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Classification Nomenclature and Isomerism
Classification Nomenclature and Isomerism
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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
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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
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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
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• 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,
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Aromatic heterocyclic compounds: Heterocyclic compounds
which resemble benzene in most of their properties are called
Aromatic heterocyclic compounds. For example,
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Classification, NomenclatureName of Institution
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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.
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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).
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I.U.P.A.C.NomenclatureofAlkanes
(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
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• There are a few common branched hydrocarbons
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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.).
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• 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 19
chain).
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• Commas are used between numbers and dashes are used
between letters and numbers. There are no spaces in the
name. Here are some examples:
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• Rules for Nomenclature of Aldehydes
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.
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• Here are some examples
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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 as they must occur at the
ends).
• 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.
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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 (notice that the e is left
off, en instead of ene).
• 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. 31
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• Remember it is not necessary to specify the location of the
carboxyl group because it will automatically be carbon #1.
See below for examples. Again, the carboxyl gets priority
in the numbering of the parent chain.
• Here are some examples:
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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
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different.
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• 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.
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However, the compounds butane and isobutane are isomers, since
they have the same general formula, but their 3D arrangement is
different.
Different structures
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• 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.
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Chain isomerism
•In chain isomerism, or skeletal isomerism, components of the
(usually carbon) skeleton are distinctly re-ordered to create
different structures.
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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.
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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.
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• 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.
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• 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.
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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.
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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.
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Pharmaceutical Analysis Name of Institution
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