follow for more ochem content Source crash course ochem "Today let’s talk about a set of reactions of aromatic amines, that variously are catalogued under “amines” and “aromatic compounds”, depending on the textbook. It involves converting an aromatic amino group (NH2) into a tremendously good leaving group (N2) which can then be replaced by various nucleophiles. However, N2 is such a good leaving group that the method only works well for aromatic amines; alkyl (“aliphatic”) amines tend to lose N2 too rapidly, making the method much less useful in that case. Treatment of an aromatic amine with nitrous acid (or sodium nitrite, which is converted to nitrous acid in the presence of acid) in the presence of a strong acid like HCl results in the loss of H2O and the formation of a new N-N triple bond. The resulting species is called a “diazonium ion”. One way to transform diazonium salts is by treating them with various compounds of copper. These are known as Sandmeyer reactions, after Traugott Sandmeyer who first discovered the reaction in 1884 (with copper acetylide!). Three key examples are: CuCl transforms aryl diazonium salts into aryl chlorides CuBr transforms aryl diazonium salts into aryl bromides CuCN transforms aryl diazonium salts into aryl cyanides (nitriles)."
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