National Higher School of Technology and Engineering- Annaba

Preparatory classes of sciences and technology

Second year
University year: 2023/2024

Organic chemistry course

Chapter 1 : Nomenclature of organic compounds
-Part 1-

Dr. A. AMIRA

Email : [email protected]

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 What is organic chemistry ?
It is a science that studies the structure, properties, composition, reactions,
and preparation of carbon-containing compounds, derived principally
from living system, and has been broadened to synthestic organic
compounds.
Basic unit of life Plants Animals

DNA & RNA Clothes Morphine Milk

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 What is organic chemistry ?

Natural gaz and petroleum Fermentation Organic synthesis

Cooking gaz Gasoline Chocolate Plastic

Organic chemistry occupies a central role in the world around us,

in our body, food, and products we use.

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 What is an organic compound ?
Most organic compounds contain carbon and hydrogen linked by covalent
bond, but they may also include any number of other elements (e.g.,
nitrogen, oxygen, halogens, phosphorus, silicon, sulfur).

Electron configuration and representation of valence shell of carbon:

In ground state: In excited state:

2 2 2 2 1 3
12 12
6𝐶: 1s 2s 2p 6𝐶: 1s 2s 2p

Carbon atom is able to form four covalent bonds.

Application : Give the electron configuration and the representation of valence shell of the
following atoms: 1𝐻, 7𝑁, 8𝑂, 17𝐶𝑙, then draw their Lewis structure.
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 Some exceptions to the definition of an organic compound

These compounds lacking C-H bonds but traditionally considered organic compounds.

This compound contain C-H bond but traditionally considered inorganic compound.

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 Molecular formulas of organic compounds

Structural formulas Molecular formula

C5H12

 It shows the number of each

 All bonds are shown  C-H bonds are not shown type of atom present in the compound

Skeletal formula
Condensed formula (Bond line formula)
Commonly
used
 Zigzag format
 Bonds are not drawn, atoms or groups
 Line ends represent carbons
of atoms are clustered together, when possible
 Heteroatom and H attached to heteroatom
must be drawn

Application : Show the different formulas of this compound

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 Nomenclature of hydrocarbons
Hydrocarbons are the simplest organic compounds, there are composed only of
the elements carbon (C) and hydrogen (H).
Hydrocarbons are the basis of the nomenclature for all types of organic
compounds.
Hydrocarbons

Aliphatic Aromatic

Acyclic (open chain) Alicyclic (closed chain)

Saturated Unsaturated
Cycloalkane Cycloalkene Cycloalkyne

Alkane Alkene Alkyne

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 Nomenclature of hydrocarbons
IUPAC
name ?

to write name in perfect way

The IUPAC (International Union of Pure and Applied Chemistry) name or

systematic name of a molecule must contain all the information on :

 the number of carbons in the molecule,

 The nature and position of multiple bonds,
 The position of branched (alkyl) groups.

A correct name allows to establish the same molecule from its systematic name.

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 Nomenclature of hydrocarbons
-Alkanes-
Type 1. Straight-chain alkanes

The name of a straight-chain alkane is composed of two parts:

Greek root
(number of carbon atoms) + Suffix: ane

4 carbones (but)+ suffix (ane) : The name of this alkane is butane

Greek roots :

(1C): meth (2C): eth (3C): prop (4C): but (5C): pent (6C): hex

(7C): hept (8C): oct (9C): non (10C): dec (11C): undec (12C): dodec
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 Nomenclature of hydrocarbons
-Alkanes-
Type 2. Branched-chain alkanes with simple alkyl groups

The name of the simple alkyl is :

Greek root
(number of carbon atoms) + Suffix: yl

2 carbones (eth)+ suffix (yl) : The name of alkyl is ethyl

Question: Name the following hydrocarbons.

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 Nomenclature of hydrocarbons
-Alkanes-
Type 2. Branched-chain alkanes with simple alkyl groups

 Choose the longest chain (parent chain) in the structure containing the greatest
number of substituents.
 Number the parent chain in both directions, choosing the direction that gives
the substituents the lowest number at the first difference.
 Classify alkyl groups alphabetically, preceded by their numbers.

(Chain with 5 carbons

(Chain with 5 carbons and 1 substituent)
and 2 substituents) 11
 Nomenclature of hydrocarbons
-Alkanes-
Type 2. Branched-chain alkanes with simple alkyl groups

 If two alkyl groups are in equivalent position, the lowest number is assigned to
the substituent ranked first in alphabetical order.

 If a substituent is present several times in the molecule, its name is

preceded by an enumerative prefix (di, tri, tetra, penta, hexa, etc.)
indicating the multiplicity of the substituent, without taking this prefix into
account in alphabetical order. 12
 Nomenclature of hydrocarbons
-Alkanes-
Type 2. Branched-chain alkanes with simple alkyl groups

 If there is an equivalence in the number for the first substituent, move on to

the next substituents, assigning them the lowest numbers.
Notes on writing the name :
 No spaces between letters.
 Numbers indicating alkyl groups positions are placed before their
corresponding names and separated from the letters by a dash (-).
 In the case of two or more numbers referring to the identical alkyl groups, the
numbers are separated by a comma (,).
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 Nomenclature of hydrocarbons
-Alkanes-
Type 3. Branched-chain alkanes with complex alkyl groups

The name of a complex alkyl is derived from the branched alkane with simple alkyl
groups:

Greek root of the

num-(num-simple alkyl + longest side chain + Suffix: yl)

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 Nomenclature of hydrocarbons
-Alkanes-
Type 3. Branched-chain alkanes with complex alkyl groups

 In the case of several identical complex substituents, the name is preceded

by an enumerative prefix(bis, tris, tetrakis, pentakis,...) without taking this
prefix into account in alphabetical order.

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 Nomenclature of hydrocarbons
-Alkanes-
Table1. Common nomenclature of complex alkyl substituents

(C 2°) (C 3°)

(C 4°)

Unlike iso and neo, sec and tert are not used in alphabetical order.

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 Nomenclature of hydrocarbons
-Alkenes-
Type 1. Straight-chain alkenes

The name of a straight alkene is composed of :

Greek root + Position of

(number of carbones) unsaturation + Suffix: ene

The name of the compound is but-2-ene

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 Nomenclature of hydrocarbons
-Alkenes-
Type 2. Branched-chain alkenes/polyenes with simple alkyl groups

 Choose the parent chain containing the double bond, which is not
necessarily the longest chain.

 In the case of polyenes (hydrocarbons with several double bonds) add the
prefix (di, tri, tetra ...) before "ene" and the letter "a" at the root.
 Attribute the lowest numbers to the unsaturations , then to the substituents.
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 Nomenclature of hydrocarbons
-Alkynes-
Alkynes are named according to the rules for alkenes by replacing the suffix ene
with yne.
The base name of a straight alkyne is composed of :

Greek root Position of

(number of carbons) + unsaturation
+ Suffix: yne

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 Nomenclature of hydrocarbons
-Alkenynes-
Alkenynes are compound which contain double bond and triple bond.
The base name of a straight alkyne is composed of :

Greek root
+ -position –en + -position-yne
(number of carbones)
 Begin numbering with the end containing the first unsaturation (double or triple).

 In the case of equal numbers between the bonds, the double bond prevails over
the triple bond and receives the lowest number.

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 Nomenclature of hydrocarbons

 In the case of many multiple bonds, the numbering starts from the end giving
the lower numbered multiple bond.

 In the case of equal numbers between many multiple bonds, the double bond
prevails over the triple bond and receives the lowest number.

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 Nomenclature of hydrocarbons
-Cycloalkanes-
 Follow all the above rules for acyclic hydrocarbons, just precede the prefix
cyclo with the name of the corresponding hydrocarbon.

+ Greek root
Prefix: cyclo + Suffix: ane
(number of carbone)

Prefix (cyclo) + 4 carbones (but)+ suffix (ane)

:
The name of cycloalkane is cyclobutane

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 Nomenclature of hydrocarbons
-Cycloalkanes-
 When the ring is substituted by a longer side chain, the side chain takes over
and the ring is named as a substituent by replacing the ane ending with yl in
the name. Consider the term cyclo in alphabetical order.

 The parent chain is the one with the highest number of carbon atoms. If there
are two cycloalkanes, use the cycloalkane with the higher number of carbons
as the parent chain.

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 Nomenclature of hydrocarbons
-Cycloalkenes-

Cycloalkenes are named by the system used for the open-chain alkenes, except
that numbering always is started at one of the carbons of the double bond and
continued around the ring through the double bond so as to keep the lowest
numbers for double bonds and then substituents.

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 Nomenclature of hydrocarbons
-Cycloalkynes-

The simplest example is a ring with at least 8 C atoms. This is due to the linear
geometry of the carbons, which hybrid (sp) geometry, making the arrangement
of less than 8 carbons impossible.

cyclooctyne

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 Nomenclature of hydrocarbons

Table 2. IUPAC and (common) name of alkyl substituents with multiple bonds

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 Nomenclature of hydrocarbons
IUPAC
Application: Name the following compounds name ?

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