1. Why is it not possible to resolve the compound CH3-NH-CH2-CH3 into a pair of enantiomers? 2. Which one of the following is not affected (or is least affected) by the lone pair of electrons on an amine's nitrogen?
a. solubility in alcohols and in water.
b. hydrogen-bond formation.
c. melting point.
d. dipole moment.
e. basicity.
3. Which of the following compounds is most basic?
a. cyclohexyl amine.
b. p-nitroaniline.
c. 2,6-dimethylaniline.
d. p-methoxyaniline.
d. aniline.

1. In the compound, H3C-NH-CH2-CH3, there are no chiral centers present, chiral centers refer to the configuration in which carbon is attached with four different groups. In the molecules, as there are no chiral centers, therefore the molecule is optically inactive, that is, it will not demonstrate pair of an enantiomer is one of the essential characteristics of optically active compounds is the possession of enantiomeric pairs.  

2. On the nitrogen of aniline, the lone pair of electrons can produce hydrogen bonds, play an essential function in basicity, play an essential role in dipole moment or polarity, and wit the increase in solubility there is an increase in the formation of the hydrogen bond, eventually increasing to boiling point. However, the melting point is not affected. As the melting point is the characteristic of the packing efficacy of a molecule and does not rely upon the anilinic nitrogen's lone pairs.  

3. With the increase in the tendency to donate an electron, basicity increases. However, if the electron is taking part in resonance, the donation will not take place easily, and the compound will be the least basic. Apart from cyclohexyl amine, in all the other given compounds, the lone pair of nitrogen takes part in the process of delocalization or conjugation. Thus, cyclohexyl amine will be most basic as the lone pairs are easily available for donation.  

trigonal pyramidal

tetrahedral

trigonal planar

bent