MIDLANDS STATE UNIVERSITY
P. Bag 9055,
Gweru,
Zimbabwe
Telephone: (263) 54 260331/7 Ext 2305
Fax: (263) 54 260233 Email: chauyan@staff.msu.ac.zw
DEPARTMENT OF CHEMICAL SCIENCES
ORGANIC CHEMISTRY II: Preparation of Benzil from benzoin by
oxidation.
Principle
Here alcohol group if benzoin is oxidized to ketone group forming benzil in the presence of
concentrated nitric acid. Nitration of aromatic ring is not occurring as sulphuric acid is totally
absent in the whole process.
This is the base catalysed conversion of aromatic 1,2-diketones into salts of alpha
hydroxycarboxylic acids. The best known example is the conversion of benzyl (2) into Benzilic
acid ie:the Benzilic acid rearrangement. Kinetic studies show that the migration of the phenyl
group with its bonding pair of electrons, to the weakly positive carbon atom of the adjacent
carbonyl group is the rate determining step.
Chemicals
Benzoin 10g; Conc Nitric acid 25ml, ethanol
Glassware
Round-bottomed flask, Reflux water condenser, Beaker, Measuring cylinder, Pipette,
Procedure
(a) oxidation of benzoin(1) to benzil
I. Dissolve 3.8g benzoin in 12 ml conc HNO3 in a 50 ml round-bottomed flask.
II. Heat the mixture in a fume cupboard on a steam bath with occasional shaking for
11/2hrs or until the evolution of brown fumes stops.
III. Pour into a stirred mixture of crushed ice and water, filter off the crystalline ppt with
suction, and wash with water, why?
IV. Recrystallize the solid from boiling EtOH (CA.7ml).
V. Record yield, and IR of your product. Keep what you do not use in the next step for
marking.
Testing the presence of unoxidized Benzoin
Dissolve about 5mg of purified benzil in 0.5ml of 95% ethanol. Add 1 drop of 10%
sodium hydroxide. Observe color changes in 2-3 minutes.
Results
Calculate theoretical yield
Using the practical yield, calculate the Percentage yield and give a brief comment.
Test Observation Conclusion
Questions
1. From the balanced equation, how many moles of nitric acid required per mole of
benzoin?
2. What is the role of Nitric acid in the reaction?
3. How many steps are involved in the Mechanism if the reaction?
4. Name and describe what happens in the 2 steps involved.
5. What color is benzil?
6. Why are some organic compounds colored, but others are not?
7. What is extended conjugation system and how many carbon atoms are involved in
extended conjugation system of benzil
References
1. Mann F. G., Saunders B. C., A textbook of “practical organic chemistry”, Pearson
education, published by Dorling Kindersley (India) Pvt. Ltd., 4 th edition, page no.
234.
2. Furniss B. S., Hannaford A. J., Smmith P. W. G., Tatchell A. R., “ Vogel’s
textbook of practical organic chemistry”, ELBS and Longmans green Co. Ltd.,
London, Fifth edition, page no. 1045.
