Problems and exercisesPhysical and Bond Properties of Amines
1. Boiling points
Order from lowest to highest boiling point: propane, trimethylamine, propylamine and 1-propanol. Explain the order.
2. Nitrogen inversion
N-Methylethylamine has a nitrogen with four different substituents (counting the lone pair). Why can its enantiomers not be separated?
3. Chiral or not?
Which of these compounds can be isolated as a pure enantiomer?
- N-Ethyl-N-methylpropylamine
- Ethylmethylpropylbenzylammonium iodide
- A quinuclidine with a substituent on an asymmetric carbon
4. Solubility
Why are low-molecular-weight amines soluble in water, and why does their smell disappear when hydrochloric acid is added?