322bs06_e3_key

322bs06_e3_key - _ Professor T.E. Hogen-Esch Spring 2006...

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Unformatted text preview: _ Professor T.E. Hogen-Esch Spring 2006 Chem 322b/325b A Fri 1 5 , Z 006 Third Progress Test Initial of Family Name KEY Name: TA: Lab Time: 1. (05) 2. (05) 3. (20) 4. (14) 5. (36) 6. (20) Total (100) 1. (05) Indicate most (M) and least (L) basic: 0 H HgN—R‘NHZ O O O 2.(05) The pKa of alkyl ammonium ions (RNHC,+ fraction would be 93 k H we we M05163; : %ov~e CM Maia 5' %A 40%;. (COCH3)3 (L) HgN—fi 'NH2 NH (M) ) in aqueous media is close to 10. At a pH of 9.0 what deprotonated? Show your calculation. L4}.— C5 IV") (941/0 reflux/2‘6 —j__0 = [09 )flém 4. (14) Write the mechanisms (all intermediates, curved arrows, formal charges): (10) a. HEN! ———> RC-NH2 0K H30 II 2/7, 69 O M :1 flaw“ CLO/7’1, K? \J (9 I g mo H /O?H \ w @ at g, wow)!» <——-> (“fix/AW “1‘ H W! (MW/44‘ {46‘ H‘0 0,": ( fl\% \N’H'L o 9 \ fir/b 3 Zen/L 5. (36) Give the structure of the predominant product inc|uding stereochemistry where appropriate: (00 96 1E / b. PhCHZCOZEt + (EtO)ZCO Naoa» ~ Chi egg V4 (‘51; ‘500 66 @f’ 2) KOH, heat \ . ph-(# 1) CH3| (excess) NI "é (Wyav 0 "£1:- Mm M- 2-0% mm e. -2n OH OH "“ A n H3C¥2&—©‘COQCH3 + n Ki gI— 0 O 1. EtONa/EtOH 3 NaOH f. CH2(COQEt)2 I...» _____* 2. Br CHZCH=CHZ 4. H+, heat Cf/WClrl—cfi/cchcoo/J ‘ 1. KOH 3. H2NNH2 9- ——+2, Pa (MM 0 h 0 ' 1. NaOH/heat /‘ ’ (“OOH Wf 1 4/ _ ¢ 0 2. neutralize \ 06/ W 4" W I 1135 H ma“ 1/ £16 (dam. R Isomer CH3 Me 4 % O: L 0:0 1. RZNLil-78 °C ’0 F‘M 2. BrCHZCH=CHZ (a l k“ Q’NO 1) CH2=CHC(O)CH3, base Q a 2) 1130* (6/1. Cl/qu) (#3 catalyst I! I. CH3-N=C=O_©__:_w> (6/3 /\/- fi—O‘Iolt/ O 6. (20) Outline the synthesis of: 0 2—61 096 CO 6/79 4% 5 J1.” m f go; Mir ‘wo 51f (Ema \COO 5f <10 6/75 (I) a as! H m, (z/L (Hr C "C143 b. (12) ©——N= N—Q—OH starting with benzene as the only carbon source and using any other needed reagent \ 2.4%, F: w 5" “Wm/x 0 q, {/0 P64 ” vibe WWW” 1C ’7 ...
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This note was uploaded on 10/12/2009 for the course CHEM 322B at USC.

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322bs06_e3_key - _ Professor T.E. Hogen-Esch Spring 2006...

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