Reactions of alcohols

Reference: Chapter 10, Section 10.2, pages 335–338

Please note
• A full risk assessment should be carried out prior to commencing this experiment.
• Personal safety equipment should be worn.
• Chemicals should be disposed of safely and with due regard to any environmental considerations.

Aim
To investigate some reactions of alcohols.

Introduction
Alcohols are a class of compounds that contain the hydroxyl –OH functional group. Their characteristic properties
can be described in terms of the chemistry of this functional group, and how it is affected by its position in the
molecule. The differences between the structures of primary, secondary, and tertiary alcohols are described on
pages 320 and 321.
In this experiment we will investigate the properties of different alcohols using a variety of approaches, including
micro-scale chemistry and demonstrations. The experiments are all qualitative in nature, and the results depend
on careful observations of reactions occurring.

Pre-lab questions
1 Combustion involves oxidation. Explain why combustion reactions and oxidation reactions are described
separately for alcohols, with reference to the part of the molecule involved in the reactions.
2 Potassium dichromate is used as the oxidizing agent in these reactions. State the change in oxidation state
that it undergoes, and the accompanying colour change that will be observed.

Method
A Solubility
1 Put approximately 3 cm3 of ethanol in a test tube and add approximately the same volume of water. Add a
few drops of universal indicator solution.
2 Record the solubility of ethanol in water and its pH.

B Combustion
1 Place a few drops of ethanol on a watch glass and light carefully.
2 Repeat with drops of the other alcohols provided.
3 Make full observations and write an equation for the reaction that occurs.
4 What products might result if the combustion occurs in a limited supply of oxygen?

© Pearson Education Ltd 2014. For more information about the Pearson Baccalaureate series please visit
www.pearsonbacconline.com
C Oxidation of different alcohols: microscale
1 Use a dropping pipette to place 10 drops of the provided solution of acidified potassium dichromate into
each of 6 wells in a well-tray.
2 Add 2 drops of a different alcohol to each well as shown below.

Well 1 Well 2 Well 3 Well 4 Well 5 Well 6

control CH3OH, C2H5OH, C3H7OH, CH3CH(OH)CH3, C(CH3)3OH,

methanol ethanol propan-1-ol propan-2-ol 2-methylpropan-2-ol

(Well 1 is a control and has no alcohol.)

3 Leave the wells to stand for about 15 minutes and note any changes in colour in each well.
4 Explain the reactions that occurred and write equations showing the organic reactants and products, using [+
O] for the oxidizing agent.

D Complete oxidation of ethanol: best done as demonstration

1 Assemble the apparatus as shown below.

2 Add 10 cm3 dilute H2SO4(aq) into the pear-shaped flask and add 2–3 g K2Cr2O7.
3 Swirl gently until all the solid has dissolved. Cool the flask under running water.
For safety reasons it is essential that this stage is completed thoroughly before proceeding.
4 Set up the apparatus for reflux. Add 1 cm3 ethanol dropwise down the condenser and into the flask. Boil
under reflux for 20 minutes.

© Pearson Education Ltd 2014. For more information about the Pearson Baccalaureate series please visit
www.pearsonbacconline.com
5 When the oxidation reaction is complete, the apparatus is rearranged for distillation, and ethanoic acid can
be collected.

6 Record your observations at each stage.

E Esterification
1 Place 5 cm3 ethanol, 6 cm3 of 1.0 mol dm–3 CH3COOH and 10 drops of concentrated H2SO4 into a round-
bottomed flask and heat gently for a few minutes.
2 When the reaction is complete, pour the reaction mixture into a beaker of cold water containing sodium
carbonate, Na2CO3. Transfer the contents of the beaker to a separating funnel and separate the ester layer.
Smell the product.
3 Write an equation for the reaction that occurred.

Results and conclusion

• Record all your observations to each part clearly.
• Write equations for all reactions that occurred.
• Comment on any results that did not fit your predictions and try to explain these.

For consideration
1 With reference to the principles of Green Chemistry, what are some advantages of using micro-scale in
laboratory experiments? What are some disadvantages?
2 How could you test the purity of the ethanoic acid collected at the end of experiment D?

© Pearson Education Ltd 2014. For more information about the Pearson Baccalaureate series please visit
www.pearsonbacconline.com
3 In experiment D, what product may be obtained if the oxidation reaction is only partially complete?
4 In experiment E the sodium carbonate is used to help separate the ester product from any unreacted
alcohol. Explain how this works.
5 How could you make a sample of ethyl ethanoate, starting only from a sample of ethanol?
6 Other than oxidation, can you think of other reactions in which primary, secondary, and tertiary alcohols
may behave differently?

© Pearson Education Ltd 2014. For more information about the Pearson Baccalaureate series please visit
www.pearsonbacconline.com
Equipment list
Chemicals / materials
methanol, CH3OH
ethanol, C2H5OH
propan-1-ol, C3H7OH
propan-2-ol, CH3CH(OH)CH3
2-methylpropan-2-ol, C(CH3)3OH
universal indicator solution
acidified potassium dichromate solution: prepared from 2 g K2Cr2O7 in 80 cm3 H2O + 10 cm3 concentrated H2SO4.
K2Cr2O7(s)
concentrated H2SO4
dilute H2SO4
1.0 mol dm–3 CH3COOH
Na2CO3

Apparatus (per group of students)

well-plate, e.g. 24 wells
dropping pipettes
round-bottomed flask
hot plate

Demonstration apparatus
reflux set up
distillation set up

© Pearson Education Ltd 2014. For more information about the Pearson Baccalaureate series please visit
www.pearsonbacconline.com