CHEMISTRY

OM PANDEY , IIT Delhi

TOPICS to be covered
• Complete Organic Chemistry Revision
 Functional Group
7 Functional group 5 Functional group
O
|| – OH
—C — OH

O – SH
O
|| ||
—C —OR —C — NH2 – NH2
O O O
|| || || – SO3H
—C —O—C — R —C —Cl
O O
|| ||
—CN —C — H —C —
 28 June, 2022 (Shift-II)

The correct IUPAC name of the following compound is :

H
O 2N
O O

A 4-Methyl-2-nitro-5-oxohept-3-enal

B 4-Methyl-5-oxo-2-nitrohept-3-enal

# C 4-Methyl-6-nitro-3-oxohept-4-enal

D 6-Fonnyl-4-methyl-2-nitrohex-3-enal
29 July, 2022 (Shift-II)

Correct structure of gama-methylcyclohexane carbaldehyde is

O
O
CH2 – C – H
H
# A B

O
O
CH2 – C – H
H D
C
 06 Sept, 2020 (Shift-II)

The IUPAC name of the following compound is : OH

NH2

O2N
CHO

A 2-nitrogen-4-hydroxymethyl-5-amine benzaldehyde.

B 3-amino-4-hydroxymethyl 1-5-nitrobenzaldehyde

# C 5-amino-4-hydroxymethyl-2-nitrobenzaldehyde

D 4-amino-2-formyl-5-hydroxymethyl nitrobenzene
 06 Sept, 2020 (Shift-II)

The IUPAC name of the following compound is:

O
CH3
C – OH

Br
A 3-Bromo-5-methylcyclopentane carboxylic acid

B 4-Bromo-5-methylcyclopentanoic acid

C 5-Bromo-3-methylcylopentanoic acid

# D 4-Bromo-2-methylcyclopentane carboxylic acid

JEE MAINS 2022 /28 July/Shift-I

Match List-I with List-II

List-I List-II
(A) (I) Spiro compound
O

(B) (II) Aromatic compound

(C) (III) Non-planar Heterocyclic compound

(D) (IV) Bicyclo compound

O
Choose the correct answer from the options given below

A (A)-(II), (B)-(I), (C)-(IV), (D)-(III) B (A)-(IV), (B)-(III). (C)-(I). (D)-(II)

# C (A)-(III), (B)-(IV), (C)-(I), (D)-(II) D (A)-(IV), (B)-(III). (C)-(II). (D)-(I)

 JEE MAINS 2022 /28 July/Shift-I

The IUPAC name of the following compounds is :

A 3-ethyl-4-methylhex-4-ene

B 4, 4-diethyl-3-methylbut-2-ene

C 4-methyl-3-ethylhex-4-ene

# D 4-ethyl-3-methylhex-2-ene
 AIEEE - 2006

The IUPAC name of the compound shown below is

Cl

Br

A 2-Bromo-6-Chlorocyclohex-1-ene

B 6-Bromo-2-chlorocyclohexene

# C 3-Bromo-1-chlorocyclohex-1-ene

D 1-Bromo-3-chlorocyclohexene
 JEE Mains 2017 / 08 April

The IUPAC name of the following compounds is :

A 1, 1-Dimethyl-2-ethylcyclohexane

# B 2-Ethyl-1,1 -dimethylcyclohexane

C 2, 2-Dimethyl-1 -ethylcyclohexane

D 1-Ethyl-2,2-dimethylcyclohexane
 AIEEE - 2004

The IUPAC name of the compound is

HO

A 3, 3-dimethyl-1-hydroxycyclohexane

B 1, 1-dimethyl-3-hydroxycyclohexane

# C 3, 3-dimethyl-1-cyclohexanol

D 1, 1-dimethyl-3-cyclohexanol
JEE Mains 2017 / 08 April

Structure of the compound whose IUPAC name is 3-ethyl-2-hydroxyl-4-methylhex-

3-en-5-ynoic acid is :

# A

D
 25 Jan, 2023 (Shift-II)

List – I (Isomeric pairs) List-II ( Type of isomers )

(A) Propanamine and N-Methylethanamine (I) Metamers

(B) Hexan-2-one and Hexan-3-one (II) Positional isomers
(C) Ethanamide and Hydroxyethanimine (III) Functional isomers
(D) o-nitrophenol and p-nitrophenol (IV) Tautomers

A (A) – (III), (B) – (IV), (C) – (I), (D) – (II)

B (A) – (IV), (B) – (III), (C) – (I), (D) – (II)

C (A) – (II), (B) – (III), (C) – (I), (D) – (IV)

# D (A) – (III), (B) – (I), (C) – (IV), (D) – (II)

01 Feb, 2023 (Shift-II)

Testosterone, which is a steroidal hormone, has the following structure.

OH
CH3

CH3

O
Testosterone
The total number of asymmetric carbon atom/s in testosterone is ___________.
 JEE Mains 2020 / 5 Sept/Shift-II

Among the following compounds, geometrical isomerism is exhibited by :

CHCl CHCl

# A B
CH3

CH2 CHCl

C D
H3C CH3
Cl
QUESTION

Which of the following is optically active : –

OH OH
CH3
A # B

OH
OH CH3

C D
AIEEE - 2004

Among the following four structures I to IV.

CH3 O CH3 H CH3

C2H5 – CH – C3H7 CH3 – C – CH – C2H5 H – C C2H5 – CH – C2H5

(I) (II) (IV)
H
(III)
It is true that :

A All four are chiral compounds

# B Only I and II are chiral compounds

C Only III is a chiral compound

D Only II and IV are chiral compounds

AIEEE - 2007

Which of the following molecules is expected to rotate the plane of polarized light?

NH2
H2N
H COOH
A H B H2N H
Ph Ph
H

CHO
# C HO H D
CH2OH
SH
 AIEEE - 2004

Which of the following will have a meso-isomer also ?

A 2-Chlorobutane

# B 2, 3-Dichlorobutane

C 2, 3-Dichloropentane

D 2-Hydroxypropanoic acid
No of stereoisomers

1 Stereo centre : D – CH – CH2 – CH3 CH3 – CH = CH – CH3

CH3

2 Stereo centre :

CH3 – CH – CH – CH3 CH3 – CH – CH – C2H5 CH3 – CH = CH – CH – OH

OH OH OH OH CH3
2 Stereo centre :
CH3 – CH = CH – CH = CH –CH3 CH3 – CH = CH – CH = CH –C2H5

3 Stereo centre :

H3C(HO)HC – CH = CH – CH(OH)CH3 H5C2(HO)HC – CH = CH – CH(OH)CH3

 QUESTION

The correct stability order of the following resonating structures is :

+ – + – – + – +
H2C = N = N H2C – N = N H2C – N  N H2C – N = N
(I) (II) (III) (IV)

A (I) > (II) > (IV) > (III)

# B (I) > (III) > (II) > (IV)

C (II) > (I) > (III) > (IV)

D (III) > (I) > (IV) > (II) i) Neutral structures

ii) Greater the number of covalent bonds
iii) -ve charge on the more electronegative atom
iv) like charges should be at the maximum distance.
 Stability of Resonating structures of different molecules
(i) - -
CH2 CH2

(ii) Linear conjugated system > cross conjugation

NH2 NH2
O O
(iii) + (iv) C
+ C
NH2 OH -O S- -S S-
 Hyper Conjugation JEE Main /Advanced

De-localisation of  electron with (i) p orbital

(ii) * orbital
H H H
+ H
C—C C—C
H H
H CH2
H H

H
H
. H H C H
C—C
H
H H
 JEE (Advanced) - 2013

The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are

due to

# A  → p (empty) and  → * electron delocalisations.

B  → * and  →  electron delocalisations

C  → p (filled) and  →  electron delocalisations.

D p (filled) → * and  → * electron delocalisations.

QUESTION

The decreasing order of hydride affinity for following carbocations is:

+ + [2023/10 April/Shift-II]
(A) CH2 = CH – C – CH3 (B) C6H5 – C – C6H5

CH3 C6H5
+ +
(C) H3C – C – CH3 (D) C
CH3

Choose the correct answer from the options given below:

A (A), (C), (B), (D) # B (C), (A), (B), (D)

C (C), (A), (D), (B) D (A), (C), (D), (B)

JEE (Main) 2014

In which of the following pairs first is more stable than second ?

A B

C # D Ph3C°, (CH3)3C°
 Aromatic Compounds

O
 16 March, 2021 (Shift-I)

Among the following, the aromatic compounds are :

(A) CH2 (B) (C) (D)

⊝ 

(B), (C) and (D) only

A
(A) and (B) only
B

C (A), (B) and (C) only

# D (B) and (C) only

JEE Main - 2012

Which of the following molecules, in pure form, is (are) unstable at room

temperature ?

# B
O

C
O

D
 Basicity

NH2 NH NH2 N

NH2 NH2 NH2

CH3 NO2
 NH2 NH2

N N

NH3 RNH2 R2NH R3N

R = CH3

R = C2H5
 25 Jan, 2023 (Shift-I)

The correct order in aqueous medium of basic strength in case of methyl substituted
amines is:

# A Me2NH > MeNH2 > Me3N > NH3

B Me2NH > Me3N > MeNH2 > NH3

C NH3 > Me3N > MeNH2 > Me2NH

D Me2N > Me2NH > MeNH2 > NH3

 11 Jan, 2019 (Shift-II)
(a)
(d)
NH2
In the following compound N N (b)
N N
(e) H (c)

The favourable site/s for protonation is / are:

A a and e

# B b, c and d

C a and d

D a
 09 Jan, 2019 (Shift-I)

Arrange the following amine in the decreasing order of basicity :

I II III
N N N

H H

A I > II > III

# B III > I > II

C I > III > II

D III > II > I

 25 Jan, 2023 (Shift-II)

List – I (Amines) List-II (pKb)

(A) Aniline (I) 3.25

(B) Ethanamine (II) 3.00
(C) N-Ethylethanamine (III) 9.38
(D) N, N-Diethylethanamine (IV) 3.29

A (A) – (I), (B) – (IV), (C) – (II), (D) – (III)

B (A) – (III), (B) – (II), (C) – (I), (D) – (IV)

C (A) – (III), (B) – (II), (C) – (IV), (D) – (I)

# D (A) – (III), (B) – (IV), (C) – (II), (D) – (I)

 07 Jan, 2020 (Shift-I)

The increasing order of pKb, for the following compounds will be

(A) NH2 – CH = NH2 N

(B) N NH
(C) CH3NHCH3

A B<C<A

B C<A<B

# C B<A<C

D A<B<C
06 Sept, 2020 (Shift-I)

The increasing order of pKb values of the following compounds is :

N (CH3)2 N(CH3)2 NHCH3 NHCH3

I II III IV
CN OH
OCH3

A II < IV < III < I

# B I < II < IV < III

C II < I < III < IV

D I < II < III < IV

QUESTION
The increasing order of basicity for the following intermediates
is ( from weak to strong ) [ 2020/09 Jan/Shift-I ]
CH3
⊝ ⊝ ⊝ ⊝
H3C C⊝ H2C = CH – CH2 HC  C CH3 CN

(i) CH3 (ii) (iii) (iv) (v)

# A (v) < (iii) < (ii) < (iv) < (i)

B (iii) < (i) < (ii) < (iv) < (v)

C (v) < (i) < (iv) < (ii) < (iii)

D (iii) < (iv) < (ii) < (i) < (v)

 25 Feb, 2021 (Shift-I)

Compound(s) which will liberate carbon dioxide with sodium bicarbonate solution
is/are :
NH2 COOH OH
O2N NO2
A= B= C=
H2N NH2
OH NO2

A A and B only

B B only

# C B and C only

D C only
 25 Feb, 2021 (Shift-II)

The correct order of acid character of the following compounds is:

OH COOH COOH COOH

I II III IV

NO2 CH3

A III > II > I > IV

# B II > III > IV > I

C I > II > III > IV

D IV > III > II > I

 JEE Main-29 Jan, 2023 Shift-I

The increasing order of pKa for the following phenols is

1. 2, 4-Dinitrophenol
2. 4-Nitrophenol
3. 2, 4, 5-Trimethylphenol
4. Phenol
5. 3-chlorophenol

A 1, 5, 4, 3, 2

B 3, 4, 5, 2, 1

# C 1, 2, 5, 4, 3

D 3, 5, 4, 2, 1
 JEE Main-26 June, 2022 Shift-I

Which will have the highest enol content ?

O O
O
A B
O

O
O

# C
O
D
O
O
 M + R–X
Na
Wurtz Reaction : CH3 – Br
Dry ether

Cl
Na
Fitting Reaction : ether

Cl
Wurtz-Fitting Reaction : CH3 – Cl + Na
ether
H3C

Frankland Reaction : Zn
I 

I
Ullmann Reaction : Cu

 Cl
Zn Zn/Cu couple
H – Cl CH3 – I Ethanol

Clemmensen Reduction Wolf - Kishner Reduction

Zn-Hg N 2H 4
O O
HCl Base

O O
Zn-Hg N 2H 4
HCl Base
JEE Main-11 April, 2023 Shift-II
O

Assertion (A) : can be subjected to Wolff-Kishner reduction to give

Cl O Cl
Reason (R) : Wolff-Kishner reduction is used to convert into CH2
C

A Both (A) and (R) are true but (R) is NOT the correct explanation (A).

B (A) is true but (R) is false.

# C (A) Is false but (R) is true.

D Both (A) and (R) are true and (R) is the correct explanation of (A).
JEE Main-30 Jan, 2023 Shift-II

O
Assertion (A) : can be easily reduced using Zn-Hg/HCl to
OH OH

Reason (R) : Zn-Hg/HCl is used to reduce carbonyl group to –CH2 – group.

# A (A) Is false but (R) is true.

B (A) Is true but (R) is false.

C Both (A) and (R) are true but (R) is not the correct explanation of (A).

D Both (A) and (R) are true and (R) is the correct explanation of (A).
 Reactions of Alkene

Anti-addition Syn - addition

Br2 / CCl4 H2 / Pd

Br2 / H2O BH3 / THF

H2O2 / OH-
HOBr
Cold and Dil. KMnO4
Hg(OAc)2 / H2O
NaBH4 OsO4

RCO3H
H3O+
 JEE Main-24 Jan, 2023 Shift-II
Find out the major products from the following reactions.

Hg(OAc)2, H2O BH3, THF

B H2O2/OH–
A
NaBH4

OH
# A A= OH , B =

OH
B A= , B=
OH

OH OH
C A= , B=

D A=
OH
, B=
OH
12 April, 2019 (Shift-I)

The major product of the following addition reaction is :

H3C – CH = CH2 Cl2 / H2O

O
A CH3 – CH – CH2 B
H3C CH3
Cl OH

O
C H3C – CH – CH2 # D H3C
OH Cl
Ozonolysis Reductive Ozonolysis Oxidative Ozonolysis
i. O3 ii. Zn/H2O i. O3 ii. H2O2
DMS

CH3 CH CH CH3

CH3 — C C — CH3

NOTE : KMnO4 / H+ or alkaline KMnO4 with Heat gives same product as OO.
 12 April, 2019 (Shift-I)

But-2-ene on reaction with alkaline KMnO4 at elevated temperature followed by

acidification will give :

A One molecule of CH3CHO and one molecule of CH3COOH

B CH3 – CH – CH – CH3

OH OH
# C 2 molecules of CH3COOH

D 2 molecules of CH3CHO
 12 April, 2023 (Shift-I)

(i) O3
2 – hexene (ii) H2O
Products

The two products formed in above reaction are

# A Butanoic acid and acetic acid

B Butanal and acetic acid

C Butanal and acetaldehyde

D Butanoic acid and acetaldehyde

 08 Jan, 2020 (Shift-II)
An unsaturated hydrocarbon X absorbs two hydrogen molecules on catalytic
hydrogenation, and also gives following reaction
O3 [Ag(NH3)2]+
X Zn/H2O
A B ( 3-oxo-hexanedicarboxylic acid )
X will be

# A B

C D
 31 Jan, 2023 (Shift-I)

Choose the correct set of reagents for the following conversion

trans ( Ph-CH = CH – CH3 ) → cis ( Ph-CH = CH – CH3 )

A Br2, alc. KOH, NaNH2, Na(Liq NH3)

# B Br2 , alc. KOH , NaNH2, (H2 , Lindlar Catalyst)

C Br2, aq KOH , NaNH2, (H2, Lindlar Catalyst)

D Br2, aq KOH, NaNH2, Na(Liq NH3)

 Red hot
Preparation of benzene H—C C—H Fe tube

Red hot
CH3 — C C—H Cu tube

OH
Zn

Anhy. AlCl3
Isomerisation CH3(CH2)2CH3 HCl, 

Anhy. AlCl3
Aromatisation of Alkane : CH3(CH2)4CH3 HCl, 
 Free radical allylic and benzylic substitution reaction

NBS
CH3 – CH2 – CH = CH2

CH2CH3
Br2
UV light

CN

Al2O3
Saytzeff Alkene
P2O5
OH
ThO2
Hoffmann Alkene
WO2
 O
H3O+
Acidic Hydrolysis CH3 — C — OCH3

O — CH3 H3O+
O — CH3

O
HO-
Basic Hydrolysis CH3 — C — Cl
O O
HO-
CH3 — C — O — C — CH3

O
H 2O
R — C — NH2

H 2O
R—C N
09 Sept, 2020 (Shift-II) The major product (Y) in the following reactions is :
CH3
HgSO4, H2SO4 (i) C2H5MgBr, H2O
H3C – CH – C  CH H3O
X (ii) Conc. H2SO4 / 
Y

CH3 CH3
A CH3 – CH – C = CH2 # B CH3 – C = C – CH3
CH2 – CH3 CH2 – CH3
CH2 CH3
C CH3 – C – CH = CH3 D CH3 – CH – C = CH – CH3

CH2 – CH3 CH3

 15 April, 2023 (Shift-I) Decreasing order of reactivity towards electrophilic
substitution for the following compounds is :
CH3 OCH3
NMe2

a b CF3
d
c e

A c>b>a>d>e

# B e>d>a>b>c

C a>d>e>b>c

D d>a>e>c>b
31 Aug, 2021 (Shift-II) Identify correct A, B and C in the reaction sequence
given below :

conc. HNO3 Cl2 Fe/HCl

+

A Anhyd. AlCl3
B C
conc. H2SO4

NO2 NO2 NO2

# NO2 O2N Cl H2N Cl
A A= ,B= ,C= B A= ,B= ,C=
Cl OH

NO2 NO2 NH2 NO2 NO2 NH2

C A= ,B= ,C= D A= ,B= ,C=
Cl Cl
Cl OH
11 Jan, 2019 (Shift-II) The major product of the following reaction is :

HO
(1) HCl
(2) AlCl3 (Anhyd.)

Cl Cl
A B

#
HO HO
C D
31 Aug, 2021 (Shift-II)
The structure of A and B formed in the following
reaction are : [Ph = –C6H5]
O

O AlCl3(2eq) Zn/Hg
+ A B
HCl

Ph
Ph A=
A A= , B = Ph
, B = Ph
B O
O OH
O O
Ph Ph
# A= OH, A= OH,
C O D O
O
OH
B = Ph B = Ph
OH
Halo-Alkanes & Halo-Arenes SN1 / SN2 E1 / E2 / E1cb SN2 Ar

Br Br

HO C2H5OH NO2 Θ
C2H5OK

NaCN
CH3 — Br
Br
NaI
C2H5OH CH3 — CH — CH3
Acetone
|
Cl
Et
Et OHΘ
Et
Et
Cl H2O OHΘ
Cl
Δ
 H

CH — CH2 Alc. KOH

Δ
O2N Cl

H
Alc. KOH Δ
N C — CH — CH2 — F
SN2 Ar

F F
Cl O 2N NO2
Et – OΘK

NaOH
NO2 NO2

Br2 NaI
CH3 — CH3
hv Acetone

H2O + EtOH AgF / HgF2

Swart’s Reaction
JEE Main-24 Jan, 2023 Shift-I In the following given reaction ‘A’ is
CH3
C = CH2
+ HBr ‘A’
Major product

CH3
CH3 Br
Br
A
B

Br CH3 CH3 CH3

C CH3 # D Br
 Choose the halogen which is most reactive towards
JEE Main-08 April, 2023 Shift-I
SN1 reaction in the given compounds (A, B, C & D)
Br(a)
Br
Br(b)
A. B. I I(b) C. D.
Br(b) (a) Br(b) Br(a)
Br(a)
Me

A A-Br(b) ; B-I(b); C-Br(b); D-Br(b)

# B A-Br(a) ; B-I(a); C-Br(b); D-Br(a)

C A-Br(b) ; B-I(a); C-Br(a); D-Br(a)

D A-Br(b) ; B-I(a); C-Br(a); D-Br(a)

 JEE Main-08 April, 2023 Shift-I Consider the following reaction that goes from
A to B in three steps as shown below :

Choose the correct

Number of Rate
Number of
Activated determining
intermediates
complexes step
A 3 2 II

# B 2 3 II

C 2 2 I

D 2 3 III
JEE Main-11 April, 2023 Shift-I

Cl Nu Nu
(I)
MeO OMe

Cl Nu Nu
(II)
O2N O2N

Rate of I & II Reaction .

JEE Main-25 Jan, 2023 Shift-I The compound which will have the lowest rate
towards nucleophilic aromatic substitution on
treatment with OH– is

Cl Cl
NO2
A B

NO2 NO2
Cl Cl
NO2
C # D
NO2
 JEE Main-30 Jan, 2023 Shift-II

Decreasing order towards SN1 reaction for the following compounds is:

Cl Cl Cl Cl

NO2 OMe Cl (d)

(a) (b) (c)

A (a) > (c) > (d) > (b) B (a) > (b) > (c) > (d)

# C (b) > (d) > (c) > (a) D (d) > (b) > (c) > (a)
 JEE Main-25 Jan, 2023 Shift-II

Identify the correct order of reactivity for the following pairs towards the
respectively mechanism.
Br Br
Br > Br
(A) SN2 (B) SN1 >

Br
Cl Cl Br
(C) Electrophilic (D) Nucleophilic substitution <
substitution >
NO2
NO2

A (A), (B) and (D) only # B (A), (B), (C) and (D)

C (A), (C) and (D) only D (B), (C) and (D) only
JEE Main-15 April, 2023 Shift-I

The major product formed in the Friedel-Craft acylation of chlorobenzene is.

Cl
Cl
COCH3
# A B
COCH3
O CH3

Cl Cl

D
C CH3 CH3

O O
O CH3
JEE Main-24 Jan, 2023 Shift-I

Number of moles of AgCl formed in the following reaction is ___________.

Cl
Cl AgNO3
Cl (A) + X AgCl ↓
H

Cl
 JEE Main-29 July, 2022 Shift-I

Considering the below reactions, the compound ‘A’ and compound ‘B’, respectively are :
AgCN
‘A’ NaCN
‘B’
C2H5OH – H2O Cl
(Major Product) C2H5OH – H2O
(Major Product)

 ⊝  ⊝
A NC, NC

B CN, CN


# C NC,
⊝
CN
 ⊝
D CN, NC
 JEE Main-27 June, 2022 Shift-I

I
F ⊝ 
PhS Na
DMF

NO2

SPh I SPh SPh

F SPh F SPh
# A B C D

NO2 NO2 NO2 NO2

JEE Main-25 July, 2022 Shift-I Most stable product of the following reaction is :

OH (i) H3C SO2Cl, Pyridine

(ii) NaCN, DMF

CN
CN
#
A B

CN
CN
D
C
 JEE Main-26 Feb, 2021 Shift-II
Identify A in the given reaction. A (Major Product)
OH
SOCl2
A (Major Product)

HO CH2OH
OH OH

# A B

Cl CH2Cl OH CH2Cl
Cl Cl

C D

Cl CH2Cl OH CH2OH
 JEE Main-25 June, 2022 Shift-I

The major product in the reaction is CH3 CH3

CH3 – C – Cl -O – C – CH3 ?

CH3 CH3

A t-Butyl ethyl ether

B 2, 2-Dimethylbutane

C 2-Methylpent-1-ene

# D 2-Methylprop-1-ene
JEE Main-28 June, 2022 Shift-II

(i) Cl2, 
(A) 4-Bromophenyl acetic acid
(ii) CN–
(iii) H2O/H+

In the above reaction (A) is

Br Br

A B

CH2CH3
CH = CH2
CH3 D
# C
Br
Br
JEE Main-28 July, 2021 Shift-II

What is A in the following reaction ?

O

CH2Br
⊝
N K

O
A
⊝
(ii) OH / H2O (Major Product)
O
CH2NH2
B NH – CH2
# A

O CH2OH

C D
NH

O
 JEE Main-27 July, 2021 Shift-I
Presence of which reagent will affect the reversibility of the following reaction,
and change it to a irreversible reaction :
hv
CH4 + I2 CH3I + HI
Reversible

A HOCl

B Liquid NH3

C Dilute HNO2

# D Concentrated HIO3
JEE Main-03 Sept, 2020 Shift-I
The mechanism of SN1 reaction is given as :
𝑌⊝
R – X → RX. → R || X R – Y + X
Ion pair Solvent
separated ion pair

A student writes general characteristics based on the given mechanism as :

(A) The reaction is favoured by weak nucleophiles.
(B) R would be easily formed if the substituents are bulky.
(C) The reaction is accompanied by racemization.
(D) The reaction is favoured by non-polar solvents.
Which observations are correct ?

A (B) And (D) # B (A), (B) and (C)

C (A) and (C) D (A) and (B)

JEE Main-02 Sept, 2020 Shift-II

The major product obtained from E2-elimination of 3-bromo-2-fluoropentane is

Br F
A CH3CH2 – CH – CH = CH2 B CH3 – CH = CH – CH – CH3

Br
# C CH3CH2CH = C – F D CH3 – CH2 – C = CH – CH3

CH3
JEE Main-07 Jan, 2020 Shift-II In the following reaction sequence, structure
of A and B respectively will be

O
HBr Na

A Ether
( Intermolecular product ) B

CH2Br

Br Br Br Br

A OH B OH
& O &
CH2Br CH2Br O
OH OH OH OH
#
Br D Br
C & &
CH2Br CH2Br
Oxidising Agent

CH3CH2 — OH
H

CH3 — C — OH
Cu / 300 0C
CH3

CH3

CH3 — C — OH

CH3
Strong Oxidising Agent Weak Oxidising Agent

(i) CrO3 / H+ (i) CrO3 / Inert solvent ( CS2 / CCl4 )

(ii) H2CrO4 (ii) PCC → pyridinium chlorochromate

(iii) K2Cr2O7 / H+

(iv) KMnO4 / H+, Δ (iii) PDC → pyridinium Dichromate

(v) KMnO4 / OH–, Δ

(vi) Jones Reagent (iv) Collins Reagent → CrO3 & Pyridine

CrO3 / aq. H2SO4 / Acetone Solvent → CH2Cl2
CH3
C — CH3 CH2 — OH

KMnO4 , OH– / Δ

CH3
(i) CrO3 / (CH3COO)2O
CrO3 (ii) H3O+
H 3O+
(i) CrO2Cl2/ CS2
(ii) H3O+
10 April, 2023 (Shift-I) The major product ‘P’ formed in the given reaction is

CH2CH3

(i) alk. KMnO4,  P

COOCH3 (ii) H3O+ Major Product

CH = CH2

CH2COOH COOH

A COOH B COOH
HO H
HO H COOH
H
CH2COOH COOH

C
COOH
# D
COOH
COOH
COOCH3
 Reducing Agent O NaBH4 O

LiAlH4 — C — Cl — C — Cl
O O
|| — NO2 ||
—C — H —C — H
—C N
O
O
|| O ||
—C —CH3 || —C —CH3
O O —C — NH2
|| ||
— CH NH
—C —O—C — R — CH NH
O O
DIBAL-H
|| O O
—C —OR — C — NH — || ||
O O —C —O—C — R
||
—C —OH —C—N— —C N
 O O
LiBH4
||
C — CI —C —OR
H2 / Pd
BaSO4 O O
|| ||
H2 / Pd / C
—C — H —C —CH3
Lindlar’s Catalyst

R—C C—R — CH NH
Na / Liq. NH3
O
B2H6 ||
Na liq. NH3
R—C C—H —C —OH — CH NH
O O
SnCl2 || ||
R—C N HCl —C — H —C —CH3
Sn HCl
 (i) HCN + HCl / AlCl3
(ii) H3O+

KCN + HCl / AlCl3

H 3 O+

CO + HCl / AlCl3

Gattermann-Koch Reaction

25 Feb, 2021 (Shift-I)

Consider the following chemical reaction.

1) Red hot Fe tube, 873 K
HC  CH 2) CO, HCl, AlCl3
Product
The number of sp2 hybridized carbon atom(s) present in the product is __________.
08 April, 2023 (Shift-I) The major product formed in the following reaction is :

CO2H
(i) LiBH4/EtOH
Major product
CO2Et (ii) H3O+

OH OH
A B
CO2Et
OH

# CO2H CO2H
C D CO2H
OH
JEE Main-16 March, 2021 Shift-I

The product “P” in the above reaction is:

O
O “P”
(i) DiBAL-H, Toluene, 78°C
(ii) H3O+
(Major Product)

CHO COOH
A B
O
O–C–H OH

C # D CHO
10 Jan, 2019 (Shift-II)
The major product of the following reaction is :

O
NaBH4
CH3N

OH OH
A CH3N B CH3N

O # OH
C CH3NH D CH3NH
08 April, 2019 (Shift-II) The major product obtained in the following reaction is

CH3 O
NaOH

OHC

CH3
H3C
A H
B
O CH3
O CH3
H3C
C H
# D
O CH3
O
 JEE Main-26 June, 2022 Shift-II

Oxidation of toluene to benzaldehyde can be easily carried out with which of the
following reagents ?

A CrO3/acetic acid , H3O+

# B CrO3/acetic anhydride , H3O+

C KMnO4/HCl, H3O+

D CO/HCl , anhydrous AlCl3

 JEE Main-25 Feb, 2021 Shift-I

The major product of the following chemical reaction is:

(1) H3O+ ,
(2)SOCl3
CH3CH2CN ⎯⎯⎯⎯⎯⎯→ ?
(3) Pd/BaSO4 ,H2

A (CH3CH2CO)2O

# B CH3CH2CHO

C CH3CH2CH3

D CH3CH2CH2OH
 10 Jan, 2019 (Shift-I)

Which dicarboxylic acid in presence of a dehydrating agent is least reactive to give

anhydride?
O
CH2
COOH
# A CH 2 B CH2 COOH
COOH
CH2 CH2 COOH
CH2 CH2

CO2H
COOH
C D
COOH
CO2H
 JEE Main-25 Feb, 2021 Shift-II

The major product of the following reaction is:

H /CO
CH3CH2CH = CH2 ⎯⎯⎯⎯⎯
2 →
Rh catalyst

# A CH3CH2CH2CH2CHO

B CH3CH2C = CH2
CHO

C CH3CH2CH2CHO

D CH3CH2CH = CH – CHO
 JEE Main-27 June, 2022 Shift-I

Which of the following reactions will yield benzaldehyde as a product ?

CH2OH
COOH
(i) SOCl2 CrO3/H2SO4
i ii
(ii) H2/Pd/BaSO4

O
C – OCH3 CH3
iii (i) NaBH4
(i) CrO3, (CH3CO)2O
(ii) PCC iv
(ii) H3O+, 

A i and iii B i and ii

# C i and iv D iv and ii
 JEE Main-25 June, 2022 Shift-II

Which of the following condition or reaction sequence will NOT give acetophenone
as the major product?

A (i) C6H5 H + CH3MgBr (ii) Na2Cr2O7, H+

O

B (i) H3C H + C6H5MgBr (ii) PCC

O

# C C6H5 OC2H5 + 2CH3MgBr

O

D C6H5 Cl + CH3MgBr + CdCl2

JEE Main-16 March, 2021 Shift-II

CN
(I) C6H5MgBr, (X)
dry Ether (1.0 equivalent) Major Product
OCH3 (ii) H3O+

The structure of (X) is :

NH2 NH2
A B

C6H5 OCH3
O O
C6H5 C6H5
C C6H5 # D

OCH3
 JEE Main-25 Feb, 2021 Shift-I

Which one of the following reactions will not form acetaldehyde ?

A CH2 = CH2 + O2
Pd II / Cu II

Cu
B CH2CH2OH ⎯⎯⎯→
573 K

CrO3 −H2 SO4

# C CH3CH2OH

( i ) DiBAL − H
D CH3CN ⎯⎯⎯⎯⎯⎯
( ii ) H 2O
→
JEE Main-11 Jan, 2019 Shift-I

The major product of the following reaction is :

O
OEt (i) Ni/H2
CN (ii) DiBAL-H

H
O NH
A B
CHO

OH D N
C #
NH2
 JEE Main-15 April, 2023 Shift-I

The product formed in the following multi step reaction is :

(i) B2H6
(ii) H2O2, NaOH
CH3 – CH = CH2 (iii) PCC
(iv) CH3MgBr

OH
#
A CH3 – CH2 – CH – CH3 B CH3 – CH2 – CH2 – CH2 – OH

O OH
C CH3 – CH2 – C – OCH3 D CH3 – C – CH3

CH3
JEE Main-11 April, 2023 Shift-I

O
R
KMnO4 (i) NH2 – NH2, KOH
‘A’ (Major Product) (ii) H3O+
‘B’ (Major Product)
(R = alkyl)

CO2H
O
CHO =A
A R
CO2H B R CHO = A,

CH3 B =R CH3
B= R

CO2H O
CO2H. =A
C R # D R CO2H = A,
O
O NHNH2 CO2H
C – NH – NH2 B =R
B=R
JEE Main-11 April, 2022 Shift-I

The ratio x/y on completion of the above reaction is __________.

O x mol of OH
OH MeMgBr OH
H H
(y mole) H3O+
JEE Main-28 June, 2022 Shift-II

‘A’ in the given reaction is

H COOH
OH H+ ‘A’
Major
O

O OH O O
A # B
O O

O
C OH C O OH COOH
D
O
 JEE Main-28 June, 2022 Shift-I

The correct structure of product ‘A’ formed in the following reaction is,
O
NaOD
PhCHO + PhCHO in D2O
A + Ph – C – O–

OD OH

# A H B H
Ph H Ph H

OD
OD
C D
D D
Ph D
Ph H
 JEE Main-31 Jan, 2022 Shift-II

The number of molecules which gives haloform test among the following molecules
is ____________.
O O
O O
OEt

OH O O

OH
JEE Main-26 July, 2022 Shift-I

The products formed in the following reaction, A and B are

O
[Ag(NH3)2]+OH– NaBH4
A B

H CHO

O
H OH H OH H OH

A A= B= B A= B=
H CH2OH H CH2OH H CHO H CH2OH

O O
H OH H OH
# C A= B=
D A= B=
H COOH H COOH H COOH H CH2OH
JEE Main-25 July, 2022 Shift-I

In the given reaction

O
H3C –OEt
C – OEt

CH2 – C – CH3
O
(Where Et is –C2H5)
The number of chiral carbon/s in product A is ___________.
 JEE Main-17 March, 2021 Shift-I

The product “A” in the above reaction is :

O O
Ethylene Glycol
H+
A
OC2H5 (Major Product)

O OH
O O
A OH B O O
OC2H5 OH

O
O
# C O O D
OC2H5
OC2H5
OH
 JEE Main-20 July, 2021 Shift-I

OH
O
OH
CHO OH
(I) (II) (III) (IV)
Which among the above compound/s does/ do not form silver mirror when treated
with Tollen’s reagent ?

A only (IV)

B (III) And (IV) only

# C only (II)

D (I), (III) and (IV) only

JEE Main-20 July, 2021 Shift-I

The number of nitrogen atoms in a semicarbazone molecule of acetone is __________.

NH2 — NH — C — NH2

Semicarbazide
JEE Main-01 Feb, 2023 Shift-II

In a reaction, OH OH OCOCH3
COOCH3 COOH COOH
‘Y’ ‘X’

Reagents ‘X’ and ‘Y’ respectively are :

# A (CH3CO)2 O/H+ and CH3OH/H+, 

B (CH3CO)2 O/H+ and (CH3CO)2 O/H+

C CH3OH/H+,  and CH3OH/H+, 

D CH3OH/H+ and (CH3CO)2 O/H+

JEE Main-24 Jan, 2023 Shift-I

‘A’ and ‘B’ formed in the following set of reactions are :

OH OH
HBr HBr
 A  B
CH2OH OCH3

Br Br OH Br
A A= B= B A= B=
, ,
CH2OH Br CH2Br OCH3

OH OH # OH OH
C A= B= D A= B=
, ,
CH2Br Br CH2Br OH
JEE Main-25 Jan, 2023 Shift-I

In the cumene to phenol preparation in presence of air, the intermediate is

O CH3 O

A B

O–O–H

C # D
JEE Main-06 April, 2023 Shift-II In the following reaction, ‘B’ is

H3O+
‘B’
OH Major

A # B

O
C D
O
 JEE Main-11 April, 2023 Shift-I

Arrange the following compounds in increasing order of rate of aromatic

electrophilic substitution reaction

OH OH O OH
O
(A) (B) (C) (D)

A D, B, C, A

B B, C, A, D

# C C, A, B, D

D D, B, A, C
JEE Main-25 June, 2022 Shift-I The intermediate X, in the reaction
OH OH
CHO
(1) NaOH
CHCl3 + Aq. NaOH + [X] (2) H+

OH OH
CCl3 CHCl2
A B

O–Na+ O–Na+
CHCl2 CCl3
D
# C
JEE Main-25 Jan, 2023 Shift-II

Number of compounds giving (i) red colouration with ceric ammonium nitrate
(ii) positive iodoform test from the following is ____________

O
O OH
OH
CH3 O
, , H , , ,
OH
OH

OH ,
JEE Main-24 Feb, 2021 Shift-I

Which of the following compound gives pink colour on reaction with phthalic
anhydride in conc. H2SO4 followed by treatment with NaOH ?

CH3 HO CH3
A B
HO HO CH3

CH3 H3C CH3

# D
C
OH HO OH
 JEE Main-05 Sept, 2020 Shift-II The major product of the following reaction is :

OH
CH3 Conc. HNO3+
Conc. H2SO4

NO2

OH OH
H3C H3C NO2
A B
O2N NO2 NO2

OH OH
H3C H3C NO2
C D
NO2 NO2
#
NO2 NO2
JEE Main-11 Jan, 2019 Shift-I The major product of the following reactions is :
OH
Br2 (excess)

SO3H
OH
OH
Br
Br Br B
# A
SO3H
Br
OH OH
Br Br
C
D
Br Br
Br SO3H
Gomberg Reaction ClΘ

N N

Coupling Reaction
ClΘ

NH2 N N pH = 4-5

ClΘ

OH N N pH = 9-10

O
 Θ 
Na O — S N N N

O
Coupling Reaction N

N
OH ClΘ

OH–
 Sandmeyer Reaction

CuCl HCl

H3PO2 KI Δ
 ClΘ
N N
HBF4 KCN
CuCN

C2H5OH H 2O Δ

Cu HCl

Gattermann Reaction
 JEE Main-26 Feb, 2021 Shift-II

List-I List-II
+ Cl
N2Cl–
(A) Cu2Cl2 (I) Wurtz reaction
+ N2
HCl
+ Cl
N2Cl–
(B) Cu, HCl (II) Sandmeyer reaction
+ N2
𝐸𝑡ℎ𝑒𝑟
(C) 2CH3CH2Cl + 2Na C2H5 – C2H5 + 2NaCl (III) Fitting reaction
𝐸𝑡ℎ𝑒𝑟
(D) 2C6H5Cl + 2Na C6H5 – C6H5 + 2NaCl (IV) Gatterman reaction

A (A)-(II), (B)-(I), (C)-(IV), (D)-(III) B (A)-(III), (B)-(IV), (C)-(I), (D)-(II)

# C (A)-(II), (B)-(IV), (C)-(I), (D)-(III) D (A)-(III), (B)-(I), (C)-(IV), (D)-(II)

25 Feb, 2021 (Shift-II)

The total number of amines among the following which can be synthesized by Gabriel
synthesis is :

CH3
CH – CH2 – NH2 CH3CH2NH2
CH3

CH2 – NH2 NH2

20 July, 2021 (Shift-II)

O O
KOBr LiAlH4
NH2 (A) NH2 (B)
H3O+
(Major Product) (Major Product)
Br Br
In the above reactions, product (A) and product (B) respectively are:
NH2 NH2
NH2 B NH2
A
, ,

Br Br
NH2 NH2
NH2 NH2
C D
, ,
#
Br Br
31 Aug, 2021 (Shift-I)

The total number of reagents from those given below, that can convert nitrobenzene
into aniline is ___________. ( Integer answer )

(i) Sn - HCl (ii) Sn-NH4OH

(iii) Fe -HCl (iv) Zn-HCl
(v) H2-Pd (vi) H2-Raney Nickel
 12 April, 2023 (Shift-I)

The incorrect statement regarding the reaction given below is

Me – N – Me

‘A’ + NaNO2 + HX → ‘B’

A The electrophile involved in the reaction is NO+

# B ‘B’ is N-nitroso ammonium compound

C The reaction occurs at low temperature

D The product ‘B’ formed in the above reaction is p-nitroso compound at low
temperature.
11 April, 2023 (shift-I) HNO2
O-Phenylenediamine ‘X’ ‘X’ is
Major Product

N
# A N B NH
N

+
NN +
N2
C + D
N2 NH2
 30 Jan, 2023 (shift-I) Benzyl isocyanide can be obtained by :

CH2Br CH2NH2
AgCN CHCl3
(I) (II)
Aq. KOH

CH2–NHCH3 CH2OTs
CHCl3 KCN
(III) (IV)
Aq. KOH

Choose the correct answer from the options given below :

A I and IV B Only II

# C I and II D II and III

 09 Jan, 2019 (Shift-II) The major product of the following reaction is :

O
C
NH2 (i) Br2/hv

CH2CH3 (ii) KOH(dil)

O
NH NH
A B

C NH
# NH D
CH3
CH3
08 April, 2023 (Shift-II)

NO2 (i) Br2

(ii) H2/Pd
(P)
(iii) NaNO2, HCl, 0°C
H3C (iv) H3PO2 Product

OH Br OH

A Br B
H3C H3C

Br
C
# D
H3C Br H3C
10 Jan, 2019 (Shift-I) The major product formed in the reaction given below will be :

NH2 NaNO2
Aq. HCl, 0 –5°C

NO2
A B NO2

# OH OH
C D
09 Jan, 2019 (Shift-II)

The test performed on compound X and their interferences are

Test Interference
(a) 2, 4-DNP test Coloured precipitate
(b) Iodoform test Yellow precipitate
(c) Azo-dye test No dye formation
Compound ‘X’ is
H3C CH3
NH2 N
COCH3
CHO
A # B

NH2 OH H3C CH3

N
C CH3
D CHO
 Maltose : C1 -D-Glucose + C4 -D-Glucose AGCT DNA

Sucrose : C1 -D-Glucose + C2  -D-Fructose AGCU RNA

Lactose : C1  -D-Galactose + C4  -D-Glucose AG - Purine

CUT - Pyrimidine

A T , G C

Amino Acids

PVT TIM HALL never Tired , only Argue

(i) Amino acids with aromatic chain :

Phenylalanine, Tyrosine, Tryptophan
(ii) Amino acids with sulphur :
Methionine , Cysteine
 11 Jan, 2019 (Shift-II)

Column-I Column-II
(A) Glucose + P/HI (I) Gluconic acid
(B) Glucose + Br2/water (II) Glucose pentacetate
(C) Glucose + acetic anhydride (III) Saccharic acid
(D) Glucose + HNO3 (IV) Hexane

# A (A)-(IV), (B)-(I), (C)-(II), (D)-(III)

B (A)-(IV), (B)-(III), (C)-(II), (D)-(I)

C (A)-(III), (B)-(I), (C)-(IV), (D)-(II)

D (A)-(I), (B)-(III), (C)-(IV), (D)-(II)

 27 July, 2021 (Shift-II)

Compound A gives D-Galactose and D-Glucose on hydrolysis. The compound A is:

A Amylose

B Sucrose

C Maltose

# D Lactose
 17 March, 2021 (Shift-II)

Fructose in an example of :

A Pyranose

# B Ketohexose

C Aldohexose

D Heptose
 20 July, 2021 (Shift-I)

Which of the glycosidic linkage between galactose and glucose is present in lactose?

A C-1 of glucose and C-6 of galactose

# B C-1 of galactose and C-4 of glucose

C C-1 of glucose and C-4 of galactose

D C-1 of galactose and C-6 of glucose

26 Feb, 2021 (Shift-II)

Column-I Column-II
(A) Sucrose (I) -D-Galactose and -D-glucose
(B) Lactose (II) -D-Glucose and -D-Fructose
(C) Maltose (III) -D-Glucose and -D-Glucose

A (A)-(III), (B)-(II), (C)-(I)

B (A)-(III), (B)-(I), (C)-(II)

C (A)-(I), (B)-(III), (C)-(II)

D (A)-(II), (B)-(I), (C)-(III)

01 Feb, 2023 (Shift-I) CHO
HO H
The correct representation in six membered
HO H
pyranose form for the following sugar [X] is
H OH
H2COH CH2OH H OH
OH O H2COH
H
A H H Sugar [X]
OH H
OH
# B OH HO
HO HO OH
H OH H H

H2COH CH2OH
OH OH
HO H
C H H
H HO D H HO
H OH HO OH
H OH OH H
 18 March, 2021 (Shift-II)

Deficiency of vitamin K causes :

A Cheilosis

# B Increase in blood clotting time.

C Decrease in blood clotting time.

D Increase in fragility of RBC’s.

 29 June, 2022 (Shift-I)

Sugar moiety in DNA and RNA molecules respectively are

A -D-2-deoxyribose, -D-deoxyribose

# B -D-2-deoxyribose, -D-ribose

C -D-ribose, -D-2-deoxyribose

D -D-deoxyribose, -D-2-deoxyribose
 27 Aug, 2021 (Shift-I)

Out of following isomeric forms of uracil, which one is present in RNA ?

OH O

N B HN
A
O N HO N
H

O
OH
# C HN
N
D
O N
H HO N
 27 July, 2021 (Shift-I)

O
H3C H
N
compound ‘A’
H N O
H
The compound ‘A’ is a complementary base of ___________ in DNA strands.

A Uracil

B Guanine

# C Adenine

D Cytosine
 12 April, 2019 (Shift-I)

Which of the following statements is not true about RNA ?

# A It has always double stranded -helix structure.

B It usually does not replicate.

C It is present in the nucleus of the cell.

D It controls the synthesis of protein.

25 July, 2021 (Shift-II)

Which one of the following is correct structure for cytosine?

H3N N
N
A B
N O N O
H3C
H H

O NH2
H3C
N H # D N
C
N O N O
H H
 You
THANK

ALL THE BEST BACCHON !