Instruction sheet for students.

CHM556
Experiment 3
Esterification Reactions of Vanillin:
The Use of NMR to Determine a Structure

Refer to experiment 67, page 863 of the laboratory textbook: Introduction to Organic
Laboratory Techniques, A Small Scale Approach, 3 rd Edition by Engel, Kriz, Lapman
and Pavia.

In this experiment, you will investigate the reactions between vanillin and acetic
anhydride under two conditions, basic and acidic conditions. These reactions will
produce different products. Conduct the experiment as described in the textbook.

You are given two lab sessions to complete this experiment. The first session should
be used to conduct the reactions and obtain the products. The second session should
be used to measure melting points, obtain NMR and IR spectra and consultation with
your instructor.

Acetic anhydride used in this experiment is a controlled chemical and very difficult to
purchase. Do not waste this reagent, take only the amount needed.

Conduct the reaction under acidic condition first because this reaction requires 1 hour
of stirring. While waiting for the reaction to stir, you may start the reaction under
basic condition.

Reaction under acidic condition will involve interesting colour changes, observe these
changes and record them in your lab notebook.

Make sure you review techniques on Recrystallization before starting off with the lab
session. For recrystallization of the product under basic condition (product A), use
minimal amount (about 15 ml) of warm 95% ethanol to dissolve the crude product.
Do not heat over 60oC. Once the crystals start to appear, continue cooling in an ice
bath containing a little bit of salt.

Melting points of both products are below 100oC. Do not place the products in oven
to dry.

For both products, obtain proton NMR and IR spectra. The NMR instrument is in
room 307 and IR instrument is in 305. There will be a queue for usage of NMR and
IR, so you will need to make an appointment with En Nordin Ali (NMR) and En
Kadim (IR).

Organic Chemistry Section,

School of Chemistry and Environmental Studies,
Faculty of Applied Sciences,
Universiti Teknologi MARA.