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NEET 2024 [LECTURE NOTE - CHEMISTRY [FIRST YEAR]

CHAPTER - 12
ORGANIC CHEMISTRY - NAMING

The word organic signifies life - ie, compounds directly or indirectly derived from living beings.

Berzelius - Vital force theory


Organic compounds are produced only under the influence of some mysterious force existing in living
beings, such a force cannot be created artificially in laboratories.
In 1828 - Wohler discovered urea by heating an inorganic compound.

NH4CNO 

NH2  CO  NH2
Later Kolbe synthesis acetic acid from C and H
Berthelot synthesised methane and acetylene
Thus vital force theory was rejected and it was shown that organic compounds should be synthesised
from inorganic source.
Organic chemistry
It is the study about carbon and its compounds or hydrocarbons and their derivatives.
Hydrocarbon classsification
On the basis of nature of carbon skelton
1. Acyclic or open chain compounds
2. Cyclic or closed chain compounds
I. Acyclic or open chain compounds
Compounds containing open chains of carbon atom in their molecule. It may be straight or
branched. These are also known as aliphatic compounds. Further divided into
 Saturated hydrocarbon or alkanes or paraffins
Compounds containing carbon carbon single bond (C–C)
 Unsaturated hydrocarbon
 Alkenes or Olefins - Containing C = C
 Alkynes or Acetylene - Containing C  C
II. Cyclic or closed chain compounds
Compounds containing one or more closed chains or rings of atom

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Further divided into


a. Homocyclic :
Rings which are made up of only one kind of atom. Mainly C atom- known as carbocyclic.
i. Alicyclic compounds.
Rings containing 3 or more carbon atom

CH2 CH2 CH2

CH2 CH2 CH2 CH2

ii. Aromatic compounds.


From the greek word Aroma - Fragrant smell
a. Benzenoid aromatic compounds
Aromatic compounds containing one or more fused or isolated benzene rings.

OH CH3

Benzene
Phenol Toluene

Fused Isolated

Naphthalene Biphenyl

Anthracene Ter-phenyl

b. Non-benzenoid aromatic compound


Compounds that does not contain benzene ring but contain other highly unsaturated rings.

O O
OH

Tropone Tropolone
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Heterocyclic compounds
Cyclic compounds containing one or more hetero atom in their rings.
a. Alicyclic heterocyclic
Aliphatic cyclic compounds containing one or more hetero atom

O N
Oxirane Tetra hydro furan H
Tetra hydro pyrrole

b. Aromatic heterocyclic
Aromatic cyclic compounds containing one or more hetero atom.

O N S N
Furan Thiophene Pyridine
H
Pyrrole

Hydrocarbon

Acyclic Cyclic

Saturated Unsaturated Homocyclic Heterocyclic

Alicyclic Aromatic
Alkene Alkyne

Benzenoid Non-benzenoid

Fused Isolated

Alicyclic
Aromatic
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Nomenclature
System of naming
 Trivial system
 IUPAC system
TRIVIAL SYSTEM
Also known as common names.
For representing saturated hydrocarbon mainly 3 prefixes are used.
1. n
n - stands for normal or straight chain

CH 3 CH 2 CH 2 CH 3 CH3 CH2 CH2 CH2 CH3


n-butane n-pentane
2. Iso
The second carbon containing one methyl group

CH3 CH3

CH3 CH CH3 CH3 CH CH2 CH3


Iso-butane Iso-pentane

3. Neo
Second carbon atom containing 2 methyl group

CH3 CH3

CH3 C CH3 CH3 C CH2 CH3

CH3 CH3
Neo-pentane Neo-hexane

Saturated hydrocarbon contains 4 types of carbon atoms.

CH3 CH3

CH3 C CH CH2 CH3

CH3
Quarternary
30 20 10

Alkane 
H
 Alkyl

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CH 
4
H
 CH3 - Methyl
methane

CH3  CH3 


H
 CH3  CH2 - Ethyl

CH3  CH2  CH3 


H
 CH3  CH2  CH2 - Propyl

CH3  CH2  CH3   CH3 CH CH3 - Iso-propyl


H

CH3 CH3

CH3 CH CH3 


H
 CH3 CH CH2 - Iso-butyl

CH3 CH3

CH3 CH CH3 


H
 CH3 C CH3 - Tert-butyl

IUPAC SYSTEM
In 1892 an International Chemical Congress was held at Geneva, they started a new naming
system for organic compounds known as Geneva system of Nomenclature. This system was further
modified as IUPAC nomenclature.
Rules
Each systematic name contain
 Word root;  Suffix;  Prefix
Word root :
It denote no.of carbon atoms in the parent chain.
Primary suffix
It shows saturation or unsaturation in a chain
Nature of C-chain 1° suffix 2° suffix
C–C –ane Alkane
C=C –ene Alkene
CC –yne Alkyne
Secondary suffix
It indicates the presence of a particular group (functional group)
Functional group 2° suffix
Alcohol –ol
Aldehyde –al
Ketone –one

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Primary prefix

It is used to distinguish cyclic from acyclic compound. In case of carbocyclic compound, 1°


prefix cyclo is used.

Secondary prefix

It denote the presence of substitutent or side chain on the parent chain.

–X halo

–NO2 Nitro

–R Alkyl

–OR Alkoxy

The complete IUPAC name of compound contain:

2° prefix + 1° prefix + word root + 1° suffix + 2° suffix

Eg : 2-methyl butanoic acid  Methyl  2° prefix : but - word root : an  1° suffix : oic acid-2° suffix
fix

NAMING OF COMPLEX COMPOUNDS

 Longest chain rule

Select the longest continuous chain of carbon atom in the molecule. The continuous chain of carbon
atom is called parent chain or main chain. Carbon atom which are not included in the parent chain are
considered as substituent or side chain.

CH3
Derivative of pentane
CH3 CH2 CH CH2 CH3

 Two or more carbon chains of equal length, then the selected chain should contain maximum no.of
side chain or substituent.

CH3
CH3
CH3 C CH3
H3C C CH3

CH3 CH2 CH CH2 CH3 CH3 CH2 CH CH2 CH3

1- side chain 3- side chain (correct way)

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CH3

CH3 CH CH2

CH CH CH3

CH3 CH CH3

CH3
Derivative of heptane

 Numbering of carbon chain

The carbon atoms of longest continuous chains are numbered. The no that indicate the position
of substituent is known as Locants.

The carbon atom carrying first substituent get the lowest possible locants.

1 2 3 4 5

CH3 CH CH2 CH2 CH3 2-Methylpentane (correct); 4-methyl pentane (wrong)


3 2 1
5 4

CH3

Two or more similar substituent is attached to the parent chain, lowest set of locant is preferred. The
lowest set is determined by first point of difference rule. The rule says “when two or more different
set of locants containing same no.of term is possible, then the set of locants is compared term by
term with other set, each set in order of increasing magnitude. The set of locant is preferred which
has a lower no.at the first point of difference”.

6 5 4 3 2 1
1 2 3 4 5 6
CH CH2 CH CH CH3 CH3 CH CH2 CH CH CH3
CH3

CH3 CH3 CH3 CH3 CH3 CH3


(2, 3, 5) lowest set
(2, 4, 5) 2,3,5-Trimethyl hexane

 If there are different alkyl substituents attached to the parent chain, their names are written in
alphabetical order.

1 2 3 4 5
CH3 CH CH CH2 CH3 - 3-Ethyl-2-methyl pentane

CH3 CH2 CH3

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 If there are different alkyl substituent at equivalent positions the numbering is done in such a way that
the substituent which comes first in alphabetical order get lowest possible number.

1 2 3 4 5 6
CH CH2 CH CH CH
2 2
CH3 3-Ethyl-4-methylhexane
6 3 5 4 3 1

CH3 CH2 CH3

Naming of complex alkyl substituents

If the substituent on the parent chain is a complex, the carbon atom of this group attached to the
parent chain is given as 1.

1 2 3 4 5 6 7
CH3 CH2 CH2 CH CH2 CH2 CH3 4- (1-methyl ethyl)heptane
or
1 CH CH3 4-isopropyl heptane

2 CH3

1 2 3 4 5 6 7 8 9
CH3 CH2 CH2 CH2 CH CH2 CH2 CH2 CH3 5- (2-methylpropyl)nonane
or
1
CH2 5-isobutyl nonane

2 CH CH3

3 CH
3

 While deciding the alphabetical order of various substituents, the name of complex substituent is
considered to begin with first letter of complex name.

1 2 4 5 6 7 8 9 10 11
3
CH3 CH2 CH2 CH2 CH CH2 CH CH2 CH2 CH2 CH3

1 CH CH3 CH2 CH3

2 CH CH3 5-(1, 2-Dimethyl propyl)-7-ethylundecane

3 CH
3

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CH3
1 2 3
H3C C CH2 CH3
1 2 4 5 6 7 8 9
3
CH3 CH2 CH2 CH2 C CH2 CH2 CH2 CH3

CH2 CH
2
CH3
1 3

CH3
5-(1, 1-Dimethyl propyl)-5- (2-methylpropyl)nonane

 If two complex substituents are of equal length, then the complex substituent with larger no.of alkyl
group form a part of longest carbon chain while the other one considered as complex substituents.

CH2 CH3
6 5 1 2 3
10 9 8 7 4
CH3 CH2 CH2 CH2 CH2 CH CH2 CH CH2 CH3

4 CH2

H3C 3C
CH3

CH2 CH3
2 1

5-(2-Ethylbutyl)-3,3-dimethyldecane

 If same complex substituent occur more than once prefix such as bis(2), tris(3), tetra kis (4)..... etc
are used before the name of complex name.

CH3

CH CH3
6 5 4 2 1
3
CH3 CH2 CH2 C CH CH3

CH3
H3C CH

CH3

2-methyl-3,3-bis(1-methylethyl) hexane

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Naming of unsaturated compound


 Longest chain of carbon atom is selected to included the double or triple bond, even if it is not the
actual longest chain

6 5 4 3 2 1

CH3 CH2 CH2 CH CH CH2

CH2 CH2 CH3

 If more than one double or triple bond is present in the molecule, the selected chain should contain
maximum number of such bonds.

7 6 5 4 3 2 1
CH3 CH CH CH2 CH CH CH2

CH2 CH2 CH3

 The parent chain is numbered in a manner to give lowest number to that carbon atom linked by a
double or triple bond.

CH3 CH3

CH3 CH CH CH CH2 CH CH3


1 2 3 4 5 6 7

4,6-Dimethyl hept-2-ene

 If a compound contains both double or triple bond, such compounds are named as Alkenynes.
5 4 3 2 1
CH3  C  C  CH  CH2 Pent-1-en-3-yne

5 4 3 2 1
CH  C  CH2  CH  CH2 Pent-1-en-4-yne

5 4 3 2 1
CH3  CH  CH  C  CH Pent-3-en-1-yne

6 5 4 3 2 1
CH  C  CH  CH CH  CH2 Hexa-1,3-dien-5-yne

In some cases all the double and triple bond are not included in the parent chain, in such cases,.......

CH2   Methylene CH2  CH   vinyl/ ethenyl

CH3  CH   Ethylidene CH  C   Ethynyl


are used

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CH2
1 2 3 4 5
CH2 CH C CH CH2

3-Methylene penta-1,4-diene

Naming of compounds containing one functional group.

 Longest chain
The selected parent chain should be the one containing functional group.

CH3 CH2 CH2 CH CH2 CH3

CH2 OH

 Numbering of carbon chain


The carbon linking to functional group get the lowest possible number.
When a chain terminating group such as –CHO, –COOH, –COOR, –CONH2, –CN are present as
functional group it must be assigned as number 1.

 The last ‘e’ of the 1° suffix is dropped and the secondary suffix corresponding functional group is
added.

 Numerical prefix like di, tri, tetra etc are attached before the suffix name if the same functional group
occur more than once.
Alkyl halide
R–X CN : Alkyl halide
IUPAC : Haloalkane

CH3  CH2  Br  Ethylbromide ; Bromoethane

CH3

CH3 CH Cl  Isopropyl chloride : 2-chloropropane

Alcohol
R–OH CN : Alkylalcohol
IUPAC : Alkanol

CH3 -OH  Methanol; Methylalcohol


CH3 -CH2 -CH2 -OH  Propanol; Propylalcohol

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Ether
R–O–R CN : Dialkylether
IUPAC : Alkoxy alkane

CH3  O  CH3  Dimethyl ether CH3  O  C2H5  Ethyl methyl ether


Methoxy methane  Methoxy ethane
Carboxylic acid
–COOH
CN : Obtained from the source from which they were isolated or present in large quantity.
IUPAC : Alkanoic acid

H  COOH  Formic acid CH3COOH  Acetic acid


Methanoic acid Ethanoic acid

CH3CH2COOH  Propionic acid CH3CH2CH2COOH  Butyric acid


Propanoic acid Butanoic acid
Aldehyde
- CHO
CN : Replace the terminal -ic acid in corresponding acid by aldehyde
IUPAC : Alkanal
H – CHO  Formaldehyde ; Methanal
CH3CHO  Acetaldehyde ; Ethanal
Ketone

C
CN : Dialkylketone
IUPAC : Alkanone
CH3 – CO – CH3  Dimethyl ketone (Acetone) ; Propanone
Amine
–NH2
CN : Alkylamine
IUPAC : Alkanamine

NH2

CH3 -NH2  Methyl amine CH3 CH CH3 : Isopropylamine


Methanamine Propan-2-amine
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CH3  NH  CH3  N  methylmethana min e

CH3 CH2 N CH3  N,N-Dimethyl ethanamine

CH3
Amide

C NH2
CN : replace -ic acid by amide
IUPAC : Alkanamide

H C NH2  Formamide : Methanamide

CH3 CH2 C NH CH3  N-Methylpropanamide


Acid halide

C X
CN : Replace -ic acid by -yl halide
IUPAC : Alkanoyl halide

H C Cl  Formyl chloride : Methanoyl chloride

CH3 C Cl  Acetyl chloride : Ethanoylchloride


Acid anhydride

O O

C O C CN : Replace acid by anhydride; IUPAC : Alkanoic anhydride

O O

H C O C H  Formic anhydride : Methanoic anhydride

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O O

CH3 C O C CH3  Acetic anhydride : Ethanoic anhydride

O O

H C O C CH3  Acetic formic anhydride : Ethanoic methanoic anhydride

Ester

C O

CN : Replace - ic acid by ate

IUPAC : Alkyl alkanoate

H C O CH3 : Methyl formate : Methylmethanoate

CH3 C O CH3 : Methylacetate : Methylethanoate

Naming of compounds containing more than one functional group

A compound containing more than one functional group or more than one multiple bond is considered
as poly functional compounds.

In such compounds one functional group is considered as principal functional group and others are
substituents. The principle functional group is mentioned by its suffix name and substituent is mentioned
by its prefix name

Rules

 Select the principal functional group

 Select the parent chain, it include principal functional group (PFG)

 Numbering the chain, PFG get lowest possible number.

Numbering preference order PFG      substituent

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Functional group Prefix name Suffix name

 COOH Carboxy -oic acid

 SO 3 H Sulpho Sulphonic acid

O O
- -oic anhydride
C O C

O
Alkoxy carbonyl -oate
C O R

O
Halocarbonyl -oyl halide
C X

O
Carbamoyl -amide
C NH 2

CN Cyano -nitrile


O
Formyl -al
C H

O
Keto/oxo -one
C

 OH Hydroxy -ol

SH Mercapto thiol

NH 2 Amino -amine

C  C  - alkene

C  C  - alkyne

R Alkyl -

 OR Alkoxy carbonyl -

 NO 2 Nitro -

 NO Nitroso -

N  N  Diazo -

X halo -

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CH3 CH C COOH
4 3 2 1 3-Methyl-2-oxobutanoic acid
CH3

4 3 2 1

CH2 CH2 CH CONH2


2-Fluoro-4-hydroxy butanamide
OH F

3 2 1
NC CH2 CH2 COOH 3-Cyano propanoic acid

O NH 2

CH3 C CH CH COOH
5 4 3 2 1 2-Amino-3-hydroxy-4-oxopentanoic acid
OH

Poly functional compounds containing more than two like functional group
If an unbranched carbon chain is directly linked to more than two like functional group, the
compound is named as the derivative of parent alkane, the carbon atoms of like functional group do
not include in the numbering, in such case suffix like Tricarboxylic acid (3COOH), Tricarbaldehyde
(3CHO), Tricarbonitrile (3CN) etc are used.

COOH CHO
3 2 1
CH2 CH CH2 CH2 CH2 CH CH2
1
4 3 2
COOH COOH CHO CHO

Propane-1,2,3-tricarboxylic acid Butane-1,2,4-tricarbaldehyde

COOH OH COOH

CH2 C2 CH2
3 1

COOH
2-Hydroxy propane-1,2,3-tricarboxylic acid

If more than 2 like functional group is not directly linked to the carbon chain, then the carbon
atoms of functional group directly attached to the parent chain is included in numbering, the other
one is considered as substituent group.

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4 3 2 1

CH2 CH CH2 COOH

COOH CH2 COOH


5

3-(carboxymethyl)-pentane-1,5-dioic acid

1
7
CHO CHO
5 4 3 2
6
CH2 CH2 CH CH2 CH2

CH2 CHO

4-(Formylmethyl)heptane-1,7-dial
4-(2-oxoethyl)heptane-1,7-dial

Naming of alicyclic compound


 Cycloalkane
Names obtained by adding the prefix ‘cyclo’ before the name of a corresponding alkane.

Cyclopropane Cyclohexane

Alkyl substituted cycloalkane are known as “alkylcycloalkane”.


If same substituents are more than one is present numerical prefix di, tri, tetra, etc are used.
If different substituents are present their names are written in alphabetical order. Numbering is done
in such a way that substituent which comes first in alphabetical order get lowest possible number.
Numbering does not violate lowest set of locant rule.

CH3
CH2 CH3
1
2
3
CH3
Ethylcyclopentane 1,3-Dimethyl cyclohexane

CH3

3 1
2 2

1 3
CH2 CH3
1-Ethyl-3-methyl cyclopentane 3-Ethyl-1,1-dimethyl cyclopentane

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CH3

1
C2H5
2
3
4

CH3
2-Ethyl-1,4-dimethyl cyclohexane

The ring containing more or equal number of carbon atom than alkyl group, then the compound is
named as derivatives of ring.

CH2 CH2 CH3


CH2 CH2 CH3

Propyl cyclobutane Propyl cyclopropane

If the side chain contains more no.of carbon atom than the ring, compound is derivative of side chain.

1
CH3
1 2 3 4 5
CH3 CH CH2 CH2 CH3 2
CH CH2 CH3
3 4

2-Cyclobutyl pentane
2-Cyclopropyl butane

If more than one alicyclic ring is directly attached to the parent chain, compound is derivative of
parent chain.

CH2
2

Dicyclopropylmethane 1,2-Dicyclohexyl ethane

Cycloalkene and cycloalkyne


Adding the prefix cyclo before the name of the corresponding alkene or alkyne.

Cyclopentene Cyclohexyne

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In case of substituted cycloalkene and cycloalkyne the number of double and triple bond get lowest
possible number 1 and 2 and the substituent get lowest possible no at first point of difference rule.

CH3
3 Cl
2 3

1 1 2

3-Chlorocyclopentyne
3-Methylcyclohexene

Alicyclic compounds containing functional group


Alicyclic alcohol, amines, ketones ....... are named as corresponding aliphatic compounds by
prefixing the word cyclo.

OH
NH2
O

Cyclohexanamine Cyclopentanone
Cyclopentanol
If an alicyclic ring is directly attached to a carbon containing functional group, the carbon atom of the
functional group is not included in the parent chain. In such cases following suffix and prefix are used
Functional group Prefix Suffix
–COOH Carboxy Carboxylic acid
–CHO Formyl Carbaldehyde
–COX Halocarbonyl Carbonylhalide
–CN Cyano Carbonitrile
–CONH2 Carbamoyl Carboxamide
–COOR Alkoxy carbonyl Alkylcycloalkane carboxylate

COOH
CHO
CONH2

Cyclohexane carboxylic acid Cyclopentane carboxamide Cyclobutane carbaldehyde

If a ring containing a multiple bond and the side chain containing functional group, then the
compound is derivative of side chain.

3 2 1
CH3 CH CH2 OH

1
2
3
2-(Cyclopent-3-enyl) propanol
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If the ring and side chain contains functional group then the compound is named as derivatives
of ring or side chain which will contain principle functional group.

4 3 2 1
4
HO CH2 CH2 CH2 COOH
1

3 2

4-(4-Hydroxycyclohex-2-enyl)butanoic acid

If the ring and side chain contains some functional group, the compound is named as a derivative
of side chain or the ring, which containmore number of carbon atom.

OH
6 1
OH 2 7
CH2 CH3 OHe 3 1 CH2 CH2 CHO
1
2 CH2 CH 3 4
5
1 2

7-(3-Formylcyclopentyl)heptanal
2-(2-Hydroxybutyl)cyclohexanol

O 4

6
CH3 1
2 1 2
3

3 5
4 CH3 OH
5 ,6 Dimethyl cyclo hex 2  en  1  one 3 Cyclohexylbutan 2  ol

Nomenclature of Aromatic compound


Compounds are derivatives of benzene. The names are obtained by “substituent name + benzene”.
Most of the compounds have typical names.

CH3 OH

Methylbenzene (Toluene) Hydroxybenzene (phenol)

NH2 Cl

Aminobenzene (Aniline) Chlorobenzene

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NO2

Nitrobenzene Cyclopropyl benzene

Special case

CHO
COOH

Benzene carboxylic acid


Benzene carbaldehyde
(Benzoic acid)
(Benzaldehyde)

CONH2 COX

Benzene carboxamide Benzene carbonyl halide


(Benzamide) (Benzoylhalide)

 If more than one substituents are present names are written in alphabetical order
 If any of the substituent give a special name to the compound, then compound is derivative of that
special name.
 Numbering does not violate lowest set of locant rule.

Cl
1
2
1-Chloro-3-nitrobenzene
3
NO2

Br
3
2
1 3-bromo toluene, (m-bromotoluene)
CH3

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(The position number is indicated in IUPAC system but position name is indicated in common system)

NH2 CH3

4 2
OH
3 4-Amino phenol 1 2-Methyl phenol
1
2 p-Amino phenol o-methyl phenol

OH

OH
COOH
2-Hydroxybenzoic acid
o-hydroxy benzoic acid (salicylic acid)

If benzene ring is attached to an aliphatic chain containing a multiple bond or functional group or
substituent, benzene ring is considered as a substituent group known by phenyl.

3 2 1
CH2 CH CH2

3-Phenyl prop-1-ene

5
CH3
2 1
4 3
CH CH CH2 COOH

OH

3-Hydroxy-4-phenylpentanoic acid

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