CHAPTER

10 Nomenclature

Question Bank

Single and Multiple-choice Type

1. The IUPAC name of the compound shown here is

OH

O
O

(a) 5-Ethyl-1-hydroxyoctan-1,4-dioic acid

(b) 2-Carboxyethyl-3-hexyl ketone
(c) 3-(3-Hexylcarbonyl) propanoic acid
(d) 5-Ethyl-4-ketooctanoic acid

2. Which of the following compounds are not correctly matched?

Compound IUPAC name
OH

(a) HO OH Cyclohexane-1,2,4-triol

(b) H3C OH 4-Methylcyclohexanol

10.2 chapter ten

CH3
(c) OH 2-Ethyl-6-methylcyclohexanol

C2H5

Cl

(d) Br 3-Bromo-1-chlorocyclohexane

3. The no. of secondary C-atoms present in the following compounds respectively is

OH N
, , N

(a) 7, 9, 4 (b) 5, 12, 8 (c) 6, 9, 8 (d) 5, 9, 4

4. The organic compound (Cyclohex-3-enyl) 2-ethyl cyclobutanecarboxylate does not

contains
(a) two 3°-carbon atoms (b) two 1°-carbon atoms
(c) 9 secondary C-atoms (d) one 1°-carbon atoms

5. The IUPAC name of the compound given below is

O

OH OH

(a) 2-Hydroxy-3-(4’-hydroxyphenyl) cyloprop-2-en-1-one

(b) 2-Hydroxy-3-(4’-hydroxyphenylmethyl) cyloprop-2-en-1-one
(c) 4-(2’-Hydroxy-3’-oxocycloprop-1’-enylmethyl) phenol
(d) 4-(1’-Hydroxy-3’-oxocycloprop-1’-enylmethyl) phenol

6. The correct IUPAC name of the compound is

HO Me Br
H OCOCHCH3

(a) 2-Bromopropyl-3-hydroxy-1-methylcyclopentane carboxylate

(b) 3’-Hydroxy-1’-methylcyclopentyl-2-bromopropanoate
(c) 1’-Hydroxy-3’-methylcyclopentyl-2-brompropanoate
(d) None of these
O
7. The IUPAC name of C – NH – C6H5 is

(a) N-Cyclohexylbenzamide
(b) N-Phenyl-N-cyclohexylmethanamide
(c) N-phenylcyclohexane carboxamide
(d) N-Cyclohexyl-N-phenylmethyl amide
 nomenclature 10.3

8. The IUPAC name of the given compound is

CHO CONH2
CH3–CH–CH CH–CH–COOH
Br COCl
(a) 2-Bromo-4-carbamoyl-5-chloroformyl-3-formylhexanoic acid
(b) 5-Bromo-3-carbamoyl-3-chloroformyl-4-formylhexanoic acid
(c) 4-Formyl-2-chloroformyl-3-carbamoyl-5-bromohexanoic acid
(d) 2-Chloroformyl-3-carbamoyl-4-formyl-5-bromohexanoic acid

9. The correct IUPAC name of the compound given below is

CHCHCH2OH
(CH2)3CHOOC Br
(a) 3-(3’-isopropoxycarbonyl cyclopentylidene) propan-1-ol
(b) 3-(2’-Bromo-3’-hydroxypropylidene) cyclopentanecarboxylate
(c) Isopropyl-3-(2’-bromo-3’-hydroxypropylidenyl) cyclopentanecarboxylate
(d) Isopropyl-3-(2’-bromo-3’-hydroxypropylidene) cyclopentanecarboxylate

10. IUPAC name of isopentyl alcohol is

(a) 1-Hydroxy-2-methyl pentane (b) 3-Methyl butan-1-ol
(c) 2-Methyl propanol (d) 2-Methyl-2-butanol

11. Which of the following structure represent Dimethyl butanedioate?

(a) CH2 – CO – CH3 (b) CH3 – COOCH2
CH2 – CO – CH3 CH3 – COOCH2

(c) CH3 – OOC – CH2 (d) COOCO

CH3 – OOC – CH2 CH3 CH 2 – CH3

12. IUPAC name of the following compound is

COOH
COOH
COOH
(a) 2-(1-carboxyethyl)-4-methyl pentanoic acid
(b) 3,5-Dicarboxy-2-methyl hexanoic acid
(c) 2,4,5-Hexane tricarboxylic acid
(d) 2,3,5-Hexane tricarboxylic acid

13. Which of the following compound has incorrect IUPAC nomenclature?

(a) CH3CH2–CH2–COOC2H5 : Ethyl butanoate
(b) CH3 – CH – CH – CH3 : 2-Methyl butan-3-ol
OH CH3
(c) CH3 – CH – C – CH2 – CH3 : 2-Methyl pentan-3-one
CH3 O
(d) CH3 – CH – CH2 – CHO : 3-Methyl butanal
CH3
10.4 chapter ten

14. Select the structure with correct numbering for the IUPAC name of the given compound.

SH SH SH SH
4 6 1 1
5 OH 5 1 OH 6
OH 2 OH
3 2 6
(a) (b) (c) (d)
6 2 4 2 5 3 3 5
1 3 4 4
OH OH OH OH

15. In which of the following H-bonding is responsible for low volatility?

OH OH
(a) (b) F

NO2

OH

(c) (d) None of these

COOH

16. Which of the following is not correctly matched?

H3C O
(a) CH3 – C – C – O – C2H5 Ethyl-2-methyl-2-phenyl propanoate

(b) –CH – CCl3 1,1,1-Trichloro-2,2-diphenyl ethane

(c) 6-Ethyl-3,3-dimethyl cyclohex-1-ene

(d) H2N – CH – CH – CHO 2-Formyl-3-amino-1,4-butane dinitrile

CN CN

17. IUPAC name of the following compound is

O
CH3
–C–N
CH3
(a) N,N-Dimethyl cyclopropanamide
(b) N-Methyl cyclopropanamide
(c) N,N-Dimethyl cyclopropane carboxamide
(d) N,N-Dimethyl cyclopropolonamide
 nomenclature 10.5

18. Correct IUPAC name of the given compound

HO NH2

CHO
(a) 5-amino-3-hydroxy benzene carbaldehyde
(b) 3-amino-5-formyl benzenol
(c) 3-amino-5-hydroxy benzaldehyde
(d) 3-formyl-5-hydroxy aniline

19. The IUPAC name of the given structure is

Cl
Br
(a) 5-Bromo-6-chloro cyclohex-1-en-3-yne
(b) 6-Bromo-5-chloro cyclohex-1-ene-3-yne
(c) 6-Bromo-5-chloro cyclohex-3-ene-1-yne
(d) 4-Bromo-3-chloro cyclohex-1-ene-5-yne

OH
20. The IUPAC name of is
CH3
(a) 3-Methyl cyclobut-1-ene-2-ol
(b) 2-Methyl cyclobut-3-ene-1-ol
(c) 4-Methyl cyclobut-1-ene-3-ol
(d) 4-Methyl cyclobut-2-en-1-ol

21. Correct name for (C2H5)2C = C(CH3)CH2CO2H

(a) 4, 4-Diethyl-3-methyl-3-butenoic acid
(b) 4-Ethyl-3-methyl-3-hexenoic acid
(c) 3-Ethyl-4-methyl-3-hexenoic acid
(d) 3-Ethyl-4-methyl-3-hexen-6-oic acid

22. Which statement is incorrect in the following?

(a) Methyl acetate is the first higher homologue of methyl formate.
(b) Propanoic acid and propionic acid are identical.
(c) Vinyl alcohol is the lower homologue of propionaldehyde.
(d) CH3–NH–CH2–CH3 is the lower homologue of CH3 – CH – NH – CH3.
CH3
23. Match the following
CH3
(a) – CH – CH2    (i) Isobutyl
CH3

CH3
(b) – CH2 – CH (ii) Tert-pentyl
CH3
10.6 chapter ten

CH3
(c) –C – CH3 (iii) Isopentyl
CH2CH3
– H2C – CH2

(d) CH3– CH – CH3 (iv) Sec. butyl

(a) a - ii; b - iv; c - ii; d - iii (b) a - iv; b - i; c - iii; d - ii
(c) a - iv; b - i; c - ii; d - iii (d) a - iv; b - ii; c - i; d - iii

24. Number of C-atoms in first higher homologue of first member of ester family is
(a) 5 (b) 4 (c) 3 (d) 2

25. In a given compound if number of σ- and π-bonds are X and Y, respectively then (X + Y)
will be
OOCH

(a) 28 (b) 26 (c) 27 (d) 24

26. Which statement is correct in the following?

(a) Alicyclic compounds are acyclic compounds.
(b) In secondary amine, nitrogen is attached to 2° carbon atom.
(c) 1°, 2°, 3° amines are homologues of each other.
(d) HCOOCH3 and CH3COOH are not homologues of each other.

27. The correct systematic IUPAC name of the given compound is

OH
CH2 – C – CH2 – C – NH2
H2NCO CONH2 O

(a) 3-Carbamoyl-3-hydroxybutanediamide
(b) 2-Hydroxypropane-1,2,3-tricarbamoyl
(c) 2-Hydroxypropane-1,2,3-tricarboxamide
(d) 2-Bis(carbamoyl)-2-hydroxyethanamide

H
28. The correct name for C O is

COOC2H5
(a) 2-Oxocyclopentanecarboxylate
(b) 2-Formylcyclopentanecarboxylate
(c) Ethyl-2-formylcyclopentanecarboxylate
(d) Ethyl-2-oxocyclopentanecarboxylate

CH3
CH3
29. The IUPAC name of is
CH2CH3
 nomenclature 10.7

(a) 2, 3-Methyl-1-ethylcyclohex-4-ene (b) 5-Ethyl-3, 4-dimethylcyclohex­-1­-ene

(c) 4-Ethyl-5, 6-dimethylcyclohex-1-ene (d) 1-Ethyl-2, 3-dimethylcyclohex-4-ene

30. Which of the following names is correct?

(a) 4, 4-Dimethyl-3-ethylpentane (b) 3-Methyl-4-oxobutanoic acid
(c) 1-Ethyl-2-methylpent-4-ene (d) Bicyclo[1.2.3]heptane
CH2 – CHO
31. IUPAC name of the compound OHC – CH2 – CH2 – CH – CH2 – CHO is
(a) 4, 4-Di (formylmethyl) butanal
(b) 2-(formylmethyl) butane-1, 4-dicarbaldehyde
(c) Hexane-3-acetal-1, 6-dial
(d) 3-(formylmethyl) hexanedial

32. The correct IUPAC name of the following compound is

C2H5
CH3 – CH – C – CH2 – CH – CH3
CH3 CH3
(a) 3-Ethyl-3,5,-dimethylhexane (b) 4-Ethyl-2,4,-dimethylhexane
(c) 2,4-Dimehtyl-4-ethylhexane (d) 4-Ethyl-2,4,-dimethylhexene

33. The number of functional groups present in the following compounds is

H2N
O
O OH
H
NH
O O O

O O

(a) 5 (b) 7 (c) 6 (d) 8

34. Write the IUPAC name of the following compound

C
C–C
C–C–C–C=C–C
C–C–C
C
(a) 3-(1,1-dimethylethenyl)-3-ethyl-2-methyl-1,4 hexadiene
(b) 3-ethyl-2-methyl-3-(1,1-dimethylethenyl)-1,4 hexadiene
(c) 3-ethyl-2-2-dimethyl-3-(1-methylethenyl)-1,4 hexadiene
(d) 3-ethyl-3-(1-methylethenyl)-2-2-dimethyl-1,4 hexadiene

35. Hybridization of which atom changes in the following reaction?

O
PCl5
C6H5 – C – CH3 C6H5 – NH – C – CH3
N – OH
10.8 chapter ten

(a) C and O (b) C and N

(c) N and O (d) No change in the hybridization of any atom

⊕ –
36. C C C C ; carbon atoms a, b, c and d are in
a b c d
(a) sp2, sp3, sp2 and sp3 hybrid states respectively
(b) sp, sp2, sp and sp3 hybrid states respectively
(c) sp2, sp, sp2 and sp3 hybrid states respectively
(d) sp2, sp2, sp2 and sp3 hybrid states respectively

37. Ratio of π- and σ-bonds in Ph–COOH will be

(a) 5 : 3 (b) 3 : 5 (c) 3 : 16 (d) 4 : 15

38. Which of the following compound has incorrect IUPAC nomenclature?

(a) CH3CH2–CH2–COOC2H5 : Ethyl butanoate

(b) CH3 – CH – CH – CH3 : 2-Methyl butan-3-ol

OH CH3

(c) CH3 – CH – C – CH2 – CH3 : 2-Methyl pentan-3-one

CH3 O

(d) CH3 – CH – CH2 – CHO : 3-Methyl butanal

CH3

39. Identify incorrect matching in the following

(a) Allyl alcohol-Prop-2-en-1-ol (b) Vinyl alcohol-Ethenol
(c) Propargyl alcohol-But-3-yn-1-ol (d) Acrylaldehyde-2-Propenal

O – C – CH3
CO2H
40. IUPAC name of the following compound

(a) Aspirin (b) 2-Acetyl benzoic acid

(c) Acetyl salicylic acid (d) 2-Acetoxy benzoic acid

41. How many functional groups are present in the given molecule?
OMe O O

HO O Me
O
H2N H2N
O
(a) 4 (b) 5 (c) 6 (d) 7
 nomenclature 10.9

42. What is the ratio of number of σ- and π-bonds in the molecule HC – CH2CH2 – COOH?
O
(a) 5 (b) 6 (c) 4 (d) none of these

43. Which is not a first member of given homologous series?

(a) Alkadiene CH2=C=CH2 (b) Alkenyne HC≡C–CH=CH2
O O
(c) Ethyl ester CH3CH2 – O – C – CH3 (d) Ketone CH3 – C – CH3

44. Consider the given statements

(i) Acetone and acetaldehyde are homologues.

(ii) N is secondary amine while is a tertiary amine.

N
H

(iii) HO is a secondary alcohol while is a tertiary alcohol.

OH
O O
(iv) and both have different functional groups
Cl Cl
Which is not incorrect?

(a) i, ii, iii (b) ii, iii, iv (c) i, ii, iv (d) i, iii, iv

45. Number of functional groups present in the given compound is

O
O O
OMe
O O
N
O NH2
HO
O
(a) 5 (b) 6 (c) 7 (d) 8

46. Which of the following compounds has isopropyl group?

(a) 2,2,3,3-Tetramethyl pentane (b) 2,2-Dimethyl pentane
(c) 2,2,3-Trimethyl pentane (d) 2-Methyl pentane

47. What is the order of solubility in water of the following compounds?

OH NH2
(i) (ii)

Cl
(iii) (iv)
HO OH

(a) i > ii > iii > iv (b) iii > iv > i > ii
(c) iv > i > iii > ii (d) iv > i > ii > iii
10.10 chapter ten

48. The correct IUPAC name of the given compound is

NH2 O
CH2 C CH2 C OH
COOH COOH

(a) 3-Carboxy-3-hydroxy butane dioic acid

(b) 2-Amino propane-1,2,3-tricarboxylic acid
(c) 3-Amino butanedioic acid
(d) 2-Bis(carboxymethyl)-2-hydroxy ethanoic acid

49. Total number of isomers of group C5H11 is

(a) 5 (b) 3 (c) 8 (d) 9

50. Write the correct name from the incorrect name 2,3-, dichloro-2,4-dibromohept-4-ene
(a) 2, 4-dibromo-2,3-dichloro hept-4-ene
(b) 4, 6-dibromo-5,6-dichloro hept-3-ene
(c) 4, 6-dibromo-5,6-dichloro hept-4-ene
(d) 5, 6-dichloro-4,6-dibromo hept-3-ene

51. In IUPAC nomenclature of compounds

O O O
(i) – C – NH2 (ii) – C – OH (iii) – C – Cl
O
(iv) – C – H (v) –C≡N

The priority order of group is/are

(a) ii > i > iii > iv > v (b) ii > iii > i > v > iv
(c) ii > iii > v > i > iv (d) ii > iii > i > iv > v

52. The correct systematic IUPAC name of the given compound is

OH
CH2 C CH2 C NH2
H2NCO CONH2 O

(a) 3-Carbamoyl-3-hydroxybutanediamide
(b) 2-Hydroxypropane-1,2,3-tricarbamoyl
(c) 2-Hydroxypropane-1,2,3-tricarboxamide
(d) 2-Bis(carbamoyl)-2-hydroxyethanamide

Br
53. Br

(a) trans-1,1-dibromocyclohexene
(b) 1,1-dibromocyclohex-3-ene
(c) 3,3-dibromocyclohexene
(d) 4,4-dibromocyclohexene
 nomenclature 10.11

54.

(a) 1-Ethyl-3,3-dimethylcyclohexane (b) 3,3-Dimethyl-1-ethylcyclohexane

(c) 3-Ethyl-1,1-dimethylcyclohexane (d) 1,1-Dimethyl-3-ethylcyclohexane
O

55. C O Et

(a) ethyl 2-ethyl-3-methyl-2-butenoate

(b) O,2-diethyl-3-methyl-2-butenaote
(c) 1-ethoxy-2-ethyl-3-methyl-2-butenal
(d) 2-methyl-2-pentenyl propanaote

56.

(a) 4-Isobutyl-3-pentyloctane
(b) 5-Ethyl-4-methyl-6-(2-methylpropyl)decane
(c) 6-Ethyl-7-methyl-5-(methylpropyl)decane
(d) 4-Butyl-5-ethyl-2,6-dimethylnonane

57. (2E, 5R)-5-methylhept-2-en-4-one

O O
(a) (b)

O
O
(c) (d)

58. 2-Ethylphenol
OH

(a) (b)

OH OH

(c) (d)
10.12 chapter ten

59. (S)-(N,4)-dimethyl-3-aminopentan-2-one
O

(a) (b) O
NH NH

O O
(c) (d)
NH NH2

60. Methyl (2Z,4Z,6Z)-3,6,9-trimethyl-2,4,6,8-decatetraenoate

(a) CO2CH3 (b)

CO2CH3

CO2CH3
(c) (d)

CO2CH3
OH

61.

(a) (E)-5-methyl-3-heptanal (b) (Z)-3-methyl-3-hepten-5-al

(c) (E)-5-methyl-4-hepten-3-ol (d) (Z)-5-methyl-4-hepten-3-ol

O
62.

(a) 5,5-Dimethylcyclohexanol (b) 3,3-Dimethylcyclohexanone

(c) 1,1-Dimethylcyclohexanone (d) 3,3-Dimethylcyclohexanal

63. O

(a) Dibenzyl ether (b) Benzyl phenyl ether

(c) Benzyl phenyl ester (d) 3,3-Dibromocyclohexene

64. Which name is correct for the following compound?

CH3 – CH – C ≡ N
CH3