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Course N4. Nomenclature S1 L1 NLS 2023 2024 Part I II
Course N4. Nomenclature S1 L1 NLS 2023 2024 Part I II
Chapter 4
Nomenclature
Presented by:
-Part I+II-
Dr. HAMRANI Ouiza Academic year: 2023/2024
Ministry of Higher Education and Scientific Research
University of Algiers 1 Benyoucef BENKHEDDA
Faculty of Sciences Department of Natural and Life Sciences
Chapter 4
Hydrocarbon Nomenclature
-Part I-
Presented by:
Dr. HAMRANI Ouiza Academic year: 2023/2024
Introduction
Introduction
Page1
Introduction
Introduction
There are molecules composed of hydrogen and carbon
atoms (hydrocarbons) as well as compounds with
heteroatoms (N, O, P, S, ...). These various compositions
have been grouped based on the similarity of their properties
into different functional groups.
The nomenclature aims to designate the chemical entities,
atoms, or molecules that constitute all living or animated
matter.
In order to name molecules, very precise rules have been
developed by an international organization called IUPAC
(International Union of Pure and Applied Chemistry
Page 2
Hydrocarbon Nomenclature
Applications of Organic Chemistry
Page 3
Hydrocarbon Nomenclature
Formulas of Organic Compounds
Molecular Representation
To describe an organic molecule, several 'formulas' can be
adopted.
1- Molecular Formula ( formule brute):
The molecular formula indicates the types of atoms that
compose the molecule and their respective numbers, such
as: CxHyOZ.
Examples: CH4O, C6H8O6...
2- Structural Formula:
A structural formula represents all the atoms that make up a molecule
using letters. Moreover, the bonds between the atoms are represented
by
Page dashes.
4
Hydrocarbon Nomenclature
Formulas of Organic Compounds
Example : C2H6O
3- Semi-Structural Formula:
Similar to the previous one (structural formula), except that
the bonds with hydrogen atoms (H) are not represented
C3H8: CH3-CH2-CH3
Page 5
Hydrocarbon Nomenclature
Formulas of Organic Compounds
4- Topological Formula:
The topological formula is a simplified representation of
organic molecules in which atoms, often used when the
carbon chain becomes larger, and in which:
Carbon-carbon bonds are indicated by zig-zag segments.
Carbon atoms are not specified.
Only atoms belonging to characteristic groups are mentioned.
Examples :
C4H10O OH
Page 6
Hydrocarbon Nomenclature
Page 7
Hydrocarbon Nomenclature
Hydrocarbons
Saturated Unsaturated
Alkanes Alkenes
Alkynes
Acyclic Cyclic
Unbranched Branched
(non ramifié) (ramifié)
Page 8
Hydrocarbon Nomenclature
Chaine carbonée
Préfixe principale
Suffixe
Page 9
Hydrocarbon Nomenclature
Page 10
Hydrocarbon Nomenclature
1- Saturated Acyclic Hydrocarbons: Alkanes
The name of unbranched alkanes consists of a
numerical root (prefix corresponding to the number of
carbon atoms in the chain) and a suffix 'ane.' The
numerical root indicates the number of carbon atoms
in the chain.
Examples:
CH3-CH2-CH2-CH3, 4 carbons: prefix But, suffix ane, so
it's butane.
CH4 (methane), C2H6 (ethane), C3H8 (propane).
Page 11
Hydrocarbon Nomenclature
The names of the first 12 linear alkanes are given in the
table below.
Page 4
Hydrocarbon Nomenclature
Branched Acyclic Alkanes
Page 13
Hydrocarbon Nomenclature
Branched Acyclic Alkanes"
Page 14
Hydrocarbon Nomenclature
Examples:
2-methylbutane."
Page 15
Hydrocarbon Nomenclature
4-ethyl-2,3-dimethyloctane
CH 2CH2CH 3 CH3CHCH 3
propyl isopropyl
CH 3 CH 3
CH 2CHCH 3 CCH 3
butyl CH 3
isobutyl tert-butyl
Page 16
Hydrocarbon Nomenclature
Rules for the Nomenclature of a Hydrocarbon
According to IUPAC
1- Identify and name the longest carbon chain present in
the molecule (the one with the greatest number of carbon
atoms). This chain, whether linear or cyclic, corresponds to
the main chain, and its name forms the basis of the
nomenclature.
2- Identify the alkyl group(s) that constitute(s) the
substituent(s) of the main chain, and state its (their)
name(s) before that of the main chain. If there are multiple
substituents, arrange them alphabetically, and numbering
is chosen so that the total position indices are as small as
possible. Additionally, substituents do not take an "e"; they
endwith
Page 17
"yl."
Hydrocarbon Nomenclature
Example :
3-méthyl-5-propyloctane
3- If the main chain contains the same substituent in
multiple instances (identical), precede the name of that
substituent with a multiplicative prefix such as di, tri,
tetra, penta,... etc. Position indices on the main chain are
indicated by numbers separated by commas and placed
immediately before the name of the substituent.
Multiplicative prefixes are not considered in alphabetical
ordering.
Page 18
Hydrocarbon Nomenclature
Exemple :
3-ethyl-4,7-dimethylnonane
4- In the case of multiple branches, the side chain is
numbered starting from the carbon attached to the main
chain. If necessary, the name of the side chain is enclosed
in parentheses.
Example :
1
2
3
Page 19
5-(1-methylpropyl)decane
Hydrocarbon Nomenclature
2
1 4 6
3 5
3-ethyl-4-methylhexane
Page 20
Hydrocarbon Nomenclature
Remarks:
When identifying he primary chain, aim for the maximum
number of substituents.
H 1
H3C C CH3
2
H2 H2 3-ethyl-2-methylpentane
3HC C C C CH3
H3 4 5
Examples :
Page 22
Hydrocarbon Nomenclature
The cycle can lose the position of the main chain in favor
of lateral chains if they are more complex.
Example:
5
3
1 4
2
1-cyclobutyl- 3-methylpentane
Page 23
Hydrocarbon Nomenclature
Nomenclature Rules"
Count the number of carbons present in the cycle,
determine the corresponding alkane, and add the term
"cyclo.―
If there are multiple substituents in the cycle, number
the cycle to have the smallest sum possible.
Alphabetically order the substituents.
Each substituent has its own number (index).
Write the complete name using the same rules as for
alkanes.
Example:
2
1
3 1-ethyl-2-methylcyclopentane
4 5
Page 24
Hydrocarbon Nomenclature
Page 25
Hydrocarbon Nomenclature
Unsaturated Hydrocarbons: Alkenes and Alkynes
1 2 3 4 5
H3C HC HC C CH pent- 2-en-4-yne
Hexa-1,3-dien-5-yne
1 2 3 4
C
H
2
C
H
C
H
C
H
Buta-1,3- diene
2
Page 28
Hydrocarbon Nomenclature
1
Example :
2 3
4 5
6 7
2,5-dimethylhept-3-ene
Page 29
Hydrocarbon Nomenclature
CAUTION:
" In the case of unsaturated compounds, the main chain is
not necessarily the longest but the one that contains the
most unsaturations."
Example:
Page 30
Hydrocarbon Nomenclature
Hydrocarbons with Triple Bonds (Alkynes)
Alkynes are unsaturated hydrocarbons with the molecular
formula CnH2n-2, featuring a triple bond C≡C. The name is
derived from that of the corresponding alkane by replacing
the suffix 'ane' with 'yne' in the longest carbon chain
containing the multiple bond. The position of the triple
bond in the main chain is indicated by a numerical index
placed before the 'yne' suffix. Carbon atoms bearing the
triple bond should have the smallest indices.
Examples:
With a triple bond: With multiple triple bonds:
Page 30
Hydrocarbon Nomenclature
Page 32
Hydrocarbon Nomenclature
Cycloalkenes:
These are cyclic hydrocarbons with the general formula
CnH2n-2 that contain a double bond in the cycle
Examples:
cyclopropene cyclohexene
Cyclopenta-1,3-diene 2,3-dimethylcyclohex-1-ene
Page 33
Hydrocarbon Nomenclature
Rules for the Nomenclature of Cycloalkenes
Count the number of carbons present in the cycle,
determine the alkene, and add the prefix ‗cyclo’.
Example:
1
1,5-dimethylcyclopentene
Page 35
Hydrocarbon Nomenclature
Aromatic or Benzene Hydrocarbons:
The aromatic or benzene series includes all compounds
whose molecules contain one or more unsaturated rings;
the most well-known of these hydrocarbons is benzene,
C6H6.
In a simple aromatic molecule, benzene becomes the main
chain. The names of the side chains attached to benzene are
used as prefixes.
Example:
1-ethyl-2-methylbenzene
Page 36
Hydrocarbon Nomenclature
Position of Substituents on Benzene
1
2
3
4
Page 37
Hydrocarbon Nomenclature
Nomenclature of Disubstituted Aromatics
Prefix + Substituent Name + Cycle Name"
"Considering that the prefix indicates the relative position of
the two substituents.
Page 38
Hydrocarbon Nomenclature
Example :
2
3 1
4 6 1-butyl-3-ethyl-2-propylbenzene
5
Page 40
Hydrocarbon Nomenclature
Page 41
Hydrocarbon Nomenclature
The Phenyl Group
42
Hydrocarbon Nomenclature
Page 43
Hydrocarbon Nomenclature
Examples :
Page 44
Hydrocarbon Nomenclature
Page 45
Hydrocarbon Nomenclature
Page 46
Thank you for your attention
Ministry of Higher Education and Scientific Research
University of Algiers 1 Benyoucef BENKHEDDA
Faculty of Sciences Department of Natural and Life Sciences
Chapter 4
Functional groups Nomenclature
-Part II-
Nomenclature of Organic Compounds
Presented by:
Dr. HAMRANI Ouiza Academic year: 2023/2024
Functional groups Nomenclature
Introduction
Functional Group
Page 47
Functional groups Nomenclature
Introduction
Page 48
Functional groups Nomenclature
Nomenclature of Molecules Containing Substituents and Functional Groups
Page 49
Functional groups Nomenclature
Page 50
Functional groups Nomenclature
Page 50
Functional groups Nomenclature
Naming Molecules Containing Functional Groups from Group A—Prefix or
Suffix
•Step 1. Find the highest priority functional group.
Determine and name the longest continuous carbon chain
that includes this group.
Page 51
Functional groups Nomenclature
Naming Molecules Containing Functional Groups from Group A—Prefix or
Suffix
Page 52
Functional groups Nomenclature
General Rules:
A systematic name of an organic compound is generally
derived by identifying the parent hydrocarbon and the
functional group(s) attached to it.
Number - Prefixes + Parent (stem) + Suffix
Locates the substituents
in the molecule Identifes the
The name of the
principal (longest) principal
Substituents in Functional
alphabetical chain
group
order
Page 53
Functional groups Nomenclature
Alcohols
In organic chemistry, any alkyl group can be abbreviated
as R. An alcohol, in which a hydroxy (-OH) group is
attached to a carbon of the alkyl group, can be abbreviated
as R-OH.
The hydroxyl group (—OH) is found in the alcohol and
phenol functional groups. (Note: that‘s not the same as
hydroxide, OH- , which is ionic.)
in alcohols, a hydroxyl group is connected to a carbon
atom.
in phenols, —OH is connected to a benzene ring. (The
―parent‖ molecule of this class is also named phenol:
PhOH or C6H5OH.)
Page 54
Functional groups Nomenclature
When two carbon groups are connected by single bonds
to an oxygen, this is classified as the ether functional
group.
Classification of Alcohols
• Alcohols are classified as primary (1°), secondary (2°),
or tertiary (3°) according to how many carbon groups are
attached to the carbon bearing the OH group:
Page 55
Functional groups Nomenclature
Classification of Alcohols
Page 56
Functional groups Nomenclature
Nomenclature of Alcohols and Phenols
Step 1.
Name the longest chain to which the hydroxyl (—OH)
group is attached. The name for this chain is obtained by
dropping the final ―-e‖ from the name of the hydrocarbon
parent name and adding the ending ―–ol‖.
Step 2.
Number the longest chain to give the lowest possible
number to the carbon bearing the hydroxyl group.
Step 3.
Locate the position of the hydroxyl group by the number
of the C to which it is attached.
Page 57
Functional groups Nomenclature
Nomenclature of Alcohols and Phenols
Step 4. Locate and name any other substituents.
Step 5. Combine the name and location for other groups,
the hydroxyl group location, and the longest chain into the
final name.
If there is more than one OH group, a counting prefix (di-,
tri-, tetra-, etc.) is placed immediately in front of the
suffix -ol (diol, triol, tetraol, etc.).
– Usually, the final ―e‖ of the parent hydrocarbon is not
dropped (e.g., propane-1,2-diol).
– The position of each alcohol group is indicated by
carbon number, separated by commas
(e.g., butane -1,3- diol).
Page 58
Functional groups Nomenclature
Nomenclature of Alcohols and Phenols
For cyclic alcohols, the carbon bearing the OH is
numbered as ―1.‖
Phenols are named after the parent compound phenol;
the C bearing the OH is numbered as ―1.‖
Examples:
2 1
1 2 3 4
CH3-CH2OH
ethanol
4 1
3 2
Page 59
Functional groups Nomenclature
Nomenclature of Alcohols and Phenols
5-methylhexan-3-ol
Butane- 1,4-diol
6
5 1
4 2 2-methylcyclohexanol
3
Page 60
Functional groups Nomenclature
Nomenclature of Alcohols and Phenols
Draw structural formulas for the following molecules:
3-methylpentan-2-ol 2,4,4,5-tetramethyheptanl-2-ol
3-ethylcyclopentanol 3-ethylphenol
Page 61
Functional groups Nomenclature
The Carbonyl Group
The carbonyl group (C=O) is found in aldehydes,
ketones, and many other organic functional groups.
The carbon and oxygen in the carbonyl group are sp2-
hybridized, with bond angles of 120°.
Page 62
Functional groups Nomenclature
Nomenclature of Aldehydes
Select the longest carbon chain containing the carbonyl
carbon.
The -e ending of the parent alkane name is replaced by
the suffix -al.
The carbonyl carbon is always numbered ―1.‖ (It is not
necessary to include the number in the name.)
1
2-ethylbutanal
4 3 2
Page 64
Functional groups Nomenclature
Nomenclature of Ketones
Select the longest carbon chain containing the carbonyl
carbon.
The ―–e‖ ending of the parent alkane name is
replaced by the suffix ―-one‖.
1
2
4 5 6 7
3,3-diethylheptan-2-one
Page 66
Functional groups Nomenclature
Nomenclature of Aldehydes and Ketones
Other Nomenclature Rules
Example:
Benzaldehyde
Page 69
Functional groups Nomenclature
Name the following compounds:
Page 70
Functional groups Nomenclature
Draw structural formulas for the following molecules:
3-ethylpentan-2-one
2,4,6-trimethylheptanal
3-ethylcyclopentanone
para-nitrobenzaldehyde
4-chloro-2-phenylpentanal
2-Chloro-3-cyclopentylhex-4-enal
Page 71
Functional groups Nomenclature
Nomenclature of Alcohols and Phenols
As with many molecules with two or more functional
groups, one is given priority while the other is named as a
substituent. Because aldehydes have a higher priority than
ketones, molecules which contain both functional groups
are named as aldehydes and the ketone is named as
an "oxo" substituent.
It is not necessary to give the aldehyde functional group a
location number, however, it is usually necessary to give a
location number to the ketone.
Page 72
Functional groups Nomenclature
Nomenclature of Alcohols and Phenols
Page 73
Functional groups Nomenclature
Examples:
Examples:
Ether Nomenclature
Common names for ethers are obtained by first naming the two
carbon groups attached to the oxygen (in alphabetical order) and
then adding the word ―ether‖ to the end. If the two groups are the
same, the prefix ―di-‖ is used, although sometimes this is simply
dropped
Page 75
(―ethyl ether‖).
Functional groups Nomenclature
Ether Nomenclature
Examples:
Page 76
Functional groups Nomenclature
Carboxylic Acids:
prefix: carboxy-; suffix: -oic acid (abbreviation: —
COOH). A carboxylic acid can only be on carbon 1, so the
―1‖ is generally omitted from the name.
Page 77
Functional groups Nomenclature
2-formyl-4-oxocyclohexanecarboxylic acid
("formyl" is used to indicate an aldehyde as a substituent
when its carbon cannot be in the chain numbering)
Page 78
Functional groups Nomenclature
Esters
Esters are named as ―organic salts‖ that is, the alkyl
name comes first, followed by the name of the
carboxylate anion. (common abbreviation: —COOR)
Page 79
Functional groups Nomenclature
Examples
Vinyl
methyl 3-hydroxycyclopentanecarboxylate
Page 80
Functional groups Nomenclature
Amines:
prefix: amino-; suffix: -amine—substituents on nitrogen
denoted by ―N‖
Examples:
propan-1-amine
3-methoxycyclohexan-1-amine
("1" is optional in this case)
N,N-diethylbut-3-en-2-amine
Page 81
Functional groups Nomenclature
Amides R-CONH2
Page 82
Functional groups Nomenclature
Amides R-CONH2
Amides are derivatives of carboxylic acids and if you have
already read about the nomenclature of carboxylic
acids, you are familiar with suffixes -ic acid, -oic
acid. Now, for primary amides, all you need to do is
replace the -ic acid, or -oic acid ending with the suffix
―amide‖.
Page 83
Functional groups Nomenclature
Amides R-CONH2
Examples:
Page 84
Functional groups Nomenclature
Amides R-CONH2
All the substituents are numbered by starting from te
amide carbon (unless a higher priority group is present)
and placed alphabetically just like for naming any other
functional group, for examples:
4-ethylhexanamide 3-bromo-4-methylpentanamide
Page 85
Functional groups Nomenclature
Amides R-CONH2
When the amide group is connected to a ring, the suffix
« carboxylic acid » is replaced with « carboxamid »
Examples:
cyclopentanecarboxamide
2-bromo -5-methylcyclohaxane-1-carboxamide
Page 86
Functional groups Nomenclature
Amides R-CONH2
Naming Secondary and Tertiary Amides
Secondary and tertiary amides bear alkyl group(s) on the
notrogen and just like other substituents, these are placed
at the beginning of the name. However, these groups are
also specifically indicated with the letter « N »
Examples:
N-methylbutanamide (N-methylbutyramide)
N,N-dimethylmethanamide
Page 87
N,N-dimethylformamide (DMF)
Functional groups Nomenclature
5-chloro- N- ethyl-N-methylhexanamide
Nitriles, R−C≡N:
A nitrile is any organic compound with a −C≡N functional group
Open chain nitriles are named with the word -nitrile after the name
of the parent alkane name. Remmber to include the carbon atom of
the nitrile as part of the parent chain.
For example: CH3CN has two carbons including the nitrile carbon
Page 88
Functional groups Nomenclature
Nitriles, R−C≡N:
3
2 1
butanenitrile
2-bromopropanenitrile
Page 90
Functional groups Nomenclature
Group Prefix
-Br Bromo-
Alkyl halides result from the -Cl Chloro-
substitution of one or more -ClO Chlorosyl-
hydrogen atoms in an alkane -ClO2 Chloryl-
by one or more halogen -ClO3 Perchloryl-
atoms; in nomenclature, they -F Fluoro-
are treated as halogenated -I Iodo-
derivatives of hydrocarbons, -IO Iodosyl-
hence the name haloalkanes. -IO2 Iodyl-
Page 91
Functional groups Nomenclature
Example:
Page 92
Functional groups Nomenclature
Anhydrides Acid:
The acide anhydride functional group results when two
carboxylic acids combine and lose water. Symmetrical acid
anhydrides are named like carboxylic acids except the
ending –acid is replaced with –anhdride.
Examples:
Page 93
Functional groups Nomenclature
Anhydrides Acid:
Page 94
Functional groups Nomenclature
Page 95
Functional groups Nomenclature
7-bromo-6-hydroxyheptane-2,4-dione
meta-bromochlorobenzene
or
m-bromochlorobenzene
Page 96
Examples:
4-phenylbutanoic acid
priority function
imposes the direction
of numbering amino
C2H5 NH2
1 2
CH3 C CH C CH3
3 4 5
O OH
ketone – one 4
hydroxy
2-(1-chloroethyl)cyclohexanone
-en
Ethyl -3-chlorobutanoate
N-benzylethanamide
v
Page 101 106
Thank you for your attention