Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in decreasing order of their basic strength: (I) (II) (III)
Options
- A(III) > (II) > (I)
- B(III) > (I) > (II)
- C(II) > (I) > (III)
- D(II) > (III) > (I)
Correct answer
A. (III) > (II) > (I)
Step-by-step solution
The basic strength of an amine depends on the availability of the lone pair of electrons on the nitrogen atom for protonation. In compound (III), cyclohexylamine, the nitrogen atom is attached to an sp^3 hybridized carbon of the cyclohexane ring. The lone pair on the nitrogen atom is localized and fully available for protonation. The +I effect of the cyclohexyl group further increases electron density on nitrogen, making it the most basic. In compound (II), aniline, the lone pair of electrons on the nitrogen atom i