1. General

Review the following topics: Column chromatography, IR spectroscopy

2. Experiment

Safety note: Thionyl chloride is noxious and reacts vigorously with water (formation of HCl and SO₂). Diethyl amine is noxious and corrosive. It has a low boiling point.

All glassware that you will be using for the reaction has to be dry!

Rinse the syringe and needle with acetone before you use it for the amine.

Make sure that you do not have cracks in your column.

3. Things to think about

a. The ¹H-spectrum of the product show non-equivalent methylene protons for the diethyl amine group. Why?

b. Why do you sythesize the acid chloride first, before you convert it into the amide?

c. Can you determine the reactivity of a carbonyl compound based on the carbonyl stretching frequency?