Acid Catalysed Ioodinaton of Propanone

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THE KINETICS OF THE ACID-CATALYSED IODINATION OF PROPANONE

INTRODUCTION:
Propanone reacts with iodine in the presence of an acid catalyst according to the equation:
+
H
CH3COCH3 + I2 → CH2ICOCH3 + H+ + I-

The rate of the reaction can be followed by measuring the time taken for the yellow colour of the
iodine initially present to disappear. The rate equation can be expressed as:
Rate = k [CH COCH ]x [I ]y [H+]z
3 3 2
(where k = rate constant and x, y and z are the orders of the reactions with respect to propanone,
iodine and hydrogen ions respectively).
The aim of this practical is determine x, y and z and hence the overall order of the reaction. You will
then be asked to propose a possible mechanism for the reaction which is consistent with the rate
equation.

ENVIRONMENTAL CARE: Although propanone occurs naturally, halogenated hydrocarbons can


pose particular problems and even though you are only dealing with dilute solutions transfer all the
residues to the marked container in the fume cupboard. Do not dispose of them down the sink. The
quantities used in this experiment have been reduced from those normally recommended to limit the
effect on the environment.

SAFETY: The product, iodopropanone, is a powerful lachrymator. Even the very small vapour
pressure of it above the solution can make your eyes smart, unless you are careful to keep the tubes
securely corked except when you are transferring samples.

PROCEDURE: For each experiment (a - g) use a burette to put the suggested volume of iodine
solution into a test-tube, and add the suggested volumes of acid and water from other burettes. Put
the required amount of propanone into a separate tube. The two tubes should be added together,
mixed quickly, and the stop-clock started. Note the time taken (in seconds) until the last trace of
yellow colour disappears. At the end of the experiment pool your results with others in the class.

Reaction mixtures:
-3
Va = volume of 2.0 mol dm propanone(aq)
-3 -3
Vb = volume of 0.0050 mol dm iodine (in 0.050 mol dm KI)
-3
Vc = volume of 1.0 mol dm sulphuric acid
Vd = volume of water

3 3 3 3 +
Mixture Va / cm Vb / cm Vc / cm Vd / cm [CH3COCH3] [I2] [H ]
-3 -3 -3
/ mmol dm / mmol dm / mmol dm

a 2 2 2 4 400 1.0 400


b 4 2 2 2 800 1,0 400
c 6 2 2 0 1200 1.0 400
d 2 1 2 5 400 0.5 400
e 2 0.5 2 5.5 400 0.25 400
f 2 2 4 2 400 1.0 800
g 2 2 6 0 400 1.0 1200

QUESTIONS:
1. Calculate the values of x, y and z and hence give the overall rate equation.
2. Suggest a mechanism for the reaction which is consistent with the rate equation.

© Dr Geoffrey Neuss, InThinking


http://www.thinkib.net/chemistry 1

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