Reactions of Arylamines and Diazonium Salts
For each of the reactions on the left, predict the major organic product. Pay particular attention to the regiochemistry and stereochemistry of the reaction.Click the mouse on the reactant molecule to view the answer;
click on the reagent to briefly review the reaction.
The reaction of a simple diazonium salt with aqueous phosphorous acid (H3PO2) will convert the diazonium group directly into the corresponding arene.
The reaction of a simple diazonium salt with a tertiary arylamine will result in the coupling of the diazonium nitrogen to the para-position of the arylamine, by a simple electrophilic aromatic substitution reaction.
Arylamines, like simple aliphatic amines, are good nucleophiles and undergo acyl transfer reactions with carboxylic acid derivatives; in this case, the amide is formed.
Arylamines, like simple aliphatic amines, are good nucleophiles and undergo acyl transfer reactions with carboxylic acid derivatives; in this case, the amide is formed in the first step, which undergoes electrophilic aromatic substitution by Br2 in the second step. The para-bromo amide is then hydrolyzed to the amine in the last step.
The reaction of a simple diazonium salt with aqueous phosphorous acid (H3PO2) will convert the diazonium group directly into the corresponding arene.
The reaction of a simple diazonium salt with a tertiary arylamine will result in the coupling of the diazonium nitrogen to the para-position of the arylamine, by a simple electrophilic aromatic substitution reaction.
Arylamines, like simple aliphatic amines, are good nucleophiles and undergo acyl transfer reactions with carboxylic acid derivatives; in this case, the amide is formed.
Arylamines, like simple aliphatic amines, are good nucleophiles and undergo acyl transfer reactions with carboxylic acid derivatives; in this case, the amide is formed in the first step, which undergoes electrophilic aromatic substitution by Br2 in the second step. The para-bromo amide is then hydrolyzed to the amine in the last step.
