Organic Chemistry - Naming: Chapter - 14
Organic Chemistry - Naming: Chapter - 14
Organic Chemistry - Naming: Chapter - 14
CHAPTER - 14
ORGANIC CHEMISTRY - NAMING
The word organic signifies life - ie, compounds directly or indirectly derived from living beings.
NH4CNO
NH2 CO NH2
Later Kolbe synthesis acetic acid
Berthelot synthesised methane and acetylene
Thus vital force theory was rejected and it was shown that organic compounds should be synthesised
from inorganic source.
Organic chemistry
It is the study about carbon and its compounds or hydrocarbons and their derivatives.
Hydrocarbon classsification
On the basis of nature of carbon skelton
1. Acyclic or open chain compounds
2. Cyclic or closed chain compounds
I. Acyclic or open chain compounds
Compounds containing open chains of carbon atom in their molecule. It may be straight or
branched. These are also known as aliphatic compounds. Further divided into
Saturated hydrocarbon or alkanes or paraffins
Compounds containing carbon carbon single bond (C–C)
Unsaturated hydrocarbon
Alkenes or Olefins - Containing C = C
Alkynes or Acetylene - Containing C C
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II. Cyclic or closed chain compounds
Compounds containing one or more closed chains or rings of atom
Further divided into
a. Homocyclic :
Rings which are made up of only one kind of atom. Mainly C atom- known as carbocyclic.
i. Alicyclic compounds.
Rings containing 3 or more carbon atom
OH CH3
Benzene
Phenol Toluene
Fused Isolated
Naphthalene Biphenyl
Anthracene Ter-phenyl
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b. Non-benzenoid aromatic compound
Compounds that does not contain benzene ring but contain other highly unsaturated rings.
O O
OH
Tropone Tropolone
Heterocyclic compounds
Cyclic compounds containing one or more hetero atom in their rings.
a. Alicyclic heterocyclic
Aliphatic cyclic compounds containing one or more hetero atom
O N
Oxirane Tetra hydro furan H
Tetra hydro pyrrole
b. Aromatic heterocyclic
Aromatic cyclic compounds containing one or more hetero atom.
O N S N
Furan Thiophene Pyridine
H
Pyrrole
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Hydrocarbon
Acyclic Cyclic
Alicyclic Aromatic
Alkene Alkyne
Benzenoid Non-benzenoid
Fused Isolated
Alicyclic
Aromatic
Nomenclature
System of naming
Trivial system
IUPAC system
TRIVIAL SYSTEM
Also known as common names.
For representing saturated hydrocarbon mainly 3 prefixes are used.
1. n
n - stands for normal or straight chain
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2. Iso
The second carbon containing one methyl group
CH3 CH3
3. Neo
Second carbon atom containing 2 methyl group
CH3 CH3
CH3 CH3
Neo-pentane Neo-hexane
CH3 CH3
CH3
Quarternary
30 20 10
Alkane
H
Alkyl
CH
4
H
CH3 - Methyl
methane
CH3 CH3
CH3 CH3
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IUPAC SYSTEM
In 1892 an International Chemical Congress was held at Geneva, they started a new naming
system for organic compounds known as Geneva system of Nomenclature. This system was further
modified as IUPAC nomenclature.
Rules
Each systematic name contain
Word root; Suffix; Prefix
Word root :
It denote no.of carbon atoms in the parent chain.
Primary suffix
It shows saturation or unsaturation in a chain
Nature of C-chain 1° suffix 2° suffix
C–C –ane Alkane
C=C –ene Alkene
CC –yne Alkyne
2C = C –adiene Alkadiene
2C C –adiyne Alkadiyne
Secondary suffix
It indicates the presence of a particular group (functional group)
Functional group 2° suffix
Alcohol –ol
Aldehyde –al
Ketone –one
Primary prefix
It is used to distinguish cyclic from acyclic compound. In case of carbocyclic compound, 1°
prefix cyclo is used.
Secondary prefix
It denote the presence of substitutent or side chain on the parent chain.
–X halo
–NO2 Nitro
–R Alkyl
–OR Alkoxy
The complete IUPAC name of compound contain:
2° prefix + 1° prefix + word root + 1° suffix + 2° suffix
Eg : 2-methyl butanoic acid Methyl 2° prefix : but - word root : an 1° suffix : oic acid-2° suffix
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NAMING OF COMPLEX COMPOUNDS
Longest chain rule
Select the longest continuous chain of carbon atom in the molecule. The continuous chain of carbon
atom is called parent chain or main chain. Carbon atom which are not included in the parent chain are
considered as substituent or side chain.
CH3
Derivative of pentane
CH3 CH2 CH CH2 CH3
Two or more carbon chains of equal length, then the selected chain should contain maximum no.of
side chain or substituent.
CH3
CH3
CH3 C CH3
H3C C CH3
CH3
CH3 CH CH2
CH CH CH3
CH3 CH CH3
CH3
Derivative of heptane
1 2 3 4 5
CH3
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Two or more similar substituent is attached to the parent chain, lowest set of locant is preferred. The
lowest set is determined by first point of difference rule. The rule says “when two or more different
set of locants containing same no.of term is possible, then the set of locants is compared term by
term with other set, each set in order of increasing magnitude. The set of locant is preferred which
has a lower no.at the first point of difference”.
6 5 4 3 2 1
1 2 3 4 5 6
CH CH2 CH CH CH3 CH3 CH CH2 CH CH CH3
CH3
If there are different alkyl substituents attached to the parent chain, their names are written in
alphabetical order.
1 2 3 4 5
CH3 CH CH CH2 CH3 - 3-Ethyl-2-methyl pentane
If there are different alkyl substituent at equivalent positions the numbering is done in such a way that
the substituent which comes first in alphabetical order get lowest possible number.
1 2 3 4 5 6
CH CH2 CH CH CH
2 2
CH3 3-Ethyl-4-methylhexane
6 3 5 4 3 1
1 2 3 4 5 6 7
CH3 CH2 CH2 CH CH2 CH2 CH3 4- (1-methyl ethyl)heptane
or
1 CH CH3 4-isopropyl heptane
2 CH3
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1 2 3 4 5 6 7 8 9
CH3 CH2 CH2 CH2 CH CH2 CH2 CH2 CH3 5- (2-methylpropyl)nonane
or
1
CH2 5-isobutyl nonane
2 CH CH3
3 CH
3
While deciding the alphabetical order of various substituents, the name of complex substituent is
considered to begin with first letter of complex name.
1 2 4 5 6 7 8 9 10 11
3
CH2 CH2 CH CH2 CH CH2 CH2 CH2 CH3
CH3 CH2
1 CH CH3 CH2 CH3
3 CH
3
CH3
1 2 3
H3C C CH2 CH3
1 2 4 5 6 7 8 9
3
CH3 CH2 CH2 CH2 C CH2 CH2 CH2 CH3
CH2 CH
2
CH3
1 3
CH3
5-(1, 1-Dimethyl propyl)-5- (2-methylpropyl)nonane
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If two complex substituents are of equal length, then the complex substituent with larger no.of alkyl
group form a part of longest carbon chain while the other one considered as complex substituents.
CH2 CH3
6 5 1 2 3
10 9 8 7 4
CH3 CH2 CH2 CH2 CH2 CH CH2 CH CH2 CH3
4 CH2
H3 C 3C
CH3
CH2 CH3
2 1
5-(2-Ethylbutyl)-3,3-dimethyldecane
If same complex substituent occur more than once prefix such as bis(2), tris(3), tetra kis (4)..... etc
are used before the name of complex name.
CH3
CH CH3
6 5 4 2 1
3
CH3 CH2 CH2 C CH CH3
CH3
H3C CH
CH3
2-methyl-3,3-bis(1-methylethyl) hexane
6 5 4 3 2 1
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If more than one double or triple bond is present in the molecule, the selected chain should contain
maximum number of such bonds.
7 6 5 4 3 2 1
CH3 CH CH CH2 CH CH CH2
The parent chain is numbered in a manner to give lowest number to that carbon atom linked by a
double or triple bond.
CH3 CH3
4,6-Dimethyl hept-2-ene
If a compound contains both double or triple bond, such compounds are named as Alkenynes.
5 4 3 2 1
CH3 C C CH CH2 Pent-1-en-3-yne
5 4 3 2 1
CH C CH2 CH CH2 Pent-1-en-4-yne
5 4 3 2 1
CH3 CH CH C CH Pent-3-en-1-yne
6 5 4 3 2 1
CH C CH CH CH CH2 Hexa-1,3-dien-5-yne
In some cases all the double and triple bond are not included in the parent chain, in such cases,.......
CH2
1 2 3 4 5
CH2 CH C CH CH2
3-Methylene penta-1,4-diene
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CH2 OH
CH3
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Carboxylic acid
–COOH
CN : Obtained from the source from which they were isolated or present in large quantity.
IUPAC : Alkanoic acid
C
CN : Dialkylketone
IUPAC : Alkanone
CH3 – CO – CH3 Dimethyl ketone (Acetone) ; Propanone
Amine
–NH2
CN : Alkylamine
IUPAC : Alkanamine
NH2
CH3
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Amide
C NH2
Acid halide
C X
CN : Replace -ic acid by -yl halide
IUPAC : Alkanoyl halide
O
Acetyl chloride : Ethanoylchloride
CH3 C Cl
Acid anhydride
O O
O O
O O
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O O
Ester
C O
CN : Replace - ic acid by ate
IUPAC : Alkyl alkanoate
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O O
- -oic anhydride
C O C
O
Alkoxy carbonyl -oate
C O R
O
Halocarbonyl -oyl halide
C X
O
Carbamoyl -amide
C NH 2
O
Keto/oxo -one
C
Hydroxy -ol
OH
C C - alkene
- alkyne
C C
R Alkyl -
OR Alkoxy carbonyl -
NO 2 Nitro -
NO Nitroso -
N N Diazo -
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CH3 CH C COOH
4 3 2 1 3-Methyl-2-oxobutanoic acid
CH3
4 3 2 1
3 2 1
NC CH2 CH2 COOH 3-Cyano propanoic acid
O NH 2
CH3 C CH CH COOH
5 4 3 2 1 2-Amino-3-hydroxy-4-oxopentanoic acid
OH
Poly functional compounds containing more than two like functional group
If an unbranched carbon chain is directly linked to more than two like functional group, the
compound is named as the derivative of parent alkane, the carbon atoms of like functional group do
not include in the numbering, in such case suffix like Tricarboxylic acid (3COOH), Tricarbaldehyde
(3CHO), Tricarbonitrile (3CN) etc are used.
COOH CHO
3 2 1
CH2 CH CH2 CH2 CH2 CH CH2
1
4 3 2
COOH COOH CHO CHO
COOH OH COOH
CH2 C2 CH2
3 1
COOH
2-Hydroxy propane-1,2,3-tricarboxylic acid
If more than 2 like functional group is not directly linked to the carbon chain, then the carbon
atoms of functional group directly attached to the parent chain is included in numbering, the other one
is considered as substituent group.
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4 3 2 1
3-(carboxymethyl)-pentane-1,5-dioic acid
1
7
CHO CHO
5 4 3 2
6
CH2 CH2 CH CH2 CH2
CH2 CHO
4-(Formylmethyl)heptane-1,7-dial
4-(2-oxoethyl)heptane-1,7-dial
Cyclopropane Cyclohexane
CH3
CH2 CH3
1
2
3
CH3
Ethylcyclopentane 1,3-Dimethyl cyclohexane
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CH3
3 1
2 2
1 3
CH2 CH3
1-Ethyl-3-methyl cyclopentane 3-Ethyl-1,1-dimethyl cyclopentane
CH3
1
C2H5
2
3
4
CH3
2-Ethyl-1,4-dimethyl cyclohexane
The ring containing more or equal number of carbon atom than alkyl group, then the compound is
named as derivatives of ring.
If the side chain contains more no.of carbon atom than the ring, compound is derivative of side chain.
1
CH3
1 2 3 4 5
CH3 CH CH2 CH2 CH3 2
CH CH2 CH3
3 4
2-Cyclobutyl pentane
2-Cyclopropyl butane
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If more than one alicyclic ring is directly attached to the parent chain, compound is derivative of parent
chain.
CH2
2
Dicyclopropylmethane
1,2-Dicyclohexyl ethane
Cyclopentene Cyclohexyne
In case of substituted cycloalkene and cycloalkyne the number of double and triple bond get lowest
possible number 1 and 2 and the substituent get lowest possible no at first point of difference rule.
CH3
3 Cl
2 3
1 1 2
3-Chlorocyclopentyne
3-Methylcyclohexene
OH
NH2
O
Cyclohexanamine Cyclopentanone
Cyclopentanol
If an alicyclic ring is directly attached to a carbon containing functional group, the carbon atom of the
functional group is not included in the parent chain. In such cases following suffix and prefix are used
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Functional group Prefix Suffix
–COOH Carboxy Carboxylic acid
–CHO Formyl Carbaldehyde
–COX Halocarbonyl Carbonylhalide
–CN Cyano Carbonitrile
–CONH2 Carbamoyl Carboxamide
–COOR Alkoxy carbonyl Alkylcycloalkane carboxylate
COOH
CHO
CONH2
If a ring containing a multiple bond and the side chain containing functional group, then the
compound is derivative of side chain.
3 2 1
CH3 CH CH2 OH
1
2
3
2-(Cyclopent-3-enyl) propanol
If the ring and side chain contains functional group then the compound is named as derivatives
of ring or side chain which will contain principle functional group.
4 3 2 1
4
HO CH2 CH2 CH2 COOH
1
3 2
4-(4-Hydroxycyclohex-2-enyl)butanoic acid
If the ring and side chain contains some functional group, the compound is named as a derivative
of side chain or the ring, which containmore number of carbon atom.
OH
7 6 1
OH 2
CH2 CH3 OHe 3 1 CH2 CH2 CHO
1
2 CH2 CH 3 4
5
1 2
7-(3-Formylcyclopentyl)heptanal
2-(2-Hydroxybutyl)cyclohexanol
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Nomenclature of Aromatic compound
Compounds are derivatives of benzene. The names are obtained by “substituent name + benzene”.
Most of the compounds have typical names.
CH3 OH
NH2 Cl
NO2
Special case
CHO
COOH
CONH2 COX
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If more than one substituents are present names are written in alphabetical order
If any of the substituent give a special name to the compound, then compound is derivative of that
special name.
Numbering does not violate lowest set of locant rule.
Cl
1
2
1-Chloro-3-nitrobenzene
3
NO2
Br
3
2
1 3-bromo toluene, (m-bromotoluene)
CH3
(The position number is indicated in IUPAC system but position name is indicated in common system)
NH2 CH3
4 2
OH
3 4-Amino phenol 1 2-Methyl phenol
1
2 p-Amino phenol o-methyl phenol
OH
OH
COOH
2-Hydroxybenzoic acid
o-hydroxy benzoic acid (salicylic acid)
If benzene ring is attached to an aliphatic chain containing a multiple bond or functional group or
substituent, benzene ring is considered as a substituent group known by phenyl.
3 2 1
CH2 CH CH2
3-Phenyl prop-1-ene
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5
CH3
2 1
4 3
CH CH CH2 COOH
OH
3-Hydroxy-4-phenylpentanoic acid
Bridges BHC
2 8
7
Bicyclo [3.2.1]octane
6
3 5
2 7
6
Bicyclo [3.1.1]heptane
3 5
4
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2 6
Bicyclo [2.2.0] hexane
3 5
2 10
1
3 9
Bicyclo [4.4.0] decane
4 8
6
5 7
1 9
3
8
CH3 8-Methylbicyclo[4.3.0]nonane
4
6 7
5
2
OH
4
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Number of carbon atom in each ring enclosed in a square bracket in ascending order, separate one
another by using dots, before the name of corresponding alkane
5 4
3 Spiro [2.3] hexane
6 1
9
10
8
1
5 Spiro [4.5] decane
7 2
6
4
3
Cl
2 1
3
6
1-Chloro spiro [4.4] nonane
4 5 7
9
8
Naming of epoxide
These are cyclic ether
1. CH2 CH2
O Epoxy
1,2-Epoxy ethane (Oxirane)
3 2 1
2. CH3 CH CH2
O
1,2-Epoxy propane (Methyloxirane)
2 3
3.
1 4
O
1,4-epoxy butane
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