Elizabeth Ping | February 28, 2012| 1

Preparation of Benzilic Acid

Introduction:

The purpose of this experiment was to prepare benzilic acid by the rearrangement of the alpha-
diketone benzil as well as to determine the melting point and IR of benzilic acid

Benzil to benzilic acid

Mechanism of the rearrangement of benzil to make benzilic acid

Procedure:
See attachment.

Observations:

Dried product (Benzilic acid) 0.056 g

Percent yield 52%
Melting point Benzilic acid (expected: 150 °C) 150 °C

See IR spectroscopy sheet for benzilic acid.

 Elizabeth Ping | February 28, 2012| 2

Calculations:

Theoretical yield:

Benzil= (0.1 g)(1 mol/210.232 g) =4.757X10-4 mol Benzil

KOH = (0.25 mL)(2.044g/1 mL)(1 mol/56.097 g)=9.111X10-3 mol KOH

Therefore, Benzil is the limiting reagent.

(4.757X10-4 mol Benzil)(1 mol Benzilic acid/1 mol Benzil)(228.247 g/mol Benzilic acid/1 mol
Benzilic Acid)= 0.1086 g Benzilic acid

Percent yield =(actual/theoretical)X 100%= (0.056 g /0.1086 g)*100= 52%

Conclusion:

In this experiment, benzilic acid was prepared by a rearrangement of the alpha-diketone benzil.
The possible amount of benzilic acid was 0.1086 g; while 0.056 g was the actual amount
produced which gave a percent yield of 52%. The observed melting point of benzilic acid was
150 °C which is the same as the expected melting point of benzilic acid. This suggests that the
product is pure. The IR of benzilic acid showed an O-H at ~3400 cm-1, carboxylic acid at ~2800
cm-1 (very wide), C=O at ~1700 cm-1, C-O at ~1250 cm-1 and an aromatic at ~700 and 750 cm-1.

Sources of error may have been due to using unclean glassware that may have produced side
reactions. Some of the product may have been lost during transferring and during the filtration
process since some green/pale brown color could be seen in the Erlenmeyer flask.

Questions:

See attachment.

References:

Pavia, Donald, Gary Lampman, George Kriz, and Randall Engel. Introduction to Organic
Laboratory Techniques: A Microscale Approach. Belmont: Thomson Brooks, 2007.