IUPAC NOMENCLATURE

IUPAC SYSTEM OF NOMENCLATURE

A system of naming compounds in chemistry, IUPAC stands for:
---International ---Union of ---Pure and ---Applied ---Chemistry

IUPAC System of Naming Organic Compounds

MR.
PREFIX

WORD ROOT

AJAY

KUMAR
PRIMARY SUFFIX

Sharma
SECONDARY SUFFIX

Similarly, the compound H3C CH=CH CH2OH is systematically named as: CH3 3-Methylbut-2-ene-1-ol
PREFIX SECONDARY SUFFIX WORD PRIMARY ROOT SUFFIX

So, let us start with THE

WORD ROOT
No. of C atoms 1 2 3 4 5 Word Root Meth Eth Prop But Pent

It is the name corresponding to no. of carbon atoms in the longest chain of CARBON atoms in the organic compound. To determine the word root we need to learn the table given alongside.

6
7 8 9 10 11 12

Hex
Hept Oct Non Dec Undec Dodec

Now, let us come to the PRIMARY SUFFIX It indicates the nature of the carbon atom chain selected. primary suffix Only single bonds between C atoms -ane
(also called saturated)

Presence of double bond between C atoms Presence of triple bond between C atoms

-ene -yne

If the parent chain contains two, three or more double or triple bonds, then the numerical prefixes such as di (for two) , tri (for three), tetra (for four) , etc. are added to the primary suffix.

But what if both double and triple bonds are present between the C atoms???
CH C CH2 CH2 CH CH2

hex-1-en-5-yne

Both ene & yne are written but ene comes before -yne.

Let us now concentrate on the SECONDARY

SUFFIX

This is the word that defines the family or functional group in the organic compound. The various functional groups with their corresponding suffixes are:
Functional Group Class of compound Suffix

-COOH
-COOR -COX (X=F, Cl, Br, I)

Carboxylic acids
Ester Acyl halides

-oic acid
-oate -oyl halide

Functional Group

Class of compound

Suffix

-CONH2 -CN -CHO >C=O -OH -NH2

Acid amide Nitriles Aldehyde Ketones Alcohol Amine

-amide -nitrile -al -one -ol -amine

Thus the compound, CH3CH2CH2OH is Propanol.

Prop is the word root. -ane is the primary suffix. -ol is the secondary suffix Prop+ane+ol = Propanol.

-C=C

Alkene
Alkyne

-ene
-yne

Since the secondary suffix begins with a vowel o, the e of ane is removed.

-CC-

Let us now come to what we call as PREFIX

As the word indicates, it means something which is fixed or attached before or at the beginning. Hence a prefix is written before the word root. These are also of two types: a)) Primary Prefix b)) Secondary Prefix

It is the word which helps us to distinguish between a cyclic and an acyclic compound. The prefix CYCLO is used for cyclic compounds only.

Therefore,
CH2

CH2 CH2 CH2 CH2

is cyclopentane while CH3CH2CH2CH3 is pentane.

Functional Group
-COOH -SO3H -COOR -COCl -CONH2 -CN

Prefix
CarboxySulphoAlkoxycarbony-

Thus the compound:

1 2 3 4

Functional group

CH3 CH CH2 CH2 OH

Cl

HaloformylCarbamoylCyano-

-CHO
>C=O -OH -SH

FormylKeto-/oxoHydroxyMercapto-

Word root- But Primary suffix- -ane Secondary suffix- -ol Prefix- Chloro

IUPAC name,

3-chloro butane-1-ol

-NH2

Amino-

Certain groups in organic chemistry are written as prefixes. They are regarded as substituents. These groups along with their prefixes are as follows:
Sl no. 1 Substituent -F Secondary prefix Fluoro-

2
3 4

-Cl
-Br -I

ChloroBromoIodo-

Sl no.

Substituent

Secondary prefix

5 6 7 8 9 10 11

-NO2 -NO -N N-

NitroNitrosoDiazomethoxy ethoxy Hydroxo Amino

-OCH3 -OC2H5 -OH -NH2

Note that the word root will come after the prefix. Thus, the compound , CH3 CH CH2 CH3

Cl
is 2-chlorobutane.

Different classes of Organic Compound

Hydrocarbon
a) Saturated hydrocarbons (i) Alkanes General formula:- CnH2n+2 Suffix:- ane 1) These are the organic compounds which contain only carbon-carbon single bonds. 2)According to IUPAC system, these are named as alkanes.

Various members of the series are given below:

Formula CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3(CH2)3CH3 IUPAC name Methane Ethane Propane Butane Pentane Common name Methane Ethane Propane n-Butane n-Pentane

CH3(CH2)4CH3

Hexane

n-Hexane

(ii) Alkyl radical or Alkyl group

General formula:- CnH2n+1 Suffix: -yl 1) Alkyl group contains only one H atom less than the alkane. 2) The alkyl group is named by substituting the suffix ane of the name of the corresponding alkane by yl. For e.g.:CH4, Methane becomes CH3- Methyl

Important Alkyl group

(b) Unsaturated hydrocarbons

These are the hydrocarbons which contain carbon to carbon double bonds or carbon to carbon triple bonds in their molecules. These are further classified into two types:

(i) Alkenes (ii) Alkynes

i) Alkenes General formula: CnH2n Suffix: -ene 1) The molecules containing one carbon-carbon double bonds are called alkenes. 2) In IUPAC system, the name of alkenes is derived by replacing suffix ane of the corresponding alkane by ene. CH3-CH3 CH2=CH2 Ethane Ethene

Some Alkene group

ii) alkynes

General formula: CnH2n-2 Suffix: -yne 1) Alkynes are unsaturated hydrocarbons with a triple bond between carbon-carbon atom. 2) Alkynes are named in the same way as alkenes i.e., by replacing suffix ane of alkane by yne.

Some Alkyne group

Alkyl halides
General formula: CnH2n+1X or RX Prefix: Halo These are obtained from alkanes by the replacement of one or more hydrogen atoms by halogen atoms: RH
-H,+X

RX

(X=F, Cl, Br, I)

Alkyl halides
In the IUPAC system, they are named as halogen substituted alkanes i.e., haloalkanes. Thus the name of halogen compound is given by prefixing flouro, Chloro, bromo, iodo to the names of the alkane. For e.g. CH3Cl chloromethane, CH3CH2Cl chloroethane etc.

alcohols
General formula: CnH2n+1OH or ROH Functional group : -OH Suffix : -ol 1) These are derived by replacing one hydrogen atom from an alkane by one hydroxyl group. 2) In IUPAC system, these are called alkanols and their names have been derived by changing -e of corresponding alkane by ol

Some alkane and their alcohols

ethers
General formula: CmH2m+1OCnH2n+1 Functional group: - O Suffix: -ol These are derived from alkanes by replacing one hydrogen atom by alkoxy group(-OR). For e.g. methoxy(OCH2) ethoxy(OC2H5) etc.

aldehydes
General formula:CnH2n+1CHO(where n can be 0 also e.g. HCHO) Functional group: -CHO Suffix: -al These compounds are obtained by replacing a hydrogen atom attached to the terminal carbon atom in alkane molecule by an aldehydic (CHO) group. The first member is, however, obtained by replacing a hydrogen atom in the hydrogen molecule.

aldehydes
These are called alkanals in the IUPAC system of nomenclature and the names of individual members are derived by changing e of corresponding alkane by al.

Aldehydes and their formulas

Ketones
General formula: CnH2n+1COCmH2m+1 Functional group: >C=O Suffix: -one These are obtained by replacing two hydrogen atoms attached to the non-terminal carbon atom in alkane molecule by a divalent oxygen atom. Thus the functional group called ketonic group contains a carbon atom joined to the oxygen atom by double bond. The names of individual members are derived by replacing e of the corresponding alkane by one.

Carboxylic acid
General formula: CnH2n+1COOH Functional group: -COOH Suffix: -oic acid 1) In this compounds, one hydrogen atom in alkane molecule is replaced by a carboxyl (COOH) group. The first member is, however, obtained by replacing a hydrogen atom in the hydrogen molecule. 2) In the IUPAC system, they are named by replacing the terminal e of the corresponding alkane by oic acid.

amines
General formula: CnH2n+1-NH2 Functional group: -NH2 Suffix: -amine These are the alkyl derivatives of ammonia. They are formed by replacing one, two or all the three hydrogen atoms in ammonia with alkyl radicals. In IUPAC, the name is derived by replacing e of alkane by amine.

RULES FOR NAMING AN ORGANIC COMPOUND

1. Longest chain rule

1)Determine the longest continuous necessarily straight) chain of carbon atoms. CH3 Alkyl group (not
Longest chain

CH3 CH2 CH2 CH2 CH CH3

The base name corresponds to the number of carbon atoms in the longest chain. The full name for the alkane will include the names of any branches.

2. Position of the substituent

Number of the carbon atoms in the parent chain as 1,2,3etc. starting from the end which gives lower number to the carbon atoms carrying the substituents i.e. Always number from the end of the longest chain closest to the first branch.
WRON G

Substituent

CORRECT

X C-C-C-C-C
1 2 3 4 5

X C-C-C-C-C
5 4 3 2 1

3. Lowest set of locant rule

When two or more substituents are present, then end of the parent chain which gives the lowest set of locants is preferred for numbering. Number the chain so as to give the lowest number possible to the : FUNCTIONAL group followed by We would call DOUBLE BOND, it the TRIPLE BOND & finally the FDTS rule! SUBSTITUENT

COOH CH CH CH2 CH2 Cl So in the above compound numbering is possible as: COOH
1

CH

CH

CH2 CH2 Cl

COOH

CH CH CH2 CH2 Cl

So which one is the correct numbering according to the above rule?? 3. If you notice in the above example, in SET 1 the functional group is _COOH and it has a Carbon in it. In such cases, the Carbon of the functional group always gets the position no. 1.

4. What if the same functional group exists twice in the chain 4 1 3 2 HOH2C CH2 CH2 CH2OH Here, irrespective of the end you start from, you get the same position number both ways. PLEASE be careful not to number the oxygen in the functional group. You only have to number the C atoms in the chain. Hence the compound is, Butane-1,4-diol .
WHERE But + ane + 1,4 - diol
Word root Primary Suffix Locant Secondary Suffix

NOTE:-

The position number of each of the functional groups is expressed by the position number of Catom to which it is attached and it is known as Locant. The locants are separated from each other by commas. The locant and the word are separated by a hyphen. The numerical prefixes di, -tri, -tetra etc. are used to indicate the presence of two, three or more like groups.

Let us try naming the compound , which we had taken as an example 1 2 3 4 5 HOOC CH CH H2C CH2 Cl The compound would thus be named as,

NOTE:- If the locant is not specified, it is taken as 1

For the same substituent at equivalent position, the first point of difference rule is applicable e.g. CH3 CH3 6 1 2 3 4 5 H3C C H2C H2C CH CH3 The locant positions are 2,2,5 CH3 in Set 1 and 2,5,5 in Set 2. CH3 Notice that 1st locant is same, CH3 3 1 6 4 2 5 nd CH3 C CH2 CH2 CH CH3 in both sets, but 2 locant in Set 1 is smaller & hence Set 1 is CH3 correct.

6. What if different substituents are present in equivalent position ? CH3CH2 CH CH CH2CH3 What do YOU think would be the correct C2H5 CH3
answer??

OPTION A 3-Ethyl-4-methylhexane OPTION B 4-Ethyl-3-methylhexane

OR

When confused about substituents , always remember that we consider the ALPHABETICAL order.

Hence option A is correct. But ignore multiplying prefixes i.e. di, tri etc. while considering the alphabetical order!

RULES FOR NAMING COMPOUNDS HAVING MORE THAN ONE FUNCTIONAL GROUP & /OR SUBSTITUENT &/OR MULTIPLE BOND.
1. In a class of students one student is elected as leader, while the others are to follow. Similarly, when more than one functional groups are present, one functional group is chosen as the

PRINCIPAL FUNCTIONAL GROUPwritten as a suffix, while others are regarded as substituentswritten as a

prefixes.

2.Now how do we decide the principal functional group??

To remove any confusion, the functional groups are arranged in a preference series as follows: Carboxylic acid>Sulphonic acid>Anhydride>Ester>Acid chloride>Acid amide>Nitrile>Aldehyde>Ketone>Alcohol> Amines>Alkene>Alkyne . The group higher in the preference series is written as a Suffix While the one lower to it would be written as a Prefix.

The corresponding prefix and suffix as given earlier for each functional group can be compiled as the follows:
S.No. 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. -C Functional group -COOH -SO3H -COO -COO -COOR -COCl -CONH2 -CN -CHO O Alkoxycarbonyl HaloformylCarbamoylCyanoFormyl Keto/oxo HydroxyMercaptoAminoPREFIX CarboxySulphoSUFFIX -oic acid Sulphonic acid Anhydride Alkyloate -oyl chloride -amide Nitrile -al -one -ol -thiol -amine -ene -yne

>C=O
-OH -SH -NH2

>C=O<
C-

THANKS FOR YOUR KIND CONSIDERATION

BY:Ashwani Kumar