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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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•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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Aromatic heterocyclic compounds: Heterocyclic compounds
which resemble benzene in most of their properties are called
Aromatic heterocyclic compounds. For example,
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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.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
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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
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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• Here are some examples:
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Here are some examples
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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.
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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.
• 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 .
• 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
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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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• 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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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).
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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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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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