Aldehydes and Ketone

Aldehydes and ketones
Aldehydes and Ketones are two classes

of compounds that contain the carbonyl group.
Examples;
ALDEHYDES; Acetaldehyde, Benzaldehyde.
KETONES; Acetone, Acetophenone, Benzophenone
1
Preparing Aldehydes and Ketones
Oxidation of primary Alcohols, produce Aldehydes;
[O]
Primary alcohols Aldehydes
[O]
CH3-OH Formaldehyde +H2O
[O]
CH3CH2OH Acetaldehyde +H2O
The oxidation of secondary Alcohols, yields ketone.
[O]
2-Propanol Acetone +H2O
2
Reactions of Aldehydes and Ketones;
1-Addition reactions;
Addition to the carbonyl group is one of the major
reactions of Aldehydes and Ketones.
While this reaction appears to be similar of the
(C=C) Carbon-Carbon double bond, there is an
important difference that is due to the difference in
the polarity of the two double bonds.
3
A-Addition of water;
Most aldehydes react with water to form an equilibrium
mixture of the aldehyde an aldehyde hydrate.
Aldehyde +H2O Aldehyde hydrate
These aldehyde hydrates are 1,1’-diols
Examples;
Chloral +H2O Chloral hydrate
Hexa fluro acetone +H2O Hexa fluro acetone

Hydrate
Chloral hydrate is an example of stable hydrate. it is a

Crystalline compound that is used in veterinary medicine as an
anesthetic for animals.
4
B-Addition of alcohols (formation of hemiacetal,
acetal, hemiketal, and ketal,
Aldehydes react with alcohols in the presence of an acid
catalyst to form a hemiactal as product.
Aldehyde +Alcohol hemiacetal

A hemiactal contains alkoxy and alcohol group,
both bonded with original carbon of the carbonyl
group.
In the presence of excess alcohol, a hemiactal can
React with alcohol to form an acetal and water.
Hemiactal +Alcohol acetal +H2O

5
Ketones react with alcohols in a
similar manner to form hemiketals
and ketals.
Ketone + Alcohol Hemiketal
Hemiketal + Alcohol ketal +H2O
6
2-Reduction of aldehydes and alcohols
the reduction of aldehydes and ketones forms

alcohols. primary alcohols are formed from
aldehydes,whereas secondary alcohols are formed
from ketones.
Pt
Aldehydes + [H] Primary alcohols
Pt
ketones + [H] Secondary alcohols
7
Biological oxidation of alcohols also
occur in the body.
ALD
CH3CH2OH +NAD NADH + Acetaldehyde +H
ALD Alcohol dehydrogenase
8
3-Oxidation reactions of Aldehydes
Although aldehydes and ketones are similar in
structure and generally show the same chemical
properties, they differ in their ability to undergo
oxidation.
Aldehydes are easily oxidized, but ketones are not,
this is because the C-H bond is more reactive than the
C-R bond.
[O]
Aldehydes carboxylic acids

[O]
Ketones no.reaction
9
Since oxidation is important
chemical difference between
Aldehydes and Ketones, it is the
bases of several chemical tests used
to distinguish an Aldehyde from a
Ketone. Two tests commonly used in
the laboratory are Tollen’s test and
Benedict’s test.
10
Benedict’s test is a solution of copper (II) ion in a
complex with citrate ions, when benedict’s
reagent is added to compound containing an aldehyde
group, the aldehyde is oxidized to the carboxylic
ion,however,in the Benedict’s test
the copper (II) ion, which is blue color is reduced to the
copper (I) oxide, which is red color and precipitates
due to it is low solubility.
Aldehyde +2Cu(II) RCOO + Cu2O(I)
Ketone + 2Cu(II) No.reaction

11
Benedict’s test is used in clinical laboratories to
test for the presence of glucose (a reducing
agent) in urine, so that Benedict’s test used to
diagnosis of diabetes mellitus, because in
normal person, the glucose is not appear in
urine.
boiling
Glucose + 2Cu(II) Gluconic ion +Cu2O(I)
(In urine) Benedict’s (red color)
reagent (blue color)
12
4-Aldol condensation
The condensation reaction involves the addition of
one aldehyde to another, with bases as a catalyst.
base
Acetaldehyde +acetaldehyde 3-hydroxy
butanal
In the condensation reaction, two important thing

happen.
1-The carbon chain is increased.
2-the product has an aldehyde group and also alcohol
group, this type condensation is called an aldehyde
condensation.
13
Condensation reactions in living systems;
Carbohydrates are prepared in living systems by
an enzyme catalyzed aldol condensation. a
specific sample is the preparation of fructose-
1,6-diphosphate by the condensation of
dihydroxy acetone phosphate and glycer
aldehyde-3-phosphate
dihydroxy acetone phosphate +
glycer aldehyde-3-phosphate aldolase
fructose-
1,6-diphosphate
14
Medical uses of aldehydes and ketones
1-aldehydes;
1-formaldehyde (methanal)
Formaldehyde is a colorless gas with a very
sharp odor, it is used in the laboratory as a
water solution containing 40%, commonly
known as formalin. is an effective germicide
for the disinfection of rooms and clothing. it is
used also as preservative for biologic
specimens. Formaldehyde solutions shouldn't
be used directly in the room with the patient
because of irritating fume. 15
2-Gluteraldehyde
Gluteraldehyde is a sterilizing agent and its
also microcidal against all microorganisms,
including spores and viruses,
Gluteraldehyde does not have disagreeable odor
like formaldehyde and its less irritating to the eyes
and skin.
3-Glycer aldehyde
is an important component in the metabolism of
carbohydrates.
16
2-Ketones
1-Acetone (Propanone)
Acetone is an important product of lipid metabolism
in the body, its concentration in the blood is increased
in certain metabolic disease such as diabetes mellitus.
in diabetes, glucose utilization is inhibited and there
is excessive breakdown of fats, since acetone is one
of the normal product of fat metabolism, is excreted
in the urine. as the acetone concentration of the blood
increase, the volatile acetone is exhaled, this is a
characteristic sign of diabetes.
17
Aromatic aldehydes;
Some aromatic aldehydes are used to flavor food
and as fragrances in perfumes.
Examples;
 Benzaldehyde is found in Almonds
 Vanillin in Vanilla beans, and
 Cinnamaldehyde in Cinnamon.
18

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Aldehydes and Ketone

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Aldehydes and ketones

Aldehydes and Ketones are two classes

Chloral +H2O Chloral hydrate

Hexa fluro acetone +H2O Hexa fluro acetone

Chloral hydrate is an example of stable hydrate. it is a

Aldehyde +Alcohol hemiacetal

Hemiactal +Alcohol acetal +H2O

Ketone + Alcohol Hemiketal

Hemiketal + Alcohol ketal +H2O

the reduction of aldehydes and ketones forms

ALD Alcohol dehydrogenase

Aldehydes carboxylic acids

Aldehyde +2Cu(II) RCOO + Cu2O(I)

Ketone + 2Cu(II) No.reaction

In the condensation reaction, two important thing

 Vanillin in Vanilla beans, and

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