Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following amines can be resolved into enantiomers at room temperature? (i) (ii) (iii) (iv)
Options
- A(i) and (iv)
- B(iii) and (iv)
- C(i), (iii) and (iv)
- D(i) and (ii)
Correct answer
B. (iii) and (iv)
Step-by-step solution
Molecule (i) is an acyclic secondary amine with a chiral nitrogen atom. It undergoes rapid pyramidal inversion at room temperature, passing through an sp^2 hybridized planar transition state, which interconverts the enantiomers and prevents resolution. Molecule (ii) has two identical methyl groups attached to the nitrogen atom. It possesses a plane of symmetry, making it achiral and impossible to resolve. Molecule (iii) is an aziridine derivative where the nitrogen atom is a chiral center. In a three-membered ring,