Lecture 29 Diazonium Chemistry and Eliminations

Lecture 29 Diazonium Chemistry and Eliminations - O H O H2N...

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O O NaNO 2 , HCl H H H O O H H 2 N NaNO HCl O HO 2 C O S configuration 2 , HCl O O H H A. S N 2 O O H N N B. S N 1 C. S N 2 twice S configuration H N O O O O HO C H O H N HO C H O 2 2 H 2 A B C O O NaNO 2 , HCl H H H O O H H 2 N NaNO HCl O HO 2 C O 2 , HCl O O H H O H H O O H N N O O H O O O H O H Which of these is the intermediate? O O H H H O O O H O H O H O O 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 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. H O HBF KI H PO Ar-OH 2 Ar-N 2 4 Ar-F Ar-N 2 Ar-I Ar-N 2 3 2 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 H 2 O HBF KI H PO Ar-OH Ar-N 2 4 Ar-F Ar-N 2 Ar-I Ar-N 2 3 2 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 NO 2 F Cl Br H 2 S O 4 HNO 3 1) NaNO 2 , H 3 O 0 o -5 o C 2) H 3 PO 2 NH Br Cl NH 2 H 2 Ni 2 H 2 /Ni HNO 3 H S O F F 1) NaNO 2 , H 3 O Br 2 FeBr Br F Cl 2 FeCl Br F Cl 2 4 NO 2 0 o -5 o C 2) HBF 4 3 NO 2 3 NO 2 Choose a method for performing the following transformation.
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