4. S
O
CH3 CH3
H — C — N
O
CH3
CH3
CH3 — C — N
O
CH3
CH3
Solvents Polar Protic Aprotic
Dimethyl sulphoxide
Dimethyl formamide
Dimethyl acetamide
5. Electrophile
Electron deficient species.
Having vacant orbital with incomplete octet .
Species having complete or partial ve charge on central atom.
NO2 N = O X
R – C = O
BH3
BF3
AlCl3
ZnCl2
FeCl3
Partial ve charge having species :
O C O
S
O
O O
P
O
Cl Cl
Cl
R C Cl
O
R
C
R
O
C
Cl
Cl Cl
Cl
6. Nucleophile
ve charge loving species
Charged : R– H– Cl– Br– SH– OH– R — O–
Neutral : H — O
H
R — O
H
NH3 R — NH2
R— CH CH — R R — C C — R
7. Cl + SbCl5
BF3 / BCl3 / AlCl3 / SbCl5
+ AlCl3
3
3
3
CH
|
CH —C—Cl
|
CH
+ AlCl3
O
||
R —C—Cl
HI / HCl / H2SO4 / HNO3
Formation of Carbocation
14. 27 Aug, 2021 (Shift-I)
A B
C D
Cl
+ Mg
dry
ether
[A]
ethanol
P
CH2CH3 O – CH2CH3
15. M + R – X
Wurtz Reaction : CH3 – Br
Na
Dry ether
Fitting Reaction :
Cl
Na
ether
Wurtz-Fitting Reaction : CH3 – Cl +
Cl
H3C
Na
ether
Frankland Reaction : I
Zn
Ullmann Reaction :
I
Cu
16. Zn
H – Cl
Cl
CH3 – I
Zn/Cu couple
Ethanol
Br – CH2 – CH2 – CH2 – Br Na
ether
OH
Br Na
20. 08 April, 2019 (Shift-II)
Which one of the following alkenes when treated with HCl yields majorly an anti
Markovnikov product ?
F3C – CH = CH2
Cl – CH = CH2
CH3O – CH = CH2
H2N – CH = CH2
A
B
C
D
21. 06 Sept, 2020 (Shift-I) The major product of the following reaction is :
A B C D
2HBr
CH3
NO2
H3C
NO2
Br
Br
CH3
NO2
Br
Br
CH3
NO2
Br
Br
NO2
Br
CH3
Br
24. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is (are)
A B
C D
JEE ( Advanced ) - 2015
CH3
H3C
Br
H
CH3
H2C
Br
H
CH3
H2C
Br
H
CH3
CH3
H2C
Br H
31. 08 Jan, 2020 (Shift - I) The major product of the following reaction is :
H3C
H3C H3C
OH
dil. H2SO4
H3C
H3C OH
CH3
OH
OH
CH3
OH
CH3
H3C
CH3
OH
CH3
H3C
H3C
H3C
HO CH3
OH OH
A B
C
D
32. CH3 CH CH2
Hg(OAc)2
H2O
(i) Addition of water by Markovnikov’s Rule
(ii) Formation of cyclo-merquric ion [ Non – classical carbocation ]
(iii) Rearrangement is not possible.
(iv) Attack of H2O as nucleophilic on more substituted partial carbocation.
Oxymercuration – Demercuration
33. CH3 CH CH2
BH3
THF
(i) Syn-Addition of water by Anti-Markovnikov’s Rule
(ii) Formation of 4 membered transition state
Hydroboration – Oxidation
34. R — C C — R
CH3 CH CH2
Syn-Dihydroxylation by Baeyer’s Reagent
42. R2O2/hv
R — CH CH2 + HBr
Mechanism :
hv
R — O — O — R
R — O• + H — Br
R — CH CH2 + Br•
R — CH — CH2 — Br + H — Br
•
Kharasch Effect or Peroxide Effect Reagents : HBr / R2O2 , hv
44. ENu
R— C C —H
Br2
R — C C — H CCl4
HBr
R — C C — H
Electrophilic addition reaction of Alkynes
Br2
R — C C — H H2O
KMnO4
R — C C — H
OH-
HOBr
R — C C — H
45. Br2
R — C C — R CCl4
KMnO4
R — C C — R OH-
Reddish orange colour of the solution of bromine in carbon tetrachloride is decolourised.
Test for Unsaturation
Br2
R — CH CH — R CCl4
R — CH CH — R
KMnO4
OH-
Colour changes from Pink purple (Bayer’s reagent) to Brown .
Br2
R — C C — R H2O
Br2
R — CH CH — R H2O
Red Brown colour of the solution of bromine water is decolourised due to unsaturation.
46. H2 / Pd / C
Lindlar’s Catalyst
Na / Liq. NH3
R — C C — R
H2 / Pd
R — C C — R
Hydrogenation
R — C C — H
Na
Liq. NH3
47. 16 March, 2021 (Shift-I)
Which of the following is Lindlar catalyst?
Partially deactivated palladised charcoal
Cold dilute solution of KMnO4
Zinc chloride and HCl
Sodium and Liquid NH3
A
B
C
D
48. JEE Adv. 2021
The major product formed in the following reaction is :
A B
C D
NaNH2
Na
liq. NH2
49. Br2 / CCl4
Br2 / CCl4
CH3 — C C — CH3
Na
Liq. NH3
CH3 — C C — CH3
D2 / Pd
CaCO3
Stability :
Solubility :
Melting Point :
Boiling Point :
Dipole moment :
50. 01 Feb, 2023 (Corrected ) But-2-yne is reacted separately with one mole of
Hydrogen as shown below :
(B) , (C) (B), (C)
(C) only (A) and (B)
A B
C D
Identify the incorrect statements from the options given below:
(A) A is more soluble than B.
(B) The boiling point & melting point of A are higher and lower than B respectively.
(C) A is more polar than B because dipole moment of A is zero.
B CH3 – C C – CH3 A
Na
liq. NH3
Pd/C
52. HgSO4 , H2SO4
Me — C C — H
H2O
Addition of H2O
BH3
Me — C C — H
THF
53. 24 Feb, 2021 (Shift-I)
Which one of the following carbonyl compound cannot be prepared by addition of
water on an alkyne in the presence of HgSO4 and H2SO4?
CH3 – CH2 – C – H
A B
C
D
O
CH3 – C – CH2CH3
O
C – CH3
O
D CH3 – C – CH3
O
55. Reductive Ozonolysis Oxidative Ozonolysis
CH3 CH CH2
CH3 — C C — CH3
CH3
CH3 CH CH
NOTE : KMnO4 / H+ or alkaline KMnO4 with Heat gives same product as in Oxidative
Ozonolysis with alkene and alkyne
56. 12 April, 2019 (Shift-I)
But-2-ene on reaction with alkaline KMnO4 at elevated temperature followed by
acidification will give :
One molecule of CH3CHO and one molecule of CH3COOH
A
B
C
D
CH3 – CH – CH – CH3
2 molecules of CH3COOH
2 molecules of CH3CHO
OH OH
57. 12 April, 2023 (Shift-I)
2 – hexene Products
Butanoic acid and acetic acid
Butanal and acetic acid
Butanal and acetaldehyde
Butanoic acid and acetaldehyde
A
B
C
D
The two products formed in above reaction are
(i) O3
(ii) H2O
59. 13 Jan, 2023 (Shift-II)
A hydrocarbon ‘X’ with formula C6H8 uses two moles of H2 on catalytic hydrogenation
of its one mole. On ozonolysis, ‘X’ yields tow moles of methane dicarbaldehyde. The
hydrocarbon ‘X’ is:
Hexa-1, 3 , 5-triene
1-methylcyclopenta-1, 4-diene
Cyclohexa-1, 3-diene
Cyclohexa-1, 4-diene
A
B
C
D
60. 08 April, 2023 (Shift-I)
Molar mass of the hydrocarbon (X) which on ozonolysis consumes one mole of O3 per
mole of (X) and gives one mole of ethanal and propanone is __________ g mol–1 (Molar
mass of C : 12 g mol–1, H : 1 g mol–1)
61. 0
1
2
4
The number of optically active products obtained from the complete ozonolysis of the
given compound is :
A
B
C
D
IIT-JEE-2012
CH3 – CH = CH – C – CH = CH – C – CH = CH – CH3
H
CH3
CH3
H
63. 12 April, 2019 (Shift-I)
The major product(s) obtained in the following reaction is/are :
(i) KOtBu
(ii) O3/Me2S
Br
A B
C D
OHC
CHO
OHC
CHO
OtBu
OHC
CHO
OHC CHO
and OHC – CHO
65. 26 Feb, 2021 (Shift-I)
For the given reaction :
CH3CH2CH2NH2
A B
C D
HC 1. NaNH2
2. Red hot iron
tube, 873 K
CHBr
CH3
(A)
(major product)
What is ‘A’?
H3C CH3
H3C
HC = CH – NH2
CH3
67. 1. Formation of sigma complex.
E+
2 . Loss of a proton gives the substitution product.
Electrophilic substitution reaction
Rate of ESR :
68. Substituent groups
Reactivity
Effect on rate
Directing nature
Effect on orientation
1. –O– , – NH- , – NHR , – NR2 , – OH
Very strongly
activating
Ortho-para directing
2.
–OR , – NH – C – R , – O – C – R
Strongly
activating
Ortho-para directing
3. –R , – Ar , – CH = CH2 Activating Ortho-para directing
69. Substituent groups
Reactivity
Effect on rate
Directing nature
Effect on orientation
4. –X , – N = O , – CH2X , –CHX2 Deactivating Ortho-para directing
5.
– CHO , – C – R , – COOH ,
– COOR , – COCl , – C N , – SO3H
Strongly
deactivating
Meta directing
6. –NO2 , –N+H3 , –N+R3 , – S+R2 , –CF3
Very strongly
deactivating
Meta directing
70. 15 April, 2023 (Shift-I)
CH3
Decreasing order of reactivity towards electrophilic substitution for the following
compounds is :
CF3
OCH3
NMe2
a b
c
d
e
c > b > a > d > e
e > d > a > b > c
a > d > e > b > c
d > a > e > c > b
A
B
C
D
73. 31 Aug, 2021 (Shift-II)
For following sequence of reactions, the correct
products are :
A B
C D
1. Br2/Fe/
3. CH3OH
2. Mg/dry ether
Products
Br
+ Mg
H
OCH3
CH3
+ Mg
OH
Br
H
+ Mg
Br
OCH3
OCH3
+ HMgBr
74. 26 Aug, 2021 (Shift-II) Consider the given reaction, the Product A is:
A B
C D
(C2H5)2O
Br2 , AlBr3
‘A’
(Major Product)
O
O
Br O
Br
O
Br
O
Br
76. 20 July, 2021 (Shift-II)
Benzene on nitration gives nitrobenzene in presence of HNO3 and H2SO4 mixture,
where :
Both H2SO4 and HNO3 act as a bases
Both H2SO4 and HNO3 act as an acids
HNO3 acts as base and H2SO4 acts as an acid
HNO3 acts as an acid and H2SO4 acts as a base
A
B
C
D
77. 10 Jan, 2019 (Shift-II)
What will be the major product in the following mononitration reaction?
A B
C D
HNO3
Conc. H2SO4
N
H
O
N
H
O
NO2
N
H
O NO2
N
H
O
O2N N
H
O
O2N
81. 10 April, 2023 (Shift-II)
The major product ‘P’ formed in the given reaction is:
A B
C D
anhy
AlCl3
‘P’
(major)
Cl
CH3O
O2N
CH3
CH3O
O2N CH3
CH3O
O2N
OCH3
CH3O
O2N
NO3
CH3 CH3
CH3
CH3
CH3
CH3O
O2N
83. (i) Poly alkylation is possible but poly acylation is not possible .
Limitations :
84. (ii) Rearranged products may form in the Friedel Craft Alkylation reactions.
(iii) Highly reactive rings like aniline and highly deactivated rings like nitrobenzene ,
cyanobenzene do not give Friedel Craft reactions.
86. 08 Jan, 2020 (Shift-II)
In the following sequence of reactions the maximum number of atoms present in
molecule ‘C’ in one plane is
Red hot
Cu tube
A B
CH3Cl (1 eq)
Anhydrous AlCl3
C A is a lowest molecular weight alkyne
88. Addition reactions of benzene
H2 Ni
Heat
Cl2
500 K
Benzene hexachloride
BHC ( gammaxene)
Benzene on treatment with excess of chlorine in the presence of anhydrous AlCl3 can be
chlorinated to hexachlorobenzene (C6Cl6 ) .
89. 06 Sept, 2020 (Shift-I)
The major product obtained from the following reaction is :
O2N
A B
C
D
C C OCH3
Hg2+/H+
H2O
O2N
OCH3
O
O2N
OH
O
O2N
OCH3
O
O2N
OH
O
91. Wurtz reaction R — Cl
Na
Dry ether
Corey House Synthesis R — Cl
(i) Li
(ii) CuCl
(iii) R’ — Cl
92. Soda – Lime Decarboxylation
C — OH
O
CH3
NaOH
C — OH
O
CaO
Heat
93. Kolbe Electrolysis
C — OH
O
NaOH
Electrolysis
CH3
NOTE : Methane cannot be prepared by this method
94. JEE Adv. 2019
Which of the following reactions produce (s) propane as a major product?
H3C
A
B
C
D
COONa + H2O
electrolysis
H3C
COONa NaOH, CaO,
H3C
Cl Zn, dil. HCl
H3C Cl
Zn
Br
95. R — H + X2
UV Light or temp.
250° — 400°C
(i) Chain initiation :
(ii) Chain propagation :
(iii) Chain termination :
X2
UV or temp.
250° — 400°C
X• + R – H
R• + X – X
X• + X•
R• + R•
R• + X•
Free Radical Substitution Reaction
97. 10 Jan, 2019 (Shift-I)
Which hydrogen in compound (E) is easily replaceable during bromination reaction in
presence of light?
- hydrogen
- hydrogen
- hydrogen
- hydrogen
A
B
C
D
CH3 – CH2 – CH = CH2
98. 26 Feb, 2021 (Shift-I)
For the given reaction :
Br2
UV light
‘A’
(major product)
monobrominated
CH2CH3
CN
What is ‘A’?
A B C D
CH2CH3
Br
CN
CH2CH3
Br CN
CH
CN
CH3
Br
CH2CH3
Br
CN
100. Total number of isomers (including stereoisomers) obtained on
monochlorination of methylcyclohexane is __________.
JEE Mains 2022 / 26 July / Shift - II
101. 06 April, 2023 (Shift-I)
Number of bromo derivatives obtained on treating ethane with excess of Br2, in
diffused sunlight is ………
102. Rate of reaction of alkanes with halogens : F2 > Cl2 > Br2 > I2
Iodination is very slow and a reversible reaction. It can be carried out in the presence
of oxidizing agents like HIO3 or HNO3 .
Rate of replacement of hydrogens of alkanes : 3° > 2° > 1°
Fluorination is too violent to be controlled.
104. 13 April, 2023 (Shift-I) In the following reaction, ‘X’ is
CH3(CH2)4CH2Cl
Cl – CH2 – (CH2)4 – CH2 – Cl
CH3CH – (CH2)2 CH3
A
B
C
D
CH3(CH2)4CH3
Anhy. AlCl3
HCl,
‘X’
Major Procut
CH3
Isomerisation CH3(CH2)4CH3
Anhy. AlCl3
HCl,
106. 25 Feb, 2021 (Shift-I)
Identify A in the given chemical reaction.
A B
C D
Mo2O3
773 K, 10-20 atm
‘A’
major product
CH3
H2C
H2C CH2
HC
CH3
CH3
CH3
CH3
107. Physical Properties
Boiling point Pentane hexane heptane
n–Pentane Isopentane Neopentane
Boiling point
Shape approaches to spherical which results in decrease in Vanderwaal forces (as surface area decreases)
108. Melting Point :
Thus alkanes with even carbon atoms are packed closely in crystal lattice to permit greater intermolecular
attractions.
Alkanes with odd carbon atoms have their carbon atom on the same side of the
molecule and in even carbon atom alkane the end carbon atom on opposite side.
Above C17 : Waxy solids
Physical State :
C1 to C4 & Neopentane : Gas
C5 to C17 : Colourless liquids
109. 06 Sept, 2020 (Shift-II)
The increasing order of the boiling points of the major products A, B and C of the
following reactions will be :
B < C < A C < A < B
A < B < C A < C < B
A B
C D
(A)
+ HBr (C6H5CO)2
O
A
(B) + HBr B
(B) + HBr C
111. 09 Jan, 2020 (Shift-I)
The correct order of heat of combustion :
(a) < (b) < (c)
(a) < (c) < (b)
(c) < (b) < (a)
(b) < (c) < (a)
A
B
C
D
(a) (b) (c)
112. 17 March, 2021 (Shift-I)
Mesityl oxide is a common name of : A
B
C
D
17 March, 2021 (Shift-II)
The total number of C – C sigma bonds in mesityl oxide (C6H10O) is _________. (Round off
to the nearest integer).
2,4-Dimethy lpentan-3 -one
3-Methylcyclohexanecarbaldehyde
2-Methylcyclohexanone
4-Methylpent-3-en-2-one
