Nitrogen-containing compounds

Introducing reactions of nitrogen-containing compounds.

Acetone forms imine with methylamine:

Steps:

1. Acetone is protonated;
2. Lone pair on N in methylamine attacks protonated carbonyl group;
3. Hydroxyl group in the intermediate is protonated, and then the lone pair on the N facilitates the elimination of water;
4. The formed iminium ion deprotonates to form imine.

Acetone forms enamine with dimethylamine:

Steps:

1. Acetone is protonated;
2. Lone pair on N in dimethylamine attacks the protonated carbonyl group;
3. Hydroxyl group in the intermediate is protonated, and the C-H bond on adjacent methyl group is subsequently eliminated to produce enamine.

Formation and transformation of benzenediazonium salt:

Steps:

1. Nitrite is protonated, forming protonated nitrite acid;
2. Lone pair on N in aniline attacks N=O of protonated nitrite acid;
3. After proton transfer, water on the distal nitrogen is eliminated;
4. After another proton transfer, a molecule of water on the distal nitrogen is eliminated, forming benzenediazonium salt;
5. Benzenediazonium salt forms halogenated benzene under the catalysis of CuX.