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Ministry of Higher Education and Scientific Research

University of Algiers 1 Benyoucef BENKHEDDA


Faculty of Sciences Department of Natural and Life Sciences

Branch: Biological Sciences


General and Organic Chemistry Course –L1-

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

Branch: Biological Sciences


General and Organic Chemistry Course –L1-

Chapter 4

Hydrocarbon Nomenclature
-Part I-
Presented by:
Dr. HAMRANI Ouiza Academic year: 2023/2024
Introduction
Introduction

Organic chemistry studies molecules composed of


carbon and hydrogen atoms. This is the common feature
among all organic molecules.

Organic chemistry focuses on the study of substances that


make up living organisms, both plants and animals,
referred to as 'organic compounds.' It has been extended
to encompass all carbon compounds, with the exception
of a few structurally simple molecules that do not contain
carbon chains: CO, CO2, KCN.

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

Examples : C2H6O: CH3-CH2-OH

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

Nomenclature of Non-functional Hydrocarbons

Hydrocarbons are primarily composed of carbon and


hydrogen. They exist in both cyclic and acyclic forms,
saturated and unsaturated. They are named based on the
number of carbon atoms constituting the main chain. The
main chain is indicated in the hydrocarbon's name with a
prefix followed by a suffix.

Page 7
Hydrocarbon Nomenclature

Nomenclature of Non-functional Hydrocarbons

Hydrocarbons
Saturated Unsaturated

Alkanes Alkenes
Alkynes
Acyclic Cyclic

Unbranched Branched
(non ramifié) (ramifié)
Page 8
Hydrocarbon Nomenclature

Nomenclature of Non-functional Hydrocarbons

Each organic compound has a systematic name assigned


according to the rules established by the International
Union of Pure and Applied Chemistry (IUPAC).

According to IUPAC, the systematic nomenclature of an


organic compound is composed of three parts:

Prefix Main carbon chain Suffix

Chaine carbonée
Préfixe principale
Suffixe
Page 9
Hydrocarbon Nomenclature

1- Saturated Acyclic Hydrocarbons: Alkanes

 Saturated hydrocarbons are alkanes with a general


molecular formula CnH2n+2. In these compounds,
carbon atoms exhibit tetrahedral geometry (sp3
hybridization) and can freely rotate around the single
covalent bonds they form.

 The main chain is the longest chain, i.e., the one


composed of the greatest number of linked carbon
atoms

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

A branched acyclic alkane is composed of a main chain to


which substituents (alkyl groups, also called radicals,
roots, or branches) are attached.

Page 13
Hydrocarbon Nomenclature
Branched Acyclic Alkanes"

Alkyl groups are obtained by removing a hydrogen from


an alkane. These groups are symbolized by the letter R,
and their name is obtained by replacing the 'ane' ending of
the corresponding alkane with 'yl'

 The main chains are always the longest chains (those


with the most carbon atoms). They are named after the
corresponding alkanes.
•The indices indicating the location of the substituents
should be as small as possible."

Page 14
Hydrocarbon Nomenclature
Examples:

2-methylbutane."

 4 carbons in the main chain: butane.


 Numbering from right to left so that the branch has
the smallest number.
 Methyl branch on carbon 2.
 Therefore, the name of the molecule is:
2-methylbutane."

Page 15
Hydrocarbon Nomenclature

4-ethyl-2,3-dimethyloctane

Alkyl Groups in Branched Chains

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

5- When the indices of alkyl groups are the same in both


directions of numbering, the first one named will receive
the smaller index.
Example:

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

 Do not consider the prefixes di-, tri-, etc. when


Alphabetizing alkyl groups.
CH3 CH2CH3
CH3CHCHCHCH2CH2CH3
1 2 3 4 5 6 7
CH3 2,3-diméthyl-4-éthylheptane
4-ethyl-2,3-dimethylheptane
Page 21
Hydrocarbon Nomenclature
Cyclic Alkanes

With the general formula CnH2n, these alkanes are called


cyclic alkanes or cycloalkanes. They are named by
preceding the name of the corresponding alkane with the
prefix 'cyclo‗.

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

Unsaturated Hydrocarbons: Alkenes


and Alkynes

Page 25
Hydrocarbon Nomenclature
Unsaturated Hydrocarbons: Alkenes and Alkynes

Unsaturated hydrocarbons are hydrocarbons that contain


multiple bonds (double or triple bonds)

The hydrocarbon containing the double bond is called


an alkene (or olefin) with the general formula CnH2n.
The name of the alkene is derived from that of the
corresponding alkane by replacing the suffix 'ane' with
'ene'.
The hydrocarbon containing the triple bond is called an
alkyne with the general formula CnH2n-2. The name of
the alkyne corresponds to that of the corresponding
alkane by replacing the suffix 'ane' with 'yne'
Page 26
Hydrocarbon Nomenclature

Rules for the Nomenclature of Linear and


Branched Alkenes and Alkynes

1- Identify the longest chain containing the most double


and/or triple bonds.

2- Number the chain starting from the end nearest to the


multiple bond to give the smallest possible position indices
to all multiple bonds. The indices are placed before the
suffix (-ene and/or -yne), separated by a hyphen. If a
choice remains, the double bond takes priority over the
triple bond and is assigned the lower index.
Page 27
Hydrocarbon Nomenclature
Examples :

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

3- The multiple bond takes precedence over substituents


for the choice of numbering direction; it must necessarily
give the double or triple bond the smallest possible
position index.

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

Substituent with triple bonds:


-Suffix: ynyl (ynyl in the name)

Hydrocarbons with Double and Triple Bonds:

The prefix of the saturated hydrocarbon is used with the


suffix -ene-yne. Multiple bonds have the lowest possible
indices. If a choice remains, the double bond has the lower
index."

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’.

 Number the cycle, assigning a number to the double


bond. Start numbering by giving the lowest number to
the double bond (from 1 to 2). Begin closest to the first
branch. The first substituent has the lowest possible
index.

 Number each substituent; each substituent has its own


index (number).
Page 34
Hydrocarbon Nomenclature
Rules for the Nomenclature of Cycloalkenes
 Write the name, separating numbers with commas and
words with hyphens. List the substituents alphabetically.
Use prefixes (e.g., di-, tri-, etc.) if necessary.

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

Dissubstituted derivatives of benzene can exist in three


isomeric forms, for which the prefixes ortho, meta, and
para are used, often abbreviated as o, m, and p, instead of
'1,2', '1,3', and '1,4'.

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

If the molecule bears three substituents, name all the


branches attached to benzene and assign a position
index to each one.

Then, alphabetically order the alkyl substituents with


6C or fewer. Next, continue numbering in the direction
of the closest substituent.
Example :
1
6
2
5 3
4 1-ethyl-2,4-dimethylbenzene
Page 39
Hydrocarbon Nomenclature

The substituents should have the lowest possible indices.


If a choice remains, alphabetical order is used.

Example :

2
3 1

4 6 1-butyl-3-ethyl-2-propylbenzene
5

Page 40
Hydrocarbon Nomenclature

Page 41
Hydrocarbon Nomenclature
The Phenyl Group

the phenyl group (Ph-R, C6H5-R) can be formed by removing a hydrogen


from benzene and attaching a substituent to where the hydrogen was
removed.
To this phenomenon, we can name compounds formed this way by
applying this rule: (phenyl + substituent).
For example, a chlorine attached in this manner would be named phenyl
chloride, and a bromine attached in this manner would be named phenyl
bromide. (See below diagram)

42
Hydrocarbon Nomenclature

Mono-substituted benzene rings are named with benzene


being the parent name. These compounds are named as
such:
Name of the substituent + Benzene.

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

Branch: Biological Sciences


General and Organic Chemistry Course –L1-

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

The functional group may be defined as an atom or


group of atoms joined in a specific manner which is
responsible for the characteristic chemical properties of
the organic compounds.
The examples are hydroxyl group (–OH), aldehyde
group (–CHO) and carboxylic acid group (–COOH) etc.

Page 47
Functional groups Nomenclature
Introduction

NOMENCLATURE OF ORGANIC COMPOUNDS

Organic chemistry deals with millions of compounds. In


order to clearly identify them, a systematic method of
naming has been developed and is known as the IUPAC
(International Union of Pure and Applied Chemistry)
system of nomenclature.
In this systematic nomenclature, the names are correlated
with the structure such that the reader or listener can
deduce the structure from the name.

Page 48
Functional groups Nomenclature
Nomenclature of Molecules Containing Substituents and Functional Groups

A. Priorities of Substituents and Functional Groups


listed here from highest to lowest priority, except that the
substituents within Group C have equivalent priority.
Group A—Functional Groups Indicated By Prefix Or Suffix

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.

•Step 2. Number the chain so that the highest priority


functional group is assigned the lower number.

•Step 3. If the carbon chain includes multiple bonds,


replace ―ane‖ with ―ene‖ for an alkene or ―yne‖ for an
alkyne. Designate the position of the multiple bond with
the number of the first carbon of the multiple bond.

Page 51
Functional groups Nomenclature
Naming Molecules Containing Functional Groups from Group A—Prefix or
Suffix

•Step 4. If the molecule includes Group A functional


groups, replace the last ―e‖ with the suffix of the highest
priority functional group, and include its position
number.

•Step 5. Indicate all Group C substituents, and Group


A functional groups of lower priority, with a prefix.
Place the prefixes, with appropriate position numbers, in
alphabetical order before the root name.

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

The number of hydrogens on the carbon bearing the OH


group does affect some chemical properties.

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

3-methylpentane-2,4-diol meta-chloro phenol

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°.

In ketones, two carbon groups are attached to the carbonyl


carbon, while in aldehydes at least one hydrogen is
attached to the carbon.

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.)

Name the substituents attached to the chain in the usual


way.
Examples:
O
4 3 2 1
H 3C CH2 CH2 C butanal
Page 63 H
Functional groups Nomenclature
Nomenclature of Aldehydes

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‖.

 Number the chain starting with the end closest to the


ketone group (the carbonyl carbon should have the
lowest possible number). The location for the ketone
group precedes the name for the longest chain.

 Name the substituents attached to the chain in the


usual way.
Page 65
Functional groups Nomenclature
Nomenclature of Ketones
Examples:
O
5 4 3 2
H3C CH2 CH2 C
Pentan-2-one
CH3
1

1
2

4 5 6 7

3,3-diethylheptan-2-one

Page 66
Functional groups Nomenclature
Nomenclature of Aldehydes and Ketones
Other Nomenclature Rules

 In cyclic ketones, the carbonyl group is always


numbered ―1‖; this does not need to be included in the
name. The numbering continues clockwise or
counterclockwise to give the lowest number for the
next substituent.

 Molecules with more than one ketone group are named


by preceding the suffix with a counting prefix (dione,
trione, etc.); position numbers must be used for each
ketone group.
Page 67
Functional groups Nomenclature
Nomenclature of Aldehydes and Ketones
 Aromatic aldehydes (containing an aldehyde group
directly attached to a benzene ring) are named after the
parent compound benzaldehyde. (The carbon to which
the aldehyde group is attached is carbon ―1‖).

Example:

Benzaldehyde

Causes the odor of almonds and cherries, and is


Page 68
also found in apricots and peaches.
Functional groups Nomenclature
Exercise:
Name the following compounds:

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

When and aldehyde or ketone is present in a molecule


which also contains an alcohol functional group the
carbonyl is given nomenclature priority by the IUPAC
system. This means that the carbonyl is given the lowest
possible location number and the appropriate
nomenclature suffix is included. In the case of alcohols
the OH is named as a hydroxyl substituent. However,
the l in hydroxyl is generally removed.

Page 73
Functional groups Nomenclature
Examples:

4-hydroxybutan-2-one 1,5- dihydroxy pentan-3-one


Page 74
Functional groups Nomenclature
Ethers
In the ether functional group, two carbon groups are
connected to a single oxygen.

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

In the IUPAC system, ethers are named as alkoxy


substituents (—OR = alkoxy group). The -yl ending of
alkyl substituents is replaced by -oxy

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

Special case : When the chain numbering cannot include


the carbon of the COOH, the suffix ―carboxylic acid‖ is
used

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

Vinylprop-2- enoate Cyclohexyl-2-phenylacetate

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

To classify, count the number of carbons connected to the


Nitrogen

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‖.

Naming Amides: Change suffix from ―ic/oic ― to


―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

Prefix: cyano Suffixe: nitrile

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

When a nitrile is the highest priority functional group


attached to a cycloalkane, the name of the parent
cycloalkane is followed by the word -carbonitrile.
The ring carbon attached to the nitrile is numbered C1 and
the nitrile is not given a number in the name.
Page 89
Functional groups Nomenclature
Nitriles, R−C≡N:
Examples:

Page 90
Functional groups Nomenclature

Alkyl halides: R-X (X = F, Cl; Br; I)

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

Nomenclature: name of the corresponding alkane, preceded by


"halogeno" and the number of the C bearing the halogen group.

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

Page 97 3-benzyl-4-methylpentanoic acid


Examples:
priority Function
(primary)
formyl
4 CH3
O
O
C CH CH2 C
1
3 2
H OH

aldehyd Function -CHO


Secondary

3- formyl butanoïc acid 10


Page 98 3
Examples:

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

4- amino-3- ethyl-4- hydroxy pentan -2- one


Page 99
Examples:
3-amino-4-methylhex-4-enoic acid

2-(1-chloroethyl)cyclohexanone

Page 100 105


N- methylhex-4-en-2-amine

-en

Ethyl -3-chlorobutanoate
N-benzylethanamide

v
Page 101 106
Thank you for your attention

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