• ORGANIC COMPOUNDS NOMENCLATURE

• How organic compounds react and a new compound is synthesized?

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• The main classes of compounds that are synthesized by the reactions are alkanes, alkyl halides,
ethers, alcohols, and amines.
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• To learn how to name these five classes of compounds.
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• Alkanes are composed of only carbon atoms and hydrogen atoms and contain only single bonds.
Compounds that contain only carbon and hydrogen are called hydrocarbons, so an alkane is a
hydrocarbon.
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• Alkanes in which the carbons form a continuous chain with no branches are called straight-chain
alkanes (Table below).
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• Table. Nomenclature and Physical Properties of Straight-Chain Alkanes

Note: Students must learn the names of

at least the first 10 or 20, with formulae.
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• The family of alkanes shown in the table is an example of a homologous series. A
homologous series (homos is Greek for “the same as”) is a family of compounds
in which each member differs from the next by one methylene (CH2) group. The
members of a homologous series are called homologs. Propane (CH3CH2CH3)
and butane (CH3CH2CH2CH3) are homologs.

• The general molecular formula for alkanes is CnH2n+2, where n is any integer.
• There are two possible structures for a butane with molecular formula C4H10, —
a straight-chain alkane—and branched butane called isobutane.
•  Compounds such as butane and isobutane that have the same molecular
formula but differ in the order in which the atoms are connected are called
constitutional isomers—their molecules have different constitutions.
•  Isobutane got its name because it is an “iso”mer of butane.

• There are three alkanes with molecular formula C5H12 Pentane is the
straightchain alkane. Isopentane has an iso structural unit and five carbon
atoms. The third isomer is called neopentane. The structural unit with a carbon
surrounded by four other carbons is called “neo.”
• Note: the CH3— is a methyl group.
• To avoid having to memorize the names of thousands of structural units,
chemists have devised rules that name compounds on the basis of their
structures, called systematic nomenclature or IUPAC nomenclature.
• Names such as isobutane and neopentane—nonsystematic names—are called
common names and are shown in red. The systematic or IUPAC names are
shown in blue.
• Nomenclature of Alkyl Substituents
• Removing a hydrogen from an alkane results in an alkyl substituent (or an alkyl
group). Alkyl substituents are named by replacing the “ane” of the alkane with
“yl.” The letter “R” is used to indicate any alkyl group.

• If a hydrogen of an alkane is replaced by an OH, the compound becomes an

alcohol; if it is replaced by an NH2 the compound becomes an amine; and if it is
replaced by a halogen, the compound becomes an alkyl halide.
• The following examples show how alkyl group names are used to build common
names:

• Two alkyl groups—a propyl group and an isopropyl group—contain three carbon atoms. In
propyl group a hydrogen is removed from a primary carbon of propane. A primary carbon is a
carbon that is bonded to only one other carbon. An isopropyl group is obtained when a
hydrogen is removed from the secondary carbon of propane. A secondary carbon is a carbon
that is bonded to two other carbons.
• There are four alkyl groups that contain four carbon atoms. The butyl and
isobutyl groups have a hydrogen removed from a primary carbon. A sec-
butyl group has a hydrogen removed from a secondary carbon, and a tert-
butyl group has a hydrogen removed from a tertiary carbon. A tertiary
carbon is a carbon that is bonded to three other carbons.

• Like the carbons, the hydrogens in a molecule are also referred to as

primary, secondary, and tertiary. Primary hydrogens are attached to
primary carbons, secondary hydrogens to secondary carbons, and tertiary
hydrogens to tertiary carbons.
• Nomenclature of Alkanes
• Name of an alkane is obtained by following rules:
• 1. Determine the number of carbons in the longest continuous carbon
chain. This chain is called the parent hydrocarbon. The number of
carbons in parent hydrocarbon becomes the alkane’s “last name.” For
example, a parent hydrocarbon with eight carbons would be called
octane. Sometimes the chain turns a corner.
• Nomenclature of Cycloalkanes
• Cycloalkanes are alkanes with their carbon atoms arranged in a ring. Because of
the ring, a cycloalkane has two fewer hydrogens than an acyclic (noncyclic) alkane
with the same number of carbons. The general molecular formula for a
cycloalkane is CnH2n. Cycloalkanes are named by adding the prefix “cyclo” to the
alkane name.

• Cycloalkanes are almost always written as skeletal structures. Skeletal structures

show the carbon–carbon bonds as lines, and do not show carbons or hydrogens.
• Acyclic molecules can also be represented by skeletal structures. In a
skeletal structure of an acyclic molecule, the carbon chains are represented
by zigzag lines.

• In the case of a cycloalkane with an attached alkyl substituent, the ring is

the parent hydrocarbon unless the substituent has more carbon atoms
than the ring. In that case, the substituent is the parent hydrocarbon and
the ring is named as a substituent. There is no need to number the position
of substituent on a ring.