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 crystals
Benzaldehyde -the benzaldehyde solidified into white particles like a thin film
TESTS: RESULTS
 Phenylhydrazone Derivative Iodoform Test

from light orange to bright from gold orange to colorless,

orange solution, formed red
layer above
light orange solution that
formed white precipitates that
settled above the solution, test
tube felt warm
light orange solution that
formed layer, brown at the top
and cloudy white below,
temperature increased
because test tube felt warm
formed white precipitate
from gold orange to brown
solution, formed black and
brown precipitates that settled
below the solution
from gold orange to yellow
solution, formed whitish yellow
precipitate that settled below
solution

from light orange to orange to from gold orange to pale yellow

cloudy white solution, formed solution, formed brown layer that
white precipitate, settled below the solution
temperature increased
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.