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1
IIT-JEE ChEmIsTry by N.J. sIr OrGANIC ChEmIsTry
NOMENCLATURE
Rule-1 Select the longest chain
Q.1

Q.2 Q.3

Q.4

Q.5

Rule-2 If 2-chains are same length select chain with more number of branches.
Q.1

Q.2 Q.3

Rule-3 General formula
Prefix(s) + Word Root + Suffix (P) + Suffix (s)
Word Root :- Represents Number of carbon atoms in main chain.
1. No. of Carbon atoms Word Root
1 meth
2 eth
3 prop
4 but
5 pent
6 hex
7 hept
8 oct
9 non
10 dec
11 undec
12 dodec
13 tridec
14 tetradec
15 pentadec
16 hexadec
17 heptadec
18 octadec
19 nonadec
20 eicoso
30 tricont
40 tetracont
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2
Rule-4 Side chains are represented as alkyl group
C
n
H
2n+1
÷÷ alkyl
CH
3
—-
methyl (Me)
CH
3
— CH
2
— Ethyl (Et)
CH
3
— CH
2
— CH
2
— propyl (pr)
CH
3
— CH
2
— CH
2
— CH
2
— butyl (bu)

CH
3
— CH — (1-methyl ethyl)
|
CH
3



CH
3
— CH — CH
2
— (2-methypropyl)
|
CH
3


CH
3

|

CH
3
— C — (2,2,-dimethyl ethyl)
|
CH
3


Rule-5 Alkyl groups are used as prefixes

Rule-6 Numbering should be done such that 1
st
locant gets lowest possible number.


1
2
3
4
5
6

1
2
3
4
5
6


1
2
3
4
5
6
7


1
2
3
4
5
6
7

(Correct) (Incorrect) (Correct) (Incorrect)



1
2
3
4
5
6
7


1
2
3
4
5
6
7

(Incorrect) (Correct)
3-methyl 3-ethyl
5-ethyl 5-methyl

Rule-6
If first locant same then look for sum rule:-


1
2
3
4
5
6
7


1
2
3
4
5
6
7

2 + 5 + 6 = 13 2 + 3 + 6 = 11
Higher sum lower sum
Incorrect Correct
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3

7

1
2
3
4
5
6
8

7

1
2
3
4
5
6
8

3 + 5 + 6 = 14 3 + 4 + 6 = 13
Incorrect Correct

Rule-7 Suffix (P) ÷÷ Primary suffix
Alkane ÷÷ ane
Alkene ÷÷ ene
Alkyne ÷÷ yne


1
2
3
4
5
6

Prefix(s) + Word Root + Suffix (p) + Suffix (s)
3-methyl hexane

Remember ÷÷
Number, number
Number – word, number letter
No gap between 2 letters

Rule-8 Multiple substituents are represented as di, tri, tetra, penta etc.


1
5
6
4
3
2


1
2
3
4
5
6

2,3-dimethyl hexane 2,3, 4-trimethyl hexane

Rule-9 Prefixes are arranged in alphabetical order


1
2
3
4
5
6
7


1
2
3
4
5
6
7
4-ethyl-2, 3-dimethylheptane 3,5-diethyl-4-methylheptane
di, tri etc. are not considered for arranging in alphabetical order

Rule-10 Complex Substituent:-
For multiple substituents bis, tris, tetrakis, pentakis are used.

1
2
3
4
5
7
6

9
2
3
4
5 7
6 8
1

4-(1-methylethyl)heptane 4,5-bis-(1-methylethyl)nonane


1
2
3
4
5
6 8
7
9

4,5-bis-(1-methylpropyl)nonane

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4

Practice questions:÷
Q.1

Q.2

Q.3

Q.4

Q.5 Q.6

Q.7

Q.8

Q.9

Nomenclature or Spiro Compound:-

:÷ ÷ only one common carbon between 2 cyclic rings

÷ Numbering will be done from neighbouring position of common carbon.

2
3
5
4
6
8 9
7
1

÷ General formula
Spiro (x.y) + word root + Suffix(p) + Suffix(s)

X s Y ÷ Numbering is done in increasing order

2
3
5
4
6
8
7
1
Spiro [3.4] octane

Q.1
2
3
5
4
6
8
7
1
Q.2
2
3
5
4
6
8 7
1

5 – methylspiro[3.4]octane 6,7 – dimethylspiro[3.4] octane

Q.3
2
3
5
4
6
8 9
7
1
Q.4
2
3 5
4
6
8
7
1

1,2,3 – trimethylspiro[4.4] nonane 5 – methylspiro[3.4] octane


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5

Q.5
2
3
5
4
6
8
7
1
Q.6
2
3
5
4
6
8 9
7
1

Spiro [3.4] oct – 6 – ene 2 – (1-methylethyl)spiro[4.4]nonane

Q.7
Q.1 Q.2

Nomenclature of Functional group containing Compound
: ÷÷
Functional group Name Suffix(s) Prefix
1. O
||
— C — OH
Carboxylic Acid Oic acid (When Carbon
included) Carboxylic acid
(When Carbon is not
included)
Carboxy
2. — SO
3
H Sulphonic acid Sulphonic acid Sulpho

3. O
||
— C
O
— C
||
O
Anhydride Oic anyhdride (Carboxylic
anhydride)

— —
4. O
||
— C — OR
Ester Alkyl…….Oate Alkoxy Carbonyl
5. O
||
— C — Cl
Acid halide Oyl chloride (Carbonyl
Chloride)
haloformyl
6. — C — NH
2
||
O
Amide Amide (Carbamide) Carbamoyl
7. — CN Cyanide Nitrile (Carbonitrile) Cyano

8. — NC Isocyanide Carbylamine Isocyano

9. O
— C
H
Aldehyde al (Carbaldehyde) Formyl
10. O
||
— C —
Ketone One Keto/oxo
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6
11. — OH Alcohol Ol Hydroxyl
12. — SH Thiol Thiol Mercapto
13. — NH
2
Amine Amine Amino
14.
— C = C

Alkene — (ene) Sufffix(p)
15. — C ÷ C — Alkyne — (Yne) Suffix(s)
16. — NO
2
— — Nitro
— NO
— F




Nitroso
Fluoro


Nomenclature of Functional group containing Compound
: ÷÷

Functional group Name Suffix(s) Prefix
— Cl — Chloro
— Br — Bromo
— I — Iodo
— O — Epoxy
= N — Diazo
— OR — Alkoxy


Nomenclature of Bicyclo compound
:÷ Bridge positions
Prefix(s) + bicycle [x.y.z.] + word root + suffix (p) + suffix (s)
X Y Z > >
÷ Numbering is done from bridge head postion
÷ Numbering is done in decreasing order of carbon atoms
(1) (2) (3) (4)

(5)
(6) (7)

(8)

(9) (10)
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7
Ans:- (1) bicycle [2.2.2] octane (2) bicycle [2.2.1] heptane
(3) bicycle [1.1.0] butane (4) 7 – methylbicyclo [2.2.1] heptane

Nomenclature of alkens:÷
÷ Select chains such that = is included in main chain

÷ If more than one = are present, maximum double bonds should be included.

Q.1
1
2
3
4
5
6
Q.2
1
2
3
4
5
6

3–methyl hex–1–ene 3–ethyl hex–1–ene

Q.3
1
2
3
4
5
6
Q.4
1
2
3
4
5
6

3–ethyl –5–methylhex–1–ene 3–propylhexa–1, 5-diene

÷ In case of diene, triene and SD on the letter ‘a’ is placed after word root.

Q.5
5
4
3
2
1
6

Q.6
3
5
4
6
7
1
2

3,4-dipropyl hexa – 1, 4 – diene 4 – methylidene – 5 – propylhepta – 1,5 – diene



Methylidene (doubly bonded substituents are named as methyl + idene)

Ethylidene

5
4
3
2
1
7
6

4 – ethenyl – 5 – propyl hepta – 1, 5 – diene

Nomenclature of alkynes:-
Suffix (p) ÷÷ yne

Q.1
1
2
3
4
5
Q.2
1
2
3
4
5
6
Q.3 1
2
3 4
5 6
7

Pent – 1 – yne 3 – propylhex – 1 – yne hept – 1, 5 – diyne

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8
Q.4 H
3
C — C ÷ C — CH
2
— CH
CH
3
— CH
3
Q.5 H
3
C — C.C — CH — (Et)
2

Q.6 (CH
3
— CH
2
)
2
— CH — CH — (CH
2
— CH
3
)
2


Q.7
H C = CH — CH — CH — C CH
2 2 2
1 2 3 4 5 6

Hex – 1 – ene – 5 – yne X
Hex – 1 – en – 5 – yne

If ene and yne are present at same number alphabetical order is considered.
X a,i,o,u, y ÷ Remember

Q.8
H C — CH = CH — CH — CH — C CH
3 2 2
1 2 3 4 5 6 7

Hept – 1 – yne – 5 – ene X
Hept – 5 – ene – 15 – yne X
Hept – 5 – en – 1 – yne

Q.9 HC C — CH — C — CH = CH
2 2
1 2 3 4 5 6
CH
2

Q.10
2
3 5
4
6 8
7
1

3 – methylidenehex – 1 – en – 5 – yne Octa – 1, 3, 5, 7 – tetraene

Q.11 Q.12

Nomenclature of Alcohal:-
1.
OH
2.
OH

3.
HO

4.
OH

5.
Br
OH

6.
OH


Ans. 1. hexan – 2 – ol 2. 5 – propylhex – 5 – en – 2 – ol
3. 2 – ethenylhex – 5 – enol 4. 3-ethyl-5-methylidene oct – 7 – en – 2 – ol
5. 5-bromocyclo hex – 2 – en – 1 – ol 6. 5-cyclohexyl cyclopent – 2- en – 1 – ol

Q.1
O O
Me H
Q.2
Cl
O–H
Br ON

Q.3
H–O

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9
Q.4
OH
OH Br

Q.5
Cl
OH

Q.6
OH
Br Cl


Q.7
OH
Cl OH


Ans. 1. 4-methoxy hexan-2-ol 2. 3-bromo-2-chloro-4-nitrosocyclopentan-1-ol
3. 3,5-dicyclo propyl hexan-1-ol

Nomenclature of carboxylic acid:÷

÷ If carbon included in main chain
Suffix (s) ÷÷ Oic acid

÷ If carbon non included in main chain
Suffix (s) ÷÷ Carboxylic acid

1. H C — CH — C — OH
3 2
O
1 2 3
÷÷ propane-1-oic acid X
propan-1-oic acid

2. H C — CH — CH — C — OH
3 2
O
1 2
3
CH
3
4
÷÷ 3-methylbutane-1-oic acid X
3-methylbutanss-1-oic acid

3.
1
2
3
4
C — OH
O
5
6

÷÷ cyclohexane-1-carboxylic acid (correct new)
÷÷ 1-cyclohexylmethan-1-oic acid (old)

4.
1 2
CH — COOH
2
÷÷ 2-cyclohexylethan-1-oic acid

5.
COOH
COOH
÷÷ cyclohexane-1,3-dicarboxylic acid
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Q. H C CH CH
3 2
1 2 3
COOH COOH COOH

Propane-1, 2, 3-tricarboxylic acid (New)

Q.
CH —COOH
2
COOH
COOH
1
2
3
4
5
6

2-carboxymethyl cyclohexane-1, 4 dicarboxylic acid

Q.
COOH
COOH
HOOC

Cyclohexane 1, 3, 5-tricarboxylic acid

Q.
COOH
1
2
3
4
5
6
7

Bicyclo [2.2.1] heptane-2-carboxylic acid

Q. COOH
1
2
3
4

Bicyclo [1.1.0] butane-2 carboxylic acid

Q. COOH
1
2
3
4
5
6
7

Spiro [.3] heptane-2-carboxylic acid

Nomenclature of aldehyde:-
C — H
O
al ÷÷ suffix(s)


H H
C
O
Methan-1-al
1.
O
H

2.
H
O

Ans. (1) 2,4,5 trimethyl hexan-1-al (2) Octa-3,5,7-trien-1-al
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11
Q.
O
H
Cl
Br
Q.
C
H
O

Q.
O
O
C—H
C—H


Q.
O O
C—H H—C
H C CH
2 2

Q.
H C CH CH
2 2
C C C
H H H
O O O


Q.
CHO

Q.
CHO
CHO
CHO


Nomenclature of ketones:-
(1)
O
propane-2-one (2)
O

butan-2-one
(3)
O
(4)
O

(5)
O

(6)
O Cl
Br
(7)
O
(8)
Cl
O


Nomenclature of cyclic ethers:-
(1)
O
H C — CH
2 2
1,2-epoxyethane (2)
O
H C — CH — CH
2 2
1,2-epoxypropane
(3)
O
(4)
O
(5)
O
(6)
O


Nomenclature of sulphonic acid:-
— SO
3
H group.
(1)
SO H
3
cyclohexanesulphonic acid
(2)
SO H
3
1
2
3
4
5
6
hexane-2-sulphonic acid
(3)
SO H
3
1
2
3
4
butane-1-sulphonic acid
Nomenclature of Isocyanide (–NC):-
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(1) H
3
C — CH
2
— N
=
÷ C ethan-1-carbylamine

(2)
NC

cyclohexane-1-carbylamine

(3)
NC
1
2
3
4
5

pentan-2-carbylamine

(4)
C–OH
O
NC
1
2
3
4

2-ethyl-3-isocyanobutan-1-oic acid

(5)
SO H
3
1
2
3
4
5
NC

4-isocyanopentane-1-sulphonic acid

Nomenclature of thiol. (— SH):-
(1)
SH
cyclohexanethiol
(2)
SH
1
2
3
4
5

pentane-2-thiol

(3)
SH
1
2
3
4
5
6
4-methylcyclohexane-1-thiol

(4)
OH
SH
2
3
5
4
6
8
7
1
7-merceptospiro [3.4] heptan-6-Ol

(5)
OH
SH
(6)
SH
SH
(7)
SH
Cl OH

(8)
SH
Cl
OH Br

Nomenclature of compounds containing multiple functional group:-
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:÷ (1)
CH=CH
2
OH O
(2)
O
O
Cl
Br
O–H
ON


(3)
C
O
HO–C
H
O

(4)
C
H
O

Ans. (1) 5-ethenyl-6-hydroxyheptan-2-one (2) 3-bromo-4-chloro-7-nitroso-6-oxoheptan-1-oic acid
(3) 6-methyl-7-oxoheptan-1-oic acid (4) 2-propylheptan-1-al

Q.1
1
2
3
4
5
C
H
O
O
H–O
6
7
8

Q.2
NO Cl
Br
O
H CO
3
O
H

6-formyloctan-1-oic acid

Q.3
O
C
C–H
OH
OMe CH
3
O
H N
2
Q.4
C
HO
O
CH
Cl
CH = CH
CH
Br
C
O
O–H

Q.5
NH
2
OH
O
H N
2

Ans. Q.1 6-formyloctan-1-oic acid
Q.2 Methyl-3-bromo-4-chloro-2-nitroso-6-oxo-hex-4-enoate
Q.3 4-hydroxy-3-methoxy-7-methyl-8-oxo-oct-5-enamide
Q.4 2-bromo-5-chlorohex-3-ene-1,6-dioic acid
Q.5 2-amino-3-hydroxyhexanamide

Nomenclature of substituted Benzene:-


÷÷÷ Benzene

Monosubstituted Benzene:-

CH
3
Methyl benzene (Toluene)
O CH
3

Methyl benzene (Anisole)
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14

NH
2

Amino benzene (Aniline)
NO
2
Nitrobenzene


Br

Bromobenzene
OH

Hydroxybenzene (phenol)

Disubstituted Benzene:-

Br
Br

1,2-dibromobenzene (o-dibromobenzene)

Br
Br
1,3-dibromobenzene, [metadibromobenzne (m-dibromobenzene)]

Br
Br
1,4-dibromobenzene, [paradibromobenzene (p-dibromobenzne)]

NO
2
Cl
O N
2
1-chloro-2, 4-dinitrobenzene, (4-chloro 1, 3-dinitrobenzne X)

CH
3
NO
2
Cl

2-chloro-1-methyl-4-nitrobenzne

CH
3
O Me
Cl

2-chloro-4-methylanisole
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CH –CH
2 3
NH
2
CH
3

4-ethyl-2-methylaniline

OH
CH
3
CH
3

3,4-dimethylphenol

Q. Write the structure of :-
(a) o-ethylanisole (b) p-nitroaniline
(c) 2,3-dibromo-1-phenylpentane (d) 4-ethyl-1 flouro-2-nitrobenzene
Ans. (a)
O CH
3
CH –CH
2 3
(b)
NH
2
NO
2
(c)
Br
Br Ph
(d)
F
NO
2
CH –CH
2 3


Q.1

Q.2
OH
O Ph
Q.3
Cl
Ph

Q.4
CH
3
O
Q.5

Q.6
O
C — OH

Q.7
C
H
O

Q.8
C
OH
O


Common Name:-



Benzene Napthalene Anthracene Phenanthrene


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Common Name
I.U.P.A.C. Common
H C — CH —
3
CH
3


1-methyl ethyl Isopropyl

H C — CH — CH —
3 2
CH
3
2-methylbutyl isobutyl
H C — C — CH —
3 2
CH
3
CH
3
2,2-dimethylpropyl Neopentyl
H C — C —
3
CH
3
CH
3
tert.-butyl
H C — CH — CH —
3 2
CH
3
sec.butyl

Nomenclature of Amines:-
—NH
2

Suffix(a) ÷÷ Amine
Prefix ÷÷ Amino

1. H
3
C — CH
2
— NH
2
÷÷ Ethanamine
2.
NH
2

÷÷ 3,4-dimethylpentanamine
3.
NH
2
Br
÷÷ 5-bromocyclohex-3-enamine
4.
Br
NH
2

÷÷ 2-bromobut-3-enamine
5.
OH
O NH
2
2
3
5
4
1

÷÷ 3-aminobutan-1-oic acid

Q.1 NH
2
Br
Q.2
Cl
NH
2
Br

Q.3
OMe
NH
2

Q.4
Cl
NH
2

Q.5.
NH
2
Q.6
Cl
NH
2

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17
Q.7
NH
2
Br
Cl
Q.8
Cl
NH
2

Ans. Q.1 2-bromobut-3-enamine Q.2 3-bromo-5-chloro oct-7-enamine
Q.3 6-methoxyoct-7-enamine Q.4 3-chloro-4,5-dimethyl hept-4-enamine
Q.5 3-cyclopylpent-4-enamine Q.6 3-butyl-2-chloropent-4-enamine
Q.7 4-bromo-5-chlorohex-2-enamine Q.8 3-chloro-5-ethyl-6-propyl oct-7-enamine


Q.1
CH
3
N
H

N-methylaminopropane

Q.2
CH
3
N — CH
3
N, N-dimethylaminobutane

Q.3
CH
3
N
H C
3

N, N-dimethylaminobenzene

Nomenclature of Esters:-

R’ — C — OR
O

+
Alkyl
+
(Name starts with alkyl)

Q.1 H
3
C — CH
2

O
C— O — CH
3


Q.2 H C — C — O — CH — CH — CH
3 2 2 3
O

Methylpropan-1-oate propylethan-1-oate
Q.3 H C — CH — C — O — CH
2 2 3
O Br

Q.4 H C — C — O — CH — CH = CH
3 2 2
O

Methyl-3-bromo-propan-1-oate Prop-2-enylethanoate
Q.5
O
O

Cyclopropylbutanoate
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(1)
O
O
(2)
O
O


(3)
O
O — CH — CH
2 3
(4)
Br
O
Cl
O—Et


(5)
O
O
(6)
C — O — Me
O


(7)
C — O — Me
O

(8) H C — CH — C — O Me
3 2
O


Nomenclature of Anhydrides:-
R — C — OH + H — O — C — R
O O
÷÷
O O
C C
O R R
+
O
H H

÷ Formed by loss of
O
H H

÷ Suffix(s) ÷ oic anhydride (If carbon included)
÷ Carboxylic anhydride (if carbon not included)

Naming of symmetrical Anhydrides:-
:÷÷
(1)
H C — C
3
H C — C
3
O
O
O

ethanoic anhydride
(2)
H C — CH — C
3 2
H C — H C — C
3 2
O
O
O

propanoic anhydride
(3)
H C — CH — CH — C
3 2 2
H C — H C — H C — C
3 2 2
O
O
O

butanoic anhydride
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(4)
O
O
O

butane-1,4-dioic anhydride

Naming of Unsymmetrical anhydride:-
(1) H
3
C —
O
C — O —
O
C — CH
2
— CH
3
Ethanoic propanoic anhydride

(2)
O O
O

Butanoic-2-methylpropanoic anhydride

(3)
O O
O

Butanoic prop-2-enoicanhydride

(4)
O O
O

Butanoic propanoic anhydride

Nomenclature of cyanides:-

CN
Nitrile
Carbonitrile

Q.1 H
3
C — C ÷ N Q.2
CN

Q.3
CN


Q.4
CN
Q.5 CN Q.6 CN
Cl
Br Br


Q.7
CN
Q.8
CN
Br


Ans. Q.1 ethanenitrile Q.2 butanenitrile Q.3 2,4,5-trimethylhexanenitrile
Q.4 4-ethylpent-4-ene-1-nitrile Q.5 5-cyclopropylhepta-3,6-diene-1-nitrile
Q.6 4,6-dibromo-5-chloropentane-nitrile Q.7 3-methylidenepent-4-one-1nitrile
Q.8 5-bromohex-3-ene-1-nitrile

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Q.1
CN
CN

Q.2
H C — CH — CH
2 2
NC CN CN

Q.3
H C — CH
2 2
CN CN


Q.3
CN
Q.4 CH
2
—CH
2
—CN Q.5
CN
CN


Nomenclature of Amides:-
H —
O
C — NH
2
Methanamide

(1)
NH
2
O
(2)
NH
2
O
(3)
N
O
Me
H

Ans. (1) pent-2-en-1-amide, pent-2-enamide
(2) 3-cyclopropyl pent-3-en-1-amide
(3) N-methylhexan-1-amide

(4)
O
H C — C — N
3
(5)
N
O
Br
Me

N-Ethyl-N-Methylethanamide N-Bromo-3-Ethyl-N-Methylpentanamide
(6)
N
O
Pr
Me

(7)
N
O

(8)
Br
N
O
(9)
N
Me
O
Br

Nomenclature of Acid Halides:-

(1) H
3
C —
O
C — Cl ethanoylchloride
(2)
O
Cl
(3)
Cl
O
(4)
Cl
O



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