ALDEHYDES AND KETONES 6.

Have dipole-dipole interaction

7. Higher boiling point than alkenes
Aldehydes and Ketones – can be considered as
8. Lower boiling point than alcohol
derivative of hydrocarbon (HC) in which two H atoms
9. Somewhat pleasant odor and some has mild
on the same C atom have been replaced by an O
odor or odorless.
atom.
Preparation in the Laboratory
Aldehydes – the carbonyl group C=O is linked to
one C atom and one H atom. 1. Oxidation of primary alcohols
2. Reduction
Ketones – it is linked to 2 C atoms.
3. Addition
Nomenclature 4. Substitution
5. Condensation
In the IUPAC rules of naming aldehydes are 6. Dehydrogenation of primary alcohols
associated with the ending -al. Ketones with the 7. Hydration of alkynes
ending -one. In both cases, the parent chain is
identified. In numbering the C in the parent chain, Uses
the carbonyl carbon C=O is always the FIRST
1. Formaldehyde is used as a protein
carbon in an aldehyde. However, in ketones, the
preservative, germicide, fungicide,
carbonyl carbon (C) must be given the lower
deodorant, in embalming fluid, silvering
possible by numbering the C’s of the parent chain
mirror and in tanning.
from its nearest ends.
2. Aldehydes and ketones are important
Example: CH3=CH-CHO Acrolein synthetic intermediates.
3. Importance of acetone – it is to be found in
General Formula: RCHO the blood breath and urine of patient with
Structure: faulty fat metabolism. Its characteristic fruity
odor being noticeable in the breath and
urine. It is also produced as a product of one
pathway of lipid metabolism.
Test for Reducing Properties of Aldehydes
1. Fehling’s test – brick red precipitate of
cuprous oxide.
Where: R – alkyl group aldehyde
2. Tollen’s test – silver (Ag) mirror on the walls
H – hydrogen atom of the test tube.
3. Schiff’s test – magenta red color of fuchsin.
C=O – carbonyl group
4. With Phenyl Hydrazine – reaction of carbonyl
functional group of aldehydes group. Yellow solids with definite melting
point.
Physical Properties
Some Important Naturally Occurring
1. Formaldehyde and acetaldehyde are Aldehydes
colorless gases.
2. Boiling points aldehyde and ketones are 1. Benzaldehyde – colorless oily liquid with a
much lower than those of the corresponding cherry-almond like odor.
alcohols and their solubility in H2O. - It is essential oil of bitter almonds.
3. Boil somewhat higher than acid from which - Used in the preparation of
they are soluble in alcohol, ethers and other flavoring agents, perfumes, drugs
organic solvents. and dyes.
4. Aldehydes are polar molecules because 2. Cinnamaldehyde – present in oil cinnamon
C=O is a polar bond. used as a flavoring.
5. They contain O, they form H bond with water 3. Vanillin - from vanilla beans and used as
or substituent branches. flavoring agent.
 4. Glucose – a type of CHO (carbohydrate) - Used in the treatment of mental
used by the body for heat and energy. patients.

7. Acetaldehyde – production of acetic acid and

Sources of Aldehydes acetic anhydride.
- Responsible for many of the
1. Industrial Pollution unpleasant odor of ethyl alcohol
2. Pesticides consumption
3. Tobacco smoke - An extremely volatile, colorless
4. Vehicle exhaust gases liquid
5. Fossil fuel combustion - Serves as starting materials for
the preparation of organic
compounds.
Uses of Aldehydes 8. Glyceraldehyde – important component in
metabolism of carbohydrates.
1. Formaldehyde – used in killed various
9. Propionaldehyde – manufacture of plastics,
vaccine production
in the synthesis of rubber chemical.
2. Formalin – used in embalming fluid and a
- As disinfectant and preservatives
preservative for biologic specimen.
- An effective germicide for Common name of aldehydes is based on roots
disinfection of excreta, rooms and coined according to the number of atoms:
- Can irritate membrane in eyes,
nose and throat. Number of Atoms Trivial Root Name
- Used to disinfect mental surface, 1 Form-
body fluids 2 Acet-
3 Propion-
4 Butyr-
3. Glutaraldehyde – superior to formaldehyde is
5 Valer-
a sterilizing agent.
6 Capro-
- Does not have the disagreeable
7 Enanth-
odor than that of formaldehyde. 8 Capryl-
- Microbial against all 9 Pelargon-
microorganism, including pores 10 Capr-
and many viruses.
- It is less irritating to the eyes and
skin. Example:
4. Butyraldehyde (butanal) – used to impart
buttery flavor to margarine and other food.
5. Metaldehyde – used as a solid fuel called
“META”.
6. Paraldehyde – formed by polymerization of
three molecules of acetaldehyde.
- Depresses the central nervous
system
- Used as hypnotic, a sleep
producer.
- Also used in the treatment of
alcoholism
- Its disadvantages are its
disagreeable taste and
unpleasant odor.
- It is non-toxic.
- Does not depress heart action or
respiration.
 Uses of Ketone
1. Acetone (propanone) also called dimethyl
ketone.
- When isopropyl alcohol is oxidized,
the product is acetone
- Living things: by product of lipid
n-Butyraldehyde
metabolism and in small amounts.
- It is a normal component of blood and
urine.
- Maybe greatly increased in diabetes
or in people suffering from starvation.
- In some cases, acetone is detectable
on the breath
- It is a good solvent for fats and oils.
- Used in fingernail polish and in nail
polish removers.
- Solvent for cellulose acetate,
cellulose nitrate, acetylene plastic
and varnishes.
n-Valeraldehyde
- As a remover of paints, varnish and
fingernail polish.
- Solvent in the manufacture of drugs,
chemicals, smokeless powders and
high explosive cordite.

KETONE Example of aliphatic ketones:

Ketone – are named by adding the ending -ONE to

the hydrocarbon stem name. The general formula is
RCOR
- The simplest possible ketone is
propanone CH3-CO-CH3 better
known as Acetone. It is also
called dimethyl ketone

Propanone
 2. Reduced to form primary and secondary
alcohols respectively.
- The name of ketone ends in -one.
3. Can undergo similar reactions to form
Drop the ending -e and add -one
hemiketals (a secondary alcohol-ether) and
2. Acetophenone – is the simplest aromatic
ketals (a secondary diether).
ketone.
- It is used as a hypnotic but has been
supplanted (replaced) for this
purpose by nerve and safer drugs.

Acetophenone

3. Chloroacetophenone – is a lacrimatory. It is
also used as tear gas.

Chloroacetophenone

Physical Properties of Ketones

1. They are polar compounds. (the molecules
of ketones are polar)
2. Almost the same water solubility as that of
alcohol.
3. High boiling point and melting point, lower
than alcohol but higher than alkanes.
Chemical Properties of Ketones
1. Do not undergo further oxidation.
CARBOXYLIC ACID 3. Butanoic acid (butyric acid) – is a thick sour
liquid with a disagreeable odor.
Carboxylic Acid – acids maybe considered as
4. Hexadecanoic acid or palmitic acid and
derivatives of the hydrocarbon (HC), in which one or
octadecanoic or stearic acid – are colorless
more of the H atoms have been replaced by a
waxy solid.
carboxyl group -COOH.
5. Straight chain acid – the boiling point
increases and the solubility in water rapidly
decreases as the carbon content increases.
Chemical Properties
1. React with metal above hydrogen in the
activity series to liberate H2 gas.
2. Slat formation with bases, oxides and
carbonates.
General formula of acid
3. Ether formation
Preparation of acid
1. Oxidation
2. Hydrolysis of nitrites or cyanides
3. Dehydration
4. Decarboxylation
5. Substitution
Carboxyl group – functional group Uses of Carboxylic Acid
R – Alkyl group 1. Formic acid – found in sting of ants, bees and
many insects.
Two types of Acid
- has slight germicidal properties
1. Monocarboxylic acid – with only one - Find use in disinfecting hides and in
carboxylic group. brewing industries.
- It is used in coagulating latex of
Example: rubber trees and as a reducing agent.
2. Ethanoic or acetic acid – used in dilute
solution as an astringent and to check
2. Dicarboxylic acid – with two carboxyl group bleeding.
- Used in the dyeing of textiles and in
Example:
tanning of leathers.
- It is also an excellent solvent for most
organic and inorganic compounds.
- Acid present in vinegar
Physical Properties 3. Glacial acetic acid – used to remove warts.
- Used in the manufacture of lacquer,
1. Methanoic or formic acid - is a colorless, cellophane and photographic films
hygroscopic (tend to absorb moisture from - Used to prepare white lead paint and
the air) liquid, acetone, as a solvent.
- pungent irritating odor like that of 4. Butyric acid – found in rancid butter, in
SO2. cheese preparation, juices of muscles.
- It is very corrosive and irritating to the 5. Oxalic acid – found in many plants (toxic)
skin causing painful blisters. 6. Lactic acid - occurs in sour milk
2. Ethanoic acid or acetic acid – is a colorless 7. Maleic acid – found in apples
liquid with a penetrating odor and sour taste. 8. Tartaric acid – found in grapes
- Soluble in H2O, alcohol and ether in 9. Citric acid – occurs in lemons and other citrus
all proportion. fruits.
Other examples:
Compound Common IUPAC
Name
H-COOH Formic Acid Methanoic
Acid
CH3-COOH Acetic Acid Ethanoic Acid
CH3-CH2- Propionic Acid Propanoic
COOH Acid
CH3(CH2)2- Butyric Acid Butanoic Acid
COOH
CH3(CH2)3- n-Valeric Acid Pentanoic
COOH Acid
CH3(CH2)4- n-Caproic Acid Hexanoic Acid
COOH
CH2(CH2)5- Enanthoic Heptanoic
COOH Acid Acid
CH3(CH2)6- Caprylic Acid Octanoic Acid
COOH
CH3(CH2)7- Pelargonic Nonanoic Acid
COOH Acid
CH3(CH2)8- Capric Acid Decanoic Acid
COOH

Aromatic Carboxylic Acid – are those that have

the carboxyl group bonded to the aromatic ring.