EXPERIMENT 13

Aldehydes and
Ketones
 OBJECTIVES
To observe the oxidation reaction of acetone and
benzaldehyde with the action of air
To compare the oxidation rates of certain
aldehydes and ketones using KMnO4
To learn and observe the reactions of aldehydes
and ketones and be able to distinguish the two
using Fehlings test, phenylhydrazone derivative,
and iodoform test
 RESULTS
Oxidation- Action of Air

Observation
Acetone -from liquid state, the temperature decreased (the
watchglass became cold), after a while, it evaporated

-after the end of the laboratory period, the oil mixed in

benzaldehyde in the watch glass was converted to colorless
Benzaldehy crystals
-the benzaldehyde solidified into white particles like a thin
de film
 RESULTS
TESTS:
KMnO4 Fehlings Test
Acetaldehyde from purple to reddish brown to from strong blue-violet to black
brown solution, formed an solution, with brown
immiscible layer (top is precipitates below
aldehyde), rate= 3 seconds
Benzaldehyde from purple to red to brown to strong blue-violet solution
brownish yellow solution,
formed an immiscible layer
(top is benzaldehyde), rate= 7
seconds
Acetone from purple to very slight strong blue-violet solution,
reddish purple solution, rate= formed bubble-like layer at the
5 seconds top

Acetophenone from purple to red solution, strong blue-violet solution,

formed insoluble bubble-like
layer that settled at the bottom
(bottom is acetophenone),
rate= 5 seconds
Control purple solution
formed a layer with a clear
color at the top
strong blue-violet solution
 Phenylhydrazone Iodoform Test
Derivative
Acetaldehyde from light orange to from gold orange to
bright orange solution, colorless, formed white
formed red layer above precipitate
Benzaldehyde light orange solution that from gold orange to brown
formed white precipitates solution, formed black and
that settled above the brown precipitates that
solution, test tube felt settled below the solution
warm
Acetone light orange solution that from gold orange to yellow
formed layer, brown at solution, formed whitish
the top and cloudy white yellow precipitate that
below, temperature settled below solution
increased because test
tube felt warm

Acetophenone from light orange to from gold orange to pale

orange to cloudy white yellow solution, formed
solution, formed white brown layer that settled
precipitate, temperature below the solution
increased
Control light orange solution gold orange solution
 DISCUSSION
Aldehydes are easily oxidized to yield carboxylic acids, RCHO to
RCO2H, but ketones are unreactive toward oxidation. This is why
acetone just evaporated in air and not oxidized. This reactivity
difference is a consequence of structure: aldehydes have CHO proton
that can be removed during oxidation, but ketones do not.
Aldehydes that lack alpha hydrogens, such as benzaldehyde oxidizes
slower than aldehydes with alpha hydrogens such as acetaldehyde.
In the Fehlings test, aldehydes oxidized to carboxylic acids, while
ketones do not oxidized, forming immiscible layers. This explains why
acetone and acetophenone formed immiscible layers. Precipitates are
due to the formation of insoluble Cu+1 as Cu2O, which indicates the
presence of aldehyde.
In the phenylhydrazone derivative test, where after the addition of
phenylhydrazine to the carbonyl compound, it resulted in the
formation of a hydrazine.
 The reaction is a condensation reaction. A condensation
reaction is one in which the two molecules join together
with the loss of a small molecule in the process. In this
case, the small molecule is water. In terms of mechanisms,
this is a nucleophilic addition elimination reaction. The 2,4-
dinitrophenylhydrazine first adds across the carbon-oxygen
double bond (the addition stage) to give an intermediate
compound which then loses a molecule of water (the
elimination stage).
Finally, for the Iodoform test, the formation of solid
iodoform (yellow precipitate) indicates a positive test. One
should have a CH3CRO in the compound to be positive in
an iodoform test. R could be an alkyl group or a hydrogen
atom. Acetone formed whitish yellow precipitate indicating
a positive test.
 QUESTIONS
1. Only one aldehyde and only one primary alcohol give a positive iodoform
test. What are their structures?
Acetaldehyde Ethanol

One should have a CH3CRO in the compound to be positive in an iodoform test.

R could be an alkyl group or a hydrogen atom.
2. Which of the following compounds would
give a positive iodoform test?
a. CH3COCH2CH3 --- positive
b. CH3OCH2CH2CH3 ---negative
c. CH3CH2CH2CHOHCH3 --- positive
3. Explain how you could use the simple laboratory tests
performed in this experiment to distinguish between:
a. 2-pentanone and 3-pentanone
- performing the Iodoform test, a 2-pentatone will have a
positive result but 3-pentatone will not, since 2-pentanone
has a CH3CO structure while 3-pentanone doesnt have.
b. benzaldehyde and acetophenone
By performing the Fehlings test, benzaldehyde will be
oxidized and acetophenone does not. Precipitate due to the
formation of insoluble Cu+1 as Cu2O which indicates the
presence of an aldehyde.
 c. acetaldehyde and propionaldehyde
By performing the Iodoform test, acetaldehyde will be
positive and propionaldehyde will not, since acetaldehyde
is the only aldehyde that will give a positive result in an
iodoform test.
 CONCLUSION
In this experiment, it is concluded that:

Benzaldehyde was readily oxidized by air while acetone

just evaporated and did not oxidize.
Acetaldehyde was oxidized the fastest (3 sec) while
benzaldehyde was oxidized the slowest (7 sec). The
ketone samples did not oxidize well and just diluted the
color of the KMnO4.
Aldehydes can be distinguished from ketones through
the Fehlings test.
Only compounds containing CH3CRO would give a positive
result in an iodoform test. R could be an alkyl group or a
hydrogen atom.