322bs08_e1_key

322bs08_e1_key - Professor T. E. Hogen-Esch Feb. 6. Spring...

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Unformatted text preview: Professor T. E. Hogen-Esch Feb. 6. Spring 2008 Chem 322b First Progress Test Initial of Family Name - Name: .P— TA: Lab Time: 1. (10) 2. (5) 3. (10) 4. (5) 5. (10) e. (10) 7. (40) e. (10) Total (100) 1. (10) In each of (a) and (b ) below give the most (M) and least (L) stable intermediate: “3- 6H2CH=CHCH3 (5H2—<'1:=CH2 CH36=CHCH3 (CH3)36 CH20H=C(CH3)2 CH3 () () (L) () (M) f“ “(L NaCl CHBONa NH2Na CHaMgBr CHGC02Na f 40 111‘ I. (L) (l (l (M) (lot, {macaw EH— we vim/9M0“. —-—.___. a... 2. (5) Indicate which of the following is least (L) and most (M) basic: “H... ‘— “EH—‘— 3. (10) Write the hybridization symbols for the indicated atoms. 5 s ‘3 j; 5P3 z 252/ I ' ©1204; {OHS—{fist ’<. 7’ K “4‘ f 2. \ a 5.1. ‘f 4. (5) Circle and name the functional groups: 5. (10) Indicate which is aromatic (A), anti-aromatic (AA) or non-aromatic (N) [molecules are assumed to be planar]: 2 “Lack, + + + 0 C) A \ / (M) (fl) (,0) (N) (I?) 6. (10) Write the reaction mechanisms. Show all “reacting” eiectron pairs as curved arrows. Show all intermediates. 0 b) R\ /o-G-'él:r={)ll R\ _ R/cQH 5H +H20 _.... R/C=O +HCr03+H3O+ ‘7L 6.6“; mm... Ax» £2- £421. ‘f 144v 7.(40) Give the structure of the predominant product. If no reaction occurs write "no rxn”. a. _ 9'”)? Qm 1)Mglether 2) (CH3)200 ....C \ / ‘r “’3 OH —-..—il- 3) NH4C| (aq.) d- (r—Bu)2CuLi + BrCH20H=CH2 __..... 9- H20r04 2)CH3MgBr OH ——I-- ———-I- ammo: (aq.) *- NH4CI(aq.) 0:0 +CH3MgBr —-- ——n- OéCHa (excess) Hzcr04 ——’. A/a I y 2 ” «f CHO I. O + CH2=CHCH=O m”: C) “if. we... 4!? . 0 j. + O __.. 0 1 4.120. C I; @/ flight 3(10) ( 51-10(67) Starting with and alcohols having 4 carbons or fewer as the only carbon sourCes outline a synthesis of : ...
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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_e1_key - Professor T. E. Hogen-Esch Feb. 6. Spring...

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