Classification, nomenclature and isomerism of Organic compounds

Organic chemistry
Organic chemistry is defined as the study of carbon compounds. The sources of
organic compounds are plant and animals (carbohydrates, proteins, fats and oils),
natural gas and petroleum (solvents, synthetic rubber and plastics), coal,
fermentation and synthesis.
Organic Compounds
The compounds in solid, liquid or gaseous state which contain carbon in its molecule
are known as organic compounds. There are a large number of organic compounds
and therefore a proper systematic classification was required. In very simple terms
that organic compounds are simply any chemical compounds that have carbon but it
doesn’t mean that every carbon-containing compound can be known as organic, for
e.g. cyanides, carbonates and carbides. The best example of the simplest organic
compound is Methane. Few examples of Organic compounds are cyclohexane,
ethyne, ethene and ethane.
Organic compounds can be broadly classified as acyclic (open chain) or cyclic
(closed chain). Moving on to their classification in detail:

Fig. 1: Flow chart of classification of organic compounds

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Acyclic or Open-chain Compounds
Acyclic compounds are just opposite to cyclic compounds because their molecules
don’t form any ring. It is called open chain compounds because they have a linear
structure. The best examples of these compounds are acyclic aliphatic compounds
and alkanes. Open-chain compounds can be understood by straight-chain
compounds and branched-chain compounds. In the straight-chain compounds don’t
have any side chains but branched-chain compounds’ atoms have the straight chain
and one or more than one side chains are attached to it.
Straight chain compounds (Aliphatic compounds)
Substances consisting entirely of single-bonded carbon and hydrogen atoms and
lacking functional groups are called alkanes. The first four members of the series are
known by their common names (Methane, ethane, propane and butane). The names
of the larger alkanes are derived from the Greek prefixes that indicate the number of
carbon atoms in the molecule. For eg. pentane has 5 carbons, hexane has 6 and so
on.
Eg.
n-pentane n-butane
Branched chain compounds
Branched alkanes are derived from the straight-chain alkanes system by
removing one of the hydrogen atoms from a methylene group (-CH2-) and
replacing it with an alkyl group.

Eg.
Isobutane Isopentane

Prefix neo is used for alkanes which have two methyl groups attached to the second
last carbon atoms of the continuous chain.

Eg.
Neopentane

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Cyclic or Closed-chain Compounds
Cyclic compounds are also known as “Ring compounds”. As its second name
suggests, cyclic compounds are those kinds of compounds where one or more than
one number of atoms get connected to form a closed ring. It is not mandatory that
every ring of these compounds is to be of the same size. They are also categorized
into two types. They are “Homocyclic” and “Heterocyclic”
Homocyclic compounds
Homocyclic compounds are the type of cyclic compounds, unlike heterocyclic, in
which the ring structure is formed by the atoms. This ring structure is made up of the
same elements’ atoms and this element is the carbon. It is also called as called as
Carbocyclic compounds. No element other than carbon can exist in this compound.
The best examples of this compound are naphthalene, tetracene and benzene etc.
Homocyclic or carbocyclic compounds are basically divided into two types. They are
alicyclic compounds and aromatic compounds.
Alicyclic Compound
The alicyclic compound is that kind of compound which is aliphatic and cyclic
too. This compound has one or more than one all-carbon rings that can be
saturated or unsaturated. The bonds which exist in pair of atoms can be any
type of bond like single, double or triple.

Cyclopropane cyclopentane cyclopentane cyclohexane

Aromatic Compound
Aromatic compounds are those chemical compounds that contain one or more rings
with pi electrons delocalized all the way around them.
Aromatic compounds are those cyclic compounds which are unsaturated. These
compounds are also called as aromatics or arenas. They are pleasant in the smell as
their Greek meaning suggests which is “aroma”. A few examples of these
compounds are benzene, aniline and toluene.

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These aromatic compounds are mainly obtained from the benzene. These
compounds are distinguished by the existence of one or more than one
isolated or fused benzene rings additionally their derivatives in the structure.
These compounds can be arranged as Monocyclic, Bicyclic and Tricyclic on
the basis of the number of benzene rings which are fused together in the
structure. In bicyclic and tricyclic compounds there are two or more than two
rings present in the structure. A few examples of these compounds are
Phenanthrene, Naphthalene, Anthracene and so on.

Naphthalene Anthracene

Phenanthrene
Heterocyclic compounds
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at
least two different elements as members of its ring. Ring structures of these
compounds have one or more one heteroatoms mostly nitrogen, oxygen, or sulfur.

Furan Thiophene Pyridine

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Nomenclature of Organic compounds
The purpose of the IUPAC system of nomenclature is to establish an international standard
of naming compounds to facilitate communication. The goal of the system is to give each
structure a unique and unambiguous name, and to correlate each name with a unique and
unambiguous structure.
Fundamental Principle
IUPAC nomenclature is based on naming a molecule’s longest chain of carbons connected
by single bonds, whether in a continuous chain or in a ring. All deviations, either multiple
bonds or atoms other than carbon and hydrogen, are indicated by prefixes or suffixes
according to a specific set of priorities.
1. Alkanes and Cycloalkanes
‘Hydrocarbon are compounds’ that contain only carbon and hydrogen. The first four
members of the series are known by their common names like methane, ethane, propane
and butane. The name of the larger alkanes are derived from the greek prefixes that indicate
the number of carbon atoms in the molecule. Thus pentane has 5 carbons and hexane has 6
and so on.

CH4 – methane CH3[CH2]4CH3 – hexane

CH3CH3- ethane CH3[CH2]5CH3 - heptane
CH3CH2CH3 – propane CH3[CH2]6CH3 - octane
CH3[CH2]2CH3- butane CH3[CH2]7CH3 - nonane
CH3[CH2]3CH3- pentane CH3[CH2]8CH3 - decane

Cyclopropane cyclopentane cyclopentane cyclohexane

Cycloheptane cyclooctane

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In the common system all isomeric alkanes has the same parent name. For example, two
isomeric C4H10 alkanes are known as butanes. The name of various isomers is distinguished
by prefixes. The prefix indicates the type of branching present in the molecule.
1. Meaning of prefix n-:
The prefix n- is used for those alkanes in which all the carbons are in one continuous
chain. The prefix n- stand for normal or straight chain.

2. Meaning of prefix Iso:

Prefix iso is used for those alkanes in which have a methyl group (CH3-) attached to
the second last carbon atom of the continuous chain.

3. Meaning of prefix Neo:

Prefix neo- is used for those alkanes which have two methyl groups attached to the second
last carbon atom of the continuos chain.

4. Classification of carbon atom

The structures formulas if alkanes contains four types of carbons
 Primary carbon: A carbon atom attached to one other (or no other)carbon atom is
called as primary carbon (1°).
 Secondary carbon: A carbon atom attached to two other carbon atoms is called
secondary carbon (2°)
 Tertiary carbon: A carbon atom attached to three other carbon atoms is called tertiary
carbon (3°)
 Quaternary carbon: A carbon atom attached to three other carbon atoms is called
quaternary carbon (4°)

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Hydrogen atoms attached to 1°,2°,3° carbon atoms atoms are often referred to as primary,
secondary and tertiary hydrogen atoms.
Alkyl groups
An alkyl group is formed by removing one hydrogen atom from an alkane. The symbol R is
used to represent alkyl group. Alkyl group isare named by dropping –ane from the name of
the corresponding alkane, and adding the ending –yl.

Non-alkyl groups
A number of nonalkyl groups are used in naming organic compounds. Their names are
given below
F — Fluoro -NO2 – Nitro

Cl — Chloro -NO - Nitroso

Br — Bromo -NH2 - Amino

I — Iodo -OH – Hydroxy

IUPAC rules for naming the alkanes

Rule 1: Select the longest continuous carbon chain: (This chain does not have to be that
portion of the molecule that is written horizontally.
Rule 2: Name the longest chain. The longest carbon chain is chosen as the basis for the
name

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Rule 3: Number the longest chain. The carbon atom in the longest chain is numbered. The
numbering is started from that end which gives numbers having the lowest value to carbon
carrying substituents.

Rule 4: Identify the substituent: Name the substituent. Indicate its position by the number of
carbon atom to which it is attached. ( The attached group is located on carbon 2 of the chain
and it is a methyl group).
Rule 5: Prefix the position number and name of the substituent onto the parent name. The
whole name is written as one word. (the number and name of the substituent are separated by
hyphen)

2- Methyl butane
The following additional rules are used, when more than one substituent is attached to the
longest continuous carbon chain.
Rule 6: Identify the substituents by names and position numbers: When the same
substituent is present two or more times in the molecule, the prefixes di-, tri-, tetra-, penta-
etc are used. Position of each substituent is indicated by a separate number. These position
numbers, separated by commas are put just before the name of the substituent, with the
hyphen before and after the numbers when necessary.

Rule 7: When two or more different substituents are present, their names are arranged in
alphabetic order and added to the name of the parent alkane again as one word.

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Alkenes
Alkenes are hydrocarbons that contain a carbon-carbon double bond. Their common names
are obtained by changing the ending –ane of the corresponding alkane to –ylene (Alkane- ane
+ ylene).

IUPAC rules for naming the alkenes

Rule 1: Select the longest carbon chain containing the double bond. This is parent chain.
Rule 2: Name the longest chain. The name is obtained by dropping the final –ane from the
name of the corresponding alkane, adding the ending –ene.
Alkane-ane + ene = Alkene
Rule 3: Number the chain from the end closer to the double bond.
Rule 4: Indicate the position of the double bond by the number of the first (lowest numbered)
carbon atom involved in the double bond.
Rule 5: Alkyl groups and other substituents are numbered, named, and placed as prefixes in
alphabetical order. For example

Rule 6: Alkenes containing two double bonds are named as Alkadienes.

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Rule 7: In naming cycloalkenes, number the ring to give the double bonded carbon atoms the
number 1 and 2. Choose the direction of numbering, so that the substituents get the lowest
numbers. The position of the double bond is not indicated because it is known to be between
C-1 and C-2.

Alkynes
Alkynes are hydrocarbon that contains carbon-carbon triple bond. The simplest alkyne
is called as acetylene.
IUPAC rules
Rule 1: Select the longest carbon chain containing triple bond (Parent chain)
Rule 2: Name the longest chain ( The name is obtained by dropping final –ane from the name
of the corresponding alkane, and adding the ending –yne.
Alane-ane +yne =Alkyne
Rule 3: Number the chain from the end close to the triple bond
Rule 4: Indicate the position of the triple bond (number of first (lowered numbered) carbon
atom involved in the triple bond).
Rule 5: Alkyl groups and other substituents are numbered, named and placed as prefixes in
alphabetical order.

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Examples:

,
Rule 6: Alkynes containing two triple bonds are named as alkadiyne

5. Nomenclature of Molecules Containing Substituents and Functional Groups

Group A—Functional Groups Indicated By Prefix Or Suffix
Family of Structure Prefix Suffix
Compound

-oic acid
Carboxylic Acid carboxy
(-carboxylic acid)

oxo- -al
Aldehyde
(formyl) (carbaldehyde)

Ketone oxo- -one

Alcohol hydroxy- -ol

Amine amino- -amine

Group B—Functional Groups Indicated By Suffix Only

Family of Structure Prefix Suffix
Compound

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 Alkene - -ene

Alkyne - -yne

Group C—Substituents Indicated by Prefix Only

Family of Structure Prefix Suffix
Compound
Alkyl R— alkyl- -
Alkoxy R— O — alkoxy- -
Fluoro-
Chloro-
Halogen -
Bromo-
Iodo-

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