32 Chemistry for JEE Main & Advanced

Ex. 4 Draw the structure of following IUPAC name.

SOLVED EXAMPLES (i) 3-Ethypenta-1,4-diyne
(ii) 3-Methoxycarbonylpropanoic acid
Ex. 1 How may 1°, 2°, 3° and 4° carbon atoms are present
in following molecule.
CH3 Sol. (i)
CH3 CH C CH2 CH CH3
O
CH3 CH3 CH2 CH3 OCH3
Sol. 1° Carbon atoms = 6, 2° Carbon atoms = 2, (ii) HO
3° Carbon atoms = 2, 4° Carbon atom = 1 O
Ex. 5 Make the structure of following organic compounds
Note : Primary, secondary, tertiary & quaternary carbon 1. Isopropylidene Bromide
atoms in a molecule are denoted by the letters p, s, t 2. Active amylene Iodide 3. Isobutylene glycol
and q respectively. 4. Isobutylene 5. Trimethylene glycol
Ex. 2 How many 1°, 2°, 3° and 4° carbon atoms are present I
in following molecule. Br
Sol. 1. CH3 C Br 2. CH3 C CH2 I
CH3
CH3 CH2 CH3
CH3 C CH2 CH CH3
CH3 CH3 OH

1°
3. CH3 C CH2 OH 4. H 3C C = CH 2
CH3 CH3 CH 3
1° 4° 2° 3° 1°
Sol. CH3 C CH2 CH CH3 5. CH2 CH2 CH2
1°
CH3 1° CH3 OH OH
1° Carbon atoms = 5, 2° Carbon atom = 1, Ex. 6 The correct IUPAC name of the following compound
3° Carbon atom = 1, 4° Carbon atom = 1 is O=CH CH2 CH CHO
H C=O
Ex. 3 Write the IUPAC name of following compounds.
(A) 1,1-diformyl propanal
(i) H 3C CH2 CH COOH (B) 3-formyl butanedial
OC 2H5 (C) 2-formyl butanedial
(D) 1, 1,3-ethane tricarbaldehyde
SO3H
Sol. (C) The principal functional group is – CHO.
4 3 2 1
(ii) O=CH CH2 CH CHO
Br CHO
2-formyl butanedial
CH3
Ex. 7 The correct IUPAC name of compound
CH3 CH3 CH2 C CH CHO is
(iii)
CH3 O CN
(A) 2-cyano-3-oxopentanal
CN O (B) 2-formyl-3-oxopentanenitrile
(iv) CH3 CH C CH2 C Br (C) 2-cyano-1, 3-pentanedion
(D) 1, 3-dioxo-2-cyanopentane
NO2 OC2H5
Sol. (B) Here the main functional group is – CN, which
Sol. (i) 2-Ethoxybutanoic acid had nitrile suffix and CHO and CO are taken sub-
(ii) 3-Bromocyclohexane-1-sulphonic acid stituents.
(iii) 1,1,2-Trimethylcyclopentane 5 4 3 2
CH3 CH2 C CH CHO
(iv) 3-Cyano-3-ethoxy-4-nitropentanoyl bromide 1
O CN
(2-formyl-3-oxopentanenitrile)
 Nomenclature of organic compound 33

Ex. 8 IUPAC name of CH3 C CH C OCH3 Ex. 12 The type of unsaturation present in crotonic acid is
O C=O O (A)  (B) 
CH3 (C)  (D) 

(A) Methyl-2, 2-acetyl ethanoate

Sol. (A) The type of unsaturation present in crotonic
(B) 2, 2- acetyl-1-methoxy ethanone
acid is .
(C) Methyl-2-acetyl-3-oxobutanoate
(D) none of these O
Sol. (C) The principal functional groups is ester group. CH3 CH=CH C OH
4 3 2 1
CH3 C CH C OCH3 (Methyl-2-acetyl-3-
Crotonic acid or (2-Butenoic acid)
O C=O O
CH3 O
oxobutanonate) Ex. 13 IUPAC name of compound CH 3CH 2OCCH 2CH 2CH 3
Ex. 9 The IUPAC name of compound HO C=O CH3 is
CH3 C=C C H (A) Propyl propanoate (B) Ethyl butanoate
(C) Propyl butanoate (D) Ethyl propanoate
NH2 Cl
1 2 3 4
is Sol. (B) CH3 CH2 O C CH2 CH2 CH3 Ethyl
(A) 2-amino-3-chloro-2-methyl-2-pentenoic acid O
(B) 3-amino-4-chloro-2-methyl-2-pentenoic acid butanoate
(C) 4-amino-3-chloro-2-methyl-2-pentenoic acid Ex. 14 The IUPAC name of the compound given below is
(D) none of these
Sol. (B) The principal functional group is carboxylic acid
(–COOH)
1 5
HO C=O CH3 (A) Bicyclo [3,2,1] octane (B) Bicyclo [3,2,2] octane
2 3 4
CH3 C=C C H (C) Spiro [2, 2] octane (D) None of these
NH2 Cl Sol. (A)

3-amino-4-chloro-2-methyl-2-pentenoic acid Ex. 15 The structure of spiro [3, 3] heptane is

Ex. 10 How many carbons are in simplest alkyne having

two side chains?
(A) (B)
(A) 5 (B) 6
(C) 7 (D) 8

(C) (D)
Sol. (B)
Sol. (B)
Ex. 11 The compound name trichloroethane is
Ex. 16 The structure of bicyclo [1.1.0] butane is
(A) Westron (B) Perclene
(C) Westrosol (D) Orlone (A) (B)
Sol. (C) Trichloroethene is westrosol
(C) (D)
Cl Cl
C=C Sol. (D)
H Cl
1, 1, 2-trichlorethene(westrosol)
 34 Chemistry for JEE Main & Advanced

EXERCISE-0
9. O2N OH
BASIC CONCEPT BUILDER

O
Give the IUPAC names for each of the following :

10.
1. OH

11.

2.

12.

3. 13.

14.

4.

15.

5.
16.

6.
17.

7.
18.

8.
19.
 Nomenclature of organic compound 35

31.
20.

32.
21.

33.

22.

34.

23.
35. =C=O

24.
36.

25.
37.

26.
38.

O Cl
|| |
27. 39. CH 2  C  CH 2  CH  CH 3

28.
40.

29.
41.

30.
42.
 36 Chemistry for JEE Main & Advanced
8. Give the IUPAC name of
EXERCISE-1 CH3
SINGLE CHOICE TYPE QUESTIONS H3C C CH3
CH3 CH2 CH2 CH CH CH2 CH2 CH3
1. Which of the following compound’s prefix ‘iso’ is not
correct – H3C CH
(A) Iso pentane (B) Iso Hexane CH3
(C) Iso butane (D) Iso octane (A) 4-isopropyl-5-ter. butyl octane
2. A substance containing an equal number of primary, (B) 4-ter. butyl-5-isopropyl octane
secondary and tertiary carbon atoms is : (C) 2-methyl-3-propyl-4-ter. butyl heptane
(A) Mesityl Oxide (B) Mesitylene (D) 2, 2-dimethyl-3-propyl-4-isopropyl heptane
(C) Maleic acid (D) Malonic acid 9. The number of primary, secondary and tertiary carbon
atom in toluene is given by the set :
3. How many secondary carbon atoms does methyl cy-
(A) 1, 6, 0 (B) 1, 5, 1 (C) 2, 5, 0 (D) 1, 6, 1
CH3 10. C3H6Br2 can shows :
clopropane have ? (A) Two gem dibromide
(B) Three vic dibromide
(A) Nine (B) One (C) Two (D) Three (C) Two tert. dibromo alkane
4. What is not true about homologous series ? (D) Two sec. dibromo alkane
(A) All the members have similar chemical properties 11. What is the correct IUPAC name for the following com-
(B) They have identical physical properties pound ?
CH3
(C) They can be represented by a general formula
(D) Adjacent members differ in molecular mass by 14 CH3(CH2 )4CH C CH2CH2CH3
5. The IUPAC name of the following is CH3 CH2 CH3
[CH3CH(CH3)]2C(CH2CH3)C(CH3)C(CH2CH3)2 (A) 3, 4-Dimethyl-3-propyl nonane
(A) 3,5-Diethyl-4,6-dimethyl-5-[1-methylethyl]hept-3- (B) 6, 7-Dimethyl-2-propyl nonane
ene (C) 6, 7-Dimethyl-7-ethyl decane
(B) 3, 5-Diethyl-5-isopropyl-4, 6-dimethylhept-2-ene (D) 4-Ethyl-4, 5-dimethyl decane
(C) 3,5-Diethyl-5-propyl-4, 6-dimethylhept-3-ene 12. All the following IUPAC name are correct except :
(D) None of these (A) 1-Chloro-1-ethoxy propane
(B) 1-Amino-1-ethoxypropane
6. Which of the following is a heterocyclic compound
(C) 1-Ethoxy-2-propanol
HC=CH HC=COOH (D) 1-Ethoxy-1-propanamine
(A) S (B)
HC=CH HC=COOH 13. Number of 3° carbon and 1° hydrogen respectively in
the following structure are :
HC=CH HC=CH
(C) CH 2 (D) C=O Me Me Me H
HC=CH HC=CH
7. Ethyl methyl vinyl amine has the structure – H C C C C Me
Me H Me Me
(A) CH3CH2 N CH2CH=CH2
(A) 3, 21 (B) 3, 23 (C) 2, 18 (D) 3, 18
CH3 14. The correct IUPAC name for the given structure is :
(B) CH3CH2 N CH=CH2 CH3
CH3 CH3 CH CH2 CH CH2 CH3
(C) CH2=CH N CH=CH2 H3C CH CH3

CH3 (A) 3-Isopropyl-4-methylhexane

(B) 4-Isoprpyl-3-methylhexane
(D) CH3 N CH=CH2 (C) 3-Ethyl-2, 5-dimethylhexane
CH3 (D) 2-Ethyl-3-isopropylpentane
 Nomenclature of organic compound 37

Et Me O
15. The IUPAC name of is : CH2 C OH
OH
23. The IUPAC name of compound C
(A) 2, 3-Dimethyl hexane COOH
CH2 COOH
(B) 2-Ethyl-4-methyl pentane
(C) 3-Ethyl-2-methyl pentane (A) 1, 2, 3-Tricarboxypropan-2-ol
(D) 2, 4-Dimethyl hexane (B) 2-Hydroxy propane-1, 2, 3-tricarboxylic acid
16. The IUPAC name of the compound is (C) 3-Hydroxy-3-carboxypentane-1, 5-dioic acid
(D) None
Ph 24. The IUPAC name of the structure is :
CH3 CH CH NH2 H2N CH CH CHO
CH3 HOOC COOH
(A) 1-Amino-1-phenyl-2-methyl propane (A) 3-Amino-2-formyl butane-1, 4-dioic acid
(B) 2-Methyl-1-phenyl propane-1-amine (B) 3-Amino-2, 3-dicarboxy propanal
(C) 2-Methyl-1-amino-1-phenyl propane (C) 2-Amino-3-formyl butane-1, 4-dioic acid
(D) 2-Chloro-2-Methylpropane (D) 1-Amino-2-formyl succinic acid
17. The IUPAC name of the compound Br (Cl) CH.CF3 is : 25. Which of the following compound is wrongly named ?
(A) haloethane Column I Column II
(B) 1, 1, 1-triflouro-2-bromo-2-chloroethane (A) CH3CH2 CH 2CHCOOH 2-Chloro pentanoic acid
(C) 2-bromo-2-chloro-1, 1, 1-triflouroethane Cl
(D) 1-bromo-1-chloro-2, 2, 2-triflouro ethane (B) 2-Methyl hex-3-enoic acid
18. The IUPAC name of tert-butyl chloride is :
(A) 4-Chlorobutane
(C) CH3CH2CH = CHCOCH3 Hex -3- en - 2- one
(B) 2-Ethyl-2-methyl pentane
(C) 3-Ethyl-2-methyl pentane (D) CH3 CHCH2CH2CHO 4-Methyl pentanal
(D) 2-Chloro-2-Methyl propane CH3
19. The IUPAC name of is : NH2
(A) 1, 1-diethyl-2, 2-dimethyl pentane COOH
26. The IUPAC name of is
(B) 4, 4-dimethyl-5, 5-diethylpentane
(C) 5, 5-diethyl-4, 4-dimethylpentane
(A) 1-amino-2-carboxybenzene
(D) 3-ethyl-4, 4-dimethylheptane
(B) 2-amino-1-carboxy benzene
20. The correct IUPAC name of :
(C) 1-amino-2-benzenecaroxylic acid
CH3 CH2 CH CH2COCl (D) 2-aminobenzenecarboxylic acid
CH3 27. Which name is correct :
(A) 3-methyl pentanoyl chloride OHC CH3
(B) 3-methyl butanoyl chloride CH3
(C) 1-chloro-3-ethyl butanone CH3
(A)
(D) 1-chloro-3-methyl pentanone
3, 7-Dimethyloct-2, 6-dienal
21. The correct IUPAC name of CH3 CH2 C COOH
(A) 2-methyl butanoic acid CH2 (B) Spiro(3,6) decane
(B) 2-ethyl-2-propenoic acid
I
(C) 2-carboxy-1- butene
(D) None of these
22. IUPAC name will be CH2 CH CH 2
(C)
CN CN CN Et
(A) 1, 2, 3-Tricyano propane 3-Ethyl-7-iodobicyclo (2.2.1) heptane
(B) Propane-1,2,3-trinitrile
(C) 1, 2, 3-Cyano propane
(D) N N-Methyl-Ethylethanamine
(D) Propane-1, 2, 3-tricarbonitrile
 38 Chemistry for JEE Main & Advanced
28. The IUPAC name of the following compound is : 33. The correct IUPAC name of the compound

CHO COOH
C O
O
Br OH
(A) 5-Bromo-3-hyddroxybenzenecarbaldehyde (A) 2-Phenoxycarbonylbenzenecarboxylic acid
(B) 3-Bromo-5-formylphenol (B) Phenyl-2-carboxybenzenecarboxylate
(C) 3-Bromo-5-hydroxybenzenecarbaldehyde (C) 2-Benzoyloxybenzenecarboxylic acid
(D) 1-Bromo-3-formyl-5-hydroxybenzene (D) 2-Bezyloxycarbonylbenzenecarboxylic acid
38. Which of the following is oxetane ?
COOH
O

(A) (B)
O
29. The IUPAC name of the compound is :
CN O
CHO O
(C) (D)
(A) 2-Cyano-1-fromylbenzene-4-carboxylic acid
(B) 3-Cyano-4-formylbenzene-1-carboxylic acid 39. The systematic nomenclature of the following spiro
(C) 4-Careboxy-2-cyanobenzene-1-carbaldehyde compound is :
(D) 2-Formyl-5-carboxybenzene-1-carbonitrile
O Me
30. IUPAC name of Cl C O

(A) 4-Chlorophenyl benzoate, (A) 2-methyl spiro [3.4] octane

(B) Phenyl-4-Chlorobenzenecarboxylate.
(B) 3-Methyl spiro [3.4] octane
(C) Benzyl-4-chlorobenzenecarboxylate
(C) 6-Methyl spiro [3.4] octane
(D) 4-Chloro diphenylcarboxylate.
(D) 7-Methyl spiro [3.4] octane
31. The correct IUPAC name of the compound.
40. An alkane (A) having a molecular mass of 72 produces
NH-CHO one monochlorination product. Compound (A) is :
Me
Cl (A) Me (B) Me
Me Me
(A) N-Formyl-4-chlorobenzenamine
(B) N-Formyl-4-chloroaniline Me
(C) N-(4-chlolrophenyl)methanamide
Me
(D) N-(Parachlorophenyl)–N-Formylaniline (C) Me (D)
Me
COOC2H5

32. IUPAC name of the compound is 41. Which of the following is a 3º amine ?
COCl (A) Propan-2-amine (B) N-Methyl ethanamine
(A) 2-Chlorocarbonyl ethylbenzenecarboxylate (C) Allyl amine (D) N,N-Diethyl butan-1- amine
(B) 2-Carboxyethylbenzoyl chloride
(C) Ethyl 2-(chlorocarbonyl)benzenecarboxylate
(D) Ethyl 1-(chlorocarbonyl)benzenecarboxylate

EXERCISE-2
PART-1
MULTIPLE CHOICE TYPE QUESTIONS
1. Which of the following statement is /are wrong ?
(A) CnH2n is the general formula of alkanes
(B) In homologous series, all members have the same
physical properties
(C) IUPAC means International Union of Physics and
Chemistry
(D) Butane contains two 1° C atoms and 2°C atom
2. Which of the following statement is/are correct?
(A) Homologous series can be represented by a gen-
eral formula
(B) The chemical properties of an organic compound
depend on the functional group
(C) Group obtained by the removal of one H atom from
the alkane are called alkyl groups
(D) Alkynes consist of one double-bond in their mol-
ecules
3. Which of the following statement is/are correct ?
(A) Methane was named as fire damp as it formes explo-
sive mixture with air
(B) Primary suffixes are added to the root word to show
saturation or unsaturation in a C atom
(C) The IUPAC name of the valeric acid is pentanoic
acid
(D) The common name of hexanoic acid is caproic acid
4. Which of the following statement is /are correct?
(A) The IUPAC name of amyl alcohol is pentanol
(B) The IUPAC name of isoamyl alcohol is 3-methyl
butanol
(C) Wood spirit is methanol
(D) Methyl alcohol is also called carbinol
5. Which of the following statement is/are correct?
(A) The trivial names of organic compounds are called
common names
(B) The systematic names of organic compound are
obtained from the IUPAC system
(C) The systematic name of alkanes are based on the
number of C atom in the longest continues chain of C
atoms
(D) The maximum number of functional groups must be
included in the C atom chain selected even if it does not
satisfy the longest chain rule
Nomenclature of organic compound 39
6. Which of the following statement is/are wrong?
(A) Acetic acid is the systematic of vinegar
O
(B) Me C OH is an unsaturated compound
(C) Prefixes like n–, iso, sec–, tert, neo– etc. are used in
IUPAC system.
(D) The systematic names of acids are formed by drop-
ping –e of the name of parent alkane and adding –oic
acid.
7. Which of the following statement is /are correct?
O O
(A) R C O C R is an unsaturated compound
(B) Neohydrocarbons contain a 3° C atom
(C) The IUPAC name of isopropyl alcohol is propan-2-
ol
(D) The IUPAC name of (CH3CN) is ethanenitrile
8. Which of the following statement is/are correct?
(A) The common name of benzene-1, 2-diol is catechol
(B) The common name of benzene-1, 3-diol is resorcinol
(C) The common name of benzene-1, 4-diol is quinol
(D) The common name of benzene-1, 4-diol is hydro-
quinone
9. Which of the following statement is/are correct?
(A) The common name of benzene-1, 2, 3-triol is pyro-
gallol
(B) The common name of benzene-1, 2, 4-triol is
hydroxyquinol
(C) The common name of benzene-1,3, 5-triol is phloro-
glucinol
(D) The common name of (CH2 = CH – Ph) is styrene
10. Which of the following statement is/are correct?
(A) The common name of (HOOC – CH2 – COOH) is
malonic acid
COOH
(B) The common name of COOH is succinic acid
(C) The IUPAC name of (CH2 = CH – OCOCH3) is vinyl
acetate
(D) The IUPAC name of acrylonitrile is prop-2-ene ni-
trile
O
11. The compound CH3 CH2 C CH2 may be named as
CH3
(A) 2-ethyl-2-methyl oxirane
(B) 1, 2-epoxy-2-methylbutane
(C) 1, 2-oxapentane
(D) 2-methyl-2-butoxide
 40 Chemistry for JEE Main & Advanced
12. Which of the following names are not correct for the 19. Which of the following statements are correct ?
CH2 CH CH2 (A) methyl cyclopropane and methyl cyclobutane do
given compound : not show stereoisomerism
CHO CHO CHO
(A) 3-Formyl pentane-1, 5-dial (B) Both show stereoisomerism
(B) 1, 2, 3-Triformylpropane (C) Dimethyl cyclopropane shows stereoisomerism, but
methyl cyclobutane does not.
(C) 2-Formylbutane-1, 4-dial
(D) Fimethyl cyclopropane does not show stereo-isom-
(D) Propane-1, 2, 3-tricarbaldehyde
erism, but methyl cyclobutane shows
13. The name (s) of the following compound is :
(CH3)2CHCN 20. Which of the following statements are correct ?
(A) 2-Methyl propane nitrile(B) Isobutyro nitrile (A) Butan-2-one shows tautomerism
(C) Isopropyl cyanide (D) None of these (B) Compounds containing asymmetric C atoms are al-
ways optically active.
14. Which of the following are the names of cyclic ether : (C) Members belonging to the same class of com-
(A) Oxirane (B) Epoxyalkane pounds are called isomers.
(C) Alkene oxide (D) Carbional (D) Isomers have the same molecular formula.
15. The name(s) of the following compound is :
CH(OH)COOH
CH(OH)COOH
(A) tartaric acid
(B) 2, 3-dihydroxy butane-1,4-dioic acid
(C) ’-dihydroxy succinic acid
(D) None of these

16. The compound C6H5 – CH = CH – COOH may be called

as :
(A) Succinic acid (B) 3-phenylprop-2-en-1-oic acid
(C) Mandelic acid (D) Cinnamic acid

17. Which of the following names are correct for the com-
pound :
O
CH3 C CH2 COOH
(A) 3-ketobutan-1-oic acid
(B) 4-Carboxy butan -2-one
(C) 3-oxo butan-1-oic acid
(D) 3-Carboxy acetone

18. Which of the following statements is/are wrong ?

(A) Acetic acid is the systematic name of vinegar
O
(B) is an unsaturated compound
Me – C – OH
(C) Prefixes like n-, iso, sec–, tert, neo–, etc,,. are used in
IUPAC system.
(D) The systematic names of acids are formed by drop-
ping –e of the name of parent alkane and adding -oic
acid.
 Nomenclature of organic compound 41

PART-2
MATRIX MATCH TYPE QUESTIONS

1. Match column I with column II and select the correct answer from the given codes :
Column - I Column - II
(Compounds) (number of carbons in the bridges)

(A) (p) [3.2.1]

(B) (q) [4.3.0]

(C) (r) [4.4.0]

(D) (s) [3.2.0]

2. Column - I Column - II
Compound Containing all the functional groups

(A) HO (p) 1° amine

Vitamin D3

NH2
Ph
(B) Me (q) 2° alcohol
Amphetamine
O
Me
(C) H (r) Triene
A cockroach repellent
found in cucumbers
(s) Aldehyde and ene
3. Column - I Column - II
Compound Nature of H atoms
Me
(A) Me Me (p) 15 (1° H), 4(2° H), 1(3° H)
Me
Me Me
(B) Me Me (q) 17 (1°H), 2(2° H), 2(3°H)
Me
Me Me Me
(C) Me (r) 12(1°H), 2(2°H), 2(3°H)
Me
Me
(D) Me Me OH (s) 15(1°H), 2(2° H), 1(3°H)
Me Me
 42 Chemistry for JEE Main & Advanced
4. Column - I Column - II
Compound Containing all the functional groups
Ph
O O
O
NH Me
(A) H2N O (p) ene and diester
Aspartame
O
Ph
O Me
(B) (q) Carboxylic acid, 1° amine, amide
N Demerol
Me
O
O O
(C) (r) Ester
Asynthetic cockroach repellent
(s) 3° amine
5. Column - I Column - II
Compound Structure

(A) C8H18 with only 1° H atom (p)

Me Me

(B) C6H12 with only 2° H atoms (q) Me

Me Me Me

(C) C6H12 with only 1° and 2° H atoms (r)

(D) C8H14 and 12 secondary and 2 (s)

tertiary H atoms
Me
Me
selected containing two such similar groups at its two
PART-3
ends. The groups present in the side chain are treated
COMPREHENSION TYPE QUESTIONS as substituents and are indicated by suitable prefixes.
Comprehension # 1 Indicate whether the following IUPAC names are true
If the organic compound contains more than two simi- (A) or false (B)
lar terminal groups and all of them are directly attached COOH
to the principal chain, then none of them forms a part of
1. HOOC CH2 CH CH2 COOH
the principal chain. Special suffixes are used to name
these :- Propane-1, 2, 3-tricarboxylic acid
Functional group Suffix True (A) False (B)
––CONH2 Carboxamide CN
––CN Carbonitrile 2. NC CH2 CH CH2 CN
–– CHO Carbaldehyde 3-cyanopentane-1, 5-dinitrile
––COOH Carboxylic acid True (A) False (B)
Carbon atoms of these terminal groups are not counted CH2COOH
in the principal chain. If any one of these terminal groups HOOC CH2 CH CH2 COOH
3.
is not directly attached to the parent chain and forms
3-(carboxymethyl)-1, 5-dioic acid
the part of side chain, then the longest chain is True (A) False (B)
 Nomenclature of organic compound 43
CH2CHO
PART-4
4. OHC CH 2 CH CH 2 CHO
SUBJECTIVE TYPE QUESTIONS
3-(formylmethyl)pentane-1, 5-dial
True (A) False (B)
CONH2
1.
5. H2NOC CH2 CH CH2 CONH2
Propane-1, 2, 3-tricarboxamide
True (A) False (B)

Comprehension # 2 2.
In addition to the standard ring systems (such as cy-
clohexane), cyclic compounds can also be bicyclic, tri-
cyclic, etc. or they can be spirocyclic, bicyclic or bridge
head carbons. The point of attachment of two rings are
called bridge head atoms. 3.
The formal names of bicyclic and related ring systems
are based on
(A) Total number of atoms in the molecule.
(B) The number of atoms in each bridge connecting the
bridge head atoms. These numbers are written in square
bracket in decreasing order. 4.
Spirocyclic compounds have two fused rings, but only
bridge head atom. Spirocyclic compounds are named
like bicyclic compounds, but have the prefix spirocyclo.
Answer the following question :
5.
1.

What is the IUPAC name of the above compound ?

(A) cyclo [1.2.2] heptane (B) Bicyclo [1.2.2] heptane
(C) Bicyclo [2.2.1] heptane (D) cyclo [2.2.1] heptane
6.
2. The number of atoms in each bridge are :

(A) [3.2.1] (B) [3.1.0] (C) [1.3.0] (D) [2.1.0]

3. Select the correct statement about the following com- 7.
pounds :

8.
(A) It is a tricyclic compound
(B) It is bicyclo compound
(C) It is spiro compound
(D) Its IUPAC name is bicyclo [2.2.2] hexane
4. Which of the following is the correct structure of bicyclo 9.
[1.1.0] butane?

CH2 CH2 CH2 CH

(A) (B) (C) (D) CH2 10.
CH2 CH2 CH2 CH
 44 Chemistry for JEE Main & Advanced

EXERCISE-3 (1) 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne

(2) 3, 5-dimethyl-4-propylhept-6-en-1-yne
PART - 1 (3) 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
PREVIOUS YEAR QUESTIONS : JEE MAIN (4) 3, 5-dimethyl-4-propylhept1-en-6-yne
[JEE Main 2019]
1. The correct decreasing order of priority for the
7. The correct IUPAC name of the following compound is
functional groups of organic compounds in the IUPAC
system of nomenclature is [AIEEE -2008]
(1) –COOH, –SO3H, –CONH2, –CHO NO2
(2) –SO3H, –COOH, –CONH2, –CHO
(3) –CHO, –COOH, –SO3H, –CONH2
(4) –CONH2, –CHO, –SO3H, –COOH Cl
2. The IUPAC name of neopentane is : [AIEEE -2009] CH3
(1) 2-methylpropane (2) 2, 2-dimethylbutane
(3) 2-methylbutane (4) 2, 2-dimethylpropane (1) 2-methyl-5-nitro-1-chlorobenzene
(2) 3-chloro-1-methyl-nitrobenzene
O (3) 2-chloro-1-methyl 1-4-nitribenzene
(4) 5-chloro-4-methyl 1-1-nitrobenzene
3. The IUPAC name of compound H2C CH CH3 [JEE Main 2019]

is :- [AIEEE -2012 (Online)] 8. Which of the following compounds will show the
(1) 1, 2-Epoxy propane (2) Propylene oxide maximum ‘enol’ content ?
(3) 1, 2-Oxo propane (4) 1, 2-Propoxide (1) CH3COCH3 (2) CH3COCH2COCH3
(3) CH3COCH2COOC2H5 (4) CH3COCH2CONH2
4. The IUPAC name of the followig compounds is :
[JEE Main 2019]
[AIEEE -2012 (Online)]
9. The IUPAC name of the following compound is
CH3 OH
H3C CH CH CH2 COOH
(1) (Z) – 5– hepten – 3 – yne (1) 4,4-dimethyl-3-hydroxybutanoic acid
(2) (Z) – 2– hepten – 4 – yne
(3) (E) – 5– hepten – 3 – yne (2) 2-methyl-3-hydroxypentan-5-oic acid
(4) (E) – 2– hepten – 4 – yne (3) 3-hydroxy-4-methylpentanoic acid
5. Aspirin is known as : [AIEEE -2012] (4) 4-methyl-3-hydroxypentanoic acid
(1) Acetyl salicyclic acid (2) Phenyl salicylate [JEE Main 2019]
(3) Acetyl salicylate (4) Methyl salicylic acid 10. What is the IUPAC name of the following compound ?
6. The IUPAC name for the following compound is
CH3 CH3
H
CH3 H
CH Br
H3C CH3

(1) 3-bromo-3-methyl-1, 2-dimethylprop-1-ene

CH3 (2) 3-bromo-1, 2-dimethylbut-1-ene
CH2 (3) 2-bromo-3-methylpent-3-ene
(4) 4-bromo-methylpent-2-ene [JEE Main 2019]
 Nomenclature of organic compound 45
PART - 2 8. The carboxyl function group (–COOH) is present in :
PREVIOUS YEAR QUESTIONS : JEE ADV. [IIT-JEE 2012]
(A) picric acid (B) barbituric acid
1. Write IUPAC name of the following [IIT-JEE 2004] (C) ascorbic acid (D) aspirin
COOH
9. The IUPAC name(s) of the following compound is(are)
[IIT-JEE 2017]

NH2
H3C Cl
O
2. IUPAC name of C6H5 C Cl [IIT-JEE 06]
(A) 4-methylchlorobenzene
(A) Benzoylchloride (B) 4-chlorotoluene
(B) Benzenecarbonylchloride (C) 1-chloro-4-methylbenzene
(C) Chlorophenyl ketone (D) 1-methyl-4-chlorobenzene
(D) Phenylchloroketone

3. Write IUPAC name of the following [IIT-JEE 2005]

SO3H

CH3

4. The number of structural isomers for C6H14 is :

[IIT-JEE 2007]
(A) 3 (B) 4 (C) 5 (D) 6

5. The IUPAC name of the following compound is :

[IIT-JEE 2009]
OH

CN
Br
(A) 4-Bromo-3-cyanophenol
(B) 2-Bromo-5-hydroxybenzonitrile
(C) 2-Cyano-4-hydroxybromobenzene
(D) 6-Bromo-3-hydroxybenzonitrile

6. The total number of cyclic isomers possible for a hy-

drocarbon with the molecular formula C4H6 is/are :
[IIT-JEE 2010]

7. In allene (C3H4), the type(s) of hybridisatin of the car-

bon atoms is (are) : [IIT-JEE 2012]
(A) sp and sp3 (B) sp and sp2
(C) only sp3 (D) sp2 and sp3
 46 Chemistry for JEE Main & Advanced

ANSWER KEY
EXERCISE-0
BASIC CONCEPT BUILDER

4 5 6 7 8
1. CH 3  CH 2  CH  CH 2  CH 2  CH 2  CH 3 8. CH 3  CH  C  CH 2  OH
| |
CH 2  CH 2  CH 3 CH 2  CH 3

4-Ethyl octane 2-Ethylbut-2-en-1-ol

3 2 1
5 4 9. CH  CH  CH 2
CH3–CH–CH3 | |
NO 2 OH
2. CH3 CH 3
1
CH2 2 CH–CH3
3-nitroprop-2-en-1-ol
CH3 OH O
| ||
10. CH 2  CH  CH  C  C  CH
6 5 4 3 2 1
3-Ethyl-2,4-dimethyl pentane
4-hydroxyhex-5-en-1-yn-3-one
3. 5-Methyl hepta-1,3,6-triene
4. Hex-1-en-3-yne
11. CH 3  C  CH 2  C  CH 3
|| ||
O O
1 2 3 4 5
5. CH 2  C  CH 2  CH  CH 3
| | Pentane-2,4-dione
CH 3  CH  CH 3 CH 3
5 4 3 2
CH 3  CH 2  CH 2  CH  CHO
2-Isopropyl-4-methylpentene 12. |
or 4-Methyl-2-(methyl ethyl) pentene 1
CN
1 2 3
6. CH 2  CH  CH 2  OCH 3 2-Formyl pentane nitrile
13. 3-Ethyl-4,6-dimethyloctane
3-Methoxypropene
14. 5 Methyl cyclohexa-1,3-diene
15. 1,3-cyclobutadiene
4 3 2 1
7. CH 2  CH  C  CH 2 16. 1,2-epoxy propane
|| | 17. 1,3,4-trimethyl-1-cyclobutene
O OH
18. 1-ethyl-2-methylcyclopentane
19. 1-methyl-3-(methyl ethyl cyclohexane)
1-Hydroxybut-3-en-2-one
or isopropyl-3-methylcyclohexane
 Nomenclature of organic compound 47
20. Butyl cyclohexane 21. Isopropylidenecyclopentane
or 1-methyl ethylidene cyclopentane
22. Cyclopropanecarboxylic acid 23. Cyclopent-2-en-1-one
24. 1-(3-butenyl) cyclopentene 25. 1-cyclohexyl-1-propanone
26. Ethyl cyclohexanecarboxylate 27. 4-Bromo-2-ethyl cyclopentanone
28. 3-(hydroxymethyl)-5-methylheptanal 29. 2-Bromo-6-oxocyclohexanecarbaldehyde
30. Bicylo(2.2.1)heptane 31. spiro (2.5) octane
32. spiro(4.5) decane 33. Bicyclo(4.4.0) decane
34. Cyclopent-2-en-1-ol 35. Cyclohexylidene methanone
36. Bicyclo (3.1.0) hexane 37. Cyclohex-2-en-1,4-dione
38. 2-ethynyl cyclohexanol 39. 4-chloro-1-cyclopentyl pentan-2-one
40. 1-Aminomethyl-2-ethyl cyclohexanol 41. 4-isopropyl-1-propyl-1-cyclohexene
or 4-(1-methylethyl)-1-propyl cyclohexene
42. 2-(2-oxo cyclohexyl) propanoic acid

EXERCISE-I
1. D 2. B 3. C 4. B 5. A 6. A 7. B 8. B 9. B 10. A 11. D 12. B 13. A
14. C 15. D 16. B 17. C 18. D 19. D 20. A 21. B 22. D 23. B 24. C 25. B 26. D
27. B 28. C 29. B 30. B 31. C 32. C 33. A 34. B 35. C 36. C 37. D 38. B 39. C
40. C 41. D
EXERCISE-II
Part-I MCQ
1. A, B, C 2. A, B, C 3. A, B, C, D 4. A, B, C, D 5. A, B, C, D 6. A, B, C 7. C, D
8. A, B, C, D 9. A, B, C, D 10. A, B, D 11. A, B 12. B, C 13. A, B, C 14. A, B, C
15. A, B, C 16. B, D 17. A, C 18. A, B, C 19. A, C 20. A, D
Part-II MATRIX-MATCH
1. A  (q) , B  (r), C  (s) , D  (p) 2. A  (r, q) , B  (p), C  (s)
3. A  (r) , B (p), C  (s) , D  (q) 4. A  (q, r) , B  (r, s) , C  (p)
5. A  (q) , B  (r), C  (s) , D  (p)
Part-III COMPREHENSION
Comprehension # 1 : 1. T 2. F 3. F 4. T 5. T
Comprehension # 2 : 1. C 2. B 3. B 4. A
Part-IV SUBJECTIVE
1. 2,2,6,7-tetramethyloctane 2. Methylene cyclohexane
3. 1,2-diethenyl cyclohexene 4. 5-amino-6-(1-methyl propyl) cyclo-hex-2-enol
5. 2-bromo-2-methyl cyclopentanone 6. Methyl-2-methoxy-6-methyl-3- cyclohexene carboxylate
7. 9-methyl bicyclo(4.2.1) nonane 8. Bicyclo (1.1.0) butane
9. Bicyclo(2.2.1) heptane 10. 8-chloro bicyclo(4.2.0) oct-2-ene

EXERCISE-III
PART-A
PREVIOUS YEAR QUESTIONS [AIEEE/JEE-MAIN]
1. 1 2. 4 3. 1 4. 4 5. 1 6. 4 7. 3 8. 2 9. 3 10. 4

PART - B
PREVIOUS YEAR QUESTIONS [IIT-JEE ADVANCED]
1. 3-Aminobenzoic acid 2. B 3. 4-Methylbenzensulphonic acid 4. C 5. B
6. 5 7. B 8. D 9. B, C