Name of Institution

AMITY INSTITUTE OF PHARMACY

B PHARM II SEMESTER
PHARMACEUTICAL ORGANIC CHEMISTRY-I
Dr PAWAN KUMAR GUPTA

1
 Syllabus I- Unit
Name of Institution

UNIT-I
Classification, Nomenclature and Isomerism
• Classification of Organic Compounds
• Common and IUPAC systems of nomenclature of organic
compounds (up to 10 Carbons open chain and carbocyclic
compounds)
• Structural Isomerisms in organic compounds

2
 Classification, Nomenclature
Name of Institution
and Isomerism

• An Organic compound is generally any chemical

compound that contains carbon.
• Due to carbon's ability to form chains with other carbon atoms
millions of organic compounds are known.
• Study of the properties and synthesis of organic compounds is
known as organic chemistry.
Classification of Organic compounds:
• Based upon the structure they are classified into two types.
• Acyclic compound (open chain)
• Cyclic compound (closed chain)

3
Classification, Nomenclature
Name of Institution
and Isomerism

4
 Classification, Nomenclature
Name of Institution
and Isomerism

Acyclic (or) open chain compounds:

• These compounds contain open chain of carbon atoms in their
molecules.
• The terminal carbon atoms are completely free they are not
linked with each other.
• The chain is open so ,it is called as open chain compound.
Ex: CH₃-CH₂-CH₃ propane
Free terminal carbon atom -CH₃-CH₂-CH₃- Free terminal
carbon atom
: CH₃-CH₂-CH₂-CH₂-CH₃ pentane
: CH₃-COOH Acetic acid
• These compounds are also called as Aliphatic compounds. 5
 Classification, Nomenclature
Name of Institution
and Isomerism

Cyclic(or)closed chain compounds:

• These compounds contain one (or) more closed chains (or)
rings of atoms in their molecules.
• In these case two terminal carbon atoms are linked with each
other. In order to form a closed ring.
• It can be either a three ,four, five membered rings.

•The compounds with only one ring of atoms in the molecule are
known as monocyclic but those with more than one ring of atoms are
termed as polycyclic.
• These are further divided into two subgroups. 6
 Classification, Nomenclature
Name of Institution
and Isomerism

• Homocyclic or carbocyclic : These are the compounds having

a ring or rings of carbon atoms only in the molecule. The
carbocyclic or homocyclic compounds may again be divided
into two types:
• Alicyclic compounds: These are the compounds which
contain rings of three or more carbon atoms.
• These resemble with aliphatic compounds compounds in many
respects.
• That is why these are named alicyclic, i.e., aliphatic cyclic.
These are also termed as polymethylenes. Some of the
examples are,

7
 Classification, Nomenclature
Name of Institution
and Isomerism

•Aromatic compounds: These compounds consist of at least one

benzene ring, i.e., a six-membered carbocyclic ring having alternate
single and double bonds.
•Generally, these compounds have some fragrant odour and hence,
named as Aromatic (Greek word aroma meaning sweet smell).
•These compounds may again be divided into two types:
•Monocyclic Aromatic Ring compounds:
•Polycyclic Aromatic Ring compounds:
•These are also called benzenoid aromatics.
8
 Classification, Nomenclature
Name of Institution
and Isomerism

Monocyclic Aromatic Ring compounds

Polycyclic Aromatic Ring compounds 9

 Classification, Nomenclature
Name of Institution
and Isomerism

Non-benzenoid aromatics: There are aromatic compounds,

which have structural units different from benzenoid type and
are known as Non-benzenoid aromatics e.g. Tropolone,
azulene etc.

Heterocyclic compounds: Cyclic compounds containing one

or more hetero atoms (e.g. O, N, S etc.) in the ring are called
heterocyclic compounds.
These are of two types:
10
 Classification, Nomenclature
Name of Institution
and Isomerism
Alicyclic heterocyclic compounds: Heterocyclic compounds
which resemble aliphatic compounds in their properties are
called Alicyclic heterocyclic compounds. For example,

11
 Classification, Nomenclature
Name of Institution
and Isomerism
Aromatic heterocyclic compounds: Heterocyclic compounds
which resemble benzene in most of their properties are called
Aromatic heterocyclic compounds. For example,

12
 Classification, Nomenclature
Name of Institution
and Isomerism

Classification of organic compounds based on functional

groups
• A functional group is an atom or group of atoms in a molecule
that gives the molecule its characteristic chemical properties.
Double and triple bonds are also considered as functional
groups.
• All compounds with the same functional group belong to the
same class.
• Various classes of compounds having some of the common
functional groups are listed in the table.

13
Classification, Nomenclature
Name of Institution
and Isomerism

14
 Classification, Nomenclature
Name of Institution
and Isomerism
Nomenclature in organic chemistry
• It is important that organic compounds are correctly and
unambiguously named so that there can be absolutely no
confusion about what compounds are actually being reported
or described.
• There have been many conventions for naming organic
compounds The International Union of Pure and Applied
Chemistry (I.U.P.A.C.) periodically reviews naming practice,
attempting to standardise nomenclature.
• The following guidelines for organic nomenclature are based
on the definitive rules published by I.U.P.A.C.(the
International Union of Pure and Applied Chemistry).

15
 Classification, Nomenclature
Name of Institution
and Isomerism

I.U.P.A.C.Nomenclature of
alkanes(saturatedhydrocarbons)
The names of the straight chain saturated hydrocarbons for up
to a 5 carbon chain are shown below.
Number of Carbons Name
1 methane
2 ethane
3 propane
4 butane
5 pentane

16
 Classification, Nomenclature
Name of Institution
and Isomerism
There are a few common branched hydrocarbons

17
 Classification, Nomenclature
Name of Institution
and Isomerism
RulesforNomenclatureofAlkanes (saturated hydrocarbons).
• Identify the longest carbon chain. This chain is called the
parent chain.
• Identify all of the substituents (groups appending from the
parent chain).
• If two or more side chains are in equivalent positions,
assign the lowest number to the one which will come first
in the name.
• If the same substituent occurs more than once, the location
of each point on which the substituent occurs is given. In
addition, the number of times the substituent group occurs
is indicated by a prefix (di, tri, tetra, etc.).

18
 Classification, Nomenclature
Name of Institution
and Isomerism
• If chains of equal length are competing for selection as the
parent chain, then the choice goes in series to:
a) the chain which has the greatest number of side chains.
b) the chain whose substituents have the lowest- numbers.
c) the chain having the greatest number of carbon atoms in
the smaller side chain.
d)the chain having the least branched side chains.
• A cyclic (ring) hydrocarbon is designated by the
prefix cyclo which appears directly in front of the base
name.
• In summary, the name of the compound is written out with
the substituents in alphabetical order followed by the base
name (derived from the number of carbons in the parent
chain).
19
 Classification, Nomenclature
Name of Institution
and Isomerism
• Commas are used between numbers and dashes are used
between letters and numbers. There are no spaces in the
name. Here are some examples:

20
 Classification, Nomenclature
Name of Institution
and Isomerism

Rules for Nomenclature of Alcohols

• Alcohols are named by replacing the suffix -ane with -anol.
• If there is more than one hydroxyl group (-OH), the suffix is
expanded to include a prefix that indicates the number of
hydroxyl groups present (-anediol, -anetriol, etc.).
• The position of the hydroxyl group(s) on the parent chain
is(are) indicated by placing the number(s) corresponding to the
location(s) on the parent chain directly in front of the base
name (same as alkenes ).
Here is an important list of rules to follow:
• The hydroxyl group takes precedence over alkyl groups
and halogen substituents, as well as double bonds, in the
numbering of the parent chain.
21
 Classification, Nomenclature
Name of Institution
and Isomerism

• When both double bonds and hydroxyl groups are present,

the -en suffix follows the parent chain directly and the -ol
suffix follows the -en suffix.
• The location of the double bond (s) is(are) indicated before
the parent name as before, and the location of the hydroxyl
group (s) is(are) indicated between the -en and - ol suffixes.

22
 Classification, Nomenclature
Name of Institution
and Isomerism
• Here are some examples:

23
 Classification, Nomenclature
Name of Institution
and Isomerism

Rules for Nomenclature of Aldehyde

• Aldehydes are named by replacing the suffix ane with anal.
• If there is more than one -CHO group, the suffix is expanded
to include a prefix that indicates the number of -CHO groups
present anedial there should not be more than 2 of these
groups on the parent chain as they must occur at the ends).
• It is not necessary to indicate the position of the -CHO group
because this group will be at the end of the parent chain and its
carbon is automatically assigned as C-1.
Here is an important list of rules to follow:
• The carbonyl group takes precedence over alkyl groups and
halogen substituents, as well as double bonds, in the
numbering of the parent chain.
24
 Classification, Nomenclature
Name of Institution
and Isomerism

• When both double bonds and carbonyl groups are present,

the en suffix follows the parent chain directly and the al
suffix follows the en suffix .
• The location of the double bond(s) is (are) indicated before
the parent name as before, and the al suffix follows the en
suffix directly.
• Remember it is not necessary to specify the location of the
carbonyl group because it will automatically be carbon #1.
See below for examples.
• Again, the carbonyl gets priority in the numbering of the
parent chain.

25
 Classification, Nomenclature
Name of Institution
and Isomerism
Here are some examples

26
 Classification, Nomenclature
Name of Institution
and Isomerism

Rules for Nomenclature of Ketones

• Ketones are named by replacing the suffix ane with anone.
• If there is more than one carbonyl group (C=O), the suffix is
expanded to include a prefix that indicates the number of
carbonyl groups present (anedione, anetrione, etc.).
• The position of the carbonyl group (s) on the parent chain is
(are) indicated by placing the number (s) corresponding to the
location (s) on the parent chain directly in front of the base
name (same as alkenes).

27
 Classification, Nomenclature
Name of Institution
and Isomerism
Here is an important list of rules to follow:
• The carbonyl group takes precedence over alkyl groups and
halogen substituents, as well as double bonds, in the
numbering of the parent chain.
• When both double bonds and carbonyl groups are present,
the en suffix follows the parent chain directly and the one
suffix follows the en suffix.
• The location of the double bond(s) is (are) indicated before
the parent name as before, and the location of the carbonyl
group(s) is (are) indicated between the en and one suffixes.
• Again, the carbonyl gets priority in the numbering of the
parent chain.

28
 Classification, Nomenclature
Name of Institution
and Isomerism

• Here are some examples:

29
 Classification, Nomenclature
Name of Institution
and Isomerism
Rules for Nomenclature of Carboxylic Acids
• Carboxylic acids are named by counting the number of
carbons in the longest continuous chain including the carboxyl
group and by replacing the suffix ane of the corresponding
alkane with anoic acid.
• If there are two COOH groups, the suffix is expanded to
include a prefix that indicates the number of COOH groups
present (anedioic acid - there should not be more than 2 of
these groups on the parent chain.
• It is not necessary to indicate the position of the -COOH group
because this group will be at the end of the parent chain and its
carbon is automatically assigned as C-1.

30
 Classification, Nomenclature
Name of Institution
and Isomerism
Here is an important list of rules to follow:
• The carboxyl group takes precedence over alkyl groups and
halogen substituents, as well as double bonds, in the
numbering of the parent chain.
• If the carboxyl group is attached to a ring the parent ring is
named and the suffix carboxylic acid is added.
• When both double bonds and carboxyl groups are present,
the en suffix follows the parent chain directly and the oic
acid suffix follows the en suffix .
• The location of the double bond (s) is (are) indicated before
the parent name as before, and the oic acid suffix follows
the en suffix directly.
• Remember it is not necessary to specify the location of the
carboxyl group because it will automatically be carbon #1. 31
 Classification, Nomenclature
Name of Institution
and Isomerism
examples:

32
 Classification, Nomenclature
Name of Institution
and Isomerism
Isomerism in organic compounds
The word isomerism came from Greek word isomers (isos =
equal, meros = a share).
Two or more compounds having the same molecular formula
but different chemical and/or physical properties are called
isomers and the phenomenon is known as isomerism.
Isomerism can be broadly divided into two types,
1. Structural isomerism (constitutional isomerism)
2. Stereoisomerism (configurational isomerism)
Isomers are the compounds with the same qualitative and
quantitative composition of elements, therefore their relative
molecular weights and general formulas are identical, but
their structures including in the 3D arrangement are
different. 33
 Classification, Nomenclature
Name of Institution
and Isomerism
• The compounds propyl chloride and propane are not isomers,
since their qualitative composition of elements are different.
• The compounds propane and propene are not isomers,
although they are built from the same elements, but with
different quantitative composition of elements.
• The compounds propene and cyclohexane are not isomers,
although they are built from the same elements, with the same
ratio of elements, their relative molecular weights are
different.

34
 Classification, Nomenclature
Name of Institution
and Isomerism

However, the compounds butane and isobutane are isomers, since

they have the same general formula, but their 3D arrangement is
different.

but different structures

35
Classification, Nomenclature
Name of Institution
and Isomerism

36
Classification, Nomenclature
Name of Institution
and Isomerism

37
 Classification, Nomenclature
Name of Institution
and Isomerism

• Structural isomerism, or constitutional isomerism is a form

of isomerism in which molecules with the same molecular
formula have different bonding patterns and atomic
organization.
• As opposed to stereoisomerism, in which molecular bonds are
always in the same order and only spatial arrangement differs.
• Three categories of constitutional isomers are skeletal,
positional, and functional isomers.
• Positional isomers are also called regioisomers.

38
 Classification, Nomenclature
Name of Institution
and Isomerism

Chain isomerism
•In chain isomerism, or skeletal isomerism, components of the
(usually carbon) skeleton are distinctly re-ordered to create
different structures.
• Pentane exists as three isomers n-pentane, Iso pentene (2-
methylbutane) and Neopentene (dimethyl propane).

39
 Classification, Nomenclature
Name of Institution
and Isomerism
Position isomerism (regioisomerism)
• In position isomerism (regioisomerism) a functional group or
other substituent changes position on a parent structure.
• In the table below, the hydroxyl group can occupy three
different positions on an n-pentane chain forming three
different compounds.

40
 Classification, Nomenclature
Name of Institution
and Isomerism

• Many Aromatic isomers exist because substituents can be

positioned on different parts of the benzene ring.
• cresol or methylphenol has three isomers where the additional
methyl group can be placed on three different positions on the
ring.
• Xylenol has one hydroxyl group and two methyl groups and a
total of 6 isomers exist

41
Classification, Nomenclature
Name of Institution
and Isomerism

42
 Classification, Nomenclature
Name of Institution
and Isomerism

Functional Isomerism
• Functional isomers are structural isomers that have the same
molecular formula but the atoms are connected in different
ways so that the Functional group are dissimilar.
• For example, cyclohexane and 1-hexene both have the formula
C6H12.
• These two are considered functional group isomers because
cyclohexane is a cycloalkane and 1-hexene is an alkene.

43
 Classification, Nomenclature
Name of Institution
and Isomerism

• For two molecules to be functional isomers, they must contain

key groups of atoms arranged in particular ways.
• Some of the best examples come from organic chemistry.
C2H6O is a molecular formula.
• Depending on how the atoms are arranged, it can represent
two different compounds
• dimethyl ether CH3-OCH3 or ethanol CH3CH2-O-H.
Dimethyl ether and ethanol are functional isomers.
• The first is an ether and the second is an alcohol.

44
 Classification, Nomenclature
Name of Institution
and Isomerism

• If the functional group stay the same, but their locations

change, the structural isomers are not functional isomers
• ex- 1-Propanol and 2-propanol are structural isomers, but they
are not functional isomers.
• Both of them are alcohols. The functional group (carbon
chain-O-H) is present in both of these compounds, but they are
not the same.
• Therefore not all structural isomers are functional isomers.
• In simple terms, functional isomers are structural isomers that
have different functional groups like alcohol and ether
• Functional isomers are most often identified in chemistry
using infrared spectroscopy.
45
 Classification, Nomenclature
Name of Institution
and Isomerism
• All alcohols in liquid and solid form absorb infrared radiation
at certain wavelengths.
• Compounds with the same functional groups will all absorb
certain wavelengths of infrared light because of the vibrations
associated with those groups.
• In fact, the infrared spectrum is divided into two regions. The
first part is called the functional group region. Dimethyl ether
and ethanol would have dissimilar infrared spectra in the
functional group region.
• The second part of the infrared spectrum is called the
fingerprint region; it is associated with types of motion
allowed by the symmetry of the molecule and influenced by
the bond energies.
46
 Classification, Nomenclature
Name of Institution
and Isomerism
Metamerism Isomerism
• Metamerism is one among the five types (Chain isomerism,
positional isomerism, functional isomerism, metamerism and
tautomerism)of structural isomerism exhibited by the organic
compounds.
• They have the same molecular formula and functional group
but differ in the alkyl group present on both the sides of the
functional group. For example,
CH3CH2-O-CH2CH3 diethyl ether and
CH3-O-CH2CH2CH3 methyl propyl ether
• both contain the ether functional group, but they have different
alkyl groups attached to the oxygen atom.

47
 Classification, Nomenclature
Name of Institution
and Isomerism

Tautomerism Isomerism
• A special case of structural isomerism is tautomerism.
Tautomers are the isomer compounds differing from each
other in the position of a double bond and mobile hydrogen
atom.
• Tautomerism. It is a special type of functional isomerism in
which the isomers are in dynamic equilibrium with each other.
• For example, a hydrogen atom is attached to the oxygen atom
in vinyl alcohol, while a double bond is located between
carbon atoms.

48
 Classification, Nomenclature
Name of Institution
and Isomerism

• Tautomers are isomers of a compound which differ only in the

position of the protons and electrons.
• The carbon skeleton of the compound is unchanged.
• A reaction which involves simple proton transfer in An intra
molecular fashion is called a tautomerism.
Keto-enol tautomerism is a very common process, and is acid
or base catalysed.
• Typically the keto form of the compound is more stable, but in
some instances the enol form can be the more stable.
• There is a similar situation with pyruvic acid, which is
important for biochemical reasons.
49
 Classification, Nomenclature
Name of Institution
and Isomerism
• Tautomers regularly cannot be separated from each other, due
to the easy interconversion of them.
• For example, the enol (vinyl alcohol) is present in 0.001%,
while the oxo compound (acetaldehyde) is present in 99.999%
for the vinyl alcohol

50
Classification, Nomenclature
Name of Institution
and Isomerism

51
 Name of Institution

THANK
YOU

52