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In this experiment, N,N diethyl-m-toluamide is synthesized.
This compound The
main functional group in this molecule is an amide (Minard, 2006).
For this reaction,
amides cannot be prepared directly by mixing a carboxylic acid with an amine.
would cause an acid-base reaction.
However, if water is removed from the solution and
the resulting solid is heated strongly, water will be eliminated and the amide will be
The high temperatures required for this reaction causes very low yields
Because of this, amides are more commonly prepared by using acid
An acid chloride has a very electrophilic carbonyl carbon and the chlorine is
easily displaced by nucleophiles like amines.
For this reaction the acid chloride of m-
toluic acid is prepared by using thionyl chloride and m-toluic acid.
This acid chloride is
then directly reacted with diethylamine to produce the product (Minard, 2006).
mechanisms for these reactions are shown below.
A percent yield will be calculated for
Column chromatography will be used to separate the crude product, and gas
chromatography (GC) and gas chromatography – mass spectrometry (GC-MS) will be
performed on the desired product.
Procedure and Data/Observations:
The procedure for this lab was an adaptation from
Introduction to Organic
Laboratory Techniques: A Microscale Approach
Before conducting this
lab, a clean reaction tube with a ½” stir bar in it and 20 mL vial were placed into the oven
one lab before the experiment was performed.
This allowed the objects to thoroughly
dry, which is needed because acid chloride reacts strongly with water.
During the next lab period, a sandbath with only ¼” of sand was set up just above
a magnetic stirrer.
The Varistat was set to 30.
Next, the septum and Telfon tubing was
set up as shown in figure 1 (Minard, 2006).
Once this was set up, the reaction tube, stir
bar, and vial were removed from the oven.
When they were cool 152 mg (1.12 mmol) of
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This note was uploaded on 03/18/2008 for the course CHEM 213 taught by Professor Masters,katherinelorenzo,peterbisch,amberwilcox,jenniferlchen,ying during the Spring '07 term at Pennsylvania State University, University Park.