Which of the following compounds exsits as a nonresolvable racemic mixture?

Options

A. `CH_(3)CH(OH)COOH`
B. `C_(2)H_(5)overset(CH_(3))overset(+|)underset(C_(6)H_(5))underset(|)(N)-CH(CH_(3))_(2)Br^(-)`
C. `CH_(3)CH_(2)NHCH_(3)`
D. `CH_(3)CH_(2)CHOHCH_(3)`

Answer

C

Explanation

Because of its pyramidal shape, such an amine is chiral, the unshared pair being considered a ''fourth'' different group. However, it is not possible to separate the enantiomers because the enantiomers readily interconvert (having enough kinetic enegry at room temperature) by a process called nitrogen inversion.