Aldehydes

• An aldehyde is an organic compound containing a terminal carbonyl group. This functional

group, which consists of a carbon atom bonded to a hydrogen atom and double-bonded to an
oxygen atom (chemical formula O=CH-), is called the aldehyde group.
• The aldehyde group is also called the formyl or methanoyl group.
• The word aldehyde seems to have arisen from alcohol dehydrogenated.
• The aldehyde group is polar. Oxygen, more electronegative than carbon, pulls the electrons in
the carbon-oxygen bond towards itself, creating an electron deficiency at the carbon atom.
~PHYSICAL PROPERTIES~
• Hydrocarbons are essentially nonpolar and thus have low melting and boiling points. The
melting and boiling points of carbonyl-containing compounds are considerably higher.
• Butane (CH3CH2CH2CH3), propanal (CH3CH2CHO), and acetone (CH3COCH3) all have the
same molecular weight (58), but the boiling point of the hydrocarbon butane is 0 °C (32 °F),
while those of propanal and acetone are 49 °C (120 °F) and 56 °C (133 °F), respectively.
• Formaldehyde (HCHO) is a gas under standard conditions, and acetaldehyde (CH3CHO) boils at
about room temperature.
• Other aldehydes, except those of high molecular weight, are liquids under ordinary conditions.
• Aldehydes with fewer than about five carbon atoms are soluble in water; however, above this
number, the hydrocarbon portion of their molecules makes them insoluble.
~CLASSIFICATIO OF ALDEHYDES~
 Aliphatic Aldehydes
• A homologous series of organic compounds of carbon, hydrogen and oxygen
• Formula: CnH2n + 2 . CHO
• Named by replacing “-e” at the end of the alkane from which they are derived with “-al”

Methanal (Formaldehyde) Ethanal (Acetaldehyde)

~ALDEHYDE NOMENCLATURE~
• In compounds which contain a carbonyl group, the parent is the longest chain containing the
carbonyl carbon.
• For an aldehydethe parent alkane -> alkanal; the chain is numbered beginning with the carbonyl
carbon as #1.
• If the carbonyl carbon of an aldehyde is attached to a ring, the compound is a cycloalkane
carbaldehyde, and the carbon of the ring to which the aldehyde is attached is #1.
• In other cases, such as when a -CHO group is attached to a ring, the suffix -carbaldehyde may be
used. Thus, C6H11CHO is known as cyclohexanecarbaldehyde. If the presence of another
functional group demands the use of a suffix, the aldehyde group is named with the prefix
formyl-. This prefix is preferred to methanoyl-.
 Aromatic Aldehydes
• An aromatic compound containing the CHO radical
• Have a benzene ring or phenyl ring connected to the aldehyde group
Benzaldehyde C6H5 para tolualdehyde ethyl benzaldehyde
 Saturated Aldehydes
• Have only single bonds between carbon atoms
• Contain all hydrogen atoms they are capable of holding

Propanal Butyraldehyde

 Unsaturated Aldehydes
• Having or able to form triple carbon to carbon bonds
• Capable of additional hydrogen atoms

Citral (3,7-dimethyl-1,2,3, tricarboxylic acid) (terpene aldehyde)

Malondialdehyde CH2(CHO)2 (Propane dial)

• If the compound is a natural product or a carboxylic acid, the prefix oxo- may be used to indicate
which carbon atom is part of the aldehyde group; for example, CHOCH2COOH is named 3-
oxopropanoic acid.

• If replacing the aldehyde group with a carboxyl group (-COOH) would yield a carboxylic acid
with a trivial name, the aldehyde may be named by replacing the suffix -ic acid or -oic acid in
this trivial name by -aldehyde.

• Acyclic aliphatic aldehydes are named as derivatives of the longest carbon chain containing the
aldehyde group. Thus, HCHO is named as a derivative of methane, and CH3CH2CH2CHO is
named as a derivative of butane. The name is formed by changing the suffix -e of the parent
alkane to -al, so that HCHO is named methanal, and CH3CH2CH2CHO is named butanal.
 Number of carbons Common name for Aldehyde
1 Formaldehyde
2 Acetaldehyde
3 Propionaldehyde
4 Butyraldehyde
5 Valeraldehyde
6 Caproaldehyde
7 Enanthaldehyde
8 Caprylaldehyde
9 Pelargonaldehyde
10 Capraldehyde

~ Uses of Aldehydes ~
 Formaldehyde
• (IUPAC name methanal) is a chemical compound with the formula H2CO. It is the simplest
aldehyde. Aqueous solutions of formaldehyde are referred to as formalin.

 Acetaldehyde
• (systematically: ethanal) is an organic chemical compound with the formula CH3CHO or
MeCHO. It is a flammable liquid with a fruity smell. Acetaldehyde occurs naturally in ripe fruit,
coffee, and fresh bread, and is produced by plants as part of their normal metabolism. It is
popularly known as the chemical that causes hangovers.

 Benzaldehyde
• is an important component of the scent of almonds,
hence its typical odor. It is the primary component of bitter
almond oil extract, and can be extracted from a number of
other natural sources in which it occurs, such as apricot, cherry, and laurel leaves, peach seeds and,
in a glycoside combined form (amygdalin), in certain nuts and kernels.

 Cinnamic aldehyde or cinnamaldehyde (more precisely trans-cinnamaldehyde, the only

naturally-occurring form) is the chemical compound that gives cinnamon its flavor and odor.
• Cinnamaldehyde occurs naturally in the bark of cinnamon trees and other species of the genus
Cinnamomum like camphor and cassia.