AS Experiment 2.

10(2)

IDENTIFYING ALDEHYDES AND KETONES

INTRODUCTION
Aldehydes and ketones are carbonyl compounds containing a C=O double bond as the
functional group. For aldehydes, this is on the end of a chain with an H atom (CHO). For
ketones it is in the middle of a chain.
Both aldehydes and ketones will react with Bradys reagent to form crystals which are
yellow, orange or red in colour. This test can be used to confirm the presence of the carbonyl
group itself.
Tests to distinguish between them rely on the fact that aldehydes can be oxidised to
carboxylic acids, but ketones cannot be oxidised easily. The oxidising agents commonly used
are Fehlings solution and Tollens reagent.
Sugars like glucose, fructose, sucrose and maltose can exist in both ring and chain
formations. When the ring opens out to form the chain structure, an aldehyde or ketone
group is formed. Those which form an aldehyde group are called reducing sugars because
they can reduce both Fehlings and Tollens (though Benedicts solution is more commonly
used in Biology). Glucose and maltose fall into this category. Fructose and sucrose open out
to form ketone groups. Sucrose is a non-reducing sugar. Interestingly, although fructose has
a ketone group in the chain form of the molecule, it can be oxidised because of a molecular
rearrangement known as keto-enol tautomerism.
PRACTICAL DETAILS

Bradys Reagent
This contains the compound 2,4-dinitrophenylhydrazine. The product of the reaction
with a carbonyl compound may, if required, be purified by recrystallisation and then the
melting point can be determined. The melting point is characteristic of the original
carbonyl compound, so the specific aldehyde or ketone can be identified by looking at the
reference table in a data book.

Fehlings Solution
This is a complex containing copper (II), Cu 2+, ions. The solution has a blue colour.
When warmed with an aldehyde, the copper is reduced to copper (I) oxide, Cu 2O, which
forms as a brick-red precipitate, and the aldehyde is oxidised to a carboxylic acid. There
is no change when warmed with a ketone.
Benedicts solution is also blue. It contains a different copper (II) complex to Fehlings
solution, but forms the same brick-red precipitate of copper (I) oxide when reacted with
an aldehyde. This requires boiling, rather than just warming, of the solution and is more
suitable for non-volatile carbonyl compounds like sugars.

Tollens Reagent
This is ammonaical silver nitrate, a colourless solution containing the diammine silver (I)
ion, [Ag(NH3)2]+ ion. When warmed with an aldehyde, the silver ions are reduced to
silver metal and a silver mirror forms on the side of the test tube. The aldehyde is
oxidised to a carboxylic acid. There is no change when warmed with a ketone.
1

AS Experiment 2.10(2)

AS Experiment 2.10(2)
SOME TEST TUBE TESTS
SAFETY
Aldehydes and ketones are harmful and many are highly flammable. Keep them
away from naked flames. Dispense from the fume cupboard.
Bradys reagent is toxic. Avoid contact with the skin. Wear gloves and wash hands
after use. Use in small quantities.
Tollens reagent is explosive under certain conditions. Prepare at the time required
and dispose of any unused or part-used solutions down the sink with plenty of water.
Fehlings 2 is corrosive. Wear eye protection at all times. Avoid contact with the
skin and wash any spillages immediately with plenty of water.
1) Set up a water bath using a large beaker just over half full of water. Heat strongly till the
water boils, then turn off the gas.
2) Whilst you are waiting for the water to boil, collect several test tubes as directed by your
teacher and mix up several lots of Fehlings solution (see the instructions below). Add
different aldehydes and ketones and sugar solutions separately to the tubes and place them
in the hot water bath. Record your observations.
3) Reheat the water bath if necessary, ensuring that no flammable materials are nearby
whilst the Bunsen burner is lit. Repeat the tests with Tollens reagent after making up
several test tubes of this reagent (see instructions below). Record your observations.
4) Add a few drops of an aldehyde, ketone or a sugar solution to 1 teat pipette full of
Bradys reagent. If no crystals form immediately, cool the tube in an ice bath.
5) Empty all the test tubes down the sinks with plenty of water. Rinse the tubes and place
them in the wet tray. Leave your area clean and tidy.
To prepare Fehlings solution
Ad 10 drops of Fehlings 1 solution to a test tube. Add 10 drops of Fehlings 2 solution
whilst shaking the tube to mix the contents well. The blue precipitate formed initially should
redissolve to give a clear blue solution.
To prepare Tollens Reagent
Place 2 teat pipettes full of silver nitrate solution into a test tube. Add bench ammonia
solution dropwise, whilst shaking the test tube, until the brown precipitate that forms JUST
redissolves.

AS Experiment 2.10(2)
RESULTS
CARBONYL
COMPOUND

FEHLINGS
SOLUTION

TOLLENS
REAGENT

BRADYS
REAGENT

FEHLINGS
SOLUTION

TOLLENS
REAGENT

BRADYS
REAGENT

SUMMARY
CARBONYL
COMPOUND
ALDEHYDES
KETONES