Question

Guanidine is a neutral compound but is an extremely powerful base. In fact, it is almost as strong a base as a hydroxide ion. Identify which nitrogen atom in guanidine is so basic, and explain why guanidine is a much stronger base than most other amines.

Answer 1

See explanation

Step-by-step explanation:

The molecule called guanidine is shown in the image attached to this answer. It contains three nitrogen atoms. Two among them are sp3 hybridized while one of them is sp2 hybridized.

Guanidine is more basic than other amines because its protonanation leads to the formation of three equivalent resonance structures thereby making its protonated form quite stable. This effect is not observed in other amines.

Also, the sp2 hybridized nitrogen atom is more basic and more easily protonated because when it is protonated, three equivalent resonance structures are obtained.