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 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions

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ORGANIC CHEMISTRY
AROMATIC COMPOUND
1. Consider the following reaction scheme and choose the correct option(s) for the major products Q, R and S.
[JEE(Advanced) 2023]
Styrene  → P  → Q P  → R  →S
(i) B2 H6 (i) CrO3 , H 2SO4 (i)SOCl2 conc.H 2SO4
(ii) NaOH, H O , H O
2 2 (ii) Cl , Re d Phosphorus
2 2 (ii) NaCN
(iii) H 2O (iii) H3O+ , ∆
O O
Cl COOH Cl COOH COOH
NH2 NH2

(A) (B)
O
SO3H
Q R S Q R S

O O
O O
Cl COOH Cl
NH2 NH2

(C) (D)
O
SO3H
Q R S Q R S

2. In the given reaction scheme, P is a phenyl alkyl ether, Q is an aromatic compound; R and S are the
major products. [JEE(Advanced) 2023]
(i) NaOH
(ii) CO2 (i) ( CH CO ) O
P → QHI
 →R 
3
+ →S
2
(iii) H3O+ (ii) H3O

The correct statement about S is

(A) It primarily inhibits noradrenaline degrading enzymes.
(B) It inhibits the synthesis of prostaglandin.
(C) It is a narcotic drug.
(D) It is ortho-acetylbenzoic acid.
3. The major products obtained from the reactions in List-II are the reactants for the named reactions
mentioned in List-I. Match List-I with List-II and choose the correct option. [JEE(Advanced) 2023]
List-I List-II
(P) Etard reaction (1) Zn −Hg, HCl
Acetophenone  →
(Q) Gattermann reaction (2) (i) KMnO ,KOH, ∆
Toluene 
4 →
(ii) SOCl2
(R) Gattermann-Koch reaction (3) CH Cl
Benzene 
3
→
anhyd. AlCl3
(S) Rosenmund reduction (4) NaNO /HCl
Aniline 
2 →
273−278 K
(5) Zn, ∆ →
Phenol 
(A) P → 2; Q → 4; R → 1; S → 3 (B) P → 1; Q → 3; R → 5; S → 2
(C) P → 3; Q → 2; R → 1; S → 4 (D) P → 3; Q → 4; R → 5; S → 2
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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
"Paragraph II" for Question No. 4
A trinitro compound, 1, 3,5 tris-(4-nitrophenyl) benzene, on complete reaction with an excess of Sn/HCl
gives major product, which on treatment with an excess of NaNO2/HCl at 0°C provides P as the product.
P, upon treatment with excess of H2O at room temperature, gives the product Q. Bromination of Q in
aqueous medium furnishes the product R. The compound P upon treatment with an excess of phenol
under basic conditions gives the product S.
–1
The molar mass difference between compounds Q and R is 474 mol and between compounds P and S is
172.5 g mol–1. [JEE(Advanced) 2023]
4. The number of heteroatoms present in one molecule of R is _____.
–1
[Use: Molar mass (in g mol ): H = 1, C = 12, N = 14, O = 16, Br = 80, Cl = 35.5
Atoms other than C and H are considered as heteroatoms]
"Paragraph II" for Question No. 5
A trinitro compound 1, 3, 5 tris-(4-nitrophenyl) benzene, on complete reaction with an excess of Sn/HCl
gives major product, which on treatment with an excess of NaNO2/HCl at 0°C provides P as the product.
P, upon treatment with excess of H2O at room temperature, gives the product Q. Bromination of Q in
aqueous medium furnishes the product R. The compound P upon treatment with an excess of phenol
under basic conditions gives the product S.
–1
The molar mass difference between compounds Q and R is 474 mol and between compounds P and S is
172.5 g mol–1. [JEE(Advanced) 2023]
5. The total number of carbon atoms and heteroatoms present in one molecule of S is _____.
–1
[Use: Molar mass in g mol ]: H = 1, C = 12, N = 14, O = 16, Br = 80, Cl = 35.5
Atoms other than C and H are considered as heteroatoms
6. If the reaction sequence given below is carried out with 15 moles of acetylene, the amount of the product
D formed (in g) is ______.
iron tube Cl 1. O2
(red hot) 2. H3O+
HC≡CH A H3C B C CH3COCl
D
AlCl3 pyridine
(80 %) (50 %) –CH3COCH3 (50 %) (100 %)

The yields of A, B, C and D are given in parentheses.

[Given : Atomic mass of H = 1, C = 12, O = 16, Cl = 35] [JEE(Advanced) 2022]
7. Considering the following reaction sequence, the correct statement(s) is(are) [JEE(Advanced) 2022]

O O O

Zn/Hg, HCl SOCl

P Q R
AlCl3
AlCl3

Zn/Hg, HCl
a hydrocarbon S
(A) Compounds P and Q are carboxylic acids.
(B) Compound S decolorizes bromine water.
(C) Compounds P and S react with hydroxylamine to give the corresponding oximes.
(D) Compound R reacts with dialkylcadmium to give the corresponding tertiary alcohol.

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
 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
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8. Consider the following transformations of a compound P.

R (i) NaNH2 P (i) X(reagent) Q

(Optically active) (C9H12) (C8H12O6)
(ii) C6H5COCH3 (ii) KMnO4/H2SO4/∆
(Optically active acid)
(iii) H3O+/∆ Pt/H2

CH3

Choose the correct option(s). [JEE(Advanced) 2020]

(A) P is

(B) X is Pd-C/quinoline/H2

(C) P is

(D) R is

9. Consider the reaction sequence from P to Q shown below. The overall yield of the major product Q from

P is 75%. What is the amount in grams of Q obtained from 9.3 mL of P ?

(Use density of P = 1.00 g mL–1, Molar mass of C = 12.0, H = 1.0, O = 16.0 and N = 14.0 g mol–1)

[JEE(Advanced) 2020]

(i) NaNO2 + HCl/0–5ºC

NH2 Q
OH
(ii) + NaOH
P
(iii) CH3CO2H/H2O

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
10. Choose the correct option(s) for the following reaction sequence

CHO
i)Hg2 + , dil.H 2 SO 4 Zn − Hg

→ Q 
→ R 
ii)AgNO3 , NH 4 OH
→S
iii) Zn − Hg, conc. HCl
i)SOCl 2 pyridine
ii) AlCl3
conc. HCl

MeO

Consider Q, R and S as major products [JEE(Advanced) 2019]

OH

CO2H
(A)
MeO MeO
Q S

CO2H
(B)
MeO MeO
O
Q R

(C)
MeO MeO
O
R S

(D)
MeO MeO
O
R S

Paragraph for Question No. 11 & 12

The reaction of compound P with CH3MgBr (excess) in (C2H5)2O followed by addition of H2O gives
Q, The compound Q on treatment with H2SO4 at 0ºC gives R. The reaction of R with CH3COCl in the
presence of anhydrous AlCl3 in CH2Cl2 followed by treatment with H2O produces compounds S.
[Et it compounds P is ethyl group]
(H3C)3C
CO2Et

11. The reactions, Q to R and S to S, are -

(A) Dehydration and Friedel-Crafts acylation
(B) Friedel-Crafts alkylation, dehydration and Friedel-Crafts acylation
(C) Aromatic sulfonation and Friedel-Crafts acylation
(D) Friedel-Crafts alkylation and Fridel-Crafts acylation

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
 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
®
12. The product S is - [JEE(Advanced) 2017]
HO3S
(H3C)3C O CH3 H3COC
(H3C)3C H3C CH3
(A) (B)
COCH3

H3C CH3
COCH3 (H3C)3C
(H3C)3C CH3
(C) (D)
COCH3

13. Among the following reaction(s) which gives (give) tert-butyl benzene as the major product is(are)
[JEE(Advanced) 2016]
Br
Cl
(A) (B)
NaOC22H
NaOC H55 AlCl33
AlCl

OH
(C) (D)
H2SO
H SO4
2 4
BF33..OEt
BF OEt22

Paragraph For Q.14 & Q.15

+
Treatment of compound O with KMnO4 / H gave P, which on heating with ammonia gave Q. The
compound Q on treatment with Br2 / NaOH produced R. On strong heating, Q gave S, which on further
treatmenet with ethyl 2-bromopropanoate in the presence of KOH following by acidification, gave a
compound T. [JEE(Advanced) 2016]

(O)
14. The compound R is :
O
NH2
Br
(A) (B)
Br
NH2
O
O O
NHBr
(C) (D) NBr
NHBr
O O
15. The compound T is :
(A) Glycine (B) Alanine (C) Valine (D) Serine

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
16. In the following reactions, the product S is - [JEE(Advanced) 2015]
H3C
I. O3 NH3
R S
II. Zn,H2O

H3C H3C N
(A) N (B)

N
N
(C) (D)
H3C H3C

17. For the identification of β-naphthol using dye test, it is necessary to use [JEE(Advanced) 2014]
(A) dichloromethane solution of β-naphthol (B) acidic solution of β-naphthol
(C) neutral solution of β-naphthol (D) alkaline solution of β-naphthol

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
 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
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SOLUTIONS
1. Ans. (B)

Sol.
OH

CH = CH2 CH 2 – CH2

(1) B2 H6
(2) NaOH, H2 O2, H2O
(Styrene) (P)
CrO3 , H2 SO4
CH 2 – CH2 – Cl (O)

SOCl2
CH 2 – C – OH

O
NaCN

CH 2 – CH2 – CN (HVZ) Cl2 +

Red P

H3O /∆
CH – COOH

CH 2 – CH2 – C – OH Cl
(Q)
(R) O

Conc. H2 SO 4

O
(S)

2. Ans. (B)
Sol. P is phenyl alkyl ether
Q is aromatic compound
R and S are the major product
i.e.

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®

O–R O–H

H–I
+R–I

Phenyl alkyl ether (Q)

(1) NaOH

—
O Na + OH
COOH
(2) CO2
H2 O + (3) H3 O +

H3 O + (CH3 CO)2 O

O – C – CH3
COOH

(Aspirin)
Pain killer
Acetyl salicylic acid
(Non-narcotic analgesic)

Aspirin inhibits the synthesis of chemicals known as prostaglandin's.

3. Ans. (D)
Sol. P → 3, Q → 4, R → 5, S → 2
O
(i) Zn–Hg/HCl
Ph – C – CH3 Ph – CH2 – CH3
Acetophenone
O

CH 3 C – Cl CHO

(ii)
(i) KMnO4 , KOH / ∆ H2 Pd – BaSO4
(ii) SOCl2 Rosenmond reaction
Toluene Toluene (S)
CH 3 CHO
(iii)
CH 3 – Cl CrO2 Cl2
Etard reaction
Anhy. AlCl3 AcOAc / ∆
(P)

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 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
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N2⊕Cl

NH2 Cl

(iv) NaNO2 / HCl Cu / HCl

Gattermann reaction
273–278 K
(Q)
OH CHO
(v)
Zn / ∆ CO / HCl
Gattermann Koch reaction
AlCl3
(R)
4. Ans. (9.00)
5. Ans. (51.00)
Sol. Common solution for Q.No. 4 and 5

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
6. Ans. (135.80 - 136.20)
Sol.
O

OH O–C–CH3
Cl
Iron tube H3C 1. O2 CH3COCl
3HC ≡CH 2. H3O

Pyridine
red hot AlCl3
15 moles –CH3COCH3
4 mol 2 mol 1 mol 1 mol
80% yield 50% yield 100% yield
50% yield
C8H8O2
136 g

7. Ans. (A, B, C or A, C)
Sol.
O
O O
O C
O C OH C C
O O OH Cl

AlCl3 Zn/ Hg (R)

SOCl2
(P) HCl (Q)
Carboxylic Acid Carboxylic
Acid
AlCl3

Zn/ Hg
(S)
HCl
O

O O
C C
Cl R
(R) R2Cd

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 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
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8. Ans. (B, C)
Sol.

(P)
NaNH2 C9H12 Pd–C/quinoline CH=CH2
H2
(X)
PhCOMe KMnO4
Pt/H2 H⊕ /
H3O+/∆ ∆
CH2
||
C C–C–Ph *
COOH
COOH
COOH
(R)
optically active
C8H12O6
optically active acid
(Q)

9. Ans. (18.60)
Sol.
NH2 N2+
NaNO2+HCl
0–5ºC
OH
C6H5NH2
P + NaOH

N=N–Ph N=N–Ph
OH O–
CH3CO2H
H2O

Molecular weight of
aniline = M.wt. of C6NH7
= 72 + 7 + 14 = 93
–1
density of P = 1 gm ml
9.3 ml of P = 9.3 gm P
9.3
= = 0.1mole P
9.3

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
N=N–Ph
+
OH
The mole ratio PhNH2 : PhN2 :

=1:1:1
so the mole of Q formed will be 0.1 mole and extent of reaction is 100% but if it is 75% yield.
75
Then amount of Q = 0.1 × = 0.075 mol
100
The molecular formula of Q = C16H12ON2
so M.wt. of Q = 16 × 12 + 12 × 1 + 16 + 2 × 14
= 192 + 12 + 16 + 28
= 248 gm
so amount of Q = 248 × 0.075
= 18.6 gm
10. Ans. (B, D)
Sol.
C – CH 2 – CH 2 – CH = O
C ≡ C – CH2 – CH = O O
Hg2 +
MeO
 →
MeO H2SO4
AgNO3+ NH4 OH

C – CH 2CH 2 – CO2–
O
MeO
Zn(Hg) + conc. HCl

CH 2CH 2 CH2 – CO2H

MeO
SOCl2+ pyridine AlCl3

(R)
MeO
O

Zn(Hg) + conc. HCl

(S)
MeO

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
 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
®
11. Ans.(B)
Sol.
OH
COOEt (1) excess H2SO4/0°C
of MeMgCl
(2) H2O Friedal Craft
Alkylation + Dehydration
O
(1) Me–C–Cl/AlCl
Me–C–Cl / AlCl33ininCH
CH2Cl
2Cl2 2

(2) H
H22OO
Friedal Craft
Acylation

C–Me
O
12. Ans. (D)
Sol. OH
COOEt (1) excess H2SO4/0°C
of MeMgCl
(2) H2O Friedal Craft's
Alkylation + Dehydration
O
Me–C–Cl
(1) Me–C–Cl / AlCl
/ AlCl 3 in2Cl
3 in CH CH2 2 Cl2

H22OO Friendal
(2) H Craft's
Friedal Craft's Acylation
Acylation

C–Me
O
(S)
13. Ans. (B, C, D)
2 E
Sol. + NaOC2H5 mechanism
Br
3º alkyl bromide

+ No reaction

1,2 shift
–
+ of H +
+ AlCl3
Cl + –
AlCl4 tert-butyl benzene

+
H +
(H2SO4)

tert-butyl
benzene

– + 1,2 shift
: :

OH + F33B—OEt22 ⊕  +
—
+ of H
(D) O — BF33
+–
H HO–BF3 tert-butyl
benzene

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JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
14. Ans. (A)
15. Ans. (B)
Solution for Q.14 & 15

HOOC COOH H2NOC

+ NH2
H KMnO4 NH3 Br2
∆ NaOH NH2
(O) (P) (Q) (R)

O CH3 O
(i) KOH
N – CH – C – OEt N–H
(ii) CH3CH–C–OEt
O O O
Br O
(S)
+
H3O
CH3
COOH
+ H2N – CH – COOH
COOH (T)
Phthalic acid Alanine

Q to R is Hoffmann's bromamide degradation reaction

S to T is Gabriel's phthalimide sysnthesis
16. Ans. (A)
H
H H
C=O
C=O C=O Tautomerisation

:
O33
(1) O NH
NH33 C–NH2
Sol. (2) Zn/H
Zn/H2O C=O Paul knor C=NH
2O
reaction H
H H
–H
–H22O
O

H3C
N

17. Ans. (D)

Sol. In alkaline medium the activating nature of –OH group increases and the rate of electrophilic substitution
(Coupling Reaction) increases on aromatic ring.
—
OH —
O
OH
+ H2O

 O

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
 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
®

–OH group converts to –O
 
Electron releasing nature of –O is more than –OH
Nucleophilicity of β-napthol increases in basic medium
N–Ph
N
OH ⊕  OH
Ph–N2Cl

(Coloured dye)

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