ORGANIC

CHEMISTRY
Classroom Practice Problems
Target IIT JEE-2020

TOPIC : IUPAC CPP. NO.-1

1. Select the correct IUPAC name of the compound shown below :

Br

Cl
F
(a) 1-bromo-4-chloro-3-fluorocyclohexane
(b) 4-bromo-1-chloro-2-fluorocyclohexane
(c) 1-chloro-2-fluoro-4-bromocyclohexane
(d) 5-bromo-2-chloro-1-fluorocyclohexane

2. Indicate the IUPAC name of the compound shown below : F

(a) 2-[1-fluoroethyl]pent-1-ene (b) 3-fluoro-2-propylbut-1-ene
(c) 2-fluoro-3-propylbut-3-ene (d) 2-fluoro-3-methylidenehexane

3. Which of the given IUPAC names is incorrect?

(a) 3-ethylpentane (b) 2-ethoxybut-3-ene
(c) 2-chlorobut-2-ene (d) 4,4-dichlorobut-1-ene

4. What is the IUPAC name of the compound shown below ?

(a) 5-ethyl-1-methyl cyclohexene (b) 1-methyl-3-ethyl cyclohexene

(c) 3-ethyl-1-methyl cyclohexene (d) 2-ethyl-4-methyl cyclohexene

5. Why is 2-Ethyl-3-methylpentane a wrong IUPAC name?

(a) Position of locant (b) Numbering of chain
(c) Naming of compound (d) Selection of parent chain

6. The correct IUPAC name of compound is :

(a) 8-ethyl-4-(2-methylpropyl)-2, 5-dimethylnonane

(b) 8-ethyl-4-isobutyl-2, 5-dimethylnonane
(c) 2, 5, 8-trimethyl-4-(2-methylpropyl)decane
(d) 3, 6, 9-trimethyl-4-(2-methylpropyl)decane

9. The correct IUPAC name of the following compound is :

1
 O

O
O

OH
(a) 4-Ethoxycarbonylpentanoic acid (b) 4-Ethanoyloxybutanoic acid
(c) 4-Ethanoyloxypentanoic acid (d) Ethanoic 4-methylbutanoic anhydride

10. Choose the correct name of the constituent acids of the following anhydride.
Br
O

O O

(a) 1-bromobenzoic acid and 3-cyclobutylpropanoic acid.

(b) 2-bromo-2-phenylethanoic acid and 4-cyclobutylbutanoic acid.
(c) 1-bromo-1-phenylethanoic acid and 4-cyclobutylbutanoic acid.
(d) 2-bromo-2-phenylethanoic acid and 3-cyclobutylpropanoic acid.

11. Choose the correct IUPAC name of the following compound.

N OH
O

NH2
(a) 6-Carbamoyl-5-cyano-3-methylideneoctan-2-ol
(b) 3-Cyano-2-ethyl-6-hydroxy-5-methylideneheptanamide
(c) 3-Cyano-2-ethyl-5-(1-hydroxyethyl)hex-5-enamide
(d) 3-Cyano-2-propyl-5-(1-hydroxyethyl)hex-5-enamide

12. Which of the following compound is (non) planar?

(a) Acetylene (b) Naphthalene
(c) CH2 = C = C = CH2 (d) Ethanenitrile

COOH
HO Br
13. IUPAC name of the following compound is :

NO2
(a) 2-bromo-6-hydroxy-4-nitro cyclohexanoic acid
(b) 2-bromo-6-hydroxy-4-nitro cyclohexane carboxylic acid
(c) 6-bromo-2-hydroxy-4-nitro cyclohexane carboxylic acid
(d) 2-hydroxy-6-bromo-4-nitro cyclohexane carboxylic acid
14. What is the molecular formula of cinnamic acid?
(a) C9H6O2 (b) C9H10O2 (c) C9H8O2 (d) C9H12O2

15. Which of the following reagent is commonly used in Bollywood movies for Kidnapping?
(a) CHCl3 (b) CHBr3 (c) CHI3 (d) CH3COOH

2
16. Select the correct IUPAC name of the compound shown below :
COOMe
(a) methyl 3-chlorocarbonyl-4-formylbenzenecarboxylate.
(b) 2-formyl-5-methoxycarbonylbenzenecarbonylchloride.
CHO
(c) 2-chlorocarbonyl-4-methoxycarbonylbenzenecarbaldehyde. COCl
(d) 2-formyl-5-ethanoyloxybenzenecarbonylchloride.

17. How many functional groups in the given molecule have priority lower than cyanide as per the IUPAC
priority table of functional groups?

O H O

H2N

O COCl OH O

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

18. Select the correct statement about the compound Paracetamol.
H
N

O
HO
(Paracetamol)
(a) Its IUPAC name is N-(4-Hydroxyphenyl)ethanamide
(b) Its Index of hydrogen deficiency value is 4
(c) It has total 3 different types of functional groups
(d) Its parent chain has 6 carbon chain as per IUPAC nomenclature rules.
19. What is the maximum number of carbon atoms arranged linearly in the given molecule?
H3C–CH2–C  C–CH=C=CH2
(a) 7 (b) 6 (c) 5 (d) 4

20. What is the index of Hydrogen Deficiency (I.H.D.) for the following 3-D compound

(a) 6 (b) 7 (c) 8 (d) 9

21. Find the Double Bond Equivalent value of the following compound
O

OH
N CH3
O

(a) 13 (b) 14 (c) 15 (d) 16