Professor Dr. Md.

Shariful Islam
Department of Agricultural Chemistry

1
 Organic Chemistry
 It is the study of carbon compounds.
 It is studied as a separate discipline because of the
following reasons
 1. large number of compounds
 2.Unique Physical & chemical properties
 3. Unique character of Carbon-Catenation- carbon has
the ability to bond successively to other carbon atoms
to form chains.

2
Importance of Organic Chemistry in
Everyday life
 Food: Proteins, Fats, Carbohydrates
 Clothing: Cotton, Silk, Wool, Nylon, rayon
 Shelter: wood, paints, Varnishes
 Power & Transportation: Natural gas, petroleum products, Coal
 Medicines & Drugs: Penicillin, Streptomycin, Aspirin
 Insecticides: DDT
 Herbicides: Treflan
 Hormones & Steroids
 Vitamins & Enzymes
 Antiseptics
 Pigments & Dyes
 Paper & Inks
 Photographic films & Developers
 Perfumes & Flavours
 Plastics, rubber & resin
 Propellants & Explosives
 Soaps & Detergents
 Refrigerants

3
Types of Organic Compounds
1. Aliphatic Compounds: Compounds which consist of open chain of carbon atoms .
Ethane CH3-CH3
Ethyl alcohol CH3-CH2-OH
Acetic acid CH3-COOH

2. Saturated & Unsaturated Compounds: Compounds which contain only carbon &
Hydrogen are called Hydrocarbons.
A Hydrocarbon is said to be saturated if it contains only C-C single bonds.
Eg: CH3-CH3 Ethane
A Hydrocarbon is said to be unsaturated if it contains C=C or C≡C multiple bonds
Eg: CH2=CH2 Ethylene
HC≡CH Acetylene

3. Aromatic compounds:
a. Benzenoid Compounds: Benzene and all compounds that have structure and
chemical properties similar to Benzene
Eg:
CH3

benzene toluene naphthalene

4
 b. Non benzenoid compounds:
-
O +

cyclo pentadienyl anion Tropylium cation

Tropolone

4. Alicyclic or Carbocyclic Compounds: Cyclic compounds which consist only of

carbon & hydrogen atoms

cyclohexane cyclopentane cyclopropane

 5. Heterocyclic Compounds: Cyclic compounds in which ring atoms are C &

Heteroatoms like N,S, O
O

N N

pyridine oxirane quinoline

 Homologous Series: series of organic compounds each containing a

characteristic functional group forms a homologous series & members are
called as homologues. They differ by a –CH2 group.
 Ex: alkanes, alkenes, alkynes, haloalkanes, alcohols, carboxylic acids etc.
5
Representations of Organic Molecules
n-Pentane: C5H12
 Long Hand formula: CH3-CH2-CH2-CH2-CH3

 Short hand formula:

 Skeletal formula: C-C-C-C-C

 Condensed Formula: CH3-(CH2)3-CH3

6
 Structural formula: H H H H H

H C C C C C H

H H H H H

H H H H H

 Three dimensional: H C C C C C H

H H H
H H

 Lewis –dot formula:

7
 Principles of Nomenclature
 In early days , each new compound was given an individual name. Such
name was based on the source, some property or some other trivial
reason.
 Eg: Formic acid, it was named as it was obtained by distillation of red
ants.
 Methane from marsh gas
 Citric acid from citrus foods
 Nitrobenzene, it is named as oil of mirbane
 Curcumin from turmeric & many more……
 An ordinary name given to a compound without reference to its structure
is called a common name or trivial name

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9
 IUPAC System of Nomenclature:
 With the rapid growth of organic chemistry, over 6 million of
compounds were discovered.It was impossible to give
common names.
 In 1957, the International Union of Pure and Applied
Chemistry proposed rules to give a systematic naming to
organic compounds based on their structure. Each organic
compound has only single IUPAC name.
 According to IUPAC, name of an organic compound has the
following parts
 1. Prefix: Indicates the identity, location, and number of
substituents attached to the carbon chain
 eg: Chloro, alkyl, amino, hydroxy etc.
 2. Root word : Represents the no. of carbon atoms in the
continuous longest chain
 3.Primary suffix: Indicates the presence or absence of
saturation
 4.Secondary Suffix: Indicates the functional group present
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Root Word:
 1-Meth
 2-Eth
 3-Prop
 4-But
 5-Pent
 6-Hex
 7-Hept
 8-Oct
 9-Non
 10-Dec
 20-Eicos

Primary Suffix:
Saturated with all single bonds: -ane
Unsaturated with = bond: -ene
Unsaturated with ≡ bond: -yne

Secondary Suffix: indicates the functional group present

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Functional Groups: A functional group is an atom or group of atoms in a
molecule that gives the molecule its chemical properties.
Some Functional groups with prefixes & suffixes are given below:

Class Functional IUPAC IUPAC Example

group group group
Prefix Suffix
Alkane C-C -ane CH3-CH3
Alkene C=C -ene CH2=CH2
Alkyne C≡C -yne HC≡CH
Arenes C6H6 Benzene
Halides -X halo CH3-CH2-Br
(X=F,Cl,Br,I)
Alcohol -OH hydroxy -ol CH3-CH2-OH

Ether -O- alkoxy CH3-O-CH3

O
Aldehyde R-CHO formyl -al
H3C H

O
Ketone Oxo- -one O
R R
H3C CH3
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Class Functional IUPAC group IUPAC group Example
group Prefix Suffix
O
Carboxylic acid -COOH carboxy -oic acid
H3C OH

Ester -COOR alkoxy carbonyl -oate O

H3C OR

Acid halides -COX halo carbonyl -oyl chloride O

H3C
( X=F,Cl,Br.I) Cl

H3C O CH3
Acid anhydride R O R -anhydride
O O
O O

Amide -CONH2 carbamoyl -amide O

H3C NH2

Amine -NH2 Amino -amine CH3-NH2

Nitriles -C≡N cyano nitrile CH3-C≡N

Isonitriles N≡C isocyano Iso nitrile or CH3-N≡C
carbyl amine
Nitro -NO2 Nitro - CH3-NO2
Compounds
Sulphonic acids -SO3H sulpho Sulphonic acids CH3-SO3H 13
Alkyl groups: By removing one
hydrogen from alkane
R-H - 1H → -R alkyl group
CH4 - 1H → -CH3 methyl group
n-alkyl group: H3C CH3
-H
H3C
+
CH2

CH3 CH3

Iso- alkyl group: H3C H

-H
H3C C
+

CH3
CH3

Neo-pentyl group: CH3

-H
CH3

+
H3C CH3 H3C CH2

CH3 CH3

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Classification of Carbon atoms
CH3 CH3 Primary ( 1o )
H3C

H
Secondary ( 2o)
H3C
Quaternary (4o)
CH3
Tertiary (3O)

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Alkyl group Structure IUPAC name Abbreviation
( Prefix)

CH3- CH3- methyl Me-

CH3CH2- ethyl Et-

CH3CH2CH2- n-propyl n-Pr

CH3CHCH3 isopropyl or i-propyl i-Pr

CH3CH2CH2CH2- n-butyl n-Bu

CH3CH2CHCH3 sec-butyl s-Bu

(CH3)2CHCH2- isobutyl or i-butyl i-Bu

(CH3)3C- tert-butyl or t-butyl t-Bu

C6 H 5 - phenyl Ph
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ALKANES
Names of first 10 straight chain alkanes

Carbon atoms Name Molecular formula

1 Methane CH4
2 Ethane C2H6
3 Propane C3H 8
4 butane C4H10
5 Penatne C5H12
6 Hexane C6H14
7 Heptane C7H16
8 Octane C8H18
9 Nonane C9H20
10 Decane C10H22

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IUPAC Rules for Naming Alkanes
 Rule 1: Select the longest continuous carbon chain

Note that it does not matter if the chain is straight or it bends

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Also note that if there are two chains of equal length, pick the chain with more
substituents.

In the following example, two different chains in the same alkane have seven C
atoms.

We circle the longest continuous chain as shown in the diagram on the left, since
this results in the greater number of substituents.

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Rule 2 : Number the atoms in the carbon chain to give the first substituent the
lowest number.

If the first substituent is the same distance from both ends, number
the chain to give the second substituent the lower number.

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When numbering a carbon chain results in the same numbers from
either end of the chain, assign the lower number alphabetically to the
first substituent.

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Rule 3 : Name and number the substituents.
 Name the substituents as alkyl groups.
 Every carbon belongs to either the longest chain or a substituent, not
both.
 Each substituent needs its own number.
 If two or more identical substituents are bonded to the longest chain, use
prefixes to indicate how many: di- for two groups, tri- for three groups,
tetra- for four groups, and so forth.

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Rule 4: Combine substituent names and numbers + parent and suffix

• Precede the name of the parent by the names of the substituents.

• Alphabetize the names of the substituents, ignoring all prefixes
except iso, as in isopropyl and isobutyl.
• Precede the name of each substituent by the number that indicates
its location.
• Separate numbers by commas and separate numbers from letters
by hyphens. The name of an alkane is a single word, with no
spaces after hyphens and commas.

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 CYCLO ALKANES
1. Cycloalkanes are named by using similar rules, but the prefix
cyclo- immediately precedes the name of the parent.

Example:

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2. Name and number the substituents. No number is needed to indicate the
location of a single substituent.

3. For rings with more than one substituent, begin numbering at one substituent
and proceed around the ring to give the second substituent the lowest number.

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4. With two different substituents, number the ring to assign the lower
number to the substituents alphabetically.

Note the special case of an alkane composed of both a ring

and a long chain. If the number of carbons in the ring is
greater than or equal to the number of carbons in the longest
chain, the compound is named as a cycloalkane.
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Naming compounds containing both Ring & side alkyl chains

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1. Select the longest carbon chain containing the double bond
2. Name the longest chain- the name is obtained by dropping the final-ane from the
name of corresponding alkane, & adding the ending –ene
3. Number the chain from the end closer to the double bond
4. Indicate the position of the double bond by the number of the first (lowest
numbered) carbon atom involved in the db.
5. Alkyl groups and other substituents are numbered, named and placed as prefixes
in the alphabetical order.
CH3

H2C CH2 H3C CH2 H3C CH2

ethene Propene
2-methyl propene

6. Alkenes containing two double bonds are named as alkadienes

CH2
H2C

1,3-butadiene
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• Number the ring to give the double bonded carbons the number 1 & 2.
• Choose the direction of numbering so that the substituents get the
lowest numbers.
• The position of the double bond is not indicated because it is known to
be between C1 & C2.

CH3

cyclohexene
3-methyl
cyclopentene

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1. Select the longest carbon chain containing the triple bond
2. Name the longest chain- the name is obtained by dropping the
final-ane from the name of corresponding alkane, & adding the
ending –yne
3. Number the chain from the end closer to the triple bond
4. Indicate the position of the triple bond by the number of the first
(lowest numbered) carbon atom involved in the triple bond.
5. Alkyl groups and other substituents are numbered, named and
placed as prefixes in the alphabetical order.
CH
CH3
HC CH H3C CH H3C HC
Propyne 1,3-butadiyne
2-Butyne
2-butyne 1,3-Butadiyne
6. Alkynes containing two triple bonds are named as alkadiynes

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1.Select the longest chain to which the halogen is attached and give it the
name of the corresponding alkane
2. Prefix the name of the alkane by chloro, bromo, iodo or fluoro
3. Number the chain so as to give the carbon carrying the halogen atom the
lowest possible number
4. Other substituents are numbered, named and placed as prefixes in
alphabetic order. If there are two or more identical halogen substituents,
the prefixes di, tri, tetra , etc.. are used
Br CH3 Cl
4 3 1 5 4
2 2 3 2 1
CH H3C CH2 C CH2 Cl H3C CH2 C CH2
1 3
CH2 Br
H3C CH3
CH3 Cl
2-Bromopropane 1-chloro-2,2-dimethylbutane 1-Bromo-3,3-dichloropentane
1-Chloro-2,2-dimethylbutane 1-bromo-3,3-dichloropentane

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Alcohols
1. Select the longest chain to which hydroxyl group is attached.
2. Name the longest chain. The name is obtained by dropping the final –e from the name of the
alkane that contains the same number of carbon atoms, and adding the ending –ol
i.e., Alkane – e + ol = Alkanol
1. Number the chain to give the lowest number to the carbon attached to the –OH group
2. Indicate the position of the hydroxyl group by the number of the carbon attached to the
hydroxyl group
3. Other substituents are numbered, named and placed as prefixes in alphabetic order. For
example,
CH3-OH Methanol CH3-CH2-OH Ethanol

HO H2C OH H2C OH
4 3 1
2 H3C CH
2
CH2 CH2 OH
CH2 HC OH
CH
1 3
H3C CH3 CH3 H2C OH H2C OH
3-Methyl-1-butanol
2-Propanol 1, 3-Propanediol
1,3-Propane diol 1,2,3-Propanetriol
1,2,3- Propane triol

6. Alcohols containing two or three –OH groups are named as alkanediols and alkanetriols.
Notice that –e of the corresponding alkane name is retained

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Ethers
1. Ethers are compounds in which an oxygen atom is bonded to two organic
groups ( R-O-R).
2. In the IUPAC system, ethers are named as Alkoxyalkanes. The smaller alkyl
group plus the oxygen atom is called an alkoxy substituent.
Methoxy OCH 2CH 3 Ethoxy
CH3-CH2-CH2-O-CH3
H3C
1- Methoxypropane CH3
H3C
2-ethoxy-5-methylhexane
2-Ethoxy-5-methylhexane
Cyclic Ethers ( Epoxides)
These are also known as oxiranes
In IUPAC system, they are named as Alkyloxiranes. Substituents on the
oxirane ring require a numbering system. The oxygen atom is given the
number-1 O
O O
H2C CH2 H2C CH H2C C CH3
CH3
oxirane CH3
2-methyloxirane
2-Methyloxirane 2,2-dimethyloxirane
2-2-Dimethyloxirane

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Aldehydes
In the IUPAC system, aldehydes are named as Alkanals
1. Select the longest chain-the name is obtained by dropping the final -e from the name of
the corresponding alkane, and adding–al at the end. Alkane – e + al = Alkanal
2. Number the chain by assigning the number 1 to the aldehyde carbon. The number 1 is
not used to indicate the position of the carbonyl carbon, since it is always located at the
end of the chain
3. Other substituents are numbered, named & placed as prefixes in alphabetic order.
O
CH3 O Br
H H
CH H3C H
H3C CH2 H
O O
3-methylbutanal
3-Methylbutanal 3-bromopentanal hexanedial
3-Bromopentanal 1,6-Hexanedial
4. When there are two aldehyde groups in a molecule, it is named as alkanedial. Notice
that –e of the corresponding alkane is retained.

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Ketones
In the IUPAC system ketones are named as Alkanones.
1. Select the longest chain containing the carbonyl carbon atom
2. Name the longest chain -the name is obtained by dropping the final -e from the name of
the corresponding alkane and adding–one at ending. Alkane – e + one = Alkanone
3. Number the chain to give the lowest number to the carbonyl carbon.
4. Other substituents are numbered, named & placed as prefixes in alphabetic order.
CH3 O O
O O
CH H3C CH3
H3C CH2 CH3 H3C
CH3
4-Methyl-2-pentanone
4-methylpentan-2-one pentan-3-one
3-Pentanone
hexane-2,4-dione
2,4-Hexanedione

5. When there are two carbonyl groups in a molecule, it is named as alkanedione. Notice
that –e of the corresponding alkane is retained.

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Carboxylic acids
1. Select the longest chain containing carboxyl group (-COOH)
2. Name the longest chain. The name is obtained by dropping the final –e from the name of the
corresponding alkane & adding the ending –oic acid. Alkane - e + oic acid = Alkanoic acid
3. Number the chain starting with carboxyl carbon as number 1. the number 1 is not used to
indicate the position of the carboxyl carbon, since it is always located at the end of the chain.
4. Other substituents are numbered, named & placed as prefixes in alphabetic order.

H3C
COOH H3C COOH COOH
HOOC
CH3
Br 1,6-hexanedioicacid
acid
3-Methylbutanoic
3-methylbutanoicacid
acid 1,6-Hexanedioic
4-Bromopentanoic acid
4-bromopentanoic acid

5. When there are two carboxyl groups in a molecule, it is named as alkanedioic acid .
Notice that –e of the corresponding alkane is retained.

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Carboxylic acid derivatives: hydroxyl part of the carboxyl
group is replaced by other groups
1. Acid Chlorides: These are derived from acids by replacing –OH group by Cl
atom. They are named by changing the ending -oic acid of the corresponding
carboxylic acid by –oyl chloride.
O
O

H5C2 Cl
H3C Cl
Ethanoyl choride Propanoyl chloride

2. Esters: These are derived from acids by replacing –OH group by –OR group.
Their names consist of two words. The first word is the name of the alkyl group
attached to the oxygen atom. The second word is derived from the carboxylic
acid name with –oic acid changed to –oate

O
O O
CH3
H3C O C2 H5
H O H3C O CH3
methyl
Methyl ethanoate
ethanoate Ethyl methanoate Butyl ethanoate

37
 Carboxylic acid derivatives: contd…
3. Acid Anhydrides: These are derived from acids by replacing –OH by –OCOR. They are
named by changing the suffix acid of the parent acid to anhydride.
O O O O

H3C O CH3 H5C2 O C2H5

Ethanoic anhydride Propanoic anhydride

Asymmetric anhydrides are named in a similar fashion listing the alkyl groups in
alphabetical order. O O O
O O

H5C2 O CH3 H NH2 H3C NH2 H5C2 NH2

Butanoic Propanoic anhydride Methanamide

Butanoic propanoic anhydride Ethanamide Propanamide

4. Amides: These are derived from acids by replacing –OH by –NH2 . These are named as
alkane amides.

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Sulphonic acids: These contain –SO3H group. Their IUPAC names are
obtained by adding the suffix sulphonic acid to the alkane name
SO3H
CH3
H3C H3C SO3H

CH3
5-methylhexane-2-sulfonic
5-Methylhexane-2-sulphonic acid
acid butane-1-sulfonic acid
Butane-1-sulphonic acid
Nitro Compounds: These contain –NO2 group. Their IUPAC names are
obtained by adding prefix –nitro to the alkane name.
NO 2
H3C NO 2
CH3
H3C
2-nitrohexane
Nitromethane
nitromethane 2-Nitrohexane
Cyanides or Nitriles: These contain –CN group. In the IUPAC system they are
named as Alkanenitriles. Numbering includes the nitrile carbon atom.
CN
CN
H3C CN H3C COOH
H3C
Ethanenitrile
ethanenitrile hexanenitrile
Hexanenitrile 3-Cyanobutanoic
3-cyanobutanoicacidacid
The prefix cyano used for the nitrile group when it occurs as a substituent.
In that case, the carbon of the –CN group is not numbered.

39
 Isocyanides/Isonitriles/carbyl amines: These contain –NC (isocyano) group. In
IUPAC system, they are named as Alkyl carbylamines. The numbering does not include
carbon of the isocyano group. CN
NC COOH
H3C NC H3C H3C
Methyl carbylamine Pentyl carbylamine 3-isocyanobutanoic
3-Isocyanobutanoic acid
acid

Amines: These are derivatives of ammonia in which one or more hydrogen atoms
have been replaced by alkyl or aryl groups.
Amines are classified as primary, secondary & tertiary amines.
R-NH2 Primary amine
R2NH Secondary amine
R3 N Tertiary amine
In the common system they are named as alkylamines. If two different alkyl groups
are present, write in the alphabetical order.
Eg: CH3-NH2 Methylamine
CH3-NH-CH3 Dimethylamine
CH3-NH-CH2CH3 Ethylmethylamine

40
Amines: contd….
In the IUPAC system, primary amines are named by replacing the final –e of the
parent alkane by –amine. If necessary, a number is added to indicate the position
of –NH2 group. NH 2

NH2
H3C H3C CH3
1-Propanamine 2-Propanamine
Secondary or tertiary amines are named as N-Substituted derivatives of primary
amines. The largest of the groups attached to nitrogen is chosen as the organic
group of the primary amine. The remaining alkyl groups are named as
substituents by using the prefix N-to indicate that they are attached to nitrogen

CH3-CH2-NH-CH3 N-Methylethanamine
H3C Whenever it is necessary to name –NH2 as a
substituent, it is called the amino group
N CH3
H2N
OH
CH3
4-amino-1- butanol
N-Ethyl-N-methylbutanamine
N-ethyl-N-methylbutanamine 4-Amino-1-butanol

41
 Nomenclature of Poly functional
compounds
When a compound contains two or more different types of functional groups ( poly
functional compound), the functional group which specifies its class is called the
Principal Functional group.
The other functional groups are referred to as substituents.

substituent
OH
2
1
H3C 4 3 COOH
5 Principal functional group

4-Hydroxypentanoic acid

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The IUPAC system has laid down priority of functional groups for
determining the class of a polyfunctional compound.
 The table below shows a list of functional groups in decreasing order of priority
for citation as the principal functional group.
Class Functional group Suffix used
Carboxylic acid -COOH -oic acid
Sulphonic acid -SO3H -sulfonic acid
Ester -COOR -oate
Acid Halide -COX -oyl halide
Amide -CO-NH2 -amide
Nitrile -CN -nitrile
Aldehyde -CHO -al
ketone -CO- -one
Alcohol -OH -ol
amine -NH2 Amine
Ethers -O- Alkoxy alkanes
Alkene -C=C- -ene
Alkyne -C≡C- -yne 43
Prefixes used for functional groups
F.G Prefix F.G Prefix F.G Prefix

-Br Bromo -R Alkyl -C=O Oxo

-F Fluoro -OR Alkoxy -NO2 Nitro
-Cl Chloro -OH hydroxy -NO Nitroso
-I Iodo -NH2 Amino -CN Cyano

44
 IUPAC Rules for naming Poly functional
compounds
Rule 1 : Identify the principal functional group.
e.g., OH CH3

H3C COOH

The two functional groups in the above structure are –COOH & -OH.
Since –COOH ranks higher in the priority table, the structure is named as a
carboxylic acid

Rule 2: Number the longest chain containing functional group

from the end closer to it. OH CH3

1
H3C 4 2 COOH
5 3
Rule 3: Write the parent name corresponding to the number of carbons in
the longest chain.
Longest chain= 5 carbons, So Parent name = Pentanoic acid

45
contd…..
Rule 4 : Arrange the substituent names with position numbers in alphabetic
order
4-Hydroxy-2-methyl
Rule 5 : prefix substituent names with the parent name
4-Hydroxy-2-methylpentanoic acid
Rule 6: C-C double or triple bonds are usually indicated by integrating –ene
or –yne into the suffix, as in –enoic acid or –ynoic acid
Rule 7: compounds containing both db & tb in the main chain are named as
alkenynes. The position number of db is inserted before-alken- & that of tb
before -yne.
Rule 8: The following functional groups are always named as substituents.
-X ( all halo groups), -CN, -R, -OR, -NH2, -NO2, -NO
OH CH3

1
H3C 4 2 COOH
5 3

46
Excercises
O H3C O
H3C
Cl
NH2 CH3
Br H3C
H
Br NO 2

OCH 3
O H
OH
O H3C
COOH
CH3 CH3
CH3 NH2

OCH 3 O O
H3C O
H3C CHO CH2
C2H5
HC
Cl
OH O
CH3 CN

47
Example-1

Cl
CH3
H3C
Br NO 2
3-bromo-2-chloro-5-nitrohexane
3-Bromo-2-chloro-5-nitrohexane

The functional groups are –Br,-Cl, -NO2 .these are not Principal F.G, but taken as
substituents

Example-2 H3C O

H
2-butenal
2-Butenal

The functional groups are –CHO & C=C . The –CHO is the Principal
functional group & it ranks higher in the priority and number for –CHO group
is not indicated as it is always 1.
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Example:3 O H
H3C
O

3-oxopentanal
3-Oxopentanal

As –CHO group is highly preferred than Ketone. Compound is

named as aldehyde and ketone is taken as substituent. So named as
the prefix –Oxo.
Example:4
OCH3
H3C OH

2-methoxy-1-butanol
2-Methoxy-1-Butanol

49
 Example:5 H3C
COOH
CH3 NH2

3-Amino-5-methylhexanoic
3-amino-5-methylhexanoic acid acid

Example:6
OCH 3 O
H3C
Cl
3-Methoxypentanoyl chloride
3-methoxypentanoyl chloride

50
Example: 7 H3C O
C2H5
OH O
ethyl 3-hydroxybutanoate
Ethyl-3-hydroxybutanoate

Example: 8 O
H3C CHO

CN

6-cyano-3-oxo-4-heptenal
6-Cyano-3-oxo-4-heptenal

51
 Example9
O
H3C

Br NH2
3-bromobutanamide
3-Bromobutanamide

Example: 10 When either db and tb can be given

HC CH2 same position number, the chain is
numbered from the end closer to the
db (example 10).
pent-1-en-4-yne
1-Penten-4-yne But when both db and tb cannot be
Example: 11 given same position number then the
CH3-CH2=CH-C≡CH main carbon chain is numbered from
the end closer to the multiple bond,
3-Penten-1-yne whether db or tb (Example 11)

52
 Some Heterocyclic parent hydrides

Furan Imidazole Isoxazole Pyrrole

(1H-isomer shown) (1H-isomer shown)

Pyran Pyridine Pyrimidine

(2H-isomer shown)

53
 Purine Quinoline Isoquinoline
(7H-isomer shown)

Thiophene Selenophene Benzofuran Naphthalene

54
 Hantzsch-Widman rules for fully saturated and fully unsaturated heterocycles

1) Identify the hetroatom present in the ring and choose from the
corresponding prefix (e.g. thia for sulfur, aza for nitrogen and oxa for
oxygen).

2) The position of a single heteroatom control the numbering

in a monocyclic compound. The heteroatom is always
assigned position 1 and if substituents present are then
counted around the ring in a manner so as to take the
lowest possible numbers.

For example:
4
N1

2
3

CH3
 Hantzsch-Widman rules
3) A multiplicative prefix (di, tri, ect.) and locants are used
when two or more similar heteroatoms contained in the
ring( two nitrogen indicated by diaza) and the
numbering preferably commenced at a saturated rather
than an unsaturated atom, as depicted in the following
example: 1,3-diaza….
4
N3

5 2
1
N
H
4) If more than one type of hetroatoms present in the ring
the name will include more than one prefix with locants
to indicate the relative position of the heteroatoms.
 Atom prefixes have a strict order of priority (preference) in
which they are to be listed. For example,‘’Oxa’’(for oxygen)
always comes before ‘’aza’’ (for nitrogen) in a name (see
table 1).
 When combining the prefixes (e.g. oxa and aza) two
vowels may end up together, therefore the vowel on the
end of the first part should be omitted (oxaza).
 Hantzsch-Widman rules

 The numbering is started from the heteroatom of the highest priority

in such a way so as to give the smallest possible numbers to the other
heteroatoms in the ring (the substituents are irrelevant). For example
the prefix corresponding to the following compound is 4-Methyl-1,3-
Thiaza….
4
N3

5 2
1
S

5) Choose the appropriate suffix from (table 2) depending

on whether or not nitrogen atom is present in the ring,
the size of the ring and presence or absence of any
double bonds

6) Combine the prefix(s) and suffix together and drop the

first vowel if two vowels came together.
 Hantzsch-Widman rules
Table 2

Ring size N-present N-absent

Unsat sat Unsat sat

irine iridine irene irane

ete etane
ete etidine

ole olidine ole olane

ine a in ane

epine a
epin epane

ocine a
ocin ocane
a
9 onine onin onane

10 ecine a ecin ecane

a: means use the prefix perhydro followed by the fully
unsaturated name
 Hantzsch-Widman rules
 Examples
H
N

• This ring contains (N) Prefix is aza

• The ring is 3-membered and fully saturated
suffix is iridine
• By combining the prefix and suffix, two vowels
ended up together (azairidine), therefore the vowel on the end
of the first part should be dropped. This gives the correct
name: Aziridine
 III-Hantzsch-Widman nomenclature (IUPAC)

 Example 2:

 This ring contains nitrogen = aza-

 And oxygen = oxa-
 And is a fully saturated four-membered
 ring = -etidine
 Drop the vowels in oxa & aza
 The name = 1,2-Oxazetidine
 III-Hantzsch-Widman nomenclature (IUPAC)

 Example 3:

 This ring contains nitrogen = aza-

 And oxygen = oxa-
 And Unsaturated five-membered rings with nitrogen = –ole
 Oxygen is higher priority than nitrogen, so it is in position 1.
 The two nitrogens are therefore at positions 2 and 5
 The name = 1,2,5-Oxadiazole
 III-Hantzsch-Widman nomenclature (IUPAC)
 Example 4:

 This ring contains sulpher= thia-

 And oxygen = oxa-
 And saturated five-membered rings without nitrogen = –
olane
 Oxygen is higher priority than sulpher, so it is in position 1.
 Drop the vowel in thia
 The name = 1,3-Oxathiolane
 Hantzsch-Widman rules

N
H

The ring is 6-memberd, fully saturated with N

Prefix perhydro followed by the name of fully unsaturated 6-
memberd ring with nitrogen azine

Thus the full name is perhydroazine

 Hantzsch-Widman rules for partially unsaturated
heterocycles
 Partial unsaturation in heterocyclic
compounds can be indicated by one of the
following methods:
a) The position of nitrogen or carbon atoms which bear extra
hydrogen atoms must be indicated by numbers and italic capital
H (e.g. 1H, 2H, etc.) followed by the name of maximally
unsaturated ring.

4 3 4
3N 4 5 3
5 2 2S 1 5
O 1 6 1 2
1 N O O
H
2H, 3H-Oxole 1H-Azepine 5H-1,2,3-Oxathiazole 4H-Oxin
 Hantzsch-Widman rules for partially unsaturated
heterocycles

b) The words dihydro, or trihydro, or tetrahydro are used if two

or three or four atoms are saturated. These words are preceded
by numbers indicate the position of saturated atoms as low as
possible and followed by the corresponding fully unsaturated
Hantzsch-Widman name.
4 4 4

5 3 5 3 5 3
4 3

6 2 6 2 6 1 2 5
1 1 2
1
N N N
H H O

1,2-Dihydroazine 1,4-Dihydroazine 2,3,4,5-Tetrahydroazine 2,3-Dihydrooxole

Isomers have the same M.F.

but differ in the position of
the double bond
Hantzsch-Widman rules for partially unsaturated heterocycles
c) Alternatively, the partially unsaturated 4 and 5 rings (i.e.
rings contain one double bond) are given special Hantzsch-
Widman suffixes1 2
as in
3
table 3 and the double bond is
specified as ∆ , ∆ , ∆ , etc.. Which indicates 1 and ; 2 and 3; 3
and 4 atoms respectively have a double bond
(i.e. Name : ∆x + Prefix + special suffix )
( x= locant of the double bond)

Table 3

Ring size With N Without N

-etine -etene

-oline -olene
 Hantzsch-Widman rules for partially unsaturated heterocycles

 Examples
2 4 3 4 3

1 1 1
2 5 2 5 2
HN HN O 1 1
N O
2 2 H
 -Azetine  -Oxetene
2 -Oxolene
3
 -Azoline
3
4
NH 4 N 3

5 2 5 2
1 1
S N
4
H
 -1,3-Thiazoline 2 -1,3-Diazoline
 Some examples
6-(4-Hydroxyhex-1-en-1-yl)undeca-2,4-diene-7,9-diyne-1,11-diol

Undecane

2,4-diene-7,9-diyne-1,11-diol 4-Hydroxyhex-1-en-1-yl

68
2,3-Dichloro-6-[4-chloro-2-(hydroxymethyl)-5-oxohex-3-en-1-yl]pyridine-4-carboxylic acid

Pyridine-4-carboxylic acid
2,3-Dichloro-6-[...]-pyridine-4-carboxylic acid

4-chloro-2-(hydroxymethyl)-5-oxohex-3-en-1-yl

69
 4,4'-Dinitro-2,3'-[ethylenebis(sulfanediyl)]dicyclohexane-1,1’-carbaldehyde

Cyclohexanecarbaldehyde 2,3'-[……]dicyclohexane-1,1’-carbaldehyde

‘ethylenebis(sulfanediyl)’ denotes a bivalent linking group made up of a

central ethylene group attached to two sulfur atom. Thus-

70
Butane-1,3-diol or 1,3-Butanediol

71
72
 Carbofuran
Carbofuran is most commonly used pesticides that have 255 Trade name

IUPAC Name: PubChem: (2,2-Dimethyl-3H-1-benzofuran-7-yl)-N-methylcarbamate

Wikipedia: (2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)methylcarbamate
4 3
5 2
(CH3)H
6
N-methylcarbamate 7 1
benzofuran

N-Methylcarbamate

2,3-dihydro-1-benzofuran
Or, 3H-1-Benzofuran

73
 Carbendazim/carbendazole
Carbendazim is most commonly used fungicides that have 148 Trade name
IUPAC Name: PubChem: Methyl-N-(1H-benzimidazol-2-yl)carbamate
Wikipedia: Methyl(1H-1,3-benzimidazol-2-yl)carbamate
N-Methylcarbamate
Benzimidazole

Imidazole
(1H-isomer shown)

74
 Carbaryl/Sevin
Chemical Name: 1-Naphthyl-N-methylcarbamate
IUPAC Name : Naphthalen-1-yl-N-methylcarbamate
N-Methylcarbamate

Naphthalene

75
 Malathion/Carbafos/Sadophos
Chemical Name: O,O-Dimethyl-S-1,2-dicarboethoxyethyl dithiophosphate
IUPAC Name : Diethyl-2-[(dimethoxyphosphorothioyl)sulfanyl]butanedioate
S
2
1 3
4

Diethylbutanedioate (dimethoxyphosphorothioyl)sulfanyl

4
2 1 3

3 2
1
4

76
 Chlorpyrifos (It has 251 trade name)
Chemical Name: O,O-Diethyl-O-3,5,6-trichloropyridine-2-yl-phosphorothioate
IUPAC Name : O,O-Diethyl-O-[3,5,6-trichloro-2-pyridyl]phosphorothioate

4
5 3
Phosphorothioate

6 2

1
Pyridine
 Sumithion/Fenitrothion/Nitrophos
IUPAC Name : O,O-Dimethyl-O-(4-nitro-m-tolyl)phosphorothioate
Chemical Name : O,O-Dimethyl-O-(3-methyl-4-nitrophenyl)phosphorothioate
Phosphorothioate 6 5
1,2- Ortho (o)
4 1,3- meta (m)
1 1,4- para (p)

2 3

4-nitro-m-tolyl
 DDT
IUPAC Name : 1,1’-(2,2,2-Trichloroethane-1,1-diyl)bis(4-chlorobenzene)
Or, 1,1,1-Trichloro-2,2-bis(4-chlorophenyl)ethane
Chemical Name : p,p’-Dichlorodiphenyl trichloroethane

1,2- Ortho (o)

1,3- meta (m)
1,4- para (p)
2 1
3 3’ 3 3’
2 1 4’ 2’ 2 2 4’ 2’
4 4
1’ 1’
5 5’ 5 5’
1 1
6 6’ 6 6’
 Caffeine- It is an alkaloid
IUPAC Name : 1,3,7-Trimethylpurine-2,6-dione

Pyrimidine Imidazole Purine

1 6 7
5
8
2
4 9
3
 Gramine- It is an alkaloid
IUPAC Name : 1-(1H-indol-3-yl)-N,N-dimethylmethanamine

Indole
82
83