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documentview5 - KEY: Synthesis of Aromatic Compounds 0 H CH...

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Unformatted text preview: KEY: Synthesis of Aromatic Compounds 0 H CH CH CH2CH3 CC a Q U 2 3 (Gong) KMnO4 g - ——> —~—a———> —-——> A103 H2804 (com) 02N NEOH / A 02N 2) H —. pH 1 CH CH b CH3CH2C1 2 3 st04 1/803 0 CH2CH3 HNO3 (conc.) . ———~——--i- —~——_——-> AlCl3 [fummg H2804] “8 H2804 (cone.) (3 Ho’ \b C‘- KMHO4 Cf 0H NaOH/A CHZCH3 H2304 /Hgo / A O QCH2CH3 ‘ *—'"——— 2 H+-—> pH 1 \‘ N02 ) N02 HO/S\\O N02 9 S? CH CH 1) KMno4/H20 CC 02N CH C_ CH3CH2CI 2 3 NaOH / A 0H HNo3 (conc.) 0“ AlCl3 2) H+__> pH 1 H2804 (00110.) 9 CH CH CH CH 1) KMnO4/ H20 C~0H CH3CH2C1 2 3 Br2 2 3 NaOH/A d- ——> ——'—'—.' "'+—“—" I 9 3 CH r BI'Z FeBr3 9 0 Br 0 II H OH O O’C‘CH3 O’C‘CH3 O’C‘CH3 || OZN e CH3C 0 H2804 / $03 HNO3 (00110.) pyrldme [filmmg H2304] H2804 (conc.) (:12 0H 0H 9 0H 0H O’C‘CH3 o N (:1 o N - 0 N 2 sto4/H20 2 C' 1) Na+ 0H /H20 2 Cl <———-——*—— <——-—---———— A 2) H+—-> pH 7 O: :0 OZIS=O (l)— Na+ OH O O \\ ll ‘— CH2CH2CH3 f. 1) CH3CH2C Cl/AIC13 H2 de/C H2804 / so; 2) H20 H / alcohol [fuming H2804] CH2CH2CH3 CHzCH2CH3 CHZCH2CH3 H2804 0 C12 0 q————— \\ ‘—“— \\ Cl A ’8 Fer ’S H0 “0 HO \‘0 N02 No2 NHz g_ HN03 (conc.) Cl2 1) Fe / HCl/H20 H2804 (conc.) A1C13 Cl 2) NaOH—-> pH 12 Cl HO c1 1 I E—cx’o N‘Q CH3CHCH3 \CH B ———-———u——-—’ ——+ h' CH3 A1C13 3 3 CHg-QH 3 CH3 Br Br Br + _ BI' N—N Na .E (311213122 6) ‘ Na+ N02' lHBr NHZ Br- I, CC H cplqu CH3_C\H 20 0 CH3—C\H CH3 CH3 _ 9 CH3 NH2 NHz BF4 NEN N02 i CIZ/HZO C1 C1 Na+N02'/HBF4 Cl Cl Na+-NO2 C1 (:1 . _, H2O/00C ' —"’Cu C1 C1 Cl 0 CH3 H / O CH 1) Cl C—Cy /A1C13 CH3 3 0 / H_ / OzN Hm / . CH3 C C13 HNo3 (00110.) C C5 J. ——————> CH3 W CH3 2) H20 2 4(conc.) 1) Fe / HCl/HZO 2) NaOH—n- pH 12 {1304' N®N® [CH3 + - {CH3 0 CH3 00—121:ch 4—“wNa N02 [HZSO4NH2 CHZ-CH 1)152/fall’cfjcjalfijoal NH2 {Ll—Ci! 3 0 CH +—————-— \ H20”) C U 3 2) NaOH—n- pH DU CH3 $ [CH3 ‘0 0 /CH3 I! O 1) ,C—C AlCl II xCH3 / 3 C1 ECH/ 3 (H3? H2 /Pd/C CHz-Ctl k. _2)H—20__—’ CH3 H falcohol CH3 HNO3 (c0nc.) H2804 (60110.) C/HCH3 /CH3 [CH3 CH ' - CH -C _ 2 \CH3 Na+ N02 /HZSO4 2 {chg‘ 1) Fe II CH2 (B 4———— ‘—— /N H20 / 0 0C 2) NaOH—n- pH 12 3 N4 HZN OZN ,CH3 CH -CH Néc 0 CH H l 3 O 1) _ 3 / 3 Cl,C CECH /A1C13 5%? H2 [Pd/C CHzCH L fif—ZO—fl-B—I" CH3 H / alcohol CH3 ) H2804 / so3 [fuming H2804] [CH3 CH CH3H3 /CH3 CHZ-CH 2' CH -CH \CH3 H2804 /H20 1 A \CH3 HNO3 (00110.) 2 \CH 4—-———— ‘ 005 H2804 (cone.) 0“ 3 \ NO HO/ \O 2 HO/S\b 1) Fe /HCl/H20 2) NaOH—h- pH 12 /CH3 [CH3 {CH3 CHZ'CE + — CHZ-CH CH CH \ 2 CH3 N——>a N02 [H2304 CH3 CuCEN \CHg H20 / 0 0C e, —> O 0 O H H H H \ /C H\ H\ /C NH?‘ < 9; N \CH3 N’C‘CH3 N ‘CH3 - O Pyrl me [fummg H2804] H2804 (001100 N3+ OH 0:|S:O 0:IS:O H20 I, A m 0H OH H N02 @N BF4- \ /H No NH2 N 2 +. No2 + . NO N0 (5’ Na N02 Na No2 /HBF4 2 1) H2804/H20/A 2 Cu ‘ HZO/OOC 2) NaOH—a- pH 12 023:0 (JJ'NaJr O O 0 O H ” II II \N/C\CH3 H‘N’Cx H‘ ’C H‘ ’8: Br (:1 HNO3 (conc.) 31'2 Clz n. ————-——> _—.—> .____... H2804 (conc.) FeBr3 FeCl3 No2 No2 No2 H @N H504- I Cl Br B 1) Fe / HCl/ H20 K+1- C' ‘ Na+ Neg/112504 <—-——- 4—""—“'_'— 2) NaOH—> pH 12 H20 / 0 0C No2 N02 I 1 1 C1 7 Br Na+ N0; / HBF4 Cl Br 1) evaporate H20 Cl Br _._._._——> -—-—-——> H20 10 0C 2) A NH2 F BF - ®N$N 4 No2 ...
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This note was uploaded on 04/02/2008 for the course CHEM 301 taught by Professor Morrow during the Spring '08 term at New Mexico.

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documentview5 - KEY: Synthesis of Aromatic Compounds 0 H CH...

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