Chapter 22

Hydrocarbons

1. The main product of the following reaction is 5. The major organic compound formed by the
reaction of 1, 1, 1-trichloroethane with silver powder
conc.H 2SO 4
C 6H5 CH 2 CH(OH)CH(CH 3 )2   o? is [JEE (Main)-2014]
[AIEEE-2010] (1) Acetylene (2) Ethene

H5C6CH2CH2 (3) 2-Butyne (4) 2-Butene

(1) C = CH2 6. Which of the following compounds will exhibit
H3C geometrical isomerism? [JEE (Main)-2015]
(1) 1 - Phenyl - 2 - butene
H 5C 6 H
(2) 3 - Phenyl - 1 - butene
(2) C=C
H CH(CH 3)2 (3) 2 - Phenyl - 1 - butene
(4) 1, 1 - Diphenyl - 1 propane
C6H5CH2 CH3
7. Which compound would give 5-keto-2-methyl
(3) C=C hexanal upon ozonolysis? [JEE (Main)-2015]
H CH3
CH3 CH3
C6H5 CH(CH3)2
CH3
(4) C=C
(1) (2)
H H
2. One mole of a symmetrical alkene on ozonolysis CH3
gives two moles of an aldehyde having a molecular
mass of 44 u. The alkene [AIEEE-2010] CH3 CH3
(1) Ethane (2) Propene
H3C
(3) 1-butene (4) 2-butene (3) (4)

3. 2–Hexyne gives trans–2–Hexene on treatment with CH3

[AIEEE-2012]
(1) Li/NH3 8. The reaction of propene with HOCl (Cl2 + H2O)
proceeds through the intermediate
(2) Pd/BaSO4 [JEE (Main)-2016]
(3) Li AlH4 (1) CH3 – CH+ – CH2 – Cl
(4) Pt/H2 (2) CH3  CH(OH)  CH2
4. Which branched chain isomer of the hydrocarbon
(3) CH3  CHCl  CH2
with molecular mass 72 u gives only one isomer of
mono substituted alkyl halide? [AIEEE-2012] (4) CH3 – CH+ – CH2 – OH
(1) Neopentane 9. The trans-alkenes are formed by the reduction of
(2) Isohexane alkynes with [JEE (Main)-2018]

(3) Neohexane (1) H2 - Pd/C, BaSO4 (2) NaBH4

(4) Tertiary butyl chloride (3) Na/liq. NH3 (4) Sn - HCl

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10. The major product of the following reaction is
OH
O (1) (2)
CH3
AlCl3,'
O o
+
(3) (4)
[JEE (Main)-2019]

12. The major product of the following reaction is

CH3O
CH2Cl
(i) AlCl3 (anhyd.)
(1)
(ii) H 2O

[JEE (Main)-2019]

OCH 3
CH3
(1)

CH3O
(2)
(2)

CH3O
(3)

(3) (4) CH3O

CH 3

13. W hich hydrogen in compound (E) is easily

replaceable during bromination reaction in presence
of light?

CH3  CH2  CH CH
G J E D
(E)
(4)
[JEE (Main)-2019]
(1) J-hydrogen
(2) D-hydrogen
11. Which of the following compounds is not aromatic? (3) G-hydrogen
[JEE (Main)-2019] (4) E-hydrogen

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14. What will be the major product in the following Cl
mononitration reaction?
(2)
O
HNO3
N  o
H Conc.H SO
2 4

Cl
[JEE (Main)-2019] (3)
O NO2
(1)
N
H

(2) O2N HO
O
(4)
N
H

17. Among the following four aromatic compounds,

(3) O which one will have the lowest melting point?
N [JEE (Main)-2019]
H
NO2 O

O OH
(1) (2) OH
(4) O2N N
H O

CH3
15. Which compound(s) out of following is/are not OH
aromatic? O
(3) O
(4)

CH3

18. The major product of the following reaction is

(A) (B) (C) (D) CH3CH2CHCH2 (i) KOH alc.
(ii) NaNH2
[JEE (Main)-2019] Br Br in liq NH3

(1) (B), (C) and (D) (2) (A) and (C) [JEE (Main)-2019]
(3) (C) and (D) (4) (B) (1) CH3CH2C { CH
16. The major product of the following reaction is
(2) CH3CH = CHCH2NH2

(3) CH3CH2CH – CH2

HO
(1) HCl
NH2 NH2
(2) AlCl 3 (Anhyd.)
(4) CH3CH = C = CH2
[JEE (Main)-2019] 19. The major product in the following conversion is
HO
CH3O CH = CH – CH3 HBr (excess)
Heat ?
(1)
[JEE (Main)-2019]

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 22. Which one of the following alkenes when treated
(1) HO CH2 – CH – CH3 with HCl yields majorly an anti Markovnikov product?
Br [JEE (Main)-2019]

(2) CH3O CH2 – CH – CH3 (1) F3C–CH=CH2 (2) CH3O–CH=CH2

(3) H2N–CH=CH2 (4) Cl–CH=CH2
Br
23. Polysubstitution is a major drawback in :
(3) HO CH – CH2 – CH3
[JEE (Main)-2019]
Br (1) Reimer Tiemann reaction
(4) CH 3O CH – CH 2 – CH 3 (2) Acetylation of aniline

Br (3) Friedel Craft’s acylation

20. The major product of the following reaction is (4) Friedel Craft’s alkylation
H3C 24. The major product of the following reaction is
CH2 HCl
(i) DCl (1 equiv.)
H CH3 C { CH o(ii) DI
[JEE (Main)-2019]
[JEE (Main)-2019]
CH3
CH2– Cl (1) CH3C(I)(Cl)CHD2 (2) CH3CD(I)CHD(Cl)
(1)
(3) CH3CD(Cl)CHD(I) (4) CH3CD2CH(Cl)(I)
H
25. The increasing order of reactivity of the following
CH3
compounds towards aromatic electrophilic
CH3
substitution reaction is
(2) H
Cl Cl OMe Me CN
CH3
CH3
(3) Cl
H A B C D
CH2– Cl [JEE (Main)-2019]
CH3 (1) D < B < A < C
(4)
H (2) D < A < C < B
21. The major product of the following reaction is (3) B < C < A < D
O Cl (4) A < B < C < D
(i) AlCl3, heat 26. The increasing order of the reactivity of the following
O+
(ii) H2O compounds towards electrophilic aromatic
substitution reactions is :
O
CI CH3 COCH3
[JEE (Main)-2019]
O Cl O

(1) (2)
(I) (II) (III)
CO2H Cl
O [JEE (Main)-2019]
O (1) I < III < II
CO2H Cl (2) III < II < I
(3) (4)
(3) II < I < III
Cl
O O (4) III < I < II

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27. W hich of these factors does not govern the 31. Heating of 2-chloro-1-phenylbutane with EtOK/EtOH
stability of a conformation in acyclic compounds? gives X as the major product. Reaction of X with
[JEE (Main)-2019] Hg(OAc)2/H2O followed by NaBH4 gives Y as the
major product. Y is: [JEE (Main)-2019]
(1) Angle strain
(2) Steric interactions OH

(3) Electrostatic forces of interaction (1) Ph (2) Ph

(4) Torsional strain OH
OH
28. The major product obtained in the given reaction is:
CH3 O CH2 CH 3
AlCl 3
Product (3) Ph (4) Ph
CH2 CH
32. In the following skew conformation of ethane,
—
Cl
Hc – C – C – Hs dihedral angle is
[JEE (Main)-2019]
H
H3C O H Hc 29°
H
(1)

CH3
H 3C O CH CH3
CH2 CH
(2)
Hs
H
H 3C O CH2 [JEE (Main)-2019]
(3) CH2 CH CH2
(1) 120° (2) 58°
CH3 (3) 151° (4) 149°

O 33. Consider the following reactions

(4) CH3

(a)
29. The major product of the following addition reaction
is
Cl2 /H2O
H3C  CH CH2  o
[JEE (Main)-2019]
O
(b)
(1) H 3C CH 3 (2) CH 3–CH–CH 2
Cl OH
O
(3) H 3C (4) H 3C–CH–CH 2
OH Cl
30. But-2-ene on reaction with alkaline KMnO4 at elevated
temperature followed by acidification will give :
(c)
[JEE (Main)-2019]
(1) 2 molecules of CH3CHO
(2) 2 molecules of CH3COOH
(3) CH3–CH–CH–CH 3

OH OH (d)

(4) One molecule of CH3CHO and one molecule of

CH3COOH

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 Which of these reactions are possible? 36. Which of these will produce the highest yield in
Friedel Crafts reaction? [JEE (Main)-2020]
[JEE (Main)-2020]
(1) (b) and (d) (2) (a) and (d) CONH2
(3) (a) and (b) (4) (b), (c) and (d) OH
(1) (2)
34. The major products A and B in the following
reactions are
NH2 Cl
CN Peroxide
[A] (3) (4)
Heat

[A] + B
37. The correct order of heat of combustion for following
[JEE (Main)-2020]
alkadienes is

CN
(1) A and B CN
(a)

CN
CN
(2) A and B
(b)

CN CN (c) [JEE (Main)-2020]

(3) A and B

(1) (c) < (b) < (a) (2) (a) < (c) < (b)
(3) (b) < (c) < (a) (4) (a) < (b) < (c)
CN
(4) A and B CN 38. The number of sp2 hybrid orbitals in a molecule of
benzene is [JEE (Main)-2020]
35. The major product in the following reaction is (1) 24 (2) 18

O (3) 12 (4) 6

+
39. The major product in the following reaction is
+ H3O
H 3C CH = CH 2
CH3 +
H 3O
[JEE (Main)-2020]
Heat

O O
[JEE (Main)-2020]

(1) (2)
OH OH
CH3 CH 3 H 3C
HO CH3
(1) (2) CH3
CH 3

OH OH OH
+

(3) (4) H 3C CH 3
CH 3

CH3 CH3 (3) (4)

CH 3

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40. The major product [R] in the following sequence of 42. The major product formed in the following reaction
reactions as: is
HBr
(I) LiNH2/ether
[P] CH3CH == CHCH(CH3)2  o
HC CH
(ii) H 3C
[JEE (Main)-2020]
CH – Br
(CH 3)2CH (1) Br(CH2)3CH(CH3)2
(i) HgSO4 /H2S O4 Conc. H2SO 4 (2) CH3CH(Br)CH2CH(CH3)2
[Q] [R]
(ii) NaBH 4 ' (3) CH3CH2CH(Br)CH(CH3)2
[JEE (Main)-2020] (4) CH3CH2CH2C(Br)(CH3)2
H 3C 43. The major products of the following reaction are
(1) C CH — CH 3 CH3
(CH3)2CH ~
(i) KOtBu/ '
H 2C CH3  CH  CH  CH3  o
(ii) O3 /H2O2
CH 2 CH 3
~
(2) C OSO2CH3
CH(CH 3)2 [JEE (Main)-2020]
H3C CH 3
(3) C C(CH3)2 (1) + CH 3COOH
CH 3 O
H 3CCH2
CH3
H3C
(2) + CH 3CHO
(4) CH CH CH2 CH3 O
CH 3
(CH3)2CH
(3) + HCOOH
41. In the following reaction sequence the major CH 3 COOH
products A and B are:
CH3
O
(4) + HCHO
anhydrous 1. Zn – Hg/HCl CH 3 CHO
+ O A B
AlCl 3 2. H3 PO4 44. The major product of the following reaction is
CH3
O
[JEE (Main)-2020]
O 2HBr

(1) A = ;B=
NO2
CO2H
O [JEE (Main)-2020]
O
CH3
Br CH3
(2) A = ;B= Br

CO2H (1) (2)

O
O Br Br
NO2 NO2
(3) A = ;B=
CH3
CO2H H3C Br
Br
O
(3) (4)
(4) A = ;B=
Br Br
CO2H NO2 NO2
O
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45. The major product obtained from the following
reaction is NO2
2+ +
Hg / H 48. HNO3
O2N C C OCH3 H 2O H2SO4

[JEE (Main)-2020]
In the above reaction, 3.9 g of benzene on nitration
OCH3
O gives 4.92 g of nitrobenzene. The percentage yield
of nitrobenzene in the above reaction is
(1) _________%.

O2N (Round off to the Nearest Integer)

OH (Given atomic mass : C : 12.0 u, H : 1.0 u, O : 16.0
u, N : 14.0 u) [JEE (Main)-2021]

(2) COO H COO H

O
O2 N FeBr 3
49. + Br2 + HBr
OH
O Br

(3) Consider the above reaction where 6.1 g of Benzoic

acid is used to get 7.8 g of m-bromobenzoic acid.
O2 N The percentage yield of the product is ____.
OCH3
(Round off to Nearest Integer).
[Given : Atomic masses : C : 120 u, H : 1.0 u, O
(4) : 16.0 u, Br : 80.0 u] [JEE (Main)-2021]
O
O2N 50. Methylation of 10 g of benzene gave 9.2 g of toluene.
46. The increasing order of the boiling points of the Calculate the percentage yield of toluene _________.
major products A, B and C of the following (Nearest integer) [JEE (Main)-2021]
reactions will be 51. W hat is the major product formed by HI on
O CH3 CH
reaction with C CH 2 ?
(C 6H 5CO) 2 CH3
(a) + HBr A CH3

[JEE (Main)-2021]
(b) + HBr B CH3
(1) CH3 – C – CH – CH 3
(c) + HBr C
I CH3
[JEE (Main)-2020]
(2) CH3 – CH – CH – CH 2 – CH3
(1) A < C < B (2) C < A < B
CH 3 I
(3) B < C < A (4) A < B < C
CH3
47. In the following sequence of reactions the
maximum number of atoms present in molecule (3) CH3 – C – CH – CH 2I
‘C’ in one plane is __________. CH3H

Re d hot CH Cl (1. eq.)

A 
Cu tube
o B 
3
Anhydrous AlCl
oC CH3
3

(4) CH3 – C – CH – CH 3
(A is a lowest molecular weight alkyne)
CH3 I
[JEE (Main)-2020]
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52. Which one of the following carbonyl compounds 56. For the given reaction :
cannot be prepared by addition of water on an 1. NaNH2 (A)
alkyne in the presence of HgSO4 and H2SO4? CH = CHBr
2. Red hot iron tube, 873K (major product)
[JEE (Main)-2021] CH3

What is ‘A’? [JEE (Main)-2021]

O O
(1) C CH3 (2) CH3 – C – CH2 CH3
(1)

O O
(3) CH3 – C – H (4) CH3 – CH2 – C – H H 3C CH3

53. Identify A in the given chemical reaction. (2)

CH3
CH3
CH2 Mo2 O3
(3) CH3CH2CH2NH2
CH3 773 K, 10-20 atm ‘A’
CH2 major product CH NH2
CH (4) CH
CH2 CH3
CH3
[JEE (Main)-2021]
1 2 3 4
CH3 57. In CH2 C CH  CH3 molecule, the
(1) (2) hybridization of carbon 1, 2, 3 and 4 respectively,
are : [JEE (Main)-2021]
CH3 (1) sp2, sp2, sp2, sp3 (2) sp2, sp, sp2, sp3
(3) (4)
(3) sp3, sp, sp3, sp3 (4) sp2, sp3, sp2, sp3
54. Consider the following chemical reaction.
1) Red hot Fe tube,873 K 58. (1) Zn/HCl
CH { CH 
2) CO ,HCl,AlCl
o Product (2) Cr 2 O3 , 773 K
3
O 10 - 20 atm
The number of sp2 hybridized carbon atom(s)
present in the product is ________. Considering the above reaction, the major product
among the following is : [JEE (Main)-2021]
[JEE (Main)-2021]
55. The major product of the following reaction is: COCH2CH3 CH3
CH3
NO2 (1) (2)

H2 SO4
CH2CH 2CH3 CH2CH 3

[JEE (Main)-2021] (3) (4)

NO 2
59. Which of the following is Lindlar catalyst ?
NO 2
[JEE (Main)-2021]
(1) (2)
(1) Cold dilute solution of KMnO4

NO 2 NO 2 (2) Partially deactivated palladised charcoal

(3) Zinc chloride and HCl

(3) (4)
(4) Sodium and Liquid NH3

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 Choose the correct option. [JEE (Main)-2021]
Cl
(1) Both statement I and statement II are
A
60. incorrect
(2) Statement I is correct but statement II is
Cl
incorrect
Identify the reagent(s) ‘A’ and condition(s) for the (3) Statement I is incorrect but statement II is
reaction [JEE (Main)-2021] correct
(1) A = HCl ; Anhydrous AlCl3
(4) Both statement I and statement II are correct
(2) A = Cl2 ; UV light
64. Match List-I with List-II
(3) A = Cl2 ; dark, Anhydrous AlCl3
List-I List-II
(4) A = HCl, ZnCl2
(Chemicals) (Use/Preparation/
A
61. CH 3 CCl 4 (Major Product) Constituent)
(a) Alcoholic potassium (i) electrodes in batteries
Product “A” in the above chemical reaction is
hydroxide
[JEE (Main)-2021]
(b) Pd/BaSO4 (ii) obtained by addition
Br
Br reaction
CH 3
(1) (2)
CH 3 (c) BHC (Benzene (iii)used for E-elimination
CH 3 CH 3 hexachloride) reaction
(d) Polyacetylene (iv) Lindlar’s Catalyst
Br
Br
Choose the most appropriate match
CH3
(3) (4)
CH3 [JEE (Main)-2021]
CH3 (1) (a)-(iii), (b)-(iv), (c)-(ii), (d)-(i)
62. Choose the correct statement regarding the
(2) (a)-(ii), (b)-(i), (c)-(iv), (d)-(iii)
formation of carbocations A and B given.
(3) (a)-(ii), (b)-(iv), (c)-(i), (d)-(iii)
+ –
CH3 – CH 2 – CH2 – CH2 + Br
(4) (a)-(iii), (b)-(i), (c)-(iv), (d)-(ii)
CH 3 – CH2 – CH =CH 2 +HBr “A”
+ –
CH3 – CH 2 – CH – CH3 + Br KMnO
“B” 65. 
4 o 'A'
H2SO4 , ' major product

[JEE (Main)-2021]
(1) Carbocation A is more stable and formed KMnO

4 o 'B'
relatively at slow rate H2O, 273 K major product
(2) Carbocation A is more stable and formed
relatively at faster rate For above chemical reactions, identify the correct
statement from the following. [JEE (Main)-2021]
(3) Carbocation B is more stable and formed
relatively at slow rate (1) Compound ‘A’ is dicarboxylic acid and
compound ‘B’ is diol.
(4) Carbocation B is more stable and formed
relatively at faster rate (2) Compound ‘A’ is diol and compound ‘B’ is
dicarboxylic acid.
63. Given below are two statements :
(3) Both compound ‘A’ and compound ‘B’ are
Statement I : 2-methylbutane on oxidation with
KMnO4 gives 2-methylbutan-2-ol. dicarboxylic acids.

Statement II : n-alkanes can be easily oxidised to (4) Both compound ‘A’ and compound ‘B’ are
corresponding alcohols with KMnO4. diols.

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66. Benzene on nitration gives nitrobenzene in
O
presence of HNO3 and H2SO4 mixture, where : OH
Conc. HBr
C–OCH 3 “P”
[JEE (Main)-2021] 70. H3C
(1) HNO3 acts as a base and H2SO4 acts as an
acid Consider the above reaction, the major product “P”
(2) Both H2SO4 and HNO3 act as an acids formed is, [JEE (Main)-2021]
(3) HNO3 acts as an acid and H2SO4 acts as a
base O

(4) Both H2SO4 and HNO3 act as a bases C – OCH 3

(1) CH3
67. An Organic compounds ‘A’ C4H8 on treatment with
KMnO4/H+ yields compound ‘B’ C3H6O. Compound Br
‘A’ also yields compound ‘B’ an ozonolysis.
Compound ‘A’ is [JEE (Main)-2021]
(1) Cyclobutane O
OBr
(2) 2-Methylpropene C – OCH 3
(2) CH3
(3) But-2-ene
(4) 1-Methylcyclopropane
O
H 3C H Br
CCl4
68.  Br2 o Product “P” C – Br
H 3C H (3) CH 3

Consider the above chemical reaction. The total

number of stereoisomers possible for Product ‘P’ is
O
________. [JEE (Main)-2021] Br
C – OCH 3
OH (4) CH3
H 3PO 4 (BH 3)2
69. 120°C
A
H 2 O2/OH, H2O
A
(Major Product) (Major Product)

Consider the above reaction and identify the 71.

Product P [JEE (Main)-2021]

OH Consider the above reaction, and choose the

correct statement : [JEE (Main)-2021]
(1) (1) Both compounds A and B are formed equally
(2) Compound A will be the major product
CH 3 OH
(3) Compound B will be the major product

(2) (4) The reaction is not possible in acidic medium

72. The correct sequential addition of reagents in the
CH 3 preparation of 3-nitrobenzoic acid from benzene is:
OH
[JEE (Main)-2021]
(3)
(1) HNO3/H2SO4, Br2/ AlBr3, Mg/ ether, CO2, H3O+

OH
(2) Br2/ AlBr3, HNO3/H2SO4, Mg/ ether, CO2, H3O+
OH (3) Br2/ AlBr3, NaCN, H3O+, HNO3/H2SO4
(4) (4) Br2/ AlBr3, HNO3/H2SO4, NaCN, H3O+

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73. Excess of isobutane on reaction with Br 2 in 76. A chloro compound “A”
presence of light at 125°C gives which one of the
following, as the major product? (i) forms aldehydes on ozonolysis followed by the
hydrolysis.
[JEE (Main)-2021]
(ii) when vaporized completely 1.53 g of A, gives
CH 3 448 mL of vapour at STP.
(1) CH3 C Br (2) The number of carbon atoms in a molecule of
CH3 CH3 compound A is _____. [JEE (Main)-2021]

Br 77. Given below are two statements : one is labelled

as Assertion (A) and the other is labelled as
(3) (4) Reason (R).
CH3 CH2Br
Assertion (A) : Treatment of bromine water with
74. The major product formed in the following reaction propene yields 1-bromopropan-2-
is : ol.
Reason (R) : Attack of water on bromonium
HBr
Major product ion follows Markovnikov rule and
(excess) results in 1-bromopropan-2-ol.
[JEE (Main)-2021] In the light of the above statements, choose the
most appropriate answer from the options given
Br
below : [JEE (Main)-2021]
Br
(1) (2) (1) Both (A) and (R) are true and (R) is the correct
Br explanation of (A)
(2) (A) is true but (R) is false
(3) (4) Br
Br Br (3) Both (A) and (R) are true but (R) is NOT the
O correct explanation of (A)
Br 2
‘A’
(4) (A) is false but (R) is true
75. AlBr 3(C 2H5 )2O
(Major product) 78. Identify correct A, B and C in the reaction
Consider the given reaction, the Product A is sequence given below: [JEE (Main)-2021]
[JEE (Main)-2021]
conc. HNO3
O +
conc. H2SO4 Cl2 Fe/HCl
A B C
' Anhyd. AlCl3
(1)
Br
NO 2 NO2 NH2
O
A= ,B= ,C=
(1)

Cl OH
(2)
NO 2 NO2 NH2

Br (2) A= ,B= ,C=

Br Cl Cl
O

NO 2 NO2 Cl
(3)
(3) A= ,B= ,C=

O Cl OH

NO2
NO 2 Cl Cl NH2
(4)
(4) A= ,B= ,C=
Br

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79. The structures of A and B formed in the following 82. Given below are two statements.
reaction are : [Ph = –C6H5] [JEE (Main)-2021]
O
Statement I: The presence of weaker S-bonds
make alkenes less stable than alkanes.
AlCl3(2 eq) Zn/Hg
+ O A B Statement II: The strength of the double bond is
HCl

greater than that of carbon-carbon single bond.

O
Ph In the light of the above statements, choose the
(1) A = , B = Ph correct answer from the options given below.
O
[JEE (Main)-2022]
O

Ph
(1) Both Statement I and Statement II are
(2) OH OH correct.
A= , B = Ph
O
(2) Both Statement I and Statement II are
Ph Ph incorrect.
(3) A = , B= (3) Statement I is correct but Statement II is
O OH
incorrect.
O O
(4) Statement I is incorrect but Statement II is
Ph Ph correct.
(4) OH OH
A= , B=
O
80. In the given reaction sequence, the major product 83.
‘C’ is:

HNO Br
alcoholic
C8H10 
H SO
3
o A 
'
2
o B o
KOH
C Consider the above reaction. The number of S
2 4

electrons present in the product ‘P’ is_________.

[JEE (Main)-2022]
[JEE (Main)-2022]
84. The product formed in the following reaction.
(1)

is:
(2)
[JEE (Main)-2022]

(3) (1)

(2)
(4)

81. The major product ‘A’ of the following given reaction (3)
has ________ sp2 hybridized carbon atoms.

H
2, 7-Dimethyl-2, 6-octadiene o A
Major Pr oduct (4)
[JEE (Main)-2022]

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85. Number of grams of bromine that will completely 89. Halogenation of which one of the following will
react with 5.0 g of pent-1-ene is ______ × 10 g. –2 yield m-substituted product with respect to methyl
group as a major product?
(Atomic mass of Br = 80 g/mol) [Nearest integer]
[JEE (Main)-2022]
[JEE (Main)-2022]
86. Amongst the following, the major product of the
given chemical reaction is
(1) (2)

[JEE (Main)-2022]
(3) (4)

(1) (2) 90. ‘A’ and ‘B’ respectively are:

1 O
A  3
2 Zn  H2 O
o Ethane-1, 2-dicarbaldehyde +

Glyoxal/Oxaldehyde
(3) (4)
1 O
B  3
2 Zn H2 O
o 5  oxohexanal

87. C7H5 O2 2
hQ
o > X@ o 2C6H5  2CO2 [JEE (Main)-2022]
Consider the above reaction and identify the (1) 1-methylcyclohex-1, 3-diene & cyclopentene
intermediate ‘X’ (2) Cyclohex-1, 3-diene & cyclopentene
[JEE (Main)-2022] (3) 1-methylcyclohex-1, 4-diene & 1-
methylcyclo-pent-ene
(1) (2) (4) Cyclohex-1, 3-diene & 1-methylcyclopent-1-
ene

91. W hat will be the major product of following

(3) (4)
sequence of reactions?
88. The major product in the following reaction (i) n  BuLi,
n  C H Cl
n  Bu— {  5 11
(ii) Lindlar cat, H
o
2

[JEE (Main)-2022]

[JEE (Main)-2022]
(1)

(1) (2)

(3) (4) (2)

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 Phase-II
(3) 95. A compound ‘A’ on reaction with ‘X’ and ‘Y’
produces the same major product but different by
product ‘a’ and ‘b’. Oxidation of ‘a’ gives a
substance produced by ants.

(4)

92. The major product (P) in the reaction

is
‘X’ and ‘Y’ respectively are
[JEE (Main)-2022]
[JEE (Main)-2022]
(1) KMnO4/H+ and dil. KMnO4, 273 K
(2) KMnO4(dilute), 273 K and KMnO4/H+
(1) (2)
(3) KMnO4/H+ and O3, H2O/Zn
(4) O3, H2O/Zn and KMnO4/H+
96. Major product of the following reaction is

(3) (4)

93. Two isomers ‘A’ and ‘B’ with molecular formula C4H8
[JEE (Main)-2022]
give different products on oxidation with KMnO4/H+
results in effervescence of a gas and gives ketone.
The compound ‘A’ is
[JEE (Main)-2022] (1)

(1) But-1-ene (2) cis-But-2-ene

(3) trans-But-2-ene (4) 2-methyl propene

94. (2)

The stable carbocation formed in the above reaction

is
[JEE (Main)-2022]
(3)
† †
(1) CH3CH2 CH2 (2) CH CH
3 2

(4)
†
(3) CH3 – CH– CH3 (4)

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97. In the presence of sunlight, benzene reacts with CI2 100. Choose the correct option for the following reactions.
to give product X. The number of hydrogens in X
is _________.
[JEE (Main)-2022]
98. W hich of the following is not an example of
benzenoid compound? [JEE (Main)-2022]
[JEE (Main)-2022] (1) ‘A’ and ‘B’ are both Markovnikov addition
products
(2) ‘A’ is Markovnikov product and ‘B’ is anti-
(1) Markovnikov product
(3) ‘A’ and ‘B’ are both anti-Markovnikov products
(4) ‘B’ is Markovnikov and ‘A’ is anti-Markovnikov
(2) product

101. Which among the following pairs of the structures

will give different products on ozonolysis? (Consider
(3)
the double bonds in the structures are rigid and not
delocalized) [JEE (Main)-2022]

(4)

99. Major product ‘B’ of the following reaction

sequence is: (1)

[JEE (Main)-2022]

(2)
(1)

(2)
(3)

(3)

(4)

(4)

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102. In bromination of Propyne, with Brom ine A. p-xylene B. bromobenzene
1,1,2,2-tetrabromopropane is obtained in 27%
yield. The amount of 1,1,2,2-tetrabromopropane C. mesitylene D. nitrobenzene

obtained from 1 g of Bromine in this reaction is E. benzene

_______ × 10–1 g. (Nearest integer)
[JEE (Main)-2022]
(Molar Mass : Bromine = 80 g/mol)
(1) C < D < E < A < B
[JEE (Main)-2022] (2) D < B < E < A < C
103. Arrange the following in increasing order of (3) D < C < E < A < B
reactivity towards nitration (4) C < D < E < B < A

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Chapter 22

Hydrocarbons
1. Answer (2) 7. Answer (2)
5-keto-2-methylhexanal is
H H
OH O O O
CH3 CH3
H
CH2–CH–CH CH2–CH–CH H
CH3 CH3

CH3 O3 Zn
O O
+
CH—CH– C H
H
H (A) (B) H CH3
CH3 8. Answer (1)
(A)
CH = CH–CH +
CH3 CH2 – CH – CH3
Extension of conjugation +
(More stable) CH2=CH – CH3 + Cl Cl More stable intermediate
? Major product +
CH3 CH2 – CH – CH3
(B)
CH2–CH = C Cl
(Minor) CH3
–
+
2. Answer (4) CH2 – CH – CH3 OH
CH2 – CH – CH3
(i) O3 Cl Cl OH
CH3 CH CH CH3 CH3 CHO
(ii) Zn-H2O
44 amu 9. Answer (3)
3. Answer (1)
Na/liq. NH3 CH3 H
4. Answer (1) CH3 – C { C – CH3 C=C
5. Answer (3) H CH3
Trans alkene
So, option (3) is correct.
Cl
Ag 10. Answer (1)
2Cl—C—CH3 CH3C { CCH3 + 6AgCl
Cl OH
O
1, 1, 1-trichloroethane
CH3
+ O AlCl3
6. Answer (1)
For geometrical isomerism doubly bonded carbon
must be bonded to two different groups which is
OH OH
only satisfied by 1 - Phenyl - 2 - butene.
CH3 CH3
H H H CH3
C=C C=C O
Ph – CH2 CH3 Ph – CH2 H O
AlCl3O
cis trans

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11. Answer (4) 15. Answer (1)

is aromatic as it has 2Se– in complete

conjugation
Contain 6Se– in complete conjugation and are
aromatic.
and are antiaromatic.

is anti-aromatic as it has 4Se – in

is non aromatic
complete conjugation.
12. Answer (2)
16. Answer (1)

MeO
CH2–Cl Cl
HO HO
AlCl3
(1) HCl

MeO +
MeO
+ AlCl3

HO +
HO
+ AlCl4–

MeO (Major product)

Para attack will form major product because at

13. Answer (1) ortho position steric crowding is applicable.
hQ 17. Answer (1)
CH3 – CH2 – CH CH2  Br2 
o
In general, polarity increases the intermolecular
CH3 – CH– CH CH2 force of attraction and as a result increases the
| melting point.
Br
18. Answer (1)
14. Answer (2)

N HNO3
 o
| Conc. H SO
2 4
H

Activated Deactivated
ring ring
19. Answer (3)
? Major product will be formed as per activating
group.
HBr
CH3O CH == CH — CH3
? Product formed is O2N Excess
O

N
| HO CH — CH2 — CH3
H
Br

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 25. Answer (2)
20. Answer (3)
OCH3 CH3 Cl CN
CH 3
CH3 > > >
CH2
+
HCl C (+M) (+H) (–I > +M) (–M, –I)
26. Answer (4)
CH3
CH3 group when bonded to benzene increases the
Cl
– electron density of benzene by +I and hyper
conjugation effects and hence makes the
CH3
compound more reactive towards EAS. Cl group
C Cl decreases the electron density of benzene by –I
effect, and CH3CO group strongly decreases the
CH3 electron density of benzene by –I and –R effects.
Therefore, correct increasing order the given
compounds towards EAS is
21. Answer (2) COCH 3 Cl CH 3

< <
O (III) (I) (II)
Cl O
C 27. Answer (1)
(i) AlCl3, Heat
+ O (ii) H2O Angle strain is not present in acyclic compounds.
22. Answer (1) Cl C 28. Answer (1)
O HO
O O O
CF 3 – CH = CH 2 AlCl 3
Cl :
H+

+ + 29. Answer (4)

CF 3 – CH – CH 3 + CF 3 – CH2 – CH 2
(More stable) Cl 2
–I CH3 – CH = CH 2 CH 3 – CH — CH 2
H 2O
(Less stable – +
Cl Cl
due to –I effect
of –CF3) CF 3 – CH2 – CH 2 – Cl +
H2O, –H
anti-Markovnikov

CH 3 – CH – CH2
23. Answer (4)
Polysubstitution is a major drawback in Friedel OH Cl
Craft’s alkylation. 30. Answer (2)
24. Answer (1)
KMnO 4
CH3 – CH = CH – CH 3 2CH3COOH
OH–, '
DCl
CH3 – C { C – H CH3 – C = CH
1 eq
31. Answer (1)
Cl D EtOK /EtOH
Ph Ph (X)
DI Cl
(CH3COO)2Hg + H2O + NaBH4
OMDM
I D
CH3 – C – CH OH
3
Cl D 4 1 Ph Product
2
1-phenylbutanol
Both addition follow Markownikov’s rule.

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32. Answer (4) 37. Answer (4)
H
H Hc29°
H a b c
Trans config. Trans config. Cis config.
120° around both around one around both
Hcc H double bond double bond double bond

? Angle between Hc and Hcc = 120° + 29° = 149° Order of stability : a > b > c
33. Answer (1) Order of heat of combustion : c > b > a
Vinyl halide and aryl halide do not give Friedel 38. Answer (2)
Craft’s reaction. The reactions which are possible Each carbon atom is sp2 hybrid
are :
? 3 sp 2 hybrid orbitals are formed by each
carbon atom
Total sp2 orbitals = 6 × 3 = 18
(b) 39. Answer (3)

H 3C CH = CH 2 H3C CH – CH 3
+
H 3O
(d)

Rearrangement .

34. Answer (4)

Peroxide generates a radical that abstracts
H-atom from the C-atom adjacent to CN group to
40. Answer (3)
give more stable radical

CN Peroxide x CN
' LiNH2 /ether –
CH
H CH CH
H
[A]
Br
[A] attacks 1-pentene to give 2° radical that picks
up H-atom to give [B]
HgSO4
+ CN CN CH
H3 — CH
H — CH(CH3)2 CH
H3 — CH
H — CH(CH3)2
H2SO 4

O ==
=C C
[B]
35. Answer (4) CH3 CH
NaBH4
O OH
+
conc.¬H 2SO 4
+ CH
H3 — CH
H — CH(CH3)2 '
H3O
CH
H — OH
CH3 CH3 CH3
Product is aromatic
36. Answer (4) C(CH3) 2
+
Aniline and phenol form complex with Lewis acid. CH
H3 — C CH
H3 — C — CH(CH3 )2
? Highest yield in Friedel Craft reaction among C2 H5 CH2CH3
Cl

given species is for chlorobenzene i.e.

(after Hydride shift)

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41. Answer (1) 45. Answer (4)

2+ +
Hg /H
C C OCH3 H2 O
Hydration
O O of alkyne

O2N
O: AlCl3 OH
+ (A)
HO CH C OCH3

O O
O 2N
Tautomerisation
Zn – Hg/HCl

O
H3 PO 4 O2N CH2 C OCH3

HO

O O Ethers are least reactive and their cleavage takes

(B) place under drastic conditions.
46. Answer (3)
O
42. Answer (4) (C 6H5 CO) 2
+ HBr (A)
CH3CH == CHCH(CH3 )2 Br
+
H
H + HBr Br (B)
CH3
+
CH3CH2 – CH – C Br
CH + HBr (C)
Hydride
shift
Boiling point decreases with branching
CH3 ? order of B.P. is A > C > B
+
CH3– CH2 – CH2 – C 47. Answer (13.00)
–
CH3
Br

Br Red hot Cu tube

CH3 3 H–C {C–H
CH3– CH2CH2 – C (Lowest molecular
weight alkyne)
CH3 (B)
(A)
43. Answer (3)
H H
H
H C
CH3 CH 3 H CH3 Cl(1 eq.)
t
KO Bu/ '
CH 3 – CH – CH – CH 3 CH3 – CH – CH = CH 2 Anhyd AlCl3
H H
(ii) O3/H 2O2
OSO2CH3
(oxidative
ozonolysis)
H
(C)
CH3

CH3 – CH – COOH + HCOOH Number of atoms in one plane = 13

48. Answer (80)

44. Answer (1) NO2

CH3 CH3 CH3
Br Br HNO3
HBr HBr H2SO 4

Br
3.9
NO2 NO2 NO2 Number of moles of C6H6 = = 0.05
78

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 Theoretical moles of nitrobenzene = 0.05 52. Answer (4)
Actual number of moles of nitrobenzene CH3 – CH2 – CHO (Propanaldehyde) cannot be
4.92 prepared by addition of water on alkyne in the
= = 0.04 presence of HgSO4 and H2SO4.
123
Percentage yield of nitrobenzene O
H2O
0.04 C { CH C CH3
= u 100 Hg , H
2+ +

0.05
= 80% H2O
49. Answer (78) HC { CH 2+ +
CH3 – CHO
Hg , H
COO H COO H
O
FeBr3 H2O
+ Br 2 + HBr CH3 – C { CH 2+ +
CH3 – C – CH3
Hg , H
Br
53. Answer (2)
mass 6.1 g 7.8 g
in gram CH3

CH2 CH3 CH3

6.1 Mo2O3
moles 0.05
122 773 K, 10-20 atm
CH2 CH (Aromatisation)
1 mol of benzoic acid give 1 mol of CH2 CH3 (A)
m-bromobenzoic acid. 0.05 mol of benzoic acid will
give 0.05 mol of m-bromobenzoic acid. 54. Answer (7)
So, percentage yield is
7.8 u 100 (1) Red hot Fe tube
% yield = 77.61% CH { CH
0.05 u 201 873 K

| 78%
50. Answer (78) (2) CO, HCl, AlCl3

CH3 CHO

10
10 g of C6H6 = moles All the 7-carbon-atoms in product are sp 2
78
hybridised.
moles of methylbenzene should be obtained
55. Answer (2)
10
= mole
78
NO 2 NO 2
10 H 2SO 4
= × 92 g
78
†
9.2
% yield = u 78 u 100 78% NO 2
NO 2
10 u 92
51. Answer (1) + H
†
†
+
H

1, 2 methyl
NO 2
shift

–
I
I (Major)

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56. Answer (2) 62. Answer (4)
Carbocation B is more stable as it is secondary
(i) NaNH 2 carbocation having more number of D-hydrogens
CH3 – CH = CH – Br and having greater +I effect.
(ii) Red hot iron
tube, 873 K ? Carbocation B formed at a faster rate than
CH3 carbocation A.
63. Answer (2)
Alkanes having tertiary H can be oxidised to
H3 C CH 3 corresponding alcohols by KMnO4.
KMnO4
Mesitylene

2-methyl butane OH
So the correct option should be (2).
whereas ordinary alkanes resist oxidation.
57. Answer (2)
64. Answer (1)
CH2 C CH  CH3 x Alc. KOH causes elimination
sp2 sp sp2 sp3 x Pd / BaSO4 – Lindlar’s catalyst
x BHC is obtained by the addition reaction of Cl2
Hybridization of carbon 1, 2, 3 and 4 respectively are with benzene in presence of U.V.
sp2, sp, sp2 and sp3
x Thin film of polyacetylene can be used as
58. Answer (4) electrode in batteries.
65. Answer (1)
CH2 CH3

(1) Zn/HCl KMnO4 COOH

(2) Cr 2 O3 , 773 K H2SO4, ' COOH
O 10 - 20 atm
(A)
59. Answer (2)
Partially deactivated palladised charcoal is called OH
KMnO4
as Lindlar’s catalyst.
H2O, 273 K
60. Answer (2)
(B) OH
In presence of U.V. light, free radical substitution
reaction occurs, at allylic position. 66. Answer (1)
In the nitration of benzene using nitrating mixture,
Cl
HNO3 acts as a base and H2SO4 acts as an acid
Cl2 to generate NO2+ ion.
U.V.
H2 SO4 o H  HSO4
Cl
+ + +
HO N O + H H2O N O H2O + NO2
61. Answer (3)
O O
+ NO2 NO2
H+ +
CH 3 –H
+
CH3 CCl 4 +
+ NO2
Br
Br–
CH 3 67. Answer (2)
CH 3
KMnO4/ H+ O
(A)
2-methylpropene (A) (B)
The reaction involves the formation of 2° carbocation
Ozonolysis O
followed by methanide shift to give 3° carbocation.
Br– ion attacks the 3° carbocation to give the major
2-methylpropene (A) (B)
product.

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68. Answer (2) 72. Answer (1)

Br

H 3C H H3C H
C CCl 4 C
+ Br2
C C
H 3C H H 3C H
Br
(+ ) P

Addition of Br2 to alkene is anti addition.

Two stereoisomers are formed in the given reaction. 73. Answer (1)
69. Answer (3)
+ Br2
hQ Br +
(T = 125°C)
Br
+
OH OH2 Major Minor
Excess
+
H 3PO4 Bromination is highly selective, reactivity order –
120°C
3° >> 2° > 1
74. Answer (3)

OH
(BH 3)2 HBr
–
H 2O 2, OH
H 2O (excess)
(P) (A)

70. Answer (1)

O
OH O +
+ Br
H
H3C OCH3
H 3C OCH3 –H 2O

(Major product)

O O
75. Answer (2)
CH3 OCH 3 CH3 OCH 3
Br– + O O
Br
Br2
(Major) AlBr3, ether

71. Answer (2) Br

Ketones are meta directors.

Br2 + AlBr3 o AlBr4– + Br +

O O

+ Br+ +

Br H
Arenium ion

O AlBr 4–

Br

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76. Answer (3)
+
O O AlCl 3

••
Given mass
Mole = AlCl3
Molar mass O O

Given volume (at STP in L)

= O O
22.4
+
1.53 448 u 10 3 O AlCl 3 –
Cl3Al O
O
Molar mass 22.4 O O
1.53 u 22.4
Molar mass = = 76.5 g mol–1 O
448 u 103
There can not be more than one chlorine atom per O
O
molecule because molar mass 76.5. One of the
possible compounds is Cl – CH2 – CH = CH2. O– AlCl 3
Cl – CH2 – CH CH2
Zn/Hg
(i) O3 HCl

(ii) Zn/ ACOH
o ClCH2 – CHO  HCHO
OH
77. Answer (1)
O
Br (B)
Br
(A) : CH3–CH = CH 2 H 2O CH3 –CH–CH2 80. Answer (2)
2

OH
+
Br
Br2
(R) : CH3–CH = CH 2 CH3 –CH–CH2

..
H 2O
..

CH3–CH – CH 2–Br

OH
78. Answer (4)

NO 2
conc. HNO3
conc. H 2SO4
' 81. Answer (2)
(A)
Cl2
Anhyd. AlCl3

NH2 NO 2
Fe
HCl

Cl Cl
(C) (B)
Number of sp2 hybridised carbon atoms = 2
79. Answer (4)
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82. Answer (1) 86. Answer (1)
The S-bond present is alkenes is weaker than V-
bond present in alkanes. That makes alkenes less
stable than alkanes. Therefore, statement-I is
correct.
Carbon-carbon double bond is stronger than Carbon-
carbon single bond because more energy is required
to break 1 sigma and 1 pi bond than to break 1 87. Answer (4)
sigma bond only. Therefore, statement-II is also
correct.
83. Answer (2)

88. Answer (1)

Oxymercuration-demercuration follows

The given reaction undergoes nucleophilic Markovnik ov’s addition of water without

substitution by SN2 mechanism at room rearrangement.

temperature
? No. of S electrons present in P = 2
84. Answer (2) 89. Answer (3)

Both products are meta with respect to –CH3.

90. Answer (4)

85. Answer (1143)

CH3–CH2–CH2–CH = CH2 + Br2
p
Br
|
CH3  CH2  CH2  CH CH2
|
Br
5 5
moles of pentene will react with moles of
70 70
Br2

5
u 160
70
= 11.43 g

1143 u 102 g (B) should be 1-methylcyclopent-1-ene.

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91. Answer (3) 97. Answer (6)

Total number of hydrogens are 6.

Hence correct option is (3). 98. Answer (1) and (2)
92. Answer (3)

and are not benzenoid

compounds, since benzenoid compound contains

benzene ring.
99. Answer (2)
93. Answer (4)

94. Answer (3)


Initially CH — CH — CH2 is formed. On
3 2


rearrangement CH3 — CH— CH3 stable

carbocation is formed.
95. Answer (4)

100. Answer (2)

* Ants produces formic acid in their venom gland.

96. Answer (4)

101. Answer (3)

? in option (3) different products are produced.

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102. Answer (3) Molar mass of 1,1,2,2-tetrabromopropane = 360 g
Mass of 1,1,2,2-tetrabromopropane

1 1 27
u u u 360 g
2 160 100

2 moles Br2 {1 mole 1,1,2,2-tetrabromopropane | 3×10–1 g

103. Answer (2)
1
mole Br2 The correct order of reactivity towards nitration is
160

1 1
{ u mole 1,1,2,2-tetrabromopropane
2 160
But yield of reaction is only 27%
Moles of 1,1,2,2-tetrabromopropane

1 1 27
= u u as electron releasing groups on benzene ring
2 160 100
facilitate the nitration at benzene ring.

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