MODULE 8

ALDEHYDES AND KETONES:

PROPERTIES, SOURCES, USES, AND NOMENCLATURE
Learning Outcomes:
1. Define what are aldehydes and ketones and its characteristics;
2. Enumerate the different uses, sources, and importance of aldehydes and ketones;
3. Write the name of the aldehydes and ketones in accordance to the IUPAC rule;
4. Draw structures of aldehydes and ketones in condensed, structural, and linear form.

Course Outline:
1. Aldehydes and ketones
2. Properties of aldehydes and ketones
3. Sources of aldehydes and ketones
4. Uses of aldehydes and ketones
5. Nomenclature of aldehydes and ketones

• compounds that contain a carbonyl carbon bonded to hydrogen or carbon atoms

• occur widely in nature, and also serve as useful starting materials and solvents in industrial
processes
• all simple carbohydrates contain a carbonyl group all simple carbohydrates contain a carbonyl

group
• carbonyl carbon atom is trigonal planar, and all bond angles are 120°
• since oxygen is more electronegative than carbon, a carbonyl group is polar (the carbonyl
carbon is electron poor (δ+) and the oxygen is electron rich (δ-)
• general formula:
o aldehyde: RCHO (hydrogen is bonded to carbon atom not the O)
o ketone: RCOR (two alkyl groups are bonded to the C atom)

• Examples:
ALDEHYDE: KETONE:
CH3CHO CH3COCH3 or (CH3)2CO

IUPAC name: ethanal 2-propanone

Common name: acetaldehyde acetone or dimethyl ketone
A. PHYSICAL PROPERTIES
• Boiling Point: The boiling points of aldehydes and ketones are higher than those of hydrocarbons
of similar molecular weight due to the presence of the polar carbonyl group. Aldehydes have
lower boiling points than ketones of comparable molecular weight because they can form
hydrogen bonds with water more effectively.

CH3CH2CH2CH2CH3 CH3CH2CH2CHO CH3CH2CH2CH2OH

pentane butanal 1-butanol
bp: 36oC bp: 76oC bp: 118oC

CH3CH2COCH3
2-butanone
bp: 80oC

Increasing strength of intermolecular forces

Increasing boiling point

• Melting Point: As the molecular size (molecular weight) of aldehydes and ketones increases,
their melting points also tend to increase. Larger molecules have stronger intermolecular forces,
such as van der Waals forces, which require more energy to overcome and result in higher
melting points.

• Solubility: Both aldehydes and ketones are soluble in organic solvents such as acetone,
benzene, and ether. They have limited solubility in water due to the inability to form strong
hydrogen bonds with water molecules.
✓ Low molecular weight aldehydes and ketones (those having less than six carbons) are
soluble in both organic solvents and water.
✓ Higher molecular weight aldehydes and ketones (those having six carbons or more) are
soluble in organic solvents, but insoluble in water.

• Polarity. The carbonyl group in aldehydes and ketones is a polar functional group, with oxygen
being more electronegative than carbon. This unequal sharing of electrons results in a partial
negative charge on the oxygen atom and a partial positive charge on the carbon atom.

• Density: the density of aldehydes and ketones generally increases with increasing molecular size
or molecular weight. Larger molecules tend to have higher densities due to their greater mass
and more closely packed arrangement in the solid or liquid state.
B. CHEMICAL PROPERTIES
Ketones and aldehydes exhibit several chemical properties that arise from the presence of the
carbonyl group (-C=O). Here are some important chemical properties of ketones and aldehydes:
1. OXIDATION
• Aldehydes can be oxidized to carboxylic acids
• Ketones cannot be oxides since they contain no H atom on the carbonyl carbon
O O
[O]
‖ ‖
R–C–H R – C – OH

Since aldehydes contain a hydrogen atom bonded to the carbonyl carbon, they can be
oxidized to carboxylic acids

Example:

Aldehydes were recognized as the main constituents of human body odor in many studies.
Aldehydes are easily oxidized by oxygen in the air. One example is butanal (CH3CH2CH2CHO) which
slowly develops the characteristics smell of its oxidation product: butanoic acid (CH3CH2CH2COOH), a
compound that contributes to the distinctive odor of human sweat.
O O
‖ [O] ‖
CH3 – CH2 – CH2 – C – H CH3 – CH2 – CH2 – C – O – H
butanal butanoic acid

For lists of aldehydes constituting human body odor, visit or download:

[Link]

2. ADDITION or REDUCTION REACTION

• Aldehydes and ketones undergo addition reactions
• Reduction is the opposite of Oxidation
• Reduction results in a decrease in the number of C – O bonds or an increase in the number
of C – H bonds
\ [H] l
C=O –C–O
/ l l
H H
*The symbol [H] is often used to represent a general reduction reaction.

A. Aldehydes (RCHO)
• are reduced to 1o alcohols (RCH2OH)

R H
\ [H] l
C=O R–C–O
/ l l
H H H
Aldehyde 1o alcohol
 Example:

CH3 H
\ H2 l
C=O CH3 – C – O
/ Pd l l
H H H

ethanal ethanol
(aldehyde) (1o alcohol)

B. Ketones (RCOR)
• are reduced to 2o alcohols (R2CHOH)

R R
\ [H] l
C=O R–C–O
/ l l
R H H
Ketone 2o alcohol

Example:
CH3CH2 CH3CH2
\ H2 l
C=O CH3CH2 – C – O
/ Pd l l
CH3CH2 H H

3-propanone 3-propanol
(diethyl ketone) (sec-propanol)
Ketone 2o alcohol

When it comes to sources of aldehydes and ketones, there are primarily two main sources:
NATURAL SOURCES
Aldehydes
and ketones are
widespread in
nature, often
combined with
other functional
groups. Example
are shown in the
following diagram.
The compounds in
the top row are
found chiefly in
plants or
microorganisms.
SYNTHETIC SOURCES
Synthetic sources of ketones and aldehydes are abundant, and they are commonly produced
in chemical laboratories or industrial settings. Here are some synthetic sources of ketones and
aldehydes:
1. Oxidation of Alcohols: Ketones and aldehydes can be synthesized through the oxidation of
primary and secondary alcohols, respectively. This can be achieved using oxidizing agents such
as chromic acid (CrO3/H2SO4), potassium permanganate (KMnO4), or Jones reagent
(CrO3/H2SO4/acetone).

2. Reduction of Carboxylic Acids or Esters: Ketones can be prepared by the reduction of carboxylic
acids or esters. Reduction can be achieved using reducing agents such as lithium aluminum
hydride (LiAlH4) or sodium borohydride (NaBH4)

A. ALDEHYDES
1. Formaldehyde (HCHO)
• production of resins, plastics, textiles, and disinfectants
• preservative in biological specimens
• sterilizing agent

2. Acetaldehyde (CH3CHO)
• production of acetic acid, perfumes, dyes, and other chemicals
• flavoring agent in food and beverages
 3. Benzaldehyde (C6H5CHO)
• flavoring agent in foods, beverages, and cosmetics
• production of dyes, perfumes, and pharmaceuticals

4. Citral
• found in citrus fruits such as lemons, oranges, and limes
• fragrance and flavor industry, providing a citrusy aroma and taste
• production of perfumes, colognes, soaps, detergents, and food and beverage
flavorings

5. Vanillin
• found naturally in the vanilla bean (Vanilla planifolia)
• flavoring agent in food products, including baked goods, ice cream, candies, and
beverages
• fragrance industry and in the production of pharmaceuticals and cosmetics

6. Cinnamaldehyde
• responsible for the characteristic aroma and flavor of cinnamon
• obtained from the bark of cinnamon trees (Cinnamomum verum)
• used as a flavoring agent in food and beverages
• production of fragrances, personal care products, and as an ingredient in traditional
medicine

B. KETONES
1. Acetone (CH3COCH3)
• solvent in various industries, including pharmaceuticals, paints, coatings, and cleaning
products
• nail polish removers and as a chemical intermediate

2. Methylethylketone (MEK or Butanone)

• solvent in coatings, adhesives, and varnishes
• used in the production of plastics, textiles, and rubber

3. Dihydroxyacetone
• an active ingredient in commercial tanning agents that produce sunless tans
• it reacts with proteins in the skin, producing a complex colored pigment that gives the
skin a brown hue

4. Camphor
• camphor tree (Cinnamomum camphora)
• topical analgesic and as an ingredient in chest rubs to relieve cough and congestion.
• production of insect repellents, as a fragrance in cosmetics and personal care
products, and as a flavoring agent in food and beverages (in small quantities)

5. Menthone
• found in plants of the Mentha genus, including peppermint and spearmint
• contributes to the characteristic aroma and flavor of these plants
• a flavoring agent in food and beverages, as well as in the production of perfumes,
cosmetics, and oral care products
A. ALDEHYDES
• has at least one H atom bonded to the carbonyl group (C=O)

OHC(CH2)6CH3 CH3(CH2)8CHO
Octanal Decanal

NAMING ALDEHYDES
• aldehydes are identified by the suffix –al

1. Find the longest chain containing the CHO group, and change the –e ending of the parent
alkane to the suffix –al.
Aldehyde IUPAC name Common name
H–C–H
‖ Methanal Formaldehyde
O
CH3CH Ethanal
‖ Acetaldehyde
O
CH3CH2CH
‖ Propanal Propionaldehyde
O
CH3CH2CH2CH
‖ Butanal Butyraldehyde
O

For aldehydes with substituents:

1. Find and name the longest chain containing the CHO.
CH3
l
CH3CH2CHCH2CHCH hexane ---------> hexanal

l ‖
CH2CH3 O
2. When the longest chain has substituent, number the carbon atoms. C1 must always start at the
carbonyl group. Then, name the substituent.
3 CH3 2 1
l
CH3CH2CHCH2CHCH Methyl at C2
Ethyl at C4
l ‖
4 CH2CH3 O
3. Arrange the substituents in alphabetical order. Drop 1- in parent chain.
IUPAC name: 4-ethyl-2-methylhexanal
B. KETONE
• has two alkyl groups bonded to the carbonyl group (C=O)
• many simple ketones are naturally occurring; for example: piperitone contribute to the flavor
and odor of an orange

NAMING KETONES
• ketones are identified by the suffix –one

1. ACYCLIC KETONE
a) Find the longest chain containing the carbonyl group (C=O), and change the –e ending
of the parent alkane to the suffix –one.

O CH3
‖ l
Pentane → pentanone
CH3CCHCHCH3
l
CH3

b) Number and name substituents, making sure the carbonyl group has the lowest possible
number.

1 2 O CH3
‖ l
CH3CCHCHCH3
l
3 CH3 4

IUPAC name: 3,4-dimethyl-2-pentanone

2. CYCLIC KETONES

a) Name the ring.

cyclopentane ---------> cyclopentanone

b) Numbering always begins at the carbonyl carbon, but the "1" is usually omitted from the
name. The ring is then numbered clockwise or counterclockwise to give the first substituent
the lower number.

c) Name the molecule applying all of the usual rules of nomenclature.

IUPAC name: 2-ethyl-3-methylpentanone

3. COMMON NAMES
Most common names for ketones are formed by naming both alkyl groups on the
carbonyl carbon, arranging them alphabetically, and adding the word ketone. Using this
method, the common name for 2-butanone becomes ethyl methyl ketone.

O
‖
CH3CCH2CH3
IUPAC name: 2-butanone
Common name: ethyl methyl ketone