Identification of unknown organic compounds via

qualitative tests for functional groups

(modified ASC 12th Nov 2024)

In recent times, complete identification of unknown organic compounds is most readily carried out via advanced
instrumental techniques such as NMR Spectroscopy. However, an initial analysis of functional groups via chemical
methods is still often useful prior to making use of more advanced methods.

In this experiment, a sequence of tests will be used to identify a set of known but unlabelled compounds via analysis of
the functional groups present.

Equipment (per group)

• 22 x test tubes and spares
• 6 x bungs for test tubes (minimum)
• 1 x test tube rack (minimum)
• 12 x dropper pipettes
• 2 x well plates or spotting tiles
• 2 x beakers, 400 cm3 (for water baths)
• Hot plate

• Samples A - F (unlabelled randomly ordered samples of butanone, t-butanol, ethanol, bromobutane, ethanoic
acid and cyclohexene)

• Potassium dichromate solution 0.1 mol dm-3 (DANGER: corrosive, harmful, irritant, health hazard)
• Silver nitrate solution, 0.1 mol dm-3 (WARNING: irritant)
• Sodium hydroxide solution, 0.4 mol dm-3 (WARNING: irritant)
• Ammonia solution 1.00 mol dm-3 (WARNING: irritant)
• Brady’s reagent (DANGER: flammable, corrosive)
• Sodium or potassium hydrogen carbonate solution, 0.4 mol dm -3
• Ethanol (DANGER: flammable, harmful if swallowed, may cause damage to organs)
• Bromine water, 0.2 mol dm-3 (DANGER: corrosive, irritant)

Safety
Wear eye protection throughout.

Avoid skin contact and wear chemical resistant gloves particularly if you have any open wounds or skin conditions. Wash
hands with soap at the end of the experiment.

Avoid breathing chemicals, keep bottles closed and bungs on test tubes as much as possible. Dispose of
the reaction products after each step if possible.

Silver nitrate solution stains clothing and surfaces.

Keep all reagents away from open flames.

© 2022 Royal Society of Chemistry 1 Qualitative tests for organic functional groups | Learner instructions
Method
Plan the order to do the relevant tests listed. Tabulate the results.

Test for alcohols

1. Add 3–4 drops of acidified potassium dichromate to a well in a spotting tile. Take care to avoid skin contact and
wipe any spills immediately with a damp cloth/paper towel.

2. Add a drop of the sample to the same well.

3. Repeat steps 1 and 2 for the remaining samples.

4. Observe and record any colour changes.

5. If only one sample gives a colour change from orange to green, remove this from further testing.

Test for aldehydes

1. Add 2.5 cm3 of silver nitrate solution to a clean, dry test tube. Take care to avoid spilling silver nitrate solution
as it stains clothing and surfaces.

2. Add 1 drop of sodium hydroxide to the test tube.

3. Add ammonia dropwise with agitation until the precipitate just dissolves. This is Tollens’ reagent.

4. Heat the Tollens’ reagent in a water bath to 60–70°C.

5. Add 2 cm3 of the sample identified as an aldehyde to the test tube and give it a little shake.

6. Leave the test tube in the water bath for around 15 minutes.

7. A silver mirror will from in the presence of an aldehyde.

8. Dispose of the reaction mixture immediately down a foul-water drain.

Test for carbonyl groups

1. Add 3–4 drops of Brady’s reagent to a well in a spotting tile. Take care to avoid skin contact.

2. Add 3–4 drops of the sample to the same well.

3. Repeat steps 1 and 2 for the remaining samples.

4. Observe and record your results.

5. If only one sample gives a positive result of an orange precipitate, remove this from further testing.

Test for carboxylic acids

1. Add 2 cm3 of the sample to a labelled test tube and place a bung on top.

2. Remove the bung and add 3–4 drops of sodium hydrogen carbonate solution to the test tube.

3. Observe and record your results in a table.

4. Repeat steps 1–3 for the other remaining samples.

5. If only one sample gives a positive result of effervescence, remove this from further testing.

© 2022 Royal Society of Chemistry 2 Qualitative tests for organic functional groups | Learner instructions
Test for haloalkanes

1. Add 2 cm3 of ethanol to a labelled test tube.

2. Add 10 drops of the appropriate sample to the test tube.

3. Add 2.5 cm3 silver nitrate solution to a second labelled test tube. Take care to avoid spilling silver nitrate
solution as it stains clothing and surfaces.

4. Repeat steps 1–3 for the other remaining samples.

5. Set up two water baths, with 100 cm3 just boiled water and 100 cm3 cold tap water.

6. Place the test tubes with the sample and ethanol into one of the water baths. Place the test tubes with the
silver nitrate solution into the second water bath.

7. Warm the solutions for five minutes.

8. Remove the silver nitrate solution test tubes from the water bath.

9. Pour the first sample into the appropriately labelled silver nitrate solution test tube.

10. Observe and record your results.

11. Repeat steps 9 and 10 for the remaining samples.

12. If only one sample gives a positive result of a precipitate, remove this from further testing.

Test for unsaturated hydrocarbons

1. Add a few drops of the sample to a labelled test tube.

2. Add 1 cm3 of bromine water to the sample. Shake the test tube vigorously from side to side.

3. Observe and record your result in a table.

4. Repeat steps 1 and 2 for the remaining samples.

6. If only one sample gives a positive result of turning the bromine water colourless, remove this from further
testing.

Disposal
• Always dispose of chemicals carefully following your teacher’s instructions.
• Empty your test tubes after testing for carboxylic acids, haloalkanes and unsaturated hydrocarbons into the
labelled waste container.
• Rinse the spotting tiles used for testing alcohol and carbonyl groups.
• Dispose of the aldehyde test’s reaction mixture immediately down a foul-water drain.

© 2022 Royal Society of Chemistry 3 Qualitative tests for organic functional groups | Learner instructions
Results
Test carboxylic unsaturated carbonyl
haloalkanes alcohols aldehydes
for... acids hydrocarbons groups
acidified
Test metal bromine silver nitrate Tollen’s
potassium 2,4-DNPH
used... carbonate water solution reagent
dichromate

Sample Functional group present Identity

A
B
C
D
E
F

Discussion
1. What is the difference between qualitative and quantitative analysis?

2. Tabulate the functional group and identity inferred for each unknown.

3. Explain how the ethanoic acid was identified.

4. Explain how the butanone was identified.

5. Explain how each alcohol was identified.

6. Explain how the cyclohexene was identified.

7. Using structural formulae, write an equation for the reaction of cyclohexene with bromine water. (States not

© 2022 Royal Society of Chemistry 4 Qualitative tests for organic functional groups | Learner instructions
 required.)

8. Explain how the haloalkane was identified.

9. Suggest a mechanism for the hydrolysis of the haloalkane.

© 2022 Royal Society of Chemistry 5 Qualitative tests for organic functional groups | Learner instructions