH3)2CHCN —- ir- @— fi— CH (C “5):: @ W H o 1‘. CHacECNa + CHacOCHa—h—z—b- CL/3C‘EC- Cf-Cf/a OH 1 r'fop 50/- wr'm‘ o 1.LDA 2- (CHa)2CO(oo|d) C? 0 9' -78°C 3. neutr lize i /0” t '0 [PC C #3 C”:- 7~ % w. h. O—CH=O +CH2=PPh3 ———I- C H2 nof‘ Arc” C ‘L m5 R10) 6.(20) a. b. Synthesize from benzene and alcohols of three carbons or Iess as the oniy carbon sources and any other needed reagenf.“"—"— ' O H\// C—C CM CaHs (and/or cis ) @2020 / We, 0 CH Cece + O a (W C/{iC/IZ c”: ya 3C”: :_ 60‘”) 3 22; _ 4/3 ("/4 CH3 M q]; {cot/3 49" 4E'H3C3Cz/2‘Zc; a” 0/ 9.1 a m, 5' J mrfl‘“ net 3‘ [77$ Synthesize from gyclohexanol and any one-carbon com und as the only carbon sources. and any other needed reagent: HZNCHZ " 0 _i“_’£,. _ o HON #9” — o ,3; A Q J. r (1.15M M t A! (A), C Produc d‘ ‘0' fl 7‘47 a460,, (1‘0 Off 00"! O] 40% 4.014 9‘3 477‘” <3" [ I (Mth a, a». C” ...
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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_e2_key - Professor T.E. Hogen-Esch M a r C A 5:...

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