Lab #: 8
Title: Carbonyl compounds
Aim: To test for the carbonyl group
Materials and apparatus: Bradys reagent, Tollens reagent, Fehlings solution, sample 1A,
sample 2A, distilled water, methanal, propanone, solution of iodine in potassium iodide which
contains KI3, NaOH solution, nitric acid, methanol, test tubes, test tube rack, thongs, dropper,
Petri dish, 50ml beakers
Introduction:
A carbonyl group is a functional group composed of a carbon atom double-bonded to an
oxygen atom: C=O. Aldehydes and ketones are organic compounds which incorporate a carbonyl
functional group. The carbon atom of this group has two remaining bonds that may be occupied
by hydrogen or alkyl or aryl substituents. If at least one of these substituents is hydrogen, the
compound is an aldehyde. If neither is hydrogen, the compound is a ketone.
Aldehydess and ketones undergo nucleophillic substitution reactions and behave
differently toward oxidizing agents. Because aldehydes have a hydrogen atom directly bonded to
the carbonyl carbon it makes them more reactive to oxidation than ketones. Ketones, which have
no hydrogen attached to the carbonyl carbon atom, may be oxidized to a carboxylic acid only
under more severe conditions (stronger reagents and higher temperatures), because their
oxidation to an acid requires the rupture of a carbon-carbon bond. Under the usual oxidative
conditions they will not oxidize.
Several laboratory tests that distinguish aldehydes from ketones are based on the fact that
the two classes of compounds are oxidized under different conditions. When aldehydes or ketone
are tested with Bradys reagent, a yellow/orange crystalline precipitate indicates the presence of a
carbonyl compound. With Tollens reagent, a silver mirror inside of a clean test tube indicates the
presence of an aldehydes. When aldehydes or ketones are tested with Fehlings solution, a yellow
or red precipitate indicates the presence of an aldehyde. When an aldehyde or ketone is tested
with a solution of iodine in potassium iodide which contains KI3, a positive test gives a yellow
precipitate of iodoform. This indicates that a methyl ketone is present. A methyl ketone has the
structure C=O
CH3
Procedure:
Test for carbonyl group
Reagent: Bradys reagent, 2,4-Dinitrophenylhydrazine (2,4-DNP)
1. 3 cm3 of the 2,4-DNP was added to the compounds in the test tubes and it was shaken.
No precipitate formed immediately so the test tube was placed to warm in a water bath
and allowed to stand for 5 minutes.
2. Observations were recorded for the test with both compounds-methanal and propanone.
Test for aldehydes
Reagent: Tollens reagent (Ammonical silver)
1. 2-3 drops of the compounds in methanol was added to 2-3 cm3 of Tollens reagent
contained in clean test tubes that were rinsed with nitric acid. The test tubes were placed
in a water bath.
2
2. Observations were recorded for the test with both compounds- methanal and propanone.
Reagent: Fehlings solution
1. 2 drops of the compounds was added to 2-3 drops of Fehlings and warmed on a water
bath for 4 minutes.
2. Observations were recorded for the test with both compounds- methanal and propanone.
Test for methyl ketones
Reagent: solution of iodine in potassium iodide which contains KI3
1. 5 drops of the compounds was dissolved in 2 cm3 of water.
2. If the compounds were soluble in water, 1 cm3 of 3m NaOH solution was added. Then
iodine solution was added drop wise and with shaking until the dark colour of iodine
persisted.
3. The test tubes were allowed to stand for 2-3 minutes. If no iodoform separated at room
temperature, the test tubes were warmed in a water bath.
4.
Observations were recorded for the test with both compounds- methanal and propanone.
Test with sample 1A and 1B
1. All procedures were repeated using sample 1A and 1B.
2. Observations were recorded.
Results:
Methanal
Bradys
Fehlings
Tollens
Iodoform
Inference
reagent
Yellow
solution
Yellow
reagent
White
No
Aldehydes
orange
precipitate
precipitate
observable
present
3
precipitate
fromed
formed at
formed
whrn test
bottom of
when test
tube
test tube.
tube
warmed
Upon
warmed
reaction
waming ,
precipitate
changed
to black.
Solution
changed
to dark
Propanone
Orange
No
grey.
No
Pale
Methyl
precipitate
observable
observable
yellow
ketone
formed
change
change
precipitate
pesent
upon
Sample 1A
fomed
heating.
Orange
No
White
Pale
precipitate
observable
precipitate
yellow
formed
change
fomed
precipitate
that
fomed
disappear
ed upon
Sample 2A
Yellow
Yellow
heating
White
orange
precipitate
precipitate
obvious
compound
precipitate
formed
fomed.
change
contains
No
This
formed
This tuned
the
to black
carbonyl
upon
group and
heating
is easily
oxidized
hence it is
an
aldehyde
