Dolbier HW Solutions 540

Dolbier HW Solutions 540 - 634 AMINES (n) An aryl diazonium...

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( n ) An aryl diazonium salt is converted to an aryl iodide on reaction with potassium iodide. ( o ) Aryl diazonium f uoroborates are converted to aryl f uorides when heated. Both diazonium salt functions in the starting material undergo this reaction. ( p ) Hypophosphorous acid (H 3 PO 2 ) reduces aryl diazonium salts to arenes. ( q ) Ethanol, like hypophosphorous acid, is an effective reagent for the reduction of aryl diazo- nium salts. ( r ) Diazotization of aniline followed by addition of a phenol yields a bright-red diazo-substituted phenol. The diazonium ion acts as an electrophile toward the activated aromatic ring of the phenol. NaNO 2 , H 2 SO 4 H 2 O CH 3 H 3 C H 3 C OH CH 3 H 3 C H 3 C OH NN C 6 H 5 2,3,6-Trimethyl-4-
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