CH-2001 {Chemistry-II} Prepared by: Dr Muhammad Tahir Hussain

National Textile University, Faisalabad

A. Name the following compounds according to IUPAC system

O (4)
(2) (3)
(1)
OH

HO
O HO O
O O
O (7) OH O O
H
H O N NH2
(5) O OH
(6) (8) (9) (10)

NH 2
(16) (17)

HO

O O O
(19) (20)

O NH 2

H2N (28)
OH
O NH2 O OH
OH OH O
HO OH HO OH HO
HO
OH
HO (32) HO (33) (36) OH
NOTE: Consult chapter 8 of Organic Chemistry by B. S. Bahl for detailed study. Some answers are here, other names also exist.

1. 3,3,4-Trimethylhexane 2. 3-Ethyl-2-methyloctane 3. 2-Methylbut-2-enoic acid

4. 5-Isopropyl-4-methyl-4-nonene 5. 2-Isopropyl-3-methylbut-2-enoic acid 6. 2-Acetylcyclopentanone
7. 2-Formylbenzoic acid 8. 6-Acetylaminohexanoic acid 9. Acrylic acid
10. Acryl amide 11. Adipic acid 12. Allyl acrylate
13. Allyl butanoate 14. 2-(N-Acetylamino)propanoic acid 15. Acetyl bromide
16. 1-Vinylcyclohex-1-ene 17. 3-Amiopropene 18. 1-Allylcyclohexanol
19. Cinnamic acid 20. Allyl formate 21. 3-Ethoxypropene (Allyl ethyl ether)
22. Allyl propanoate 23. 3-Aminobenzaldehyde 24. 2-Aminobenzamide
25. 2-(4-aminophenyl)ethanoic acid 26. 2-Aminobenzenesulphonic acid 27. 4-Aminobenzophenone
28. 4,2'-Diaminobenzophenone 29. 1-Amino-5-chloro-9,10-anthracene 30. 4-Amino-2,6-dichlorophenol
31. 2-Amino-3,4,5,6-tetrahydroxyhexanal 32. 2-Amino-3,4,5,6-tetrahydroxyhexanal 33. 2,3,4,5,6-Pentahydroxyhexanal
34. 2-(2-Aminoethoxy)ethanol 35. 4-Amino-5-hydroxy-2,7-naphthalenedisulphonic acid (H-acid)
36. 6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

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CH-2001 {Chemistry-II} Prepared by: Dr Muhammad Tahir Hussain
National Textile University, Faisalabad
Exercise on Nomenclature of Aromatic Compounds
Benzene Derivatives:
Structure Name Structure Name
CH3 NH2
Toluene Aniline

OH
Phenol COOH Benzoic acid

O O
Acetophenone Benzophenone
C CH3 C

CH2Cl Benzyl chloride CHCl2 Benzal chloride

O
CHO Benzaldehyde Benzoyl chloride
C Cl

SO3H Benzenesulphonic acid CH2CH2OH 2-Phenylethanol

Cl
Cl
o-Dichlorobenzene m-Dichlorobenzene
Cl
Cl

SO3H
Biphenyl-2,2’-
Biphenyl
disulphonic acid
HO3S

OH
O2N NO2
CH2CH3 Ethylbenzene 2,4,6-Trinitrophenol
NO2

CH3
O2N NO2 OH
2,4,6-Trinitrotoluene OH
Catechol
(TNT)
NO2

OH

Resorcinol HO OH Hydroquinone
OH

OH
4-Chlorophenol
Phloroglucinol HO Cl
HO OH
p-Chlorophenol

COOH CH3
NH2 Anthranilic acid NH2 o-Toluidine

NH2 NO2

Metanilic acid m-Nitrobenzenesulphonic acid

SO3H SO3H

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CH-2001 {Chemistry-II} Prepared by: Dr Muhammad Tahir Hussain
National Textile University, Faisalabad
OH OH
CHO Salicylaldehyde COOH Salicylic acid

CH3 CH3 CH3

Mesitylene Durene
CH3 CH3 CH3 CH3

Cl CH3
Cl 1,2-Dichlorobenzene 1,3-Dimethylbenzene
CH3

CH3 OH
Cl 2-Chlorotoluene Cl 2-Chlorophenol
o-chlorotoluene o-chlorophenol

CH2CH3 Cl
1-ethyl-3- Cl 1,2,3-
propylbenzene trichlorobenzene
CH2CH2CH3 Cl

Cl OH
1,3,5- Br Br 2,4,6-
trichlorobenzene Tribromophenol
Cl Cl Br

CH2CH3 CH3 CH3

CH
3-Ethylacetophenone Cumeme
CH3
C (Isopropylbenzene)
O

CH3 CH3
CH3 o-xylene m-xylene
CH3

CH3
CH3 1,2,3-
H3C CH3 p-xylene
CH3 Trimethylbenzene
O
COOH
C CH3 o-Methylacetophenone Phthalic acid
CH3 COOH

COOH

Isophthalic acid HOOC COOH Terephthalic acid

COOH

CH CH2 Styrene C CH Phenylacetylene

2,2-di(p-
Cl
Cl chlorophenyl)-1,1-
CH2OH Benzyl alcohol Cl C CH
Cl trichloroethane
Cl
(DDT)
p-toluenesulphonic
CH3 SO3H H2N SO3H Sulphanilic acid
acid
H2N SO2NH2 Sulphanilamide H3C SO2NH2 p-toluenesulphonamide

CH2NH2 Benzylamine N N Azobenzene

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CH-2001 {Chemistry-II} Prepared by: Dr Muhammad Tahir Hussain
National Textile University, Faisalabad
NH NH Hydrazobenzene H2N NH2 Benzidine
Benzonitrile
CN O2N CN p-Nitrobenzonitrile
(Phenyl cyanide)
NH p-
N-methylaniline N N NH2
CH3 Aminoazobenzene
COOH
3,4,5-Trihydroxybenzoic
HO OH Pyrogallol
HO OH acid (Gallic acid) OH
OH

CH2COOH Phenylacetic acid CH CH COOH Cinnamic acid

5-Acetylaminoanthranilic OH
COOH
H2N NHCOCH3 2-acetylamino-6-
H2N acid
aminophenol-4-
(5-Acetylamino-3-
NHCOCH3 sulphonic acid
aminobenzoic acid) SO3H

H2N NH2
SO3H
3- Aniline-2,4-
Aminobenzenesulphonamide disulphonic acid
SO2NH2 SO3H

Methoxybenzene OCH3 o-Anisidine

OCH3 (Anisole) or NH2 (o-methoxyaniline)
(Methylphenyl ether)
OCH3 p-anisic acid
o-Anisaldehyde
CHO
CH3O COOH (4-methoxybenzoic
(o-methoxybenzaldehyde)
acid)
OH OH
CH3 o-Cresol m-Cresol
(2-Methylphenol) (3-Methylphenol)
CH3

Naphthalene Derivatives
OH
1-Naphthol NH2 2-Naphthylamine
(-Naphthol) (-Naphthylamine)

Br Br
SO3H -Naphthalenesulphonic
1,8-Dibromonaphthalene
acid

COCH3 COOH
-Acetylnaphthalene -Naphthoic acid

SO3H
SO3H
NH2 2-Naphthylamine-8- Naphthalene-1,5-
sulphonic acid disulphonic acid
SO3H

OH NH2 OH NH2 European K-acid

H-acid
(1-Amino-8-
(1-Amino-8-naphthol-3,6-
HO3S naphthol-4,6-
HO3S SO3H disulphonic acid) SO3H
disulphonic acid)

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CH-2001 {Chemistry-II} Prepared by: Dr Muhammad Tahir Hussain
National Textile University, Faisalabad
SO3H SO3H NH
NH2
K-acid 2 Koch Acid
(2-Naphthylamine-3,6,8- (1-Naphthylamine-
HO3S SO3H trisulphonic acid) HO3S SO3H 3,6,8-trisulphonic acid)

NH2 HO3S NH2

HO3S M-acid J-acid
(5-Amino-1-naphthol-3- (6-Amino-1-naphthol-3-
OH
sulphonic acid) OH sulphonic acid)

OH NH2
OH R-acid S-acid
(2-naphthol-3,6- (1-Amino-8-naphthol-4-
HO3S SO3H
disulphonic acid) SO3H sulphonic acid)

SO3H
OH
G-acid O2N
(2-naphthol-6,8- 3-Nitro-2-naphthol
disulphonic acid) OH
HO3S

SO3H
NH2 C-acid COOH BON-acid
(2-naphthylamine-4,8- (3-Hydroxy-2-naphthoic
disulphonic acid) OH acid)
SO3H

SO3H OH
NH2 Sulpho C-acid Naphthalene-1,5-
(2-naphthylamine-4,6,8-
HO3S
trisulphonic acid)
diol
SO3H OH

NH2 H
4-Aminophenyl J-acid
HO3S N NH2 (6-(4-
1,5-Diaminonaphthalene
Aminophenyl)amino-1-
NH2 naphthol-3-sulphonic acid)
OH

OH NHCOCH3
Acetyl H-acid COOCH3 BON-acid methyl ester
(1-Acetylamino-8-naphthol- (Methyl 3-hydroxy-2-
3,6-disulphonic acid) OH naphthoate)
HO3S SO3H

OH OH N-Acetyl Gamma acid

NH2
Gamma acid NHCOCH3 (2-Acetylamino-8-
(2-Amino-8-naphthol-6- naphthol-6-sulphonic
HO3S sulphonic acid) HO3S acid)
OH OH N-Phenyl J acid
1-Naphthol-4-sulphonic (6-Phenylamino-1-
acid naphthol-3-sulphonic
SO3H HO3S NH acid)
SO3H NH SO3H OH
2 Epsilon acid 1-Naphthol-3,8-
(1-Naphthylamine-3,8- disulphonic acid
SO3H disulphonic acid) SO3H

H O
OH OH Chromotropic acid
OH N C 8-Benzoylamino-1-
(1,8-Dihydroxy-3,6-
naphthol-3,6-disulphonic
naphthalenedisulphonic
acid HO3S SO3H
HO3S SO3H acid)

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CH-2001 {Chemistry-II} Prepared by: Dr Muhammad Tahir Hussain
National Textile University, Faisalabad
SO3H
NH2 Casella acid NH2
2-Aminoanaphthalene-
(2-Aminoanaphthalene-
HO3S 6-sulphonic acid
4,8-disulphonic acid)
SO3H

Anthracene and Phenanthrene Derivatives

O
OH
9-Hydroxyanthracene 9,10-Anthraquinone
O

O
SO3H SO3H
1-Anthracenesulphonic 2-Anthraquinonesulphonic
acid acid
O

O OH
OH
Alizarin 2-Methoxyanthracene
(1,2-dihydroxyanthraquinone) OCH3
O

8 9
7 10 Br

6 1 Phenanthrene 9-Bromophenanthrene
5
4 2
3
OH OH
1,10-
4,5-Dihydroxyphenanthrene
OH Dihydroxyphenanthrene
OH

Heterocyclic Compounds

N
Pyrrole Furan
(IUPAC: Azole) O (IUPAC: Oxole)
H

Thiophene or Pyridine
S (IUPAC: Thiole) N N

Indole Quinoline
N (Benzopyrrole) N (2,3-Benzopyridine)

Isoquinoline Coumarin
N O O

O Isocoumarin 2-Furansulphonic acid

O SO3H
O

N NO2 2-Nitropyrrole Furfural

O CHO
H

OCH3
Furoic acid 3-Methoxyfuran
O COOH
O

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CH-2001 {Chemistry-II} Prepared by: Dr Muhammad Tahir Hussain
National Textile University, Faisalabad
Write structures of the following compounds
1. 5-Acetylaminoanthranilic acid 46. N-Acetyl J-acid
2. Aniline-m-sulphonamide 47. N-Acetyl European K-acid
3. Aniline-2,4-disulphonic acid 48. N-Benzoyl-J-acid
4. Benzaldehyde-o-sulphonic acid 49. 1,8-Dihydroxynaphthalene-3,6-
5. Benzidine-2,2’-disulphonic acid disulphonic acid
6. Chloranil 50. 2-Aminonaphthalene-4,8-disulphonic acid
7. 4-Chloro-5-nitro-2-aminophenol 51. 3-Hydroxy-2-naphthoic acid
8. 4-Chlorometanilic acid 52. 6-Benzoylamino-1-naphthol-3-
9. 4-Chloro-2-aminophenol-6-sulphonic acid sulphonic acid
10. 2,6-Dibromo-4-nitroaniline 53. 8-Benzoylamino-1-naphthol-3,5-
11. 2,3-Dichloroaniline disulphonic acid
12. 3,4-Dichloroaniline 54. 2-Naphthol-8-sulphonic acid
13. 3,3’-Dibromobenzidine 55. 2-Naphthylamine-5-sulphonic acid
14. 2,5-Dichloronitrobenzene 56. 2,3-Dihydroxynaphthalene-6-
15. 2,5-Dichloro-p-nitroaniline sulphonic acid
16. 2,4-Dinitroaniline 57. 1,7-Dihydroxy-3-sulphonic acid
17. 2,4-DinitroChlorobenzene 58. 1-Naphthylamine-5-sulphonic acid
18. 3,5-Dinitrosalicylic acid 59. 8-(3-Aminobenzoyl)amino-1-
19. m-Aminoacetanilide naphthol-3,5-disulphonic acid
20. m-Aminoacetanilide-p-sulphonic acid 60. 7-(3-Sulphophenyl)amino-1-
21. m-Chloroaniline naphthol-3-sulphonic acid
22. m-Nitro-p-chlorobenzoic acid 61. 1-Naphthylamine-7-sulphonic acid
23. m-Nitro-p-toluidine 62. 5-Amino-1-naphthol-3-sulphonic acid
24. Metanilic acid 63. N-Benzoyl H-acid
25. Methyl anthranilate 64. 3-Methylamino-1-naphthol
26. 5-Nitroanthranilic acid 65. 6-Phenylamino-1-naphthol-3-
27. 5-Nitro-2-aminophenol sulphonic acid
28. 6-Nitro-2-aminophenol-4-sulphonic acid 66. 1-Hydroxy-8-naphthalenesulphonic acid
29. p-Anisidine-3-sulphonic acid 67. Sodium naphthalene-2,7-disulphonate
30. p-Anisidine-2,5-disulphonic acid 68. N-(4’-Ethoxyphenyl)-1-
31. 4-Chloroaniline naphthylamine
32. p-Chloro-m-cresol 69. 7-Amino-1-naphthol
33. 4-Nitrobenzoic acid 70. 8-Benzoyl-1-naphthol
34. p-Toluidine-2,5-disulphonic acid 71. 7-(2’-Methoxyphenyl)-2-naphthol
35. 2,4,5-Trichloroaniline 72. 4-Cyano-1-naphthyl amine
36. 5-Chlorosalicylic acid 73. 1,2,4-Trihydroxynaphthalene
37. 2,2’,5,5’-Tetrachloro-4,4’- 74. 2,3,6,7-Tetraethoxynaphthalene
diaminobiphenyl 75. 2,3,6,7-Tetramethoxyanthracene
38. 2-Amino-6-chloro-4-nitrophenol 76. 1,4,5,8-Tetrachlorophenanthrene
39. p-Chlorobenzophenone 77. 2,7-Dibromophenanthrene
40. p-Cyanoacetophenone 78. Phenanthrene-1,7-disulphonic acid
41. p-Methoxyphenylacetic acid 79. Anthracene-2,4,6-trisulphonic acid
42. p-Nitrobenzyl bromide 80. N-(4-Amino-3-sulpho)phenyl-J-acid
43. p-Nitrobenzyl alcohol 81. 8-Benzyl-J-acid
44. p-Toluenesulphonyl chloride 82. 2,5-Diamino-1-naphthol
45. 4-Acetylbenzonitrile 83. Methyl 3-hydroxy-2-naphthoate

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