Donné van Heerden 217028986

Experiment 3: Preparation of 2-Acetylcyclohexanone

Prelab questions:
1. Research the potential toxicity of each of the reagents you will be using in this
practical.
 Cyclohexanone – Moderately toxic and not carcinogenic.[1]
 Pyrrolidine – Can cause severe chemical burns, both when inhaled as well
when there is physical contact with the skin. Can cause headaches, nausea as
well as vomiting. Anaemia could result from exposure to high concentrations.
[2]

 Toluene-4-sulfonic acid – Can cause chemical burns, both when inhaled as

well as physical contact with the skin. Can be fatal when ingested.[3]
 Acetic anhydride – All contact should be avoided. Can cause severe chemical
burns. Very toxic.[4]
 HCl – Can cause chemical burns as well as respiratory irritation.[5]
2. You will make use of a piece of apparatus known as a Dean and Stark trap in
this experiment. (a) What is a Dean and Stark trap? Draw a sketch of a typical
Dean and Stark trap.
A Dean and Stark trap is a specialized glassware that is used for the continuous
removal of water that is formed in a chemical reaction.[6]

(b) Explain why it is necessary to use this piece of apparatus in this experiment.
What function does the Dean and Stark trap perform?
The apparatus assists in the distillation of the azeotropic mixture of water and toluene
out of the reaction, however only the toluene returns to the reactions as a result of its
density being lower than that of water.
The Dean and Stark trap facilitates the removal of water to ensure thar the reaction is
pushed to completion. The water is collected in the trap.[6]
(c) Read up about azeotropic distillation. Water readily forms azeotropes with
some organic solvents. What is an azeotrope? What is the nature of the solvent
(toluene) interaction with water?
An azeotrope is a mixture containing two or more liquids whose constituents cannot
be changed by simple distillation as a result of the vapour having the same
constituents as the unboiled mixture.[7]
Water is formed as a by-product of the reaction. When the reaction is carried out, the
steam found in the reflux condenser is an azeotropic mixture of toluene and water.
Upon condensation, two layers are formed, the top layer is toluene and the bottom
layer is water. The toluene flows back into the reaction flask when the liquid level in
the Dean and Stark trap reaches the top.[8]
(d) Discuss the significance of azeotropes in this experiment.
Forming an azeotrope and using distillation to remove the water help to achieve
product-rich extracts. The significance therein lies in ones’ ability to successfully
remove any volatile components founds in a reaction mixture. The azeotropic removal
of these volatile components can drive reactions forward.[9]
(e) Describe another method that accomplishes the removal of water from a
reaction mixture.
Molecular sieves.[10]
 Ensure that the molecular sieves are dry.
 Place the sieves in a dry flask and heat under high vacuum for at least 8 hours,
whereafter you refill it with argon.
 Add the molecular sieves to the flask containing your reaction mixture and
pour the solvent over it, allow the flask to stand for about 12 hours.
 Remove the sieves by filtration

References
1. Michael T. Musser "Cyclohexanol and Cyclohexanone" in Ullmann's
Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005
2. Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I.
A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in
Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity
Scales". The Journal of Organic Chemistry.  1019–1028.
3. Armarego, Wilfred (2003). Purification of Laboratory Chemicals. Elsevier
Science. p. 370
4. Wu, Guang; Van Alsenoy, C.; Geise, H. J.; Sluyts, E.; Van Der Veken, B. J.;
Shishkov, I. F.; Khristenko (2000), Acetic Anhydride in the Gas Phase, Studied by
Electron Diffraction and Infrared Spectroscopy, Supplemented with ab Initio
Calculations of Geometries and Force Fields, The Journal of Physical Chemistry. 
5. Noam (January 1998). Structure of Concentrated HCl Solutions. The Journal of
Physical Chemistry.
6. E. W. Dean and D. D. Stark (1920). A convenient method for the determination of
water in petroleum and other organic emulsions". The Journal of Industrial &
Engineering Chemistry.
7. Moore, Walter J. Physical Chemistry, 3rd e, 1962, pp. 140–142
8. Isac-Garcia J, Dobado J. A., Calvo-Flores F. G., Martinez-Garcia H.,
Experimental Organic Chemistry, 2016
9. Anderson N, Practical Process Research and Development, 2nd e, 2012.
10. Williams, D. B. G., Lawton, M., "Drying of Organic Solvents: Quantitative
Evaluation of the Efficiency of Several Desiccants", The Journal of Organic
Chemistry 2010