Practical Endorsement GCE Chemistry

PAG5 Synthesis of an organic liquid

5.3 Oxidation of ethanol
LEARNER

5.3 Oxidation of ethanol LEARNER

Introduction
When ethanol is heated with acidified sodium dichromate(VI), it can be partially oxidised to ethanal, CH3CHO, or
completely oxidised to ethanoic acid, CH3COOH. For complete oxidation, the reagents undergo sustained heating
under reflux to ensure complete reaction and to minimise loss of substances by evaporation. The final product is
then purified by distillation. For partial oxidation, the reagents undergo reaction in a distillation setup so that the
volatile aldehyde is purified before complete oxidation occurs.

 Partial oxidation
CH3CH2OH + [O]  CH3CHO + H2O

ethanol + ‘oxygen’  ethanal + water

 Complete oxidation

CH3CH2OH + 2[O]  CH3COOH + H2O

ethanol + ‘oxygen’  ethanoic acid + water

In this activity, you will carry out the partial and complete oxidation of ethanol.

Aims and Skills

 To synthesise and purify an organic liquid
 To use reflux and distillation apparatus in an organic synthesis
 To use a water bath or electric heater or sand bath for heating
 To carry out a risk assessment

Intended class time

 2 hours and time to complete the risk assessment

This document may have modified from the original – check the master version on OCR Interchange if in doubt.
© OCR 2015-16 Page 1 v2.1 – 9 March 2016
 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.3 Oxidation of ethanol
LEARNER

Chemicals
You are provided with the following:

Label Identity Hazard information

Use CLEAPSS resources or similar to find this
ethanol ethanol, C2H5OH(l)
information
sodium dichromate(VI)-2-
water, Na2Cr2O7.2H2O(s)
Na2Cr2O7.2H2O Use CLEAPSS resources or similar to find this
(preweighed) information
2 g and 4 g preweighed
samples
2.0 mol dm-3 2.0 mol dm–3 aqueous Use CLEAPSS resources or similar to find this
H2SO4(aq) sulfuric(VI) acid, H2SO4(aq) information

3.0 mol dm-3 3.0 mol dm–3 aqueous Use CLEAPSS resources or similar to find this
H2SO4(aq) sulfuric(VI) acid, H2SO4(aq) information

sodium carbonate solid, Use CLEAPSS resources or similar to find this

Na2CO3(s)
Na2CO3(s) information
0.100 mol dm-3 potassium
acidified potassium
dichromate(VI), K2Cr2O7(s), Use CLEAPSS resources or similar to find this
dichromate
in 0.100 mol dm-3 information
solution
sulfuric(VI) acid solution
< 1% w/v commercial
universal indicator Use CLEAPSS resources or similar to find this
formulation or follow
solution information
CLEAPSS Recipe Book #47.

Equipment – the same equipment is needed for each experiment

 eye protection
 anti-bumping granules
 test tubes
 measuring cylinders (25 cm3)
 thermometer (10 – 110 °C)
 Quickfit apparatus:
o pear-shaped or round-bottom flask (50 cm3)
o still head
o Quickfit thermometer (10 – 110 °C) or Quickfit adaptor (or thermometer pocket) for
thermometer
o Liebig condenser and tubing
o receiver
 wide-necked funnel
 water bath or electric heater or sand bath
 Bunsen burner
 retort stands, bosses and clamps
 dropping pipette
 glass marker pen
 beaker (250 cm3) with ice – for ice-water bath

This document may have modified from the original – check the master version on OCR Interchange if in doubt.
© OCR 2015-16 Page 2 v2.1 – 9 March 2016
 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.3 Oxidation of ethanol
LEARNER

Health & Safety

Before beginning the procedure, you must complete a risk assessment. This should:
 identify the hazard information and precautions for the chemicals you will be using and producing –
use CLEAPSS resources (Student Safety Sheets) or similar,
 consider the actions you will take during the procedure,
 plan the precautions you will take to minimise the risk.
Have your risk assessment approved by your teacher before beginning the procedure.

Procedure
Before starting your practical work, read the information below.
Decide how you will organise your practical work, and which observations you need to make and/or which
measurements you need to take. Ensure that you record all of your results in a suitable format.

Experiment 1: Complete oxidation of ethanol

1. Add the pre-weighed 4.0 g sodium dichromate(VI)-
2-water to the pear-shaped/round-bottomed flask
using the funnel. [Note carefully the amount
here.]
2. Slowly add 20 cm3 3.0 mol dm-3 sulfuric(VI) acid
into the pear-shaped/round-bottomed flask using
the funnel. [Note carefully the concentration
here.]
3. Add a few anti-bumping granules and swirl the
flask to dissolve the solid.
4. Cool the solution by swirling the flask in an ice
water bath for 2-3 minutes, until the solution is ice
cold (< 10C).
5. Carefully add 0.5 cm3 ethanol to the flask dropwise
with swirling in the ice-water.
6. Continue to swirl the mixture in the ice-water,
monitoring the temperature of the reaction with a
thermometer – you will observe an increase in
temperature.
7. When a maximum temperature has been reached,
repeat steps 4-6 with a second 0.5 cm3 ethanol.
8. Clamp the flask by the neck, position in your Figure 1: Reflux setup
heating apparatus (water bath/electric heater/sand
bath) and arrange the condenser above the flask in
a reflux setup, as shown in Figure 1. Turn on the
condenser water flow.
9. Heat the reaction mixture under reflux for about 20 minutes.

This document may have modified from the original – check the master version on OCR Interchange if in doubt.
© OCR 2015-16 Page 3 v2.1 – 9 March 2016
 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.3 Oxidation of ethanol
LEARNER

10. Allow the apparatus to cool for 5 minutes, then rearrange into a distillation setup as shown in Figure 2.

Figure 2: Distillation setup

11. Dry the outside of the flask with a paper towel.

12. Heat the reaction mixture gently with a low blue Bunsen flame until you have distilled off 2-3 cm3 of clear
colourless distillate – stopper the test tube and make a note of the boiling point of the distillate.
13. Cautiously smell the distillate, then separately test a few drops of the distillate with:
a. universal indicator solution
b. anhydrous sodium carbonate solid (the tip of spatula’s worth)
c. a few drops of 2.0 mol dm-3 sulfuric acid(VI) and a few drops acidified potassium dichromate(VI)
solution.
Record your observations.
14. IF YOU HAVE TIME: Allow the apparatus to cool for 5 minutes, then redistill your distillate – make a note of
the boiling point of the redistillate.

This document may have modified from the original – check the master version on OCR Interchange if in doubt.
© OCR 2015-16 Page 4 v2.1 – 9 March 2016
 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.3 Oxidation of ethanol
LEARNER

Experiment 2: Partial oxidation of ethanol

1. Add the pre-weighed 2.0 g sodium dichromate(VI)-2-water to the pear-shaped/round-bottomed flask
using the funnel. [Note carefully the amount here.]
2. Slowly add 20 cm3 2.0 mol dm-3 sulfuric(VI) acid into the pear-shaped/round-bottomed flask using the
funnel. [Note carefully the concentration here.]
3. Add a few anti-bumping granules and swirl the flask to dissolve the solid.
4. Cool the solution by swirling the flask in an ice-water bath for 2-3 minutes, until the solution is ice cold
(< 10C).
5. Carefully add 0.5 cm3 ethanol to the flask dropwise with swirling in the ice-water.
6. Continue to swirl the mixture in the ice-water, monitoring the temperature of the reaction with a
thermometer – you will observe an increase in temperature.
7. When a maximum temperature has been reached, repeat steps 4-6 with a second 0.5 cm3 ethanol.
8. Remove the flask from the ice-water bath, dry the outside with a paper towel and allow to warm to room
temperature.
9. Clamp the flask by the neck, arrange the Quickfit apparatus in a distillation setup, as shown in Figure 2.
Turn on the condenser water flow.
10. Heat the reaction mixture gently with a low blue Bunsen flame until you have distilled off 2-3 cm3 of clear
colourless distillate in a test tube – stopper the test tube and make a note of the boiling point of the
distillate.
11. Cautiously smell the distillate, then separately test a few drops of the distillate with:
a. universal indicator solution
b. anhydrous sodium carbonate solid (the tip of spatula’s worth)
c. a few drops of 2.0 mol dm-3 sulfuric(VI) acid and a few drops acidified potassium dichromate(VI)
solution.
Record your observations.
12. If have learnt how to make Tollens’ reagent, you could test your distillate with this as another
confirmation of the presence of an aldehyde – discuss this with your teacher.

Analysis of results
1. Interpret the results of the chemical tests on your reaction products.
2. Discuss another observation that you made that indicated that an oxidation was occurring?

Extension opportunities
1. The full equations for the formation of ethanoic acid (Experiment 1) and ethanal (Experiment 2) are
shown below.
Experiment 1: 3CH3CH2OH + 16H+ + 2Cr2O72–  3CH3COOH + 11H2O + 4Cr3+

Experiment 2: 3CH3CH2OH + 8H+ + Cr2O72–  3CH3CHO + 7H2O + 2Cr3+

Explain how the different quantities of Na2Cr2O7.2H2O and different reaction conditions allow different
organic products to be formed. Density of ethanol = 0.78 g cm–3

2. A common step in the purification of organic liquid products is shaking with water followed by separation
using a separating funnel. Explain why this would not be appropriate for purifying ethanoic acid.

3. Write an equation for the reaction between ethanoic acid and sodium carbonate. Discuss how your
results provide evidence for the higher acid strength of ethanoic acid compared with ethanal.

This document may have modified from the original – check the master version on OCR Interchange if in doubt.
© OCR 2015-16 Page 5 v2.1 – 9 March 2016
 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.3 Oxidation of ethanol
LEARNER

To submit
As evidence for the Practical Endorsement, you should have recorded evidence of all of your observations and
measurements. If you completed a risk assessment for this practical, you should also include this in your records.
All work should be clearly dated.

In addition, in preparation for the assessment of practical work in the written examinations and to help you
develop your understanding of the underlying chemical theory, you should complete the questions in the Analysis
and Extension opportunities sections.

This document may have modified from the original – check the master version on OCR Interchange if in doubt.
© OCR 2015-16 Page 6 v2.1 – 9 March 2016