604

15
IUPAC NAME

Level - 1
O
Cl Br
1. C—OH

Total number of substituent present in the above compound :

(a) 1 (b) 2
(c) 3 (d) 4
2. CH IUPAC name will be :

(a) Hex-5-en-1-yne (b) Hex-1-en-5-yne

(c) Hex-6-en-1-yne (d) Hex-1-en-6-yne
CH3 CH3
OEt
3. IUPAC name of is :

(a) 1-Ethoxy-2, 2-dimethylcyclohexane (b) 2-ethoxy-1, 1-dimethyl cyclohexane

(c) 1, 1-Dimethyl-2-ethoxycyclohexane (d) 2-methyl-1, 1-ethoxy cyclohexane

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 605
4. How many secondary carbon and hydrogen atoms are present in the molecule given below
respectively ?
Br

Br
(a) 2, 3 (b) 2, 2 (c) 3, 3 (d) 2, 0
5. Which IUPAC name is correct for the given compound ?
OHC CH3

CH3
(a) 3, 7-dimethylocta-2, 6-dienal (b) 2, 6-dimethyloct-2, 6-dienal-8
(c) 7-formyl-2, 6-dimethylhept-2, 6-diene (d) 7-aldo-2,6-dimethylhept-2, 6-diene
6. Write the IUPAC name of the following compound :
CO—O—C2H5

CO—Cl
(a) ethyl-2-(chlorocarbonyl) benzoate (b) ethyl-2-(chlorocarbonyl) hexanoate
(c) 2-(thoxycarbonyl) benzoyl chloride (d) None of these
Cl CH2CH3
7. The IUPAC name of the compound C == C is :
H3C I
(a) trans-2-chloro-3-iodo-2-pentene (b) cis-2-chloro-3-iodo-2-pentene
(c) trans-3-iodo-4-chloro-3-pentene (d) cis-3-iodo-4-chloro-3-pentene
8. The IUPAC name of the compound is :
CONH2
CHO

(a) 2-methyl-6-oxohex-3-enamide (b) 6-keto-2-methyl hexanamide

(c) 2-carbamoylhexanal (d) 2-carbamoylhex-3-enal
F

9. The IUPAC name of is:

I Cl
Br
(a) 1-Bromo-2-chloro-3-fluoro-6-iodo benzene
(b) 2-Bromo-1-chloro-5-fluoro-3-iodo benzene
(c) 4-Bromo-2-chloro-5-iodo-1-fluoro benzene
(d) 2-Bromo-3-chloro-1-iodo-5-fluoro benzene

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 606
O
10. The IUPAC name of CH3—CH2—CH—C—OCH3 is:
C2H5

(a) Methyl 2-ethylbutanoate (b) 1-methoxy-2-ethylbutanone

(c) 3-Methoxycarbonylpentane (d) 1-methoxy-2-ethylbutanal
O
||
11. The IUPAC name of CH 3 — CH == CH — C — OH is:
(a) But-1-en-4-oic acid (b) 1-hydroxybut-2-en-1-one
(c) But-2-en-1-oic acid (d) But-2-en-4-oic acid
OCH3
12. The IUPAC name of CH3—CH ==C—CH 3 is:
(a) 1-Methoxy-1-methylpropene (b) 2-Methoxybut-2-ene
(c) dimethylpropeneether (d) none of these
Me O
13. The IUPAC name of CH2 ==C—C—OC 2H 5 is:
(a) Ethyl 2-methylprop-2-enoate (b) Ethyl 2-methylprop-1-enoate
(c) 1-Ethoxy-2-methylprop-2-enone (d) 1-Ethoxy-2-methylprop-2-enal
CH 3 CH 3
| |
14. The IUPAC name of CH 3 — CH — CH — CH 2 NH 2 is:
(a) 2, 3-Dimethylbutan-4-amine (b) 2, 4-Dimethylbutan-1-amine
(c) 2,4-Dimethylbutan-4-amine (d) 2, 3-Dimethylbutan-1-amine
O
||
15. The IUPAC name of CH 3 — C — CH — CH — CH 3 is:
| |
C 2H 5 CH 3
(a) 3-(Methylethyl) pentan-2-one (b) 3-(Methylethyl)pentan-4-one
(c) 3-Ethyl-4-methylpentan-2-one (d) 3-Ethyl-2-methylpentan-4-one
O
16. The IUPAC name of CH3—CH—CH2—C—Br is:

CH3
(a) 2-Methylbutanoyl bromide (b) 2-Methylbutan-4-oyl bromide
(c) 1-Bromo-3-Methylbutanone (d) 3-Methylbutanoyl bromide

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 607
17. The IUPAC name of CH 3 — CH — CH 2 — OH is:
|
C 6H 5
(a) 2-Phenylpropan-1-ol (b) 2-Phenylpropan-3-ol
(c) 1-(2-Hydroxy-1-methylethyl) benzene (d) 1-((Hydroxymethyl)ethyl) benzene
CH 3
|
18. The IUPAC name of CH 3 — C — CH — CH — CH 2 — CH 3 is:
| | |
CH 3 CH 3 I
(a) 3-Iodo-4,5,5-trimethylhexane (b) 4-Iodo-1, 1, 3-trimethylhexane
(c) 4-Iodo-2, 2-dimethylheptane (d) 4-Iodo-2, 2, 3-trimethylhexane
CH 3
|
19. The IUPAC name of CH 3 — CH 2 — CH — CH — C — CH 3 is:
| | |
Cl CH 3 OH
(a) 4-Chloro-2, 3-dimethylhexane-2-ol (b) 4-Chloro-2-hydroxy-2, 3-dimethylhexane
(c) 4-Chloro-1, 1, 2-trimethylpentan-2-ol (d) 3-Chloro-2, 3-dimethylhexane-2-ol
CH3

20. The IUPAC name of CH—CHO is:

(a) 2-Phenylpropan-3-al (b) Formylethylbenzene

(c) 2-Phenylpropanal (d) Ethylformylbenzene
O
CH3
21. The IUPAC name of CH3—C—CH is:
CH3
(a) 2-Methylbutan-3-one (b) 3-Methylbutan-2-al
(c) 2-Methylbutan-3-al (d) 3-Methylbutan-2-one
CH3—CO
22. The IUPAC name of O is:
CH3—CH2—CO

(a) Ethanoic propanoic anhydride (b) Propanoic ethanoic anhydride

(c) 1-Ethanoyloxypropanone (d) 3-Ethanoyloxypropan-3-one
23. The IUPAC name of CH 3 — CH — CH — CH 2 — OH is:
| |
OH C 2H 5
(a) 3-Ethylbutane-2, 4-diol (b) 2-Ethylbutane-1, 3-diol
(c) 3-Ethylbutane-1, 3-diol (d) 2-Ethyl-1-methylpropane-1, 3-diol

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 608
24. The IUPAC name of CH 3 — C — C — CH 3 is:
|| ||
O O
(a) Butane-2, 3-dial (b) Butane-1, 3-dione
(c) Butane-2, 3-dione (d) 1, 2-dimethylethanedione
25. The IUPAC name of CH 2 == CH — CH == CH 2 is:
(a) Butane (b) Buta-1, 3-diene (c) Butane-1, 3-diene (d) none of these
26. The IUPAC name of CH 2 — CH 2 — CH 2 is:
| |
COOH COOH
(a) Pentane-1, 5-dioic acid (b) Pentane-1, 5-dicarboxylic acid
(c) Propane-1, 3-dioic acid (d) none of these
27. The IUPAC name of CH 2 — CH == CH — CHO is:
|
CHO
(a) propene-1, 3-dial (b) Propene-1, 3-dicarbaldehyde
(c) Pent-3-ene-1, 5-dial (d) Pent-2-ene-1, 5-dial
28. The IUPAC name of CH 2 — CN is:
|
CH 2 —CN
(a) Butane-1, 4-dicarbonitrile (b) Ethane-1, 2-dicarbonitrile
(c) Ethane-1, 2-dinitrile (d) Butane-1, 4-dinitrile

29. The IUPAC name of CH 2 — CH — CH 2 — CH 2 is:

| | |
NH 2 CH 3 NH 2
(a) 2-Methylbutane-1, 4-diamine
(b) 3-Methylbutane-1, 4-diamine
(c) 3-(Aminomethyl)butanamine
(d) 2-(Aminomethyl)butan-4-amine
CH 2Cl
|
30. The IUPAC name of CH 2 — CH — CH 2 is:
| |
Cl Cl
(a) Tris(chloromethyl) methane
(b) 1, 3-Dichloro-2 (chloromethyl) propane
(c) 1-Chlorobis(chloromethyl) ethane
(d) none of these

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 609
CH 3
|
31. The IUPAC name of CH 3 — CH — CH — CH — C — CH 3 is:
| | | |
OH CH 3 OH CH 3

(a) 3, 5, 5-Trimethylhexane-2, 4-diol (b) 2, 2, 4-Trimethylhexane-3, 5-diol

(c) 1, 2, 4, 4-Tetramethylpantane-1, 3-diol (d) 2, 2, 4, 5-Tetramethylpantane-3, 5-diol
32. The IUPAC name of HOOC — CH == CH — COOH is:
(a) But-2-ene-1, 4-dicarboxylic acid (b) But-2-ene-1, 4-dioic acid

(c) Ethene dicarboxylic acid (d) Ethene dioic acid

OCH 3
|
33. The IUPAC name of CH 3 — CH — CHO is:
(a) 1-Formyl-1-methoxyethane (b) 2-Methoxypropan-3-one
(c) 2-Methoxypropanal (d) 2-Methoxypropan-3-al
CH 3
|
34. The IUPAC name of CH 2 == C — COOCH 3 is:
(a) Methyl-2-methylprop-1-en-3-oate (b) 2-Methoxycarbonylpropene
(c) 2-Methoxycarbonylprop-2-ene (d) Methyl-2-methylprop-2-enoate
35. The IUPAC name of CH 3 — CH == CH — COOH is:
(a) But-2-ene-1-oic acid (b) But-1-ene-1-oic acid
(c) But-2-ene-1-carboxylic acid (d) Propene-1-carboxylic acid
OH
|
36. The IUPAC name of CH 3 — CH — COOH is:
(a) 2-Hydroxypropanoic acid (b) 1-Hydroxypropanoic acid
(c) 1-Hydroxyethane carboxylic acid (d) 1-Hydroxyethanoic acid
37. The IUPAC name of HO — CH — COOH is:
|
HO—CH—COOH
(a) 2, 3-Dihydroxybutane-1, 4-carboxylic acid
(b) 2, 3-Dihydroxybutane-1, 4-dioic acid
(c) 1, 2-Dihydroxyethane dicarboxylic acid
(d) none of these

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 610
38. The IUPAC name of is:

(a) 3-Methyl-2-oxobutanecarboxylic acid (b) 2-Methyl-3-oxobutan-4-oic acid

(c) 3-Methyl-2-oxobutanoic acid (d) 3-Methyl-1,2-dioxobutanoic acid
39. The IUPAC name of NC — CH 2 — CH 2 — COOH is:
(a) 3-Carboxy propanenitrile (b) 4-Cyanobutanoic acid
(c) 2-Cyanoethane Carboxylic acid (d) 3-Cyanopropanoic acid

40. The IUPAC name of is:

(a) 3-Carboxy-3-hydroxypentanedicarboxylic acid

(b) 2-Hydroxypropane-1, 2, 3-tricarboxylic acid
(c) 2-Hydroxypropane-1, 2, 3-trioic acid
(d) 3-Hydroxypropane-1, 2, 3-tricarboxylic acid
O
||
41. The IUPAC name of CH 3 — C == CH — CH 2 — C is:
| |
COOC H OH
2 5

(a) 4-ethoxycarbonylpent-3-enoic acid

(b) 4-ethanoyloxypent-3-enoic acid
(c) 3-ethoxycarbonylbut-2-enecarboxylic acid
(d) 3-ethoxycarbonylpent-3-enoic acid
42. The IUPAC name of CH 3 — CH — C — C — NH is:
| || || |
CH 3 O O Br
(a) (N-Bromo)-2-keto-3-methylbutanamide
(b) (N-Bromo)-2-keto-4-methylbutanamide
(c) (N-Bromo)-1, 2-diketo-3-methylbutanamine carboxamide
(d) (N-Bromo)-1-keto-2-methylpropane
43. The IUPAC name of CH 2 — C == CH — CH 2 OH is:
| |
Cl CH 3
(a) 4-Chloro-3-methylbut-2-en-1-ol (b) 1-Chloro-2-methylbut-2-en-4-ol
(c) 4-Chloro-1-hydroxy-3-methylbut-2-ene (d) 1-Chloro-4-hydroxy-2-methylbut-2-ene

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 611
O
||
44. The IUPAC name of CH 2 — CH — C — CH 2 — CH 3 is:
| |
Br CONH 2
(a) 2-(Bromomethyl)-3-oxopentane carboxamide
(b) 1-Bromo-2-carbamoylpentan-3-one
(c) 5-Bromo-4-carbamoylpentan-3-one
(d) 2-(Bromomethyl)-3-oxopentanamide
45. The IUPAC name of (CH 3 ) 3 C ◊ CH 2 CH 2 Cl is:
(a) 2, 2-Dimethyl-4-chloro butane
(b) 1-Chloro-3, 3-dimethylbutane
(c) 4-Chloro-2, 2-dimethyl butane
(d) none of these
46. The IUPAC name of CH 3 — CH — CH — CH — CHO is:
| | |
CH 3 OH OH
(a) 2, 3-Dihydroxy-4-methylpentanal
(b) 1-oxo-2, 3-Dihydroxy-4-methylpentane
(c) 2,3-Dihydroxy-4-methylpentanone
(d) 1, 2-Dihydroxy-3-methylbutanecarbaldehyde

47. The IUPAC name of CH 3 — CO — CH — CH 2 — CH 2 Cl is:

|
CH 3
(a) 1-Chloro-3-methylpentan-4-one
(b) 1-Chloro-2-(oxoethylbutane)
(c) 5-Chloro-3-methylpentan-2-one
(d) 3-(2-Chloroethyl)butan-2-one
OH O
| ||
48. The IUPAC name of CH 3 — C — CH 2 — C — CH 3 is:
|
H
(a) 2-Hydroxypentan-4-one
(b) 4-Hydroxypentan-2-one
(c) 4-oxopentan-2-ol
(d) 2-oxopentan-4-ol

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 612
49. The IUPAC name of CH 3 — CH — CH — CH — CH 3 is:
| | |
Cl Br OH
(a) 3-Bromo-4-chloropentan-2-ol
(b) 3-Bromo-2-chloro-4-hydroxypentane
(c) 3-Bromo-2-chloropentane-4-ol
(d) none of these
Br Cl
| |
50. The IUPAC name of CH 3 — CH 2 — C — CH — CH 2 — Cl is:
|
OH
(a) 3-Bromo-4, 5-dichloropentan-3-ol
(b) 3-Bromo-1, 2-dichloro-3-hydroxypentane
(c) 3-Bromo-1, 2-dichloropentan-3-ol
(d) 3-Bromo-4, 5-dichloro-3-hydroxypentane
51. The IUPAC name of CH 3 — CH — CH 2 — O — C 2 H 5 is:
|
OH

(a) 1-Ethoxypropan-2-ol (b) 3-Ethoxypropan-2-ol

(c) 1-Ethoxy-2-hydroxypropane (d) none of these
NH2

52. The IUPAC name of is:

Br

(a) 4-Bromo benzenamine (b) 4-Amino-1-bromobenzene

(c) 4-Bromo benzenamide (d) 1-Bromo benzencarboxamide

53. The IUPAC name of is:

(a) N, N-Dimethyl aminobenzene (b) N, N-Dimethyl benzenamine

(c) (a) and (b) both are correct (d) none of these

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 613
OH
54. The IUPAC name of is:
O

(a) 2, 6-Dimethylhepta-2, 5-dienoic acid

(b) 3, 7-Dimethylhepta-2, 5-dienoic acid
(c) 1-Hydroxy-2, 6-dimethylhepta-2, 5-dienone
(d) none of these
55. The IUPAC name of is:
CHO

(a) 3-Methylpent-1-en-4-al (b) 3-Methylpent-4-enal

(c) 3-Methylpent-4-carbaldehyde (d) 3-Methyl-5-oxopent-1-ene
O
56. The IUPAC name of is:

(a) 2-Phenyl ethanone (b) 1-Phenyl ethanone

(c) 1-(Oxoethyl)benzene (d) 1-(Ethyaloxo)-benzene
OH
OH
57. The IUPAC name of is:

(a) 2-Hydroxybenzenol (b) 1, 2-Dihydroxybenzene

(c) Benzene-1, 2-diol (d) 2-Hydroxyphenol
OH O

58. The IUPAC name of OH is:

(a) 2-Carboxyphenol (b) 2-Hydroxybenzoic acid

(c) 1-Carboxy-2-hydroxybenzene (d) 2-Carboxy-1-hydroxybenzene
OH
59. The IUPAC name of is:

(a) 1,3-Dimethyl phenol (b) 1-Hydroxy-2-6-dimethyl benzene

(c) 2, 6-Dimethyl benzenol (d) 2-Hydroxy-1-3-dimethylbenzene

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 614
O
||
60. Ph æ CH == CH æ C æ OH
The IUPAC name is :
(a) 3-phenyl prop-2-enoic acid (b) 3-phenol prop-1-enoic acid
(c) 3-carboxy-prop-1-ene benzene (d) but-2-enoic acid

61. The IUPAC name of Cl is:

(a) Chloromethylbenzene (b) Chlorophenylmethane

(c) (a) and (b) both (d) none of these
62. The IUPAC name of the compound having the formula is :
CH 3
|
H 3 C — C — CH == CH 2
|
CH 3

(a) 3, 3, 3-Trimethylprop-1-ene (b) 1, 1, 1-Trimethylprop-2-ene

(c) 3, 3-Dimethylbut-1-ene (d) 2, 2-Dimethylbut-3-ene
63. The IUPAC name of the compound CH 2 == CH — CH(CH 3 ) 2 is :
(a) 1, 1-Dimethylprop-2-ene (b) 3-Methylbut-1-ene
(c) 2-Vinyl propane (d) none of these
64. The number of sigma and pi-bonds in 1-butene 3-yne are :
(a) 5 sigma and 5 pi (b) 7 sigma and 3 pi
(c) 8 sigma and 2 pi (d) 6 sigma and 4 pi
65. The IUPAC name of C 6 H 5 COCl is :
(a) Benzoyl Chloride (b) Benzene chloro ketone
(c) Benzene carbonyl chloride (d) Chloro phenyl ketone
66. The IUPAC name of the following compound is :
OH

CN
Br
(a) 4-Bromo-3-cyanophenol (b) 2-Bromo-5-hydroxybenzonitrile
(c) 2-Cyano-4-hydroxybromobenzene (d) 6-Bromo-3-hydroxybenzonitrile

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 615
67. Many organic compounds contain more than one functional group. Which of the following is
both an aldehyde and an ether ?

O
O O
O O
O H
O
(ii) O (iv)
(i)
(iii)
O

OCH3
O
(v)

(a) (i) only (b) (i) and (iv)

(c) (ii) and (v) (d) (iii) and (iv)
68. What is the sum of positions assigned to bromine while numbering the Parent Chain in the
below compounds ?
Br Br Br
Br

(I) (II) (III) (IV)

(a) 13 (b) 14 (c) 15 (d) 16
69. How many number of compounds, which have same IUPAC name ?
OH
OH
OH

OH

OH
OH
OH
OH
(a) 0 (b) 1 (c) 2 (d) 3

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 616
70. How many total number of substituents are present in the following compound ?
Br

Cl

(a) 3 (b) 4 (c) 5 (d) 6

71.

Correct IUPAC name :

(a) 1-methyl-3-ethylcyclohexene (b) 5-ethyl-1-methylcyclohexene
(c) 2-ethyl-4-methylcyclohexene (d) 3-ethyl-1-methylcyclohexene

ANSWERS — LEVEL 1
1. (c) 2. (b) 3. (b) 4. (b) 5. (a) 6. (a) 7. (a) 8. (a)
9. (b) 10. (a) 11. (c) 12. (b) 13. (a) 14. (d) 15. (c) 16. (d)
17. (a) 18. (d) 19. (a) 20. (c) 21. (d) 22. (a) 23. (b) 24. (c)
25. (b) 26. (a) 27. (d) 28. (d) 29. (a) 30. (b) 31. (a) 32. (b)
33. (c) 34. (d) 35. (a) 36. (a) 37. (b) 38. (c) 39. (d) 40. (b)
41. (a) 42. (a) 43. (a) 44. (d) 45. (b) 46. (a) 47. (c) 48. (b)
49. (a) 50. (c) 51. (a) 52. (a) 53. (b) 54. (a) 55. (b) 56. (b)
57. (c) 58. (b) 59. (c) 60. (a) 61. (b) 62. (c) 63. (b) 64. (b)
65. (c) 66. (b) 67. (b) 68. (c) 69. (a) 70. (c) 71. (b)

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 617

Level - 2
Give the IUPAC name of the following compounds

Cl
1. OH 2. OH 3. OH
Br

HO Cl OH
OH
4. Cl 5. Br 6.
Cl
Br
Br

HO Cl
Br
7. 8. 9. OH
Cl Br
HO OH

HO HO OH
10. 11. 12.
Br
Cl
OH

Cl
Br Cl
Cl
13 OH 14. 15.
OH
HO OH

Cl
HO HO
16 OH 17 18.

HO OH OH
Br

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 618

19. 20. 21.

22. 23. 24.

25. 26. 27.

28. 29. 30.

OH O
Cl
31. 32. 33. O
Br
Br

O
O
O
34. O 35. 36.
O
O

O O
O
37. 38. 39.
O

O O
O
O
40. 41. 42.
O
O

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 619

O
43. 44. 45. O

O
O Cl Cl O
46. 47. NH 48.
NH Br Cl NH Br
Br Br

Br
O O O
Br
49. N 50. 51.
NH Cl NH
Cl

Cl
Br O O O
52. Cl 53. 54.
NH NH Cl NH
Cl

Br Cl Br
O O O Br
Br
55. Cl 56. 57.
NH Br NH Br NH
Br Cl Br

O
O O
58. Br 59. 60. O
NH Cl
O

O O
61. 62.
O

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 620

Br O
63. O 64.
O
OH OH
Cl

O
O
O NH
65. 66. O
Br Br OH Cl
Br OH

O
O O
O
67. 68.
O

O Cl

69. 70.

O OH
O S O

71. +O 72.
N O
-
O
O O
HO O

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 621

-
Br O +O
N
Br
73. 74. 75.
Br
Cl
Cl

O OH
O OH O OH
O
OH
S
76. O 77. 78.
Cl
Cl O O
O Cl

O OH
O OH

79. 80. 81.

O
Br HO
Cl
Br Br Cl
82. Br 83. 84.
Cl
Cl O
O

HS
HO
O O Cl
Br Br
85. 86. 87.

O O
Br Cl
Br

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 622

O
O O O

88 89. 90.
Br O
SH
Cl O
O
O O
Cl
91. 92. 93.

Br
Br
Br O
O O Cl
94. 95. 96. O
N+
Br Cl Br
Cl O–

O OHO
O
N+ CH3 O
O– C — O — CH3
97. 98. 99.
C — NH 2
+
–O N
O
O
Br O
CH2 — CHO O CO2H
100 C — O — CH3 101. 102.
C
H

O
CO2H
103. 104.
HO – CH2 – C – CH == CH – CH2 – CO2H

CH3

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 623

Cl
O
CO2Et
105. 106. CH3 — NH — CHO 107.

Br
OH

Cl O CN
OH
108. 109. C — NH — Ph 110.
Br

CHO CONH2 CHO

Br
111. 112. 113.

CO2H CO2H

CO2H OH
Cl
114. 115. 116.
CN
O2N
CN NO2

CO2H
CO2H
Cl

117. 118. 119. C O

NH2
OH
O

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 624

Br
120. 121. 122. O
N+
Cl
O–

–
O O
N+ N+
O O–
123. 124. O 125.
N+

O–
N +
O– O

N+
O–
126. 127. 128.
H2 N
O == S== O

OH

129.

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 625
130. Give the IUPAC name of the following compounds :
CH 3 CH 3
| |
(a) CH 3 - CH 2 - CH - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH - CH 3
OH CH 3
| |
(b) CH 3 - CH 2 - CH - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH 2 - CH - CH 3
CH3

(c) CH3 – CH2 – CH2– CH2 CH2 – CH3 (d)

| |
CH3 – CH2 – CH – CH – CH3
CH3 CH3
CH3

CH3
(e)
CH3

CH3

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 626
131. Give the IUPAC name of the following :
CH3
|
CH3 CH2—CH—CH3
| |
CH3—CH—CH2—CH2—CH—CH2—CH2 —CH2—CH3
(a) 1 2 3 4 5 6 7 8 9
CH3
|2 1 3
CH3 CH2—CH—CH3
| |
CH3—CH—CH2—CH2—CH—CH2 —CH2—CH3
(b) 8 7 6 5 4
CH3 CH3
| |
CH3 CH2—CH—CH—CH3
| |
CH3—CH2—CH—CH2—CH2—CH —CH2—CH2—CH2—CH2—CH3
(c) 1 2 3 4 5 6 7 8 9 10 11

OH
5 6
5 6
6 1 6 1
(d) 4 5 2 1
(e) 4 5 2 1
4 3
4 3 2
2 3
3

4
1
4 3 5
5 5 3 2 6
(f) 4
1 2 3 (g) 2 7
CH3
1
2 6
(h) 1
CH3
4 5
3
7

5 3 1 2
(i) 6 2 (j) 3 1
7 2 6 8
8 4
3 1 4 5 7 9

CH3

CH3 CH—CH3

CH3—CH—C—CH2—CH3

(k) CH3—CH2—CH2—CH2—CH—CH2 —CH2—CH2—CH3

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 627
132. Match the Column :
Column (I) Column (II)
Compound IUPAC Name
Cl

(a) (p) 1, 3-dibromo-2-chlorocyclopropane

Br
Br

(b) (q) 1, 2-dibromo-3-chlorocyclopropene

Cl
Br

(c) (r) 3-bromo-1-chlorocyclopropene

Cl Br
Cl

(d) (s) 1-bromo-3-chlorocyclopropene

Br Br
133. Match the Column :
Column (I) Column (II)
Cl Cl
Br
(a) (p) 1-butyl-4-methyl cyclohexane

(b) (q) 2-bromo-1,1-dichloro cyclohexane

COOEt
(c) (r) 1-Bromo-1,2-dichloro cyclohexane
CHO
Br Cl
Cl
(d) (s) Ethyl-2-formyl cyclohexane carboxylate

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 628

Subjective Problems
F
1.
When IUPAC name of following compound is given, then double bond and substituent gets
respectively
( x and y) number so the sum of ( x + y) will be

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 629

ANSWERS – IUPAC Name

1. pent-4-yn-1-ol 2. pent-4-en-1-ol

3. (5E)-2-bromo-3-chlorohept-5-en-1-ol 4. 3-bromo-2-chloro-6-ethenylcyclohexanol

5. 4-bromo-3-chloro-5-cyclopropylcyclohexanol

6. 3-bromo-2-chloro-5-methylidenecyclohexanol

7. 3-bromo-2-chloro-5-methylidenecyclohexane-1,4-diol

8. 2-bromo-4-chloro-5-ethynylcyclohexanol 9. cyclopenta-1,3-dien-1-ol

10. 2-bromo-5-chlorocyclopenta-2,4-dien-1-ol

11. cyclopenta-2,4-dien-1-ol 12. dodec-10-en-4-yne-3,8-diol

13. 1-chloro-3-methylbut-3-en-2-ol 14. 4-bromo-2-chlorooct-6-ene-3,5-diol

15. 3-chloro-5-(1-methylethenyl)cyclopenta-1,3-dien-1-ol

16. 2-bromo-5-chloro-3-methylidenecyclopentanol

17. cyclohexane-1,3,5-triol 18. cyclohexane-1,3-diol

19. cyclopenta-1,3-diene 20. (6E)-oct-6-en-1-yne

21. but-1-en-3-yne 22. (3Z)-pent-3-en-1-yne

23. buta-1,3-diyne 24. (2E)-dec-2-en-5-yne

25. (6Z)-dodec-6-en-2-yne 26. pent-1-en-4-yne

27. 4-ethynyl-1-methylcyclohexene 28. cyclooctyne

29. (2E)-hex-2-en-4-yne 30. 5-ethynylcyclopenta-1,3-diene

31. 5-(prop-2-enyl) cyclopenta-1,3-diene

32. 3,5-dibromo-2-chloro-4-ethenylcyclohexanol

33. cyclopropylmethyl cyclobutanecarboxylate

34. cyclobutylmethyl cyclopropanecarboxylate

35. ethyl ethanoate 36. 2-methylpropyl butanoate

37. prop-2-enyl 3-ethylpent-4-enoate 38. 4-methylpentan-2-one

39. 2,5-dimethylheptan-3-one 40. octa-1,7-dien-4-one

41. 3,4-dimethylheptane-2,6-dione 42. 9-ethyl-3-methylundecane-2,5,10-trione

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 630

43. 5-methyloctanal 44. but-3-enal

45. 3-ethylheptanal 46. N,3-dibromobutanamide

47. 4-chloro-N-(3-chlorobutyl)butanamide

48. 3-bromo-N-(2-bromoethyl)-4-chloropentanamide

49. N,3-diethyl-N-propylpentanamide

50. 3-cyclopropyl-N-(3-cyclopropylbutyl)pentanamide

51. 4-bromo-N-(3-bromo-2-chloropropyl)-3-chloropentanamide

52. 3-bromo-4,5-dichloro-N-(2-chloroethyl)hexanamide

53. (5E)-N-(prop-2-en-yl)oct-5-enamide

54. 3-chloro-N-(2-cyclopentylpropyl)-4-cyclopropylpentanamide

55. 5,6-dibromo-3,4-dichloro-N-(2-chloroethyl)heptanamide

56. 3-bromo-N-(3-bromobutyl)butanamide

57. 3,4-dibromo-N-(3,4-dibromobutyl)pentanamide

58. 4-bromo-N-(3-chloro-2-cyclopropylpropyl)-3-(cyclopenta-2,4-dien-yl)butanamide

59. 2-oxopropanal 60. 4-oxopentanal

61. 3-oxobutanal 62. 3,4-dicyclopropyloct-7-yn-2-one

63. (2E,6E)-4-bromo-5-chloro-8-cyclopropyl-10-oxodeca-2,6-dienoic acid

64. 4,5,6,7,8,9-hexaethynyldodec-11-ynoic acid

65. (2E,6E)-5,9-dibromo-4-cyclopropyl-6-formylundeca-2,6-dienoic acid

66. 3-bromo-5-chloro-6-(formylamino)hexanoic acid

67. ethyl 3-phenylpropanoate 68. ethyl methyl benzene-1,3-dicarboxylate

69. ethenylbenzene 70. benzoyl chloride

71. methyl 4-acetyl-2-nitrobenzoate 72. 2-formyl-4-sulphobenzoic acid

73. 1,2-dibromo-4-chlorobenzene 74. octylbenzene

75. 2-bromo-1-chloro-4-nitrobenzene 76. 4-formyl-2-sulphobenzoic acid

77. 3-(trichloromethyl)benzoic acid 78. 4-(ethoxycarbonyl)benzoic acid

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79. 4-ethenylbenzoic acid 80. 4-benzylbenzoic acid

81. biphenyl 82. 1,2,5-tribromo-3,4,6-trichlorobenzene

83. ethyl 4-acetylbenzoate 84. 2-bromo-6-chlorophenol

85. 2, 4, 6-tribromophenol 86. ethyl 4-bromo-3-chlorobenzoate

87. ethyl 3-chloro-4-mercapto/sulpho benzoate 88. ethyl 4-(chlorocarbonyl)benzoate

89. 3-bromo-4-sulphobenzaldehyde 90. benzene-1, 3-dicarbaldehyde

91. 4-bromo-2-chlorobenzaldehyde 92. 1-phenylpentan-1-one

93. 1-(3-bromophenyl)hexan-1-one

94. 4-bromo-1-(3-bromo-4-chlorophenyl)pentan-1-one

95. 1-(3-bromo-5-chlorophenyl)-2-chloroethanone

96. 1-(3-nitrophenyl)ethanone 97. 2,4-dinitrobenzoic acid

98. methylcyclohexane carboxylate 99. 2-methylcyclopentane carboxamide

100. methyl-2-bromocyclohexane carboxylate 101. 2-(2-methylcyclobut-1-enyl)ethanal

102. 4-formyl-2-oxocyclohexane-1-carboxylic acid

103. 5-cyclohexyl-6-hydroxy-5-methylhex-3-en-1-oic acid

104. 2-oxocyclohexane-1-carboxylic acid 105. ethyl-2-oxocyclohexane-1-carboxylate

106. N-methylmethanamide 107. 2-bromo-4-chloro-5-ethynylcyclohexanol

108. 2-bromo-6-chloro-3-methylidene-cyclohexanol

109. N-phenylcyclohexane carboxamide 110. cyclohexane carbonitrile

111. cyclopentanecarbaldehyde 112. cyclohexanecarboxamide

113. 2-bromo-6-methyl-cyclohexanecarbaldehyde

114. cyclopropane carboxylic acid

115. 4-cyno-2-hydroxy-5-nitrocyclohexane carboxylic acid

116. 6-chloro-5-cyno-4-nitrocyclohex-2-ene carboxylic acid

117. 6-chloro-4-(3-oxo cyclobutyl)cyclohex-2-ene carboxylic acid

118. 4-(2-amino-4-hydroxycyclopentyl cyclohex-2-enecarboxylic acid

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 632

119. cyclohexylidenemethanone 120. 2-bromo-4-chloro-1-methylbenzene

121. 1,2-diethyl-3-methyl-4-propylbenzene 122. 1-ethyl-3-nitrobenzene
123. 2-methyl-1, 3, 5-trinitrobenzene 124. 1-methyl-3-nitrobenzene
125. Diphenylmethane 126. 4-Methyl-3-nitrobenzene sulphonic acid
127. 1-ethenyl-4-methylbenzene 128. heptan-3-amine
129. 2-methylpentan-3-amine
130. (a) 2,11-dimethyltridecane
(b) 12-methyl-tridecan-3-ol
(c) 4-ethyl-3-methyloctane
(d) 1,2,7-trimethylcyclopentadecane
(e) 1,1,2,5-tetramethylcyclopentane
131. (a) 5-isobutyl-2-methylnonane, 5-2-methylnonane (2-methylpropyl)
(b) 2,7-dimethyl-4-propyloctane
(c) 6-(2,3-dimethylbutyl) 3-methyl undecane
(d) 1,1,2,6-tetramethylcyclohexane
(e) 2,2,3-trimethylcyclohexanol
(f) 1,2,4-trimethylcyclopentane
(g) 2-methylbicyclo[3.1.1] heptane
(h) 2-methylbicyclo[3.1.1] heptane
(i) 2,2,6,6,7-pentamethyloctane
(j) 4-(1methylpropyl)-2,3,5-trimethyl nonane Not 2-butyl
(k) 5-(1-ethyl-2-methyl-1-(1-methylethyl)propyl) nonane
132. a - r; b - s; c - q; d - p
133. a - q; b - p; c - s; d - r

Subjective Problems
1. 4

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