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The IUPAC Systematic Approach To Nomenclature
The IUPAC Systematic Approach To Nomenclature
By-- S.K.SINHA
Number the chain:-Number the atoms in the parent chain, beginning at the end nearer the first
branch point. If there is branching an equal distance from both ends, then consider the next branch
point.
Identify the substituents:- Identify and number the substituents. Remember there must be as many
numbers as there as substitutents.
Writing the name:- Write out the name as a single word, using hyphens to separate the different
prefixes and commas to separate the numbers. If two or more different substitutents are present, cite
them in alphabetical order. With identical substituents, use the prefix di-, tri-, tetra- etc. as required.
Ignore these prefixes when alphabetising.
If a substituent has subranching (ie. its complex) then reapply the first 4 steps as if it were a
compound. Numbering must begin at the point of attachment. Now set this substituent in
parentheses.
Naming the parent chain: Here is a list of the root names for the hydrocarbon chains
C1 = meth- C2 = ethoctC9 = non-
C3 = propC10 = dec-
Suffix if Highest
Precedence
-oic acid
-carboxylic acid
-sulfonic acid
-oic anhydride
alkyl -oate
alkyl carboxylate
-oyl halide
-carbonyl halide
-amide
-carboxamide
-nitrile
-carbonitrile
-al
-carbaldehyde
-one
-ol
-thiol
-azane (-amine)
-azane (-imine)
-ene
-yne
-
Prefix if Lower
Prededence
carboxysulfoalkoxy-oxohalo-oxohalocarbonylamino-oxoaminocarbonylcyanooxoformyloxohydroxysulfanylazanyl- (-amino)
azanylidene*
**
halo-, alky-l, alkoxyaryl-, nitronitroso-, azidodiazo-, (R)-sulfanyl-
(C) designates a carbon atom included in the parent hydrocarbon (part of the longest chain or ring.
Ph-0744-2422383
.Mo-93149-05055
By-- S.K.SINHA
* and ** These are always used as a suffix. If a higher priority group is present in the molecule the suffix
is changed to en or yn and is followed by the suffix of the higher priority group.
Step 2
Determine the parent hydrocarbon (principle chain or ring system system):
(a)
If the principle group occurs in a chain, the principle chain is selected as
(i) the chain containing the functional group of the highest seniority as the parent.
OH
2-(propan-1-yl)pentan-1-ol
(ii) If more than one such choice is possible, select the chain with the maximum number of
multiple bonds.
2-(hexan-1-yl)buta-1,3-diene
(iii) If (i) and (ii) together are not definitive, then choose the longest chain.
(iv) If two chains of the same length are possible, choose the one with the maximum number of
substituent groups.
O
2-(butan-1-yl)-4-methylhexanal
The parent chain here contains six carbon atoms.
If the principle functional group occurs in a cyclic system, that cyclic system forms the parent.
(b)
OH
2-(octan-1-yl)cyclohexanol
2-(hexan-1-yl)cyclopentene
Step 3 Name the parent structure of and the principle group(s). Give the parent name the same name as
if it were an alkane, but replace ane with the suffix characteristic of the functional group of the highest
priority (Table 1). Note: Multiple unsaturation in hydrocarbons is indicated by the numerical prefixes di-,
tri-, etc. In such cases, however, the ending ane of the parent alkane is replaced with adiene, atriene,
etc. leaving the a in the root alkane name whenever the first letter of the suffix is a consonant to make
the name easier to pronounce. Thus we get alkadienes, alkatrienes, alkadiynes, etc.
Step 4 Complete the number system.
(a) Number the carbon atoms consecutively from the end of the chain nearer the functional group of the
highest priority.
1
2
4,5-dimethylhexan-3-one
4
O
(b)
1
If the same number for the functional group of highest priority is obtained in both directions, the
correct IUPAC name is the one that contains the lowest substituent numbers.
(c)
(d)
2,4-dimethylhex-3-ene
The substituent numbers are 2 and 4. If we numbered from the other end, the substituent numbers
would have been 3 and 5. 2+4 is a lower numbering system than 3+5.
If the first substituents occur at an equal didtance from each end of the chain, number the end
nearer a second substituent. If still the same, continue until the first point of difference.
If numbering for either end gives the same set of numbers, number from the end with the substituent
that comes
first in alphabetical order.
6
2
5
4
2-chloro-5-methylhex-3-ene
3
Cl
Ph-0744-2422383
.Mo-93149-05055
By-- S.K.SINHA
In monosubstituted cycloalkanes and benzene derivatives. The carbon to which the substituent is
bonded is always number 1. If there is only one substituent, the locant number 1 is omitted.
However, the number one is required in polysubstituted compounds.
NO 2
CH3
OH
I
Cl
(f)
Br
Cyclopentanol
1-chloro-2-methylcyclohexane
2-bromo-4-iodo-1-nitrobenzene
In polysubstituted cyclic compounds, the starting point and the direction of numbering are chosen to
give the lowest numbering system. The starting point is chosen according to the following factors:
(i) The principle functional group named as the suffix is always given the lowest possible number.
Because certain cyclic systems have fixed numbering systems, it is not always possible to place a
substituent on carbon number 1.
6
HO
NO 2
1
CH3
Br
OH
7
6
N
1
5
4
IUPAC: 3-nitrobenzen-1-ol
3-methylazabenzene
7-bromonaphthalene-2-ol
(3-nitrophenol accepted) (3-methylpyridine accepted ) (7-bromo-2-naphthol accepted)
Note: When one heteroatom is present in the ring the number 1 is assigned to that atom. If more than
one is present then we use the number 1 on the O, S, or N in that order of priority.
4
3
4
3
4
N3
5 N
S 2
O
O
1
1
IUPAC: oxole(Furan accepted)
1,2-oxathiolane
(ii) Lowest numbering for multiple bonds in cyclic compounds.
5
2
N
1
1,3,5-triazine
Cl
OH
CH3
5
CH3
5-chloro-3-methylcyclohexene
6-methylcyclohex-3-en-1-ol
Note: In naming cycloalkenes, the double bond is located between C1 and C2, and the 1 is
usually omitted in the name. The ring is numbered clockwise or counterclockwise to give the first
substituent the lower number. However, when functional group with a higher priority than an
alkene is present, the carbon bonded to the higher priority group becomes C1 and then multiple
bonds are considered for lowest possible numbering.
(iii) Lowest numbering for first substituent (or first point of difference).
Cl
CH3
3
2
4
5 6 1
OH
CH2CH2CH3
5 6 1
4
2
3
Cl
CH3
4-chloro-2-methylcyclohexan-1-ol
4-chloro-2-methyl-1-(propan-1-yl)cyclohexane
(iv) If the same numbers will result from numbering in either direction, give the lowest number for
the substituent that is cited first in the name.
4
Br
CH3
3
2
1
4
5
CH2CH3
Cl
3
6
2
1
O
2-ethyl-3-methylnaphthalene
3-bromo-5-chlorocyclohexanone
Step 5 Name alkyl groups, halides, and other substituents and determine their position on the chain by
the numbering system established by step 4.
Step 6 Assign the stereochemistry to chiral carbon atoms (stereocenters) and the double bond(s):
B-7. JAWAHAR NAGAR.Main Road ,Kota.
Ph-0744-2422383
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(a)
By-- S.K.SINHA
Disubstituted alkenes may be named in two ways: (i) using terms cis- and trans- or (ii) using terms
(E) or (Z). Note: Use of (E) and (Z) stereocenters is preferred. However, the cis-trans terms are
accepted.
(E)-pent-2-ene or trans-pent-2-ene
(Z)-hex-3-ene or cis-hex-3-ene
(b)
Triand
tetrasubstituted
alkenes
may
only
be
named using the (E-Z) system.
6
1
5
(E)-2,3,5-trimethylhex-3-ene
(c)
cis-1-chloro-4-methylcyclohexane
(R-S) system not applicable here
Cl
CH3
trans-3-methylcyclopentanol
(1R,3R)-3-methylcyclopentanol
Chiral carbon atoms are assigned (R) or (S) configuration.
H
HO
(d)
(S)-5-methylhexan-3-ol
H
HO
OH
H
COO
(2S,3R)-2-amino-3-hydroxybutanoic acid
common name: threonine
H3N
(e)
When both (R-S) and (E-Z) stereodescriptors are present, they are placed in parentheses followed
by a hyphen; each stereodescriptor is immediately preceded by its associated number and they are
arranged in numerical
order.
H OH
Cl
CH3
(3S,4E)-6-methylhept-4-en-3-ol
(2Z,4E,6R)-6-chloro-6-methylocta-2,4-diene
Step 7 Compounds with multiple bonds and triple bonds have the following suffixes: adiene,
adiyne, atriene, atetraene, and so on. Specify the location of each multiple bond by a locant number
placed between the a and diene, diyne, triene, etc.
(E)-2-ethylhexa-1,4-diene
previously: (E)-2-ethyl-1,4-hexadiene
Step 8 Compounds with both double and triple bonds are called enynes. Start the numbering of enynes
from the end nearest the first multiple bond, regardless of type. When a double bond is the same distance
8 number.
from one end as a triple bond from the other end, assign the double bond the lower
7
6
4
5
(E)-hept-5-en-1-yne
(E)-oct-2-en-6-yne
Step 9 Write the complete name of the compound as a single word with the correct locant numbers for
all substituents, which are listed in alphabetical order. The prefixes di, tri, tetra, etc. do not alter the
alphabetical ordering of the substituents. The stereochemistry is indicated by placing the appropriate
prefix within parentheses followed by a hyphen in front of the name.
Cl
1
6
2
5
4
(E)-5-chloro-3-methyl-3-en-2-one
3
O
4-ethyl-2,5-dimethylhexanal
(a)
Ph-0744-2422383
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By-- S.K.SINHA
Step 10
A complex substituent is named by applying the above steps just as if the substituent were a
compound itself. We begin numbering the sidechain at the point of attachment to the parent hydrocarbon
giving the carbon at the point of attachment the locant of C1. We then give this substituent the suffix yl.
We put this name in parentheses and in front of the parentheses we place the locant number on the
parent hydrocarbon.
SH
OH
Br
2-(bromomethyl)benzenethiol
OH
3 2
3
3-(4-methylcyclohexyl)propane-1,2-diol
When a complex sidechain contains a chain that is attached to the parent hydrocarbon at a position other
than at the end of the chain, the carbon of attachment is still numbered as C1 and the other part of the
chain is named as a substituent group to that chain.
1
3
(1-ethylbutyl)benzene
1-(2-ethyl-1-methylbutyl)-2-methylcyclohexane
Note: An alternate method of numbering the sidechain is to find the longest chain and begin numbering
at the end closest to its attachment to the parent hydrocarbon. The yl ending is added to the chain
parent name and the position of the attachment is placed before the yl ending.
1
2
1-(3-ethylpentan-2-yl)-2-methylcyclohexane
The table below shows some examples of IUPAC names for commonly known compounds. The IUPAC
system allows the trivial names of these compounds to be retained as official IUPAC names and, for
some, to be used in naming substituted compounds such as 4-bromobenzoic acid. The IUPAC systematic
name for this compound would be 4-bromobenzenecarboxylic acid.
OH
IUPAC:
Trivial (retained)
azabenzene
pyridine
1,2-dehydrobenzene
benzyne
NH2
benzenol
phenol
NH2
NH2
CH3
IUPAC:
Trivial (retained)
phenylazane
benzenamine
aniline
O
2-methylphenylazane
2-methylbenzenamine
ortho-toluidine
naphthalene-2-ylazane
naphthalene-2-amine
2-naphthylamine
OH
OCH3
IUPAC:
Trivial (retained)
benzenecarboxylic acid
benzoic acid
methyl
benzenecarboxylate
methyl benzoate
Ph-0744-2422383
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propiophenone
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By-- S.K.SINHA
CH3
CH CH2
IUPAC:
Trivial (retained)
H3C
methylbenzene
toluene
CH3
propan-2-one
(ethenyl)benzene
styrene
acetone
Many other trivial names are also retained but can only be used for the unsubstituted compound. For
example, the names butanoic acid (systematic) and butyric acid (trivial retained) are both approved by the
4-bromobutanoic acid and
IUPAC. However, BrCH2CH2CH2COOH must be named systematically as
cannot be named as 4-bromobutyric acid.
Hantzsch-Widman System
Element Valence Prefix
Element Valence
Silicon
IV
Sila
Oxygen
II
Sulfur
II
Thia
Tin
IV
Selenium
II Selena
Tellurium II
Boron
III
Bora
Nitrogen
III
Stems for the Hantzsch-Widman System
The stem for six-membered rings depends on the least
heteroatom whose name directIy precedes the stem.
Prefix
Oxa
Stanna
Tellura
Aza
Phosphorus III
Phospha
To determine the proper stem for six-membered rings, select the set below that contains the least
preferred heteroatom before consulting the table.
Ring size
3
4
5
Unsaturated
irene
ete
ole
Saturated
irane
etane
olane
Ring size
7
8
9
Unsaturated
epine
ocine
onine
Saturated
epane
ocane
onane
Common nomenclature Common nomenclature is an older system of naming organic compounds. Instead of using the prefixes
for the carbon skeleton above, another system is used. The pattern can be seen below.
Number of
carbons
Prefix as in new
system
Meth
Formaldehyde
Formic acid
Eth
Acetaldehyde
Acetic acid
Prop
Propionaldehyde
Propionic acid
But
Butyraldehyde
Butyric acid
Pent
Amyl alcohol
Valeraldehyde
Valeric acid
Hex
Caproaldehyde
Caproic acid
Hept
Enanthyl alcohol
Enanthaldehyde
Enanthoic acid
Oct
Capryl alcohol
Caprylaldehyde
Caprylic acid
Non
Pelargonaldehyde
Pelargonic acid
10
Dec
Capric alcohol
Capraldehyde
Capric acid
Ph-0744-2422383
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1
2
or
6
5
benzene
3
5
naphthalene
10
anthracene
B. Monosubstituted Benzenes
1. Most substituents keep their designation, followed by the word benzene:
Cl
NO2
CH2CH3
chlorobenzene
nitrobenzene
ethylbenzene
COOH
benzoic
acid
SI
C
N
H I H
E IT A
M
IS
TR
Y
2. Some common substituents change the root name of the ring. IUPAC accepts these as root
names, listed here in decreasing priority:
SO3H
CHO
benzenebenzaldehyde
sulfonic acid
OH
NH2
phenol
aniline
OCH3
anisole
CH3
toluene
C. Disubstituted Benzenes
1. Designation of substitutiononly three possibilities:
X
X
Y
common:
IUPAC:
ortho1,2-
Y
para1,4-
meta1,3-
OCH3
Br
CHO
3-aminobenzoic acid
1,4-dibromobenzene
2-methoxybenzaldehyde
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3-methylphenol
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D. Polysubstituted Benzenes
CH3
Cl
HN
CH3
O2N
COOCH2CH3
NO2
Cl
OH
NO2
3,4-dichloro-N-methylaniline
NH2
E. Aromatic Ketones
A special group of aromatic compounds are ketones where the carbonyl is attached to at least one
benzene ring. Such compounds are named as phenones, the prefix depending on the size and
nature of the group on the other side of the carbonyl. These are the common examples:
O
O
C CH3
C CH2CH3
propiophenone
SI
C
N
H I H
E IT A
M
IS
TR
Y
acetophenone
O
C CH2CH2CH3
butyrophenone
O
C
benzophenone
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14
Homologous series
Compounds with the same functional group, differing only in the number of CH2 units in their
skeleton are said to be in the same homologous series. They are part of the same family of
compounds with similar reactions and characteristics that differ only in the number of carbon
atoms that make up the chain. Members of a series will have formula that are linked by a general
formula. For example, all alkanes have the general formula CnH2n+2.
All organic compounds have six identifying characteristics each.
1. Molecular formula - showing the actual number of atoms of each element in that compound.
E.g. C2H4O2 for ethanoic acid, meaning there are two carbon atoms, four hydrogen atoms and
two oxygen atoms.
2. Empirical formula - the simplest whole number ratio of the atoms of each element in that
compound. E.g. CH2O for ethanoic acid, meaning there is a ratio of 1:2:1 of C:H:O atoms.
SI
C
N
H I H
E IT A
M
IS
TR
Y
3. Structural formula - showing how those atoms are arranged. E.g. CH3CO2H for ethanoic acid,
meaning three hydrogen atoms are attached to one carbon atom, which in turn is attached to
another carbon atom, which in turn has two oxygen atoms attached to it, one of which has a
hydrogen atom attached to it.
4. Graphical formula - showing how these atoms are arranged in space and the bonds between
them. Lines represent covalent bonds (shared pairs of electrons) between atoms. E.g. for
ethanoic acid, where = represents a double covalent bond and represents a single covalent
bond.
H
H
C
H
O
C
O
5. Skeletal formula showing an abbreviated form of the carbon chain, with each line segment
understood to have a carbon atom at each end. These structures may or may not show terminal
(end of chain) carbons. E.g. for ethanoic acid
O
OH Or
H3C
OH
6. Name - based upon an accepted system for naming compounds (IUPAC nomenclature). E.g.
CH3CO2H, is called ethanoic acid.
Ph-2422383,
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18
ALKANES
1. Name the following compounds
i) CH3C(CH3)2CH2CH3
ii) CH3CH2C(C2H5)2CH2CH2CH3
iii) CH3CH(CH3)CH2CH(CH3)CH3
iv) CH3CH2CH(CH3)CH(C2H5)CH2C(CH3)2CH3
2. Draw graphical formula for the following compounds
2-methylpropane
3-methylheptane
2,3-dimethylbutane
2,2,6-trimethyloctane
1,3-diethylcyclobutane
SI
C
N
H I H
E IT A
M
IS
TR
Y
i)
ii)
iii)
iv)
v)
CH3CH2CH=CH2
CH3CCCH3
CH3CH2CH(CH3)CCCH3
CH3CCCH(CH3)2
CH2=CHCH=CH2
2,3-dimethylbut-2-ene
4-methylhex-1-yne
3,4-diethylhex-2-ene
4-ethylcyclohex-1-ene
4-ethylcyclohex-1-ene
HALOGEN COMPOUNDS
5. Name the following compounds
i) CH3CH2CH2CH2CH2I
Br
O
ii)
iii)
(CH3)2CHBr
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19
SI
C
N
H I H
E IT A
M
IS
TR
Y
i) CH3CH2CH2CHO
ii) CH3CH(CH3)COCH3
iii) CH3CH(CH3)CHO
iv) CH3CH(CH3)COCH3
10. Draw graphical formula for the following compounds
i) cyclohexanone
ii) 3-methylbutanal
iii) 2,2-dimethylpropanal
iv) 3-chlorobutan-2-one
CARBOXYLIC ACIDS & DERIVATIVES
11. Name the following compounds
i) CH3CH2CO2H
ii) CH3CH2CH(OH)CH2COOH
iii) (CH3)3CCO2H
Cl
H3C
iv) H3C
3-aminopentane
Ph-2422383,
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Br
Cl
Br
Cl
10
11
12
Br
Cl
1.
2.
3.
4.
O
OH
5.
6.
HO
H
O
O
O
7.
8.
OH
O
H
O
9.
10.
O
O
O
11.
12.
O
OH
13.
14.
O
Br
O
O
.
:
1.1
g)
k)
l) CH3 CH2
C
Br
1.2
b) CHCl3
Br
C
CH3
CH3
|
|
CH3 CH2 CHCH 2 CHCHCH 3
|
CH2 CH2 CH3
CH3
|
CH3 CH2 C-CC-CH(CH 3 )2
|
CH3
m) CH3 CH2
C
CH3 CH2
H
C
H
b) 3,3-dimethyl-1-butanol
c) 4-ethyl-2,2-dimethylhexane
d) 1,2-dibromo-2-methylpropane
e) 4-methyl-2-pentyne
f) cis-1-bromo-2-pentene
2.1
2.2
3.1
d) Cl
Cl
c) 4-isopropylcyclohexene
b)
c) Cl
d)
CH3
3.2
4.1
d) FC(CH3 )3
d) sec-butyl bromide
4.2
5.1
5.2
6.
d) ethylene
1.2
a) 2,2-dimethylbutane
CH3
|
CH3 CCH2 CH3
|
CH3
b) 3,3-dimethyl-1-butanol
CH3
|
HOCH 2 CH2 CCH3
|
CH3
c) 4-ethyl-2,2-dimethylhexane
d) 1,2-dibromo-2-methylpropane
CH3 CH2 CH3
CH3
|
|
|
CH3 CCH2 CHCH 2 CH3
CH2 CCH3
|
|
|
CH3
Br Br
e) 4-methyl-2-pentyne
CH3 CCCHCH 3
|
CH3
f) cis-1-bromo-2-pentene
BrCH2
CH2 CH3
C
C
H
H
2.1
a) cycloheptane
c) 2-methylcyclobutanol
2.2
3.1
3.2
b) isopropylcyclopentane
d) 1,4-dichlorocyclohexene
b)
CH(CH 3 )2
c)
CH2 CH3
4.1
4.2
a) methyl iodide
b) isobutyl alcohol
CH3 I
(CH3 )2 CHCH 2 OH
5.1
a) cyclopentyl alcohol
5.2
a) cyclopropyl chloride
a) propylene
CH3 CH=CH 2
(CH3 )2 CHOH
b) cyclohexyl alcohol
d) sec-butyl bromide
CH3 CHBrCH 2 CH3
c) cyclobutyl bromide
b) cyclohexyl iodide
Cl
6.
c) isopropyl alcohol
b) acetylene
H-CC-H
c) ethylacetylene
CH3 CH2 CC-H
23
d) ethylene
H2 C=CH 2