Lab Aldehydes and Ketones

Objectives:

Observe the reactions of aldehydes and ketones

Identify unknown chemicals as aldehydes or ketones or neither.

Background:
The major similarity between an aldehyde and a ketone is the carbonyl group. A carbonyl group
is a carbon atom doubly bonded to an oxygen atom, as depicted below.

O
C
Both molecules have a carbonyl group, the aldehyde and ketone differ in what atom is bonded
to the carbonyl carbon. The carbonyl carbon of an aldehyde is bonded to two hydrogens or one
hydrogen and one carbon. The carbonyl carbon of a ketone is bonded to two carbons. See the
below pictures
O
O
R C H
aldehyde

R C R
ketone

Remember that the R symbolizes any carbon side-chain, from one carbon to a million carbons.
What it comes down to is that in an aldehyde the carbonyl group is on the terminal (last) carbon
and the ketones carbonyl group is not.
Three test reagents will be used in this experiment. Dinitrophenylhydrazine, chromic acid and
Tollens reagent. Dinitrophenylhydrazine, DNP for short, reacts with aldehydes and ketones to
form a light orange precipitate. Both chromic acid and Tollens reagent are used to differentiate
between aldehydes and ketones. Aldehydes may be oxidized relatively easily, while ketones
are not easily oxidized. The chromic acid will change in color from orange to green when it is
reduced by, in this case by an aldehyde. The Tollens reagent, composed of a silver-ammonium
ion, will have its silver reduced by an aldehyde. This silver will plate a glass surface creating a
mirror.

Procedure:
1. Your observations are the most important aspect of this lab. Remember to be as descriptive
as possible and highly organized. Record all observations of a separate sheet of paper,
identifying each observation as to what reactants were allowed to react.
2. In a test tube, add 2 drops of an aldehyde and add 10 drops of DNP.
3. In a test tube, add 2 drops of a ketone and add 10 drops of DNP.
4. In a test tube, add 20 drops of acetone, add 2 drops of an aldehyde, agitate and add 1 drop
of chromic acid and agitate again.
5. In a test tube, add 20 drops of acetone, add 2 drops of a ketone, agitate and add 1 drop of
chromic acid and agitate again.
6. In a test tube, add 15 drops of 6M NaOH and wait two minutes.
7. Empty the test tube, do not rinse or clean, add 15 drops of .1M silver nitrate.
8. Add 15 drops of 6M ammonium hydroxide and agitate until the precipitate is dissolved.
9. Add 5 drops of an aldehyde.

10. In a test tube, add 15 drops of 6M NaOH and wait two minutes.
11. Empty the test tube, do not rinse or clean, add 15 drops of .1M silver nitrate.
12. Add 15 drops of 6M ammonium hydroxide and agitate until the precipitate is dissolved.
13. Add 5 drops of an ketone.
14. Using all the data you have just collected, identify the unknowns as aldehydes, ketones or
neither.

Concluding Questions:
1. Identify the unknowns:
a.
b.
c.
2. Explain how you came to these conclusions.

3. What product is formed as the liver metabolizes the alcohol found in wine? Explain.

4. What product is formed as the liver metabolizes the alcohol found in an antiseptic? Explain.

5. Draw the structures for two aldehydes and two ketones and name each.