Fundamentals of Organic ChemistryChemistryAmines
Consider the three amines shown below: Which of the following statements regarding their relative basicity is correct?
Options
- AAniline is the strongest base, and cyclohexylamine is the weakest base.
- B4-Nitroaniline is the strongest base, and cyclohexylamine is the weakest base.
- CCyclohexylamine is the strongest base, and 4-nitroaniline is the weakest base.
- DCyclohexylamine is the strongest base, and aniline is the weakest base.
Correct answer
C. Cyclohexylamine is the strongest base, and 4-nitroaniline is the weakest base.
Step-by-step solution
The basicity of amines depends on the availability of the lone pair of electrons on the nitrogen atom for protonation. Cyclohexylamine is an aliphatic amine. The lone pair of electrons on the nitrogen atom is localized and not involved in any resonance. Therefore, it is readily available for protonation, making cyclohexylamine the strongest base among the three. Aniline is an aromatic amine. The lone pair of electrons on the nitrogen atom is delocalized into the benzene ring through resonance. This delocalization r