Homework%209%20b - NO 2 a. Br Br Br b. Starting with...

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Homework 9 b Fall 2009 Last part of problems related to the material covered on Wednesday will be given as extra sheet on Friday. 1. Write product of electrophilic monosubstitution of the aromatic ring OH NO 2 HNO 3 H 2 SO 4 HNO 3 H 2 SO 4 Br 2 /FeBr 3 Cl CHO OCH 2 CH 3 Br 2 /FeBr 3 Cl 2 /FeCl 3 HNO 3 /H 2 SO 4 COCH 3 CN Br 2 /FeBr 3 Cl 2 /FeCl 3
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2. Write the product (if any): OH NO 2 Cl CHO OCH 2 CH 3 Cl 2 /FeCl 3 HNO 3 /H 2 SO 4 COCH 3 CN Br 2 /FeBr 3 Cl 2 /FeCl 3 1.CH 3 COCl/AlCl 3 2. H 2 O workup 1.CH 3 COCl/AlCl 3 2. H 2 O workup NH 2 NH 2 /HO - NO 2 ? O O CH 3 NH 2 OH/H + LiAlH 4 H 2 /Pt Zn(Hg)/HCl LiAlH 4 ? 3. Write the product (if any):
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NHCOPh Cl CHO OCH 2 CH 3 Cl 2 /FeCl 3 HNO 3 /H 2 SO 4 Br 2 /FeBr 3 1.CH 3 COCl/AlCl 3 2. H 2 O workup NO 2 O O CH 3 MeO NC Me O 2 N HNO 3 /H 2 SO 4 HNO 3 /H 2 SO 4 4. How would you accomplish the synthesis of the alcohol given below, starting with 1,4-dimethylbenzene. You  can use no more than two-carbon compounds and any reagents needed: OH 5. Complete the following syntheses: 
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Unformatted text preview: NO 2 a. Br Br Br b. Starting with anisole propose step by step synthesis of 4-cyclopentenylanisole. OCH 3 6. Show how you would synthesize the following product starting with anisole. NH 2 OCH 3 Cl 7. Design a short synthesis for the following ether starting with anisole using no more than 3-carbons compounds and any reagents you want within the reason. OCH 3 OCH 3 O 8. Write products formed in each step of the following reaction sequences: NO 2 NH 2 NaNO 2 HCl CuCN a. b. NO 2 1. Sn/HCl HNO 2 /HCl 2. HO-HO-/Cu + c. NO 2 CH 3 1. Sn/HCl MeCOCl pyridine Cl 2 /FeCl 3 OH-HNO 2 /HCl H 3 PO 2 2. HO-deprotection or hydrolysis...
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This note was uploaded on 10/11/2010 for the course CHM 2211 taught by Professor Castalleano during the Spring '06 term at University of Florida.

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Homework%209%20b - NO 2 a. Br Br Br b. Starting with...

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