UNIVERSITY OF THE VALLEY

ACADEMIC VICE-RECTORATE

DIRECTION OF UNENROLLED EDUCATION

COURSEOF

GENERAL ORGANIC CHEMISTRY

AUTHOR:

LUZ MARINA JARAMILLO PhD

Full Professor
Faculty of Sciences - Department of Chemistry

SantiagodeCali,2001

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Classification and Nomenclature of the
Organic Compounds

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 Classification and Nomenclature of Compounds
Organic
Specific Objectives
Introduction
2.1 Classification of Organic Compounds and the Concept of Functional Group 61
2.2 Isomerism 63
2.3 Hydrocarbons: Classification 65
2.3.1 Nomenclature of Straight ChainAlkanes 69
2.3.2 Nomenclature of Branched ChainAlkenes 70
2.3.3 Nomenclature ofAlkenes 80
2.3.4 Nomenclature ofAlkynes 82
2.3.5AlicyclicHydrocarbons 83
2.4 Nomenclature ofAromatic Hydrocarbons 86
2.5 Nomenclature ofAlcohols,Thiols, and Phenols 89
2.6 Nomenclature of Ethers andThioethers 92
2.7NomenclatureofAldehydesandKetones 95
2.8NomenclatureofCarboxylicAcids 98
2.9 Nomenclature of CarboxylicAcid Derivatives 100
2.10 Nomenclature ofAmines 103
2.11 Order of Priority of Functional Groups 105

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Specific Objectives

At the end of the study of this material, the student will be able to:
Classify and define the different classes of hydrocarbons.
•Write the names and formulas studied of alkanes, cycloalkanes, alkenes and
main alkynes.
Given the molecular formula of an organic compound where one or
two hydrogens by another atom or functional group, write the structures of the
position isomers.
Given the complete structural formula of a simple organic compound, identify
its dominant functional group and classify it within one of the families
representatives of organic compounds.
Given the complete structural formula of any simple organic compound
name it according to the IUPAC system or by the common naming system.

Introduction

An appropriate way to become familiar with the countless and different compounds
organics is understanding the concept of functional group (or most reactive site) that
characterizes a set or group of organic compounds.
On the other hand, it is absolutely necessary to know the language of chemistry.
organic through the learning and handling of the main nomenclature rules
systematics that have been formulated to name organic compounds.
The study of this chapter will allow for the classification of organic compounds.
simple due to their functional group, name them once their structural formula is given and
write the structure for a given systematic name.

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2.1 Classification of Organic Compounds and the Concept of Group

Functional

The study of the properties of the millions of known organic compounds is

has made it easier by grouping them into classes or families based on their particularities

structural. Consequently, the members of each class of compounds contain

an atom or group of characteristic atoms that distinguishes them and is called a group

functional.
The functional group (or function) is the atom or group of atoms that defines the
structure of a particular family of organic compounds and at the same time
determines its chemical properties. Thus, each class of compounds exhibits
similar chemical properties as a result of having a common functional group.
For example, the hydroxyl group (-OH) is the functional group that characterizes the family.
of alcohols, the double bond (-C=C-) to the alkene family, the carboxyl
(-COOH) to carboxylic acids, etc.
On the other hand, a family of compounds constitutes a homologous series.
equal) with the following characteristics:

All compounds in the series contain the same elements and can
to be represented by a very simple general formula.
The molecular formula of each homologue differs from the one preceding it and from the one that follows.

it happens due to unmetileno (-CH2).

There is a gradual variation in physical properties with the increase of

molecular mass.
All the compounds in the series exhibit similar chemical properties.
Therefore, the homologous series of alkanes, alkenes, and alcohols will be obtained.
carboxylic acids, etc. Table 2.1 shows the main families or series
homologs of organic compounds, with their general structure based on the group
functional, generic name and a representative example.

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Table2.1ClassesofOrganicCompounds

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Tabel21.CalsesoO
f rganciCompounds(Contn
iued)

TheleterR
' 'isusedtoindicateanyalkylradical.

2.2 Isomerism

The fundamental importance of molecular structure is illustrated through the

concept of isomerism. In organic compounds, the capacity of the atom of
carbon to form single and multiple bonds with itself and with other atoms
leads to various structures for molecules with the same molecular formula. To these
Structures are called isomers, from the Greek isos = equal and meros = part.
One class of isomers is structural (or constitutional) isomers, the
which differ from each other by the bonding sequence of their atoms in the molecule and in
its physical and chemical properties. They are subdivided into:

a. Chain Isomers, in which the alkyl chains (hydrocarbon) are

they branch out in a different way.
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 Table2.2StructuresandBoilingPointsofsomeStructuralIsomers

Position Isomers, which differ in the location of a chemical function in

the hydrocarbon chain.
c. Functional Isomers, which belong to different families because their
Functional groups are different; however, they have the same molecular formula.

Table 2.2 shows various examples for the three mentioned classes with their
respective boiling points.

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It is to be expected that the number of potential structural isomers will

increases as the number of carbon atoms in the chain increases
hydrocarbonated. For example, in the family of alkenes, there are two compounds with
formula C4H10six with the formula C6H14seventy-five with C10H22, etc.
Finally, there is another level of isomerism that is more subtle where molecules with the

they have the same molecular formula but their atoms or groups are joined in the same order

they differ only in the spatial arrangement. These isomeric molecules are called
denominates stereoisomers and their study constitutes a branch of chemistry known
Stereochemistry (from the Greek stereos = solid) that studies molecular structure
in three dimensions. (see Chapter 6).

2.3 Hydrocarbons: Classification

The term hydrocarbon refers to compounds formed exclusively by atoms

of carbon and hydrogen through covalent bonds. Based on its structure,
Hydrocarbons are divided into two main classes: Aliphatic and Aromatic.
First, they are divided into families: Alkenes, Alkynes, and their analogs.
Cyclic compounds, also known as Alicyclic (Figure 2.1).

Hydrocarbons

Aliphatic Aromatics

Let us go Alkenes Alkynes Alicyclics

Figure21.GeneralClassificationofHydrocarbons

Aliphatic hydrocarbons in general are made up of open chains

of carbon atoms (alkanes, alkenes or alkynes), or by cyclic structures
(alicyclic hydrocarbons).

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Originally, many of the early aliphatic hydrocarbons that were studied

they were obtained from fatty acids, therefore they were assigned the name of aliphatic
(from Greek aleiphatos = fat).
If each carbon atom is bonded to four other atoms of
carbon and/or hydrogen we have saturated hydrocarbons or alkenes
the general formula is CnH2n+2

(Table 2.3).

Table2.3Formulasofsomealiens

Also the so-called cycloalkanes (Table 2.4) with general formula CH2nson

saturated hydrocarbons that constitute a homologous series. Cyclopropane is the

simplest cycloalkane, has three carbons and its structure is triangular, with
slightly bent links.
There are also unsaturated aliphatic hydrocarbons where not all
Carbon atoms are bonded by four single bonds to four others.
atoms, but can only be found bonded to two or three atoms. In this
a case may present at least a double or a triple bond between two atoms of
carbon. This is how alkenes result:

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Table 2.4 Formulas of some cycloalkanes

general formula CnH2nand the alkynes with the general formula CnH2n-2 ( Table 2.5).

Aromatic hydrocarbons, for their part, constitute a special group of

cyclic compounds that generally contain six-membered rings, in which
all carbon atoms possess sp hybridization2and where the p electrons are
each carbon atom is delocalized over the plane of the ring,
occupying the lowest energy orbitals.

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Table2.5AlkenesandAlkynes

The simplest member of the series is benzene. These hydrocarbons exhibit a

very different chemical behavior from aliphatic hydrocarbons.

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Given the ability of the carbon atom to form single and multiple bonds
with itself and with other atoms, among the carbon compounds arise structures
molecules with different properties but that exhibit the same molecular formula.

2.3.1 Nomenclature of Straight-Chain Alkenes

So far, the names of a number of organic compounds have been used without
specify its systematic origin. The development of a formal system for naming the
organic compounds emerged in the late 19th century. Before that time, they had already
numerous compounds have been discovered and their names reflected the natural source, such as acid

acetic (from Latin acetum = vinegar), formic acid (from Latin formicae — ant), etc.
These ancient names are now referred to as common or trivial names. Many of
they are extensively used by chemists, biochemists, and companies that sell
reactives. For this reason, it is still necessary to learn to name numerous in this way.
organic compounds.
Systematic names formulated by the system will mostly be used.
International Nomenclature (known as International Union of Pure and Applied Chemistry)

Applied, in English International Union of Pure and Applied Chemistry = IUPAC.

The IUPAC met for the first time in Geneva (Switzerland) to launch a simple system,
unambiguously, naming organic compounds. This organization reviews the
system at regular intervals of time, to keep it updated.
A fundamental principle rests in the IUPAC system of nomenclature. Each
A different compound will have a different name. The IUPAC system for naming alkenes.
It is quite simple and its rules extend to compounds from other families.
The ending of all alkanes is an, and the first four compounds of the
series are named methane, ethane, propane, and butane (see Table 2.6). Starting from
five carbon atoms the names are derived from the Greek or Latin prefix (penta, hexa,
hepta, octa, nona, deca, undeca, etc.) for the particular number of carbons in the
composed, resulting in: pentane, hexane, heptane, etc. Notice, when joining the prefix and the

ending year, an 'a' is removed.

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The names of many families of organic compounds are

intimately related, for example: propane, propene, propanol, propanoic, etc.

Table2.6MolecularstructuresandIUPACnamesofthe
first twenty straight-chain alkanes

2.3.2 Nomenclature of Branched Chain Alkanes

Before proceeding to the description of the stages for correctly naming a
alkane, a systematic approach will be very helpful to write all of them
isomers corresponding to a molecular formula, whose writing can be difficult or
impossible, when done at random.

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Remember that a systematic approach is important to avoid

Duplications. Always keep these two important points in mind:
All structural isomers must correspond to the molecular formula. Avoid
write duplicate structures. It should always compare the last one with all the others
previous structures. For example, if you need to write the structural isomers
from heptane C7H16, follow the following steps:
Start with the linear chain structure of seven carbons, for which there is only
a possible: CH3-CH2-CH2-CH2-CH2-CH2-CH3
Consider the closest isomers with a continuous chain of six carbons.
where a group or radical CH3it must be bonded to one of the carbon atoms
no terminals to give branched string structures:

•Note that structures 1' and 2' are duplicates of 1 and 2. You must be
Sure to understand it!!
Next, consider a continuous chain of 5 carbon atoms, where it is possible
join two groups (or radicals) -CH3to the non-terminal carbon atoms or a radical
CH3CH2to the third atom (from either end) of the chain.

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• Finally, consider a continuous chain of four carbon atoms where the

three remaining carbon atoms would join as three -CH radicals3, or like a
group CH32- and one -CH3Observe. Will structure 9 be a duplicate of the
structure 7 ? Why?

In conclusion, there are nine structural isomers (linear and the structures 1
a 8) with molecular formula C7H16
An alternate method for drawing structural isomers uses skeletons.
carbonados (the hydrogens are omitted and only bare carbons are used). When using
This method must be careful to go back and add the number.
appropriate hydrogen atoms in such a way that each carbon has four
links. For example:

Exercise 2.1 (application) Which of the following pairs of compounds

Do they represent identical structures? What are structural isomers?

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Exercise 2.2 (study) Draw the structural isomers of:

a) All hexanes (C6H14).
b) All octanes (C8H18with a continuous chain of five carbon atoms.
c) The four chlorobutanes (C4H9CI).

Rental Groups
The so-called alkyl groups (or alkyl radicals R) are substituents that replace
a hydrogen atom in a hydrocarbon chain, in branched alkanes.
These groups are fragments of alkanes from which one hydrogen has been removed.
They take the name of the alkane with the same number of carbons from which they are derived.

taking into account the carbon where hydrogen was removed and changing the suffix
anoporilo.
When naming the compound of which an alkyl group is a part, its name is
places it before the alkane pattern, locating it with the number of the carbon to which it is attached.

united and using the suffix in place of. The same alkyl groups can be at
they are branched. In such cases, they take the name of the precursor alkane.
(branched). The IUPAC recognizes eight trivial names of alkyl groups.
most common branched. In Table 2.7 some are observed.

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Table 2.7 Most common alkyl groups.

Steps to follow for correctly naming an alkane:

Step 1. Select the longest continuous carbon chain. The name of
this chain (or pattern compound) will be derived from the corresponding normal alkane.
The various groups called substituents are named as will be indicated later.
forward.
For example, isobutane can be considered to be derived from propane.
by replacing a hydrogen atom with a methyl group -CH3The name would be
then methyl propane.

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Stage 2. The carbon atoms are listed consecutively starting from the
closest end to the substituent (if there is only one), if the carbon chain
when the chosen one has several substituents, the order of enumeration that is selected

correspond to the lowest combination of numbers Example:

Step 3. Identify each substituent attached to the parent compound and locate it.
through the carbon number to which it is linked.
When the halogens F, Cl, Br, and I appear as substituents in a
carbon chain, the prefixes fluoro, bromo, chloro or iodo are used respectively,
with the pattern name of the alkane. But such compounds can also be designated
using the trivial names of alkyl radicals and the prefixes fluoride, chloride,
bromide and iodide. Below are two examples of compounds.
halogenated, named according to IUPAC and trivial nomenclature.

Stage 4. If the same alkyl radical substituent, halogen or other group

appears more than once, use the prefixes di, tri, tetra, etc. to indicate how many of
they are present. Precede them with the numbers of the carbons to which they are attached
united (the number of digits must exactly match the prefix used).

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Stage 5. If several different substituents are present, name them in

alphabetical order, previously they were named in increasing size or
complexity. When the substituents are alphabetized, the prefixes di, tri are ignored,
tetra, etc. that specify the number of some type of substituent. Thus, eletil
precede dimethyl. For alphabetical order, prefixes that are separated are also ignored.
for a dash (or italicized) used in the trivial names of some alkyl radicals
as:n, secbutyl. Thus tert-butyl precedes n-propyl. In change the
prefix iso, neo, cyclo should be ignored, for example isopropyl precedes methyl and
cyclopropyl to octyl.
The alphabetical order is the preferred order in Chemical Abstracts (which is the
reference work in the general literature of chemistry) and it is the
what will be used in this text. The following examples illustrate how to name
IUPAC taking into account the previous rules:

Example 1: Name the following hydrocarbon according to IUPAC:

Stage 1 The longest chain consisting of 6 carbon atoms is selected.

with the name hexane pattern.

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Stage 2 There are two ways to number the chosen string

Stages 3 and 4 There are three methyl groups: two at C-2 and one at C-4. Because of this

there are three identical substituents (methyl groups) in the molecule, we will name them

grouped in the trimethyl expression. To identify their binding positions we will say
2,2,4-trimethyl.
number and name.
Stage 5 Finally the correct IUPAC name is 2,2,4trimethylhexane.

Example 2 Write the correct name of:

Stages 1 and 2. When choosing the chain and numbering it in both directions, it

determined which of them corresponds to the lowest combination of numbers for the
substituents at C-3 and C-5:

Stages 3, 4 and 5. We have a methyl group at position 3, a chlorine atom.

also at position 3 and an ethyl group at position 5, which gives the following order: 3-
chloro-5-ethyl-3-methyl
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It should be noted that the halogen always precedes

the alkyl groups. When combining the above with the pattern name, we will have 3-chloro-
5-ethyl-3-methyloctane If two chains of equal length are competing for the chain
boss, the selection is made for the chain that has the highest number of
substituents.

Example 3: Name the compound correctly:

Step 1 The competing chains are pointed out, breaking down the molecule and
It is observed that they have 6 carbon atoms.

Stages 2, 3, and 4 The correct chain is chosen using the combination of

lowest numbers for the substituents. These are identified as methyl at C-2,
ethyl at C-3, and methyl at C-6. Resulting in 2,6-dimethyl and 3-ethyl.

Stage 5 The name of the parent alkane is combined with the substituents in
alphabetical order to give: 3-ethyl-2,6-dimethylheptane. The alternative name 5-isopropyl-
2-methylheptane using the other chain is incorrect!!!!.

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Please note that the methyl group can be represented as –Me, the ethyl as -
It is o –C2H5,isopropyl as iso-C3H2the isobutyl as iso-C4H5and the n-butyl as
n-C4H9., etc.

Exercise 2.3 Draw the structure for l-bromo-3,3-diethyl-4-isobutylnonane.

Solution. The name is analyzed completely and separated as follows:

The parent chain has 9 carbon atoms. The substituents are: a bromine at C-
1, two ethyl groups on C-3 and one isobutyl on C-4.

We then place the indicated substituents on the carbons.

corresponding and hydrogen atoms are added to all the carbons in such a number that
satisfy the tetravalency of carbon.

Exercise 2.4 Write the correct IUPAC names for the following structures.
Note that the structures have been given slightly condensed.

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Exercise 2.5 Write the correct IUPAC names for all the isomers of
heptane, from page 75.

Finally, it is important to recognize the types of carbon atoms that

arise depending on the degree of branching in a molecular structure
carbogenic (carbonated). Thus, the terms primary (1o), secondary (2o) and tertiary
(3o), designed carbon atoms of a particular substitution pattern in chemistry
organic. These designations are summarized:

2.3.3 Nomenclature of Alkenes

Alkenes, also called olefins, are hydrocarbons that have one or more
double C-C bonds. They are unsaturated hydrocarbons, as they do not contain the number
maximum number of hydrogen atoms that each carbon can accommodate.
According to IUPAC, the fundamental name of an alkene is formed using
the same prefixes as for alkanes, but changing the ending to -eno.
The IUPAC rules for the nomenclature of alkenes are similar to those of the
let's go.
Step 1 The position of the double bond is indicated by numbering the main chain
from the closest end to the double bond.
Stage 2 The longest continuous chain of carbon atoms that contains the
The double bond is taken as the basis for the fundamental name of the alkene. For the
so, the positions

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of the substituents in the main chain that contain the double bond, are indicated of
according to the numbering already established by the presence of the double or multiple bonds.

In the following examples, the trivial names are found in parentheses.

some alkenes:

Exercise 2.6 Write the correct systematic name for each of the following
structures.

Alkenyl Groups. There are also fragments of alkenes that result from removal
of a hydrogen. Its name as a substituent ends in 'enyl'. This branching
(or side chain) is numbered from the point of connection with the main chain.
Three important alkenyl groups are known that are usually named with names.
trivial when they appear as substituents. They are:

2.7
2,4-dimethyl-2-pentene

Dieno, Trieno and Polieno

Several of the most important organic compounds have two or more double bonds. The
Hydrocarbons with two double bonds are called dienes, with three they are called trienes, and so on.

successively. Those with multiple double bonds are called polyenes.

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 The dienes whose double bonds are separated by a single bond
they constitute a group of compounds of great importance, they are known as the
conjugated dienes have chemical properties that distinguish them from
simple alkynes. Conjugated polyenes, for their part, constitute numerous
natural origin compounds such as vitamin A, carotenoids, oils
essentials and polymers like natural rubber.
When the double bonds of dienes and polyenes are separated by more than
a simple bond, they are not conjugated and are chemically similar to alkenes
simple.
To name such compounds, they are numbered from the end closest to the
double links, indicating their position and adding the ending dieno,
triene, tetraene, etc. to the root of the corresponding alkane.

Exercise 2.8 Systematically name the following compound:

Exercise 2.9 Write the structure for 3-ethyl-1,3,7-octatriene.

2.3.4 Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons that have one or more triple bonds.
carbon-carbon. The simplest among them is the important ethyne or acetylene gas
(C2H2Alkynes are often referred to as acetylenes (a name not
systematic). They follow the same naming rules as alkenes: the chain
longer carbonada that contains triple

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link will be the basis of the fundamental name; the ending -inose adds to the root
Numerical. The numbering starts from the end closest to the triple bond.
Alkynes are also named as derivatives of acetylene. In the
Examples below will provide both names where possible, placing the
trivial in parentheses. If in the main string there are both doubles and triples
links, the ending becomes serenino. The numbering is done without considering.
if the lowest number corresponds to -enoo-ino, in such a way that the numbers of
the double and triple links should be as low as possible,

When both alternatives lead to the same numbers the priority of the
the lowest number is given to the hemp. Examples:

Exercise 2.10 Name the following compounds:

a)(CH)
3 2C=C-CH3. b) HC-C=C-CH
3 2-CH=CH-CH-CH2.

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2.3.5 Alicyclic Hydrocarbons

The compounds where the carbon atoms are arranged to form rings
they are called cyclic or acyclic compounds.
Cycloalkanes. In this family, the smallest ring is made up of three carbon atoms.
and corresponds to cyclopropane:

Cyclic hydrocarbons that have a ring are named by placing the prefix
the name of the open-chain hydrocarbon with an equal number of carbons. A
the following are examples of the most common cycloalkanes, represented in
polygonal formulas

The substituents are identified by naming them as prefixes to the name of the
cycloalkane. When there is more than one substituent, the position of each one must
to be indicated by numbering around the ring starting from the substituent that is being named

First. The combination of the lowest numbers is always chosen.

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Cycloalkenes. Cycloalkenes are cyclic hydrocarbons with double bonds.

Examples:

In substituted cycloalkenes, the carbons of the double bond are numbered.

1 and 2. The numbering of the substitute(s) must correspond to the number(s)
lower(s).

For cycloalkenes with more than one double bond, they will be used as in the
polyunsaturated the endings diene, triene, tetraene, etc. Examples:

Finally, when a ring (or more) is attached to an aliphatic chain with a

large number of carbons, the rings are named as substituents and through
the same

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principles used for radicals. The following presents some

Monocyclic Substituent Groups:

Examples:

Important!!! The following compound would be better named as a derivative.

of cyclohexene since the side chain has a lower number of carbons than it
ring

Exercise 2.11 Draw the structures corresponding to the following names:

cyclopentylcyclohexane
4-chlorocyclohexene
3-cyclopentyl-2-methylheptane

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2.4 Nomenclature of Aromatic Hydrocarbons

Aromatic hydrocarbons are a type of polyenes clearly

differentiated from the rest of the alkenes, being the molecule of benzene (C6H6) the most
Simple of them. Benzene consists of six carbon atoms with sp hybridization.2,
connected in a cycle that can be represented through Lewis structures
equivalents (or resonant) I and II or of the unique structure III:

Structure III emphasizes that it is not about three fixed double bonds,
but of a complete delocalization of the 6 electronsπ contributed by the 6
atomic orbitals perpendicular to the plane of the sp hybrid orbitals2.
Following them in order of complexity are the Arenes, which are derivatives of benzene.

and are made up of an aliphatic fraction and an aromatic one. The sands are
they are called derivatives of benzene or related structures. It is enough with
prioritize the name of the substituent group (in this case an alkyl radical) to the
word benzene like, for example:

When there are two substituents on a benzene ring, their positions are
they are indicated by the prefixes orto (o), meta (m), and para (p). The ortho prefix indicates that

the substituents are found in relative positions 1,2; meta and para represent
posiciones 1,3 y 1,4 respectivamente. Ejemplos

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If there are more than two substituents on the ring, they are named by numbering them.
positions, such as in:

When conceptually removing a hydrogen from benzene, the radical or results.

phenyl group; (C6H5-). That can be represented as:

Sometimes the benzene ring is referred to as a substituent of

a standard aliphatic hydrocarbon.

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Benzene derivatives do not only refer to an aromatic ring.

attached to an alkyl fragment but can be attached to various groups
functional groups such as carboxyl (-COOH), hydroxyl (OH), amino (NH)2), etc.. The
resulting compounds will exhibit mixed chemical properties, that is, they will undergo
typical reactions of the benzene ring (partially modified), as well as
some of the typical reactions of the functional group. The nomenclature of such
derivatives will be studied as the other groups are presented
functional.

2.5 Nomenclature of Alcohols, Thiols, and Phenols

The functional group of an alcohol is the hydroxyl (-OH) attached to an alkyl group. An
Alcohol can be considered a derivative of water by substitution of an atom.
of hydrogen by an organic radical (alkyl, alkenyl, or alkynyl). Many of
The properties of low molecular weight alcohols are similar to those of water.

Water Alcohol

According to the IUPAC nomenclature system, alcohols are named using

the suffix -ol. The chain continues longer on which the group is attached
hydroxylose is taken as the main chain. The end of the name of the corresponding
hydrocarbon is replaced by the suffix -ol The numbering takes place from one end
from the main chain, so that the hydroxyl group receives the most number
small possible.

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Compounds that contain two, three, or more hydroxyl groups are called
polyols, comodols, triols, etc. The 1,2-diols are commonly referred to as
glycols. Examples

When a compound contains more than one different functional group, it is necessary to

decide which group is chosen for the fundamental name. The IUPAC nomenclature
design a priority order for functional groups. For example, alcohols
they take priority over alkenes, in that case the numbering will be done in such a way that
the carbon bonded to the hydroxyl group receives the lowest number, disregarding that
the double bond forms part of the main chain or not. Examples.

In the example of cyclic alcohol, it is not necessary to precede the number 1.

from the suffix -ol because it is understood that the numbering starts at the carbon that is

joined to the hydroxyl function.

If there is another functional group in the molecule that takes precedence over the alcohol, the

The -OH group would be named as the hydroxyl substituent.

A common subdivision of alcohols is based on the number of atoms of
carbon attached to the one carrying the hydroxyl group. Thus, 1-propanol is an alcohol.
primary (1obecause the carbon attached to the hydroxyl group is only attached to a
carbon, while 2-propanol is a secondary alcohol (2 o) and 2-methyl-2-
propanol is tertiary (3o).

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Thiols are the sulfur analogs of alcohols, in which the atom of

oxygen has been replaced by a sulfur atom. The functional group here is the
sulfhydryl (-SH) or simply thiol. Thiols were known in ancient times as
mercaptans. To name them, the name of the corresponding alkane is added with the
sufijotiol.Examples:

If the hydroxyl group is directly attached to the benzene ring, we have the
the simplest member of the phenol family is phenol (or benzol).

Phenol

Alcohols and phenols are frequently studied separately, as

the chemical properties of the latter are different.
Many phenols are known by their common or trivial names. For example
Phenols with two hydroxyl groups in positions 1,2; 1,3; and 1,4 are known as
names of catechol, resorcinol and hydroquinone respectively, but they are no longer very
accepted by IUPAC.

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Methyl phenols are also known as cresols.

The hydroxyphenols are pyrogallol and phloroglucinol.

2.6 Nomenclature of Ethers and Thioethers

Ethers are compounds in which two carbon atoms are attached to one.
oxygen atom. Its general formula is:

R-OR, Ar-O-R or Ar-O-Ar Ar =

It is known as the aryl group or benzene ring. replaced

after the conceptual removal of a hydrogen.
Two systems accepted by IUPAC will mainly be discussed for
name the ethers. The first consists of naming the two alkyl groups attached to the
oxygen and then the word ether. Examples:

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In the second naming system, one of the groups and the oxygen are
they name as an alkoxy substituent the other group that is considered as the
main structure. This system is common when one of the groups does not have
simple name. For example:

In some compounds it is possible to use both systems:

There are also cyclic ethers, where oxygen is part of the ring. These
compounds with an element other than carbon within the ring are known as
Heterocyclics. The smallest ring of cyclic ethers is three.
members, which has been called oxirane (oxacyclopropane, ethylene oxide, or
simply epoxide). The organic rings that contain this oxirane ring
are generically known as epoxides. Below are some names of ethers.
cyclic

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In these examples, oxygen is counted as a carbon and is designated with the

prefix oxa. For its part, the thioethers are sulfur analogs of the ethers.
they are called thioether or alquiltio-derived (by comparison with alkoxy). Examples:

2.12

Exercise 2.13 Write the IUPAC name of each of the following structures

Exercise 2.14 Write a structure for each compound:

2-cyclohexylethanol. m-bromoisopropylbenzene.
diphenylacetylene. trans-1,2-phenylethylene.

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e) 2-isopropyl-5-methylcyclohexanol (menthol). ethylthiopropane.

g) 3-methyl-oxacyclohexane

2.7 Nomenclature of Aldehydes and Ketones

Aldehydes and ketones are substances with a general formula.

Aldehydes and ketones contain the carbonyl group C=O and are often thus
They are called Carbon Compounds. The IUPAC names of aldehydes follow a pattern.
common: The longest chain that contains the -CHO group is considered the parent structure (or
(patron) and is named by replacing the alkane ending with "al". The position of a
the substituent is indicated considering the carbon of the CHO group as number one.
The so-called common nomenclature is also commonly used for aldehydes and
it derives from the trivial names of the corresponding carboxylic acids, taken in their
majority of natural fixatives.. In the common name of aldehydes the point of union of the
substituents are indicated with the Greek letters a, p, y, 5, etc.

Table 2.8 shows some IUPAC names and common names (in parentheses) of
Frequent use aldehydes and ketones. Below are some examples of aldehydes.
substituted:

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Table2.8.CommonAldehydesandKetones

The suffix carb aldehyde (or carboxaldehyde, -CHO) is used when the group
aldehyde is attached to a ring. Examples:

The standard compound that contains the aldehyde group directly attached to the ring

benzenic is called benzaldehyde, this is:

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If the -CHO group is secondary compared to another, the prefix formyl is used.
example:

According to the IUPAC, the suffix is used to name a ketone. It must

start numbering from the end where C=0 receives the lowest number
possible. It is also common to name aliphatic ketones using the name of the
alkyl groups united to the carbonyl and then the word ketone.
Table 2.9 shows some IUPAC names, common names (in parentheses) and
common ketone structures.

The ketones where the carbonyl group (C=O) is part of a ring, are
They are named by changing the ending of the corresponding cycloalkane to the suffix -one.
(see Table 2.9). The substituents on the ring are named by indicating their position with the
combination of the lowest numbers starting from numbering the carbonyl carbon as the
C-1. Examples:

Exercise 2.15. Write the IUPAC name and common name (where possible) of the
following structures:

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Exercise 2.16. Write the structural formula for the following names of
carbonyl compounds.
a) Methyl isobutyl ketone. 3-Hydroxypentanal
c) 1,3-Diphenyl-2-propen-1-one d) 3-Phenylpropenal.
e) Phenylacetaldehyde. f) 2-Bromocyclopentanecarbaldehyde.
Ethyl phenyl ketone

2.8 Nomenclature of Carboxylic Acids

The most important acids in organic chemistry are members of a family of

compounds called carboxylic acids. They were among the first compounds
organic compounds studied by ancient chemists and are present in various
natural products, which is why many trivial names are related to it
natural origin of the respective acid. The characteristic functional group of these
the carboxyl group -COOH, which can be attached to a group
I rent (RCOOH) in aliphatic acids or in a ring (ArCOOH) in aromatic acids.
The IUPAC names for carboxylic acids follow the usual scheme. They
consider the longest chain that contains the carboxyl group and is named
replacing the alkane suffix with the oic suffix
preceding the word acid.

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Table 2.9 shows some IUPAC names and common names (in parentheses) of
common carboxylic acids.

Table 2.9 Common carboxylic acids

Examples of substituted carboxylic acids:

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Note that the substituent in position 3 or p is a phenyl group that is also

replaced, therefore chlorine is named indicating its position with the prefix para (p) or the
number 4. If the carboxylic acid contains a double bond in the main chain, it is referred to as
prefixenoic, if it has two double bonds it will be dienoic and so on.
There are many dicarboxylic acids in nature (with two groups
carboxylic), which are named using the suffix -oic (Table 2.9)
When the carboxyl group is directly attached to the benzene ring, the acid becomes
classified as aromatic. The simplest of them is benzoic acid, which has other
substituents will be named according to the nomenclature rules for the
aromatic hydrocarbons as derivatives of benzoic acid.

2.9 Nomenclature of Carboxylic Acid Derivatives

The compounds in which the hydroxyl group of the carboxylic acid has been replaced by a
heteroatom or by a group, are known as derivatives of carboxylic acids. The group
Hydroxyl may have been replaced by (-Cl) in acid chlorides, by an alkoxyl (-OR)

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in the esters and by an amino(-NH2. -NHR, -NR2) in amides. Because it is very
related to their reactions, these derivatives will be considered together

Acid chlorides are named by replacing the suffix 'oic' of the parent acid with 'oyl'.

suffix oil, similarly the word acid is replaced by chloride of.

Carboxylic anhydrides (or acid anhydrides) are named after the acid.
appropriate carboxylic replacing the word acid with anhydride. If the groups attached to
oxygen are different, separate words are used to indicate the two acids
carboxylics.

The esters of carboxylic acids are named using a combination

from the names of the alcohol and the original carboxylic acid. The name of the radical of the
alcohol is used (with the suffix -ilo) as if it were a substituent. This name
is preceded by that of the carboxylic acid with the suffix -oate instead of -oic. The
the word acid is omitted.
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The salts of these acids are named using the suffix at the end of the name of the
cation.

The suffix amide is used instead of the suffix oic to designate amides.

The nitrites (R-CNoAr-CN) are considered along with the other groups.
previous because the -CN easily transforms into carboxylic acid. The nitrile suffix
is added to the main name. The numbering includes the atom of the -CN group. When
the group -CN is named as a substituent, the word cyano is used:

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Exercise 2.17 Name the following compounds according to IUPAC and common nomenclature:

Exercise 2.18. Write a structure for each compound:

4-bromobutanoic acid. b) m-Methylbenzoic acid.
c) Phenylmalonic acid. Sodium phenylacetate.

e) m-bromophenyl benzoate. 3-methylbutanoyl chloride.

benzoic methanoic anhydride

2.10 Nomenclature of Amines

Amines are organic derivatives of ammonia (NH3They are compounds of a nature

basic but important aspects of organic chemistry. In amines, the hydrogens of ammonia
they have been replaced by one, two, or three groups, giving rise to primary amines,
secondary or tertiary respectively. Note that the use of these terms does not
has the same structural meaning as in alcohols. While in amines, those
terms refer to the number of carbons bonded to the nitrogen atom, in alcohols
they refer to the number of carbons bonded to the carbon that has the OH group.

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In IUPAC nomenclature, the suffix amine is added to the main name when
designate the primary amines, in this case the atom of is neither counted nor numbered
nitrogen. Secondary and tertiary amines are considered primary amines
replaced, using the letter N to indicate that the substituent is located on the
nitrogen atom. However, it is common to use the hydrocarbon radical as if
a substituent followed by the suffix amine. This is equivalent to naming amines.
as if they were derivatives of ammonia:

In other compounds with dominant functional groups, the amino group or

Alquilamino is named as a substituent of the parent compound.

When the amino or alkylamino group is directly attached to the ring.

Aromatic we have aromatic amines, derived from the pattern compound.
phenylaminoaniline

Substituted anilines are also known on the nitrogen or on the aromatic ring.

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Amines salts usually take their name by replacing amine.

for ammonium (or aniline for anilinium) and by placing the name of the anion first (chloride of..,

nitrate of., sulfate of.., etc.

There are also cyclic amines where one or more nitrogen atoms make
part of the ring. They are also heterocyclic compounds. The nitrogen in the ring is
name with the prefix 'aza', when using the systematic nomenclature of IUPAC.
Examples

There are also amines with nitrogens that are part of a ring.
Aromatic. They are common:

2.11 Order of Priority of Functional Groups

When two or more functional groups are part of the same molecule, it is
it is necessary to choose among them the one that forms part of the main name. Both the suffix
as the name of the radical and the numbering will depend on this choice.
The IUPAC numbering system includes an order of priorities,
assigning the maximum to the carboxyl group (-COOH) of carboxylic acids and to the group
acilo(-C(O)-G) of the acid derivatives, which must be located at the end of
the carbon chain and are named with the suffixes sico, oilo, amide, etc. A
the following are functional groups

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as aldehyde (-CHO) with the suffix -al, ketonic (-CO-) with -one, alcohol (-OH) with
Groups like ol, etc. can also be formulated as substituents in front of a
dominant group, using the prefixes: methanoyl (or formyl), oxo, hydroxy,
respectively. The lowest priority is assigned to halogens that do not have a suffix and
that are always referred to as substituents.
Table 2.10 shows a list of functional groups, ordered by
from highest to lowest priority.

Table 2.10 Functional Groups in orderof priority

from greater to lesser

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Excluding the naming of double and triple bonds, in the IUPAC system
only a suffix is used in the fundamental name. The suffix means that it is part of
of the fundamental name. The prefix is used when the group is named as
substitute. Examples:

In these two cases, since the carboxyl group (-COOH) is dominant, the
hydroxyl groups (-OH) and carbonyl groups (C=O) are named as substituents using the
corresponding prefixes.

Exercise 2.19. Name the following compounds and indicate the functional group
used as the basis of the pattern name.

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 BIBLIOGRAPHY

Morrison, T.M. and Boyd, N.B. 'Organic Chemistry', 4th Ed., Educational Fund
Inter-American, 1985.

Ref. 2. Fessenden, R.J. and Fessenden, J.S., 'Organic Chemistry', Wadsworth

International/Ibero-American, 1983.

Ref. 3. Solomons, T.W.G., "Organic Chemistry", Limusa Publishing, Mexico, 1985.

Ref. 4. Pine, S.H., Hendrickson, J.B., Cram, D.J. and Hammond, G.S., "Chemistry
Organic

Ref. 5.Baum, S.J., "Introduction to Organic and Biological Chemistry", 1st ed., Editorial
Continental, S.A., Mexico, 1981.

Ref. 6. Wingrove, A.S. and Caret, R.L., 'Organic Chemistry', Harper&Row, Publishers,
New York, 1981.

7.Reusch, W.H., "Organic Chemistry", Mc Graw-Hill, Mexico, Bogota, 1979.

Ref. 8. Allinger, N.L., Cava, M. P., De Jongh, D.C., Johnson, C.R., Lebel, N.A. and
Stevens, C.L., "Organic Chemistry", Reverté Publishing, S.A., Barcelona, 1976.

Ref. 9. Oullette, R.J., "Introduction to Organic Chemistry", Harper & Row

Latin American, 1973.

Ref. 10. Holum, J.R., "Organic and Biological Chemistry", John

Wiley&Sons, New York, 1978.

Ref. 11. Neckers, D.C. and Doyle, M.P. "Organic Chemistry", John Wiley & Sons, New York,

1977.

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 RECOMMENDED BIBLIOGRAPHY

Ref. 4, p.: 30-70

-Ref. 6, p.: 79-92

-Ref. 11, p.: 34-42; 54-56; 105-107; 162-163; 176-178

Fletcher, J.H., Dermer, O.C. and Fox, R.B., 'Nomenclature of

Organic Compounds, American Chemical Society, 1974.

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