Lecture 29 Diazonium Chemistry and Eliminations

Lecture 29 Diazonium Chemistry and Eliminations - O O NaNO...

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Unformatted text preview: O O NaNO 2 , HCl H H H O O H H 2 N H H NaNO HC O HO 2 C O S configuration NaNO 2 , HCl O O H H A. S N 2 O O H N N H H B. S N 1 C. S N 2 twice S configuration N H 2 N O O O O HO C H O H N H HO 2 C H O H 2 N O HO 2 C H HO 2 C A B C O O NaNO 2 , HCl H H H O O H H 2 N H H NaNO HC O HO 2 C O NaNO 2 , HCl O O H H O H H O O H N N H H O O H O O O O H O H Which of these is the intermediate? O O H H H O O O H O H O O H O O H A B C HX/CuX heat HX/CuX, heat X = Cl, Br X I K I F heat N N HBF 4 BF 4 N N O KCN/CuCN heat C N H P OH O H H 3 PO 2 heat H hypophosphorous acid (reducing agent, H- ) Give a method for performing the following transformation. H2O HBF4 KI H PO Ar-OH 2 Ar-N 2 HBF4 Ar-F Ar-N 2 KI Ar-I Ar-N 2 H3PO2 Ar-H Ar-N 2 Ar-Cl HCl CuCl Ar-N 2 Ar-Br HBr CuBr Ar-N 2 Ar-CN KCN CuCN Ar-N 2 Cl F Br H2O HBF4 KI H3PO2 Ar-OH Ar-N 2 4 Ar-F Ar-N 2 KI Ar-I Ar-N 2 H3PO2 Ar-H Ar-N 2 Ar-Cl HCl CuCl Ar-N 2 Ar-Br HBr CuBr Ar-N 2 Ar-CN KCN CuCN Ar-N 2 F NO2 Br F C Cl Br H2S O4 HNO3 1) NaNO2, H3O o-5 o C 2) H3PO2 NH Br Cl NH2 H 2 Ni NH2 H 2 /Ni HNO3...
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This note was uploaded on 10/18/2010 for the course CHE 326 taught by Professor Fowler during the Fall '08 term at SUNY Stony Brook.

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Lecture 29 Diazonium Chemistry and Eliminations - O O NaNO...

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