Practice Questions On Nomenclature

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IIT-JEE ChEmIsTry by N.J. sIr

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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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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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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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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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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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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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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

3methyl hex1ene 3ethyl hex1ene

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

3ethyl 5methylhex1ene 3propylhexa1, 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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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
OH
Br ON

Q.3
HO

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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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Q.
O
H
Cl
Br
Q.
C
H
O

Q.
O
O
CH
CH

Q.
O O
CH HC
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)
COH
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
OH
ON

(3)
C
O
HOC
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
HO
6
7
8

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

6-formyloctan-1-oic acid

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

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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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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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
OEt

(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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IIT-JEE ChEmIsTry by N.J. sIr

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