NOMENCLATURE_merged_removed

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 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions

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NOMENCLATURE
1. Which one of the following structures has the IUPAC name
3-ethynyl-2-hydroxy-4-methylhex-3-en-5-ynoic acid ? [JEE(Advanced) 2020]
OH
(A) CO2H
(B) HO2C
OH
OH
(C) CO2H
OH
(D) CO2H
2. The IUPAC name(s) of the following compound is(are) [JEE(Advanced) 2017]
H3C Cl
(A) 4-methylchlorobenzene
(B) 4-chlorotoluene
(C) 1-chloro-4-methylbenzene
(D) 1-methyl-4-chlorobenzene
1
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ORGANIC CHEMISTRY
GENERAL ORGANIC CHEMISTRY
Paragraph for Q.1 and Q.2
The amount of energy required to break a bond is same as the amount of energy released when the same
bond is formed. In gaseous state, the energy required for homolytic cleavage of a bond is called Bond
Dissociation Energy (BDE) or Bond Strength. BDE is affected by s-character of the bond and the stability
of the radicals formed. Shorter bonds are typically stronger bonds. BDEs for some bonds are given below:
[JEE(Advanced) 2021]
1. Correct match of the C–H bonds (shown in bold) in Column J with their BDE in Column K is
Column-J Column-K
–1
Molecule BDE (kcal mol )
(P) H–CH(CH3)2 (i) 132
(Q) H–CH2Ph (ii) 110
(R) H–CH=CH2 (iii) 95
(S) H–C ≡ CH (iv) 88
(A) P – iii, Q – iv, R – ii, S – i (B) P – i, Q – ii, R – iii, S – iv

(C) P – iii, Q – ii, R –i, S – iv (D) P – ii, Q – i, R – iv, S – iii
2. For the following reaction
CH4(g) + Cl2(g) 
→ CH3Cl(g) + HCl (g)
light
the correct statement is

(A) Initiation step is exothermic with ∆H° = – 58 kcal mol–1.
(B) Propagation step involving CH3 formation is exothermic with ∆H° = – 2 kcal mol .
• –1
(C) Propagation step involving CH3Cl formation is endothermic with ∆H° = + 27 kcal mol .
–1
(D) The reaction is exothermic with ∆H° = – 25 kcal mol .

–1
3. With respect to the compounds I-V, choose the correct statement(s). [JEE(Advanced) 2020]
H
H
H
H–CH3 H H
I II III IV V
(A) The acidity of compound I is due to delocalization in the conjugate base.
(B) The conjugate base of compound IV is aromatic.
(C) Compound II becomes more acidic, when it has a -NO2 substituent.
(D) The acidity of compounds follows the order I > IV > V > II > III.
1
JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ®
4. Consider the following four compounds I, II, III, and IV. [JEE(Advanced) 2020]
NH2 H3C N CH3
NH2 H3C N CH3 O2N NO2 O2N NO2
NO2 NO2
I II III IV
Choose the correct statement(s).

(A) The order of basicity is II > I > III > IV.
(B) The magnitude of pKb difference between I and II is more than that between III and IV.
(C) Resonance effect is more in III than in IV.
(D) Steric effect makes compound IV more basic than III.
5. The correct order of acid strength of the following carboxylic acids is - [JEE(Advanced) 2019]
O O O OH
H H OH MeO H3C
OH OH O
H
I II III IV
(A) I > III > II > IV (B) III > II > I > IV
(C) II > I > IV > III (D) I > II > III > IV
6. Choose the correct option(s) that give(s) an aromatic compound as the major product.
i) alc.KOH
H3C
Br →
ii) NaNH 2
(1) + Cl (excess) 
UV, 500K
→ (2)
2 iii) red hot iron tube,873 K
Br
Br
NaOEt NaOMe
(3)  → (4)  →
7. Among the following, the number of aromatic compound (s) is- [JEE(Advanced) 2017]
 ⊕ ⊕
⊕ 
2
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8. The order of basicity among the following compounds is [JEE(Advanced) 2017]
NH
NH NH2 2
NH
NN NH
NH HN
HN N
N
HH3CC
3
NH2 2
NH HH2NN
2 NH
NH
II II
II III
III IV
IV
(A) II > I > IV > III (B) IV > II > III > I (C) I > IV > III > II (D) IV > I > II > III
9. The correct order of acidity for the following compounds is: [JEE(Advanced) 2016]
CO2H CO2H CO2H CO2H
HO OH OH
OH
OH
I II III IV
(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > IV > II
10. The number of resonance structures for N is : [JEE(Advanced) 2015]
OH
NaOH
N
3
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ORGANIC CHEMISTRY
ISOMERISM
1. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the
molecular formula C4H8O is ______. [JEE(Advanced) 2019]
SOLUTIONS
1. Ans. (10.00)
O * O O O
* * *
O O
(1) , (2) (1) , (2) (3) (1)
Sol. , , R,R ,
(R + S)
(R + S) R,S
S,S
1
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ORGANIC CHEMISTRY
STRUCTURAL ISOMERISM
1. The correct combination of names for isomeric alcohols with molecular formula C4H10O is/are-
(A) tert-butanol and 2-methylpropan-2-ol
(B) tert-butanol and 1, 1-dimethylethan-1-ol
(C) n-butanol and butan-1-ol
(D) isobutyl alcohol and 2-methylpropan-1-ol
2. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown in the figure.
I and II and III
The correct order of their boiling point is [JEE(Advanced) 2014]

(A) I > II > III
(B) III > II > I
(C) II > III > I
(D) III > I > II
1
JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
ALLEN®
ORGANIC CHEMISTRY
STEREOISOMERISM
1. The total number of chiral molecules formed from one molecule of P on complete ozonolysis (O3, Zn/H2O) is
________. [JEE(Advanced) 2022]
OH OH
HO HO OH
P
2. Among the following, the conformation that corresponds to the most stable conformation of
meso–butane–2,3–diol is – [JEE(Advanced) 2021]
OH OH
OH OH Me OH H OH
H H OH
Me
(A) (B) (C) (D)
H Me Me H
Me H H Me H Me
OH Me
3. Given
CHO
H OH
HO H HNO3 P
H OH
H OH [a]D = +52.7°
CH2OH
D-Glucose
The compound(s), which on reaction with HNO3 will give the product having degree of rotation, [a]D = –52.7º
is (are) [JEE(Advanced) 2021]
CHO CHO CHO CHO
HO H HO H HO H H OH
(A) HO H (B) HO H (C) H OH (D) H OH
H OH H OH HO H HO H
H OH HO H HO H H OH
CH2OH CH2OH CH2OH CH2OH
4. Newman projections P, Q, R and S are shown below :
OH
CH3 H3C CH3 CH3
CH3
HO CH3 H H C2H5 CH(CH3)2
C2H5 H
H3C C2H5 H C2H5 H H
HO CH3
CH3 CH3 C2H5 OH
P Q R S
Which one of the following options represents identical molecules ? [JEE(Advanced) 2020]
(A) P and Q (B) Q and S (C) Q and R (D) R and S
1
JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions ALLEN®
5. The Fischer projection of D-erythrose is shown below. [JEE(Advanced) 2020]
CHO
H OH
H OH
CH2OH
D-Erythrose
D-Erythrose and its isomers are listed as P, Q, R, and S in Column-I. Choose the correct relationship of
P, Q, R, and S with D-erythrose from Column II.
Column-I Column-II
HO H
OHC
P. 1. Diastereomer
H OH
OH
OHC OH
Q. HO H 2. Identical
H OH
H OH
OHC
R. 3. Enantiomer
H OH
OH
OHC OH
S. HO OH
H H
(A) P ® 2, Q ® 3, R ® 2, S ® 2 (B) P ® 3, Q ® 1, R ® 1, S ® 2
(C) P ® 2, Q ® 1, R ® 1, S ® 3 (D) P ® 2, Q ® 3, R ® 3, S ® 1
6. An organic compound (C8H10O2) rotates plane-polarized light. It produces pink color with neutral FeCl3
solution. What is the total number of all the possible isomers for this compound?
7. For the given compound X, the total number of optically active stereoisomers is______.
8. In the following monobromination reaction, the number of possible chiral products is

CH2CH2CH3
Br2(1.0 mole)
H Br
300°C
CH3
(1.0 mole)
(enantiomerically pure)
2
JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions
ALLEN®
9. For 'invert sugar', the correct statement(s) is (are)

(Given : specific rotations of (+)-sucrose, (+)-maltose, L-(–)-glucose and L-(+)-fructose in aqueous
solution are + 66°, +140°, –52° and + 92°, respectively) [JEE(Advanced) 2016]
(A) 'invert sugar' is prepared by acid catalyzed hydrolysis of maltose
(B) 'invert sugar' is an equimolar mixture of D-(+) glucose and D-(–)-fructose
(C) specific rotation of 'invert surgar' is –20°
(D) on reaction with Br2 water, 'invert sugar' forms saccharic acid as one of the products
10. The total number of stereoisomers that can exist for M is : [JEE(Advanced) 2015]
H 3C CH3
H3 C
M O
11. The total number(s) of stable conformers with non-zero dipole moment for the following compound is
(are) [JEE(Advanced) 2014]
Cl
Br CH3
Br Cl
CH3
12. Consider all possible isomeric ketones including stereoisomers of MW = 100, All these isomers are
independently reacted with NaBH4 (NOTE : stereoisomers are also reacted separately). The total number
of ketones that give a racemic product(s) is/are [JEE(Advanced) 2014]
3
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ORGANIC CHEMISTRY
HYDROCARBON
1. The reaction of 4-methyloct-ene (P, 2.52 g) with HBr in the presence of (C6H5CO)2O2 gives two isomeric
bromides in a 9 : 1 ratio, with combined yield of 50%. Of these, the entire amount of the primary alkyl
bromide was reacted with an appropriate amount of diethylamine followed by treatment with eq. K2CO3
to given a non-ionic product S in 100% yield. The mass (in mg) of S obtained is _____.
–1
[Use molar mass (in g mol ) : H = 1, C = 12, N = 14, Br = 80] [JEE(Advanced) 2023]
2. The number of isomeric tetraenes (NOT containing sp-hybridized carbon atoms) that can be formed from
the following reaction sequence is ________. [JEE(Advanced) 2022]
1. Na, liquid NH3

2. Br2 (excess)
3. alc. KOH
3. The number of -CH2- (methylene) groups in the product formed from the following reaction sequence is
________. [JEE(Advanced) 2022]
1. O3, Zn/H2O
2. KMnO4
3. NaOH, electolysis
4. Cr2O3, 770 K, 20 atm
4. The major product formed in the following reaction is [JEE(Advanced) 2021]

NaNH
→ 2
Na liq.NH 3
(A) (B)
(C) (D)
Question Stem for Q.5 and Q.6

For the following reaction scheme, percentage yields are given along the arrow :
NaNH2 red hot iron

H2O MeI tube 873 K
Mg2C3 P Q R
75% 40%
(4.0 g) (x g)
Hg2+ / H+ 100%
333 K
Ba(OH)2 NaOCl
S T U (decolourises
heat 80% 80%
(y g) Baeyer's reagent)
x g and y g are mass of R and U, respectively.

–1
(Use : Molar mass (in g mol ) of H, C and O as 1, 12 and 16, respectively)
1
5. The value of x is______. [JEE(Advanced) 2021]
6. The value of y is______. [JEE(Advanced) 2021]
7. In the reaction given below, the total number of atoms having sp2 hybridization in the major product P is
______. [JEE(Advanced) 2021]
1. O3 (excess)
then Zn/H2O
P
2. NH2OH (excess)
8. Which of the following reactions produce(s) propane as a major product? [JEE(Advanced) 2019]
H 3C electrolysis
(A) COONa + H 2O
(B) H 3C NaOH, CaO, ∆

COONa
Cl Zn, dil. HCl

(C) H3C
Br
(D) H C Br Zn
3
9. Total number of hydroxyl groups present in a molecule of the major product P is ______.
i) H , Pd − BaSO , quinoline

2 4
ii) dil. KMnO (excess), 273 K
→P
4
10. The major product U in the following reactions is : [JEE(Advanced) 2015]

+
CH2=CH–CH 3,H radical initiator, O2
high pressure, heat T U
H
O
O H3C CH3
CH3 O
(A) (B) O H
H
O
O
CH2 CH2
O H
(C) O
(D)
2
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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.
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
1
"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.
2
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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)
(i) NaNO2 + HCl/0–5ºC

NH2 Q
OH
(ii) + NaOH
P
(iii) CH3CO2H/H2O
3
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
4
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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)
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
5
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
6
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ORGANIC CHEMISTRY
HALOGEN DERIVATIVE
1. Match the reactions in List-I with the features of their products in List-II and choose the correct option.
List-I List-II
(P) (-)-1-Bromo-2-ethylpentane aq. NaOH (1) Inversion of configuration

(single enantiomer) SN2 reaction
(Q) (-)-2-Bromopentane aq. NaOH (2) Retention of configuration

(R) (-)-3-Bromo-3-methylhexane aq. NaOH (3) Mixture of enantiomers

(S) (4) Mixture of structural isomers

aq. NaOH
Me H Me Br
SN1 reaction
(Single enantiomer)
(5) Mixture of diastereomers
(A) P → 1; Q → 2; R → 5; S → 3 (B) P → 2; Q → 1; R → 3; S → 5
(C) P → 1; Q → 2; R → 5; S → 4 (D) P → 2; Q → 4; R → 3; S → 5
2. Consider the following reaction. [JEE(Advanced) 2022]
OH
red phosphorous
Br2
R (major product)
Br
On estimation of bromine in 1.00 g of R using Carius method, the amount of AgBr formed (in g) is ______.
[Given : Atomic mass of H = 1, C = 12, O = 16, P = 31, Br = 80, Ag = 108]
3. The weight percentage of hydrogen in Q, formed in the following reaction sequence, is ______.
Cl
1. NaOH, 623 K, 300 atm
Q (major product)
2. conc. H2SO4 and then
conc. HNO3
[Given : Atomic mass of H = 1, C = 12, N = 14, O = 16, S = 32, Cl = 35]
1
4. The correct statement(s) for the following addition reactions is(are) [JEE(Advanced) 2017]
H
(i) H3C Br2 /CHCl3
M and N
H CH3
H 3C C H3 Br2 / CHCl3
(ii) O and P
H H
(A) (M and O) and (N and P) are two pairs of diastereomers
(B) Bromination proceeds through trans-addition in both the reactions
(C) O and P are identical molecules
(D) (M and O) and (N and P) are two pairs of enantiomers
5. For the following compounds, the correct statement(s) with respect of nucleophilic substitution reactions
is(are): [JEE(Advanced) 2017]
(I) Br (II) (III) (IV)
(A) I and II follow SN2 mechanism

(B) The order of reactivity for I, III and IV is : IV > I > III
(C) I and III follow SN1 mechanism
(D) Compound IV undergoes inversion of configuration
6. Which of the following combination will produce H2 gas? [JEE(Advanced) 2017]
(A) Zn metal and NaOH(aq)
(B) Au metal and NaCN(aq) in the presence of air
(C) Cu metal and conc. HNO3
(D) Fe metal and conc. HNO3
7. In the following reaction, the major product is - [JEE(Advanced) 2015]
CH3
1 equivalent HBr
CH2
H2C
CH3 CH3
CH3 CH2
(A) CH2 (B) H3C
Br Br
CH3 CH3
(C) (D)
H2C Br H3C Br
2
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®
8. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is (are) –
H Br
H Br
(A) (B) H2C CH3
H3C CH3
H Br
H2C Br H
(C) CH3 (D) CH3
H2C
CH3
9. The reactivity of compound Z with different halogens under appropriate conditions is given below-
OH Mono halo substituted derivative when X2=l2
X2
di halo substituted derivative when X2=Br2
C(CH3)3
tri halo substituted derivative when X2=Cl2
The observed pattern of electrophilic substitution can be explained by - [JEE(Advanced) 2014]
(A) The steric effect of the halogen
(B) The steric effect of the tert-butyl group
(C) The elctronic effect of the phenolic group
(D) The electronic effect of the turt-butyl group
3

®
ORGANIC CHEMISTRY
ALCOHOL, PHENOL & ETHER
1. In the following reaction sequence, the correct structure(s) of X is (are) [JEE(Advanced) 2018]
X  →
3 21) PBr , Et O
2) Nal, Me2 CO
3) NaN3 ,HCONMe2
Me OH
(A) (B)
(C) (D)
Me OH
2. The correct statements(s) about of the following reaction sequence is(are) [JEE(Advanced) 2016]
(i) O22 CHCl
CHCl33/NaOH
/NaOH
Cumene(C99H
H1212)) ++ P Q (major) + R (minor)
(ii) H
H33O
NaOH
Q S
PhCH22Br
PhCH Br
(A) R is steam volatile
(B) Q gives dark violet coloration with 1% aqueous FeCl3 solution
(C) S gives yellow precipitate with 2, 4,-dinitrophenylhydrazine
(D) S gives dark violet coloration with 1% aqueous FeCl3 solution
3. The number of hydroxyl group(s) in Q is [JEE(Advanced) 2015]
+ aqueous dilute KMnO
KMNO44 (excess)
H H+
H
P Q
heat 0°C
HO
H
H33C
C CH
CH33
4. The acidic hydrolysis of ether (X) shown below is fastest when [JEE(Advanced) 2014]
acid
OR OH + ROH
[X]
(A) one phenyl group is replaced by a methyl group
(B) one phenyl group is replaced by a para-methoxyphenyl group
(C) two phenyl groups are replaced by two para-methoxyphenyl group
(D) no structural change is made to X
1

®
ORGANIC CHEMISTRY
ORGANOMETALLIC COMPOUNDS
1. The major product in the following reaction is [JEE(Advanced) 2014]
O
Cl 1. CH3MgBr, dry ether, 0ºC
CH3 2. aq. acid
OH
(A) O (B)
H3C H2C CH
CH3 CH3 3
(C) (D)
CH3
O CH2 O CH3
1

®
ORGANIC CHEMISTRY
CARBONYL COMPOUND
1. In the following reactions, P, Q, R, and S are the major products. [JEE(Advanced) 2023]
(i) PhMgBr, then H O⊕
CH3CH 2 CH(CH3 )CH 2 CN  3
(ii) PhMgBr, then H O
→P
2
O
|| (i) anhyd. AlCl3
Ph – H + CH3CCl Q
(ii) PhMgBr, then H2O
O
|| 1
(i) (PhCH ) Cd
2 22
CH3CH2CCl R
(ii) PhMgBr, then H O
2
( i ) PhMgBr, then H 2O
PhCH 2 CHO 

(ii) CrO3 , dil.H 2SO 4
(iii) HCN
→S
(iv) H 2SO4 , ∆
The correct statement(s) about P, Q, R, and S is(are)

(A) Both P and Q have asymmetric carbon(s).
(B) Both Q and R have asymmetric carbon(s).
(C) Both P and R have asymmetric carbon(s).
(D) P has asymmetric carbon(s), S does not have any asymmetric carbon.
2. In the reaction scheme shown below Q, R and S are the major products. [JEE(Advanced) 2020]
O
CH3
H3C H3C CH3 O
H3C (i) CH3MgBr
O (i) Zn-Hg/HCl (ii) H3O+
Q R S
AlCl3 (ii) H3PO4 (iii) H2SO4/∆
P
The correct structure of
CH3 CH3
H3C H3C
H3C CH3 H3C CH3
H3C H3C
(A) S is (B) Q is
CH3 HO2C O
CH3 CH3
H3C H3C
H3C CH3 H3C CH3
H3C H3C
(C) R is (D) S is H3C
1
3. Choose the correct option(s) for the following set of reactions [JEE(Advanced) 2019]
C6H10 O  →
i) MeMgBr
Q  →
Conc. HCl
S
ii) H2O
(major)
20% H3PO 4, 360 K
i) H , Ni
T ← 2
 R 
ii) Br2, h ν ∆ → U
HBr, benzoyl peroxide
(major) (major) (major)
H3C Br CH3 CH 3
H3C Cl
Cl Br
(A) (B)
U S S U
CH3 H3C Br CH3 H3C Br

Cl Br
(C) (D)
S T U T
4. The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is (are) [JEE(Advanced) 2018]

O
Conc. H2SO4 heated iron tube
(A) (B) Me H
∆ 873 K
O
1) Br2 , NaOH CHO
2) H3O+
(C) (D) Zn/Hg, HCl
3) sodalime, ∆
OHC CHO
O O
5. In the following reaction sequence, the amount of D (in g) formed from 10 moles of acetophenone
is_______.
–1
(Atomic weight in g mol : H = 1, C = 12, N = 14, O = 16, Br = 80. The yield (%) corresponding to the
product in each step is given in the parenthesis) [JEE(Advanced) 2018]
O
NaOBr NH3 , ∆ Br 2 /KOH Br 2 (3 equiv)

A B C D
+
H3O (60%) (50%) (50%) AcOH (100%)
6. Positive Tollen's test is observed for [JEE(Advanced) 2016]

H O OH
CHO Ph O
(A) H (B) (C) Ph (D)
H O Ph Ph
H
2
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®
7. The major product of the following reaction sequence is : [JEE(Advanced) 2016]
O
(i) HCHO (excess) / NaOH, heat

+
(ii) HCHO / H (catalytic amount)
O OH
O O O O OH O O
HO
(A) (B) (C) (D)
OH
8. Reagent(s) which can be used to bring about the following transformation is(are)
O O O O
C O C
H OH
COOH O COOH O
(A) LiAlH4 in (C2H5)2O (B) BH3 in THF
(C) NaBH4 in C2H5OH (D) Raney Ni / H2 in THF
9. The major product of the following reaction is - [JEE(Advanced) 2015]
O
I. KOH, H2O
CH3
II. H+, Heat
O
CH3 CH3
O
O O O
CH3 CH3
(A) (B) (C) (D)
10. Among the following the number of reaction(s) that produce(s) benzaldehyde is –
CO,
CO, HCl
HCl
I.
Anhydrous AlCl33/CuCl
Anhydrous AlCl /CuCl
CHCl
CHCl22
II. H
H22O
100°C
COCl
COCl
III. H22
Pd-BaSO
Pd-BaSO44
CO
CO2Me
Me
DIBAL-H
DIBAL-H
IV.
Toluene,–78ºC
Toluene, –78°C
H22O
H O
3
Paragraph For Questions No. 11 and 12
In the following reaction [JEE(Advanced) 2015]
Pd-BaSO4 (i) B2H6
C8H6 C8H8 X
H2 (ii) H2O2, NaOH, H2O
H2O
HgSO4, H2SO4
(i) EtMgBr, H2O

C8H8O + Y
(ii) H , heat
11. Compound X is :
O OH
OH
CH33 CH3
(A) (B)
OH
OH CHO
CHO
(C) (D)
12. The major compound Y is :
CH33 CH33
(A) (B)
CH
CH33
CH
CH22
CH33 CH
CH33
(C) (D)
4
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®
ORGANIC CHEMISTRY
CARBOXYLIC ACID & THEIR DERIVATIVE
1. The total number of sp2 hybridised carbon atoms in the major product P (a non-heterocyclic compound)
of the following reaction is _______. [JEE(Advanced) 2023]
NC CN (i) LiAlH4 (excess), then H2O
P
NC CN (ii) Acetophenone (excess)
2. In the following reaction, compound Q is obtained from compound P via an ionic intermediate
CO2CH3
C6H5 C6H5
Conc. H2SO4
Q (A colored compound)
C6H5
P
What is the degree of unsaturation of Q ? [JEE(Advanced) 2020]
3. Answer the following by appropriately matching the lists based on the information given in the
paragraph.
List-I includess starting materials and reagents of selected chemical reactions. List-II gives structures of
compounds that may be formed as intermediate products and/or final products from the reactions of List-I.
List-I List-II
i) DlBAL-H
CN
ii) dil, HCl
CHO
(I) O (P)
iii) NaBH 4
O iv) conc. H2SO4
CO2H
i) O3
OH
(II) ii) Zn, H2O (Q) OH
CO2H iii) NaBH4
iv) conc. H2SO4
Cl i) KCN
ii) H3O, ∆
+
(III) (R)
CO2CH3 iii) LiAlH4
O
iv) conc. H2SO4
CO2Me OH
(IV) i) LiAlH4 (S)
CO2Me
ii) conc. H2SO4 CO2H
CO2H
(T)
CO2H
(U) O
O
1
Which of the following options has correct combination considering List-I and List-II?
(A) (III), (S), (R)
(B) (IV), (Q), (R)
(C) (III), (T), (U)
(D) (IV), (Q), (U)
4. Answer the following by appropriately matching the lists based on the information given in the
paragraph
List-I includess starting materials and reagents of selected chemical reactions. List-II gives structures of
compounds that may be formed as intermediate products and/or final products from the reactions of List-I.
List-I List-II
i) DlBAL-H
CN CHO
(I) O ii) dil, HCl (P)
iii) NaBH 4
O iv) conc. H2SO4 CO2H
i) O3 OH
(II) ii) Zn, H2O (Q)
CO2H
OH
iii) NaBH4
iv) conc. H2SO4
Cl i) KCN
ii) H3O, ∆
+
(III) (R)
CO2CH3 iii) LiAlH4 O
iv) conc. H2SO4
CO2Me OH
(IV) i) LiAlH4 (S)
CO2Me
ii) conc. H2SO4 CO2H
CO2H
(T)
CO2H
(U) O
Which of the following options has correct combination considering List-I and List-II?
(A) (I), (Q), (T), (U) (B) (II), (P), (S), (U)
(C) (II), (P), (S), (T) D) (I), (S), (Q), (R)
2

®
5. Different possible thermal decomposition pathways for peroxyesters are shown below. Match each
pathway from List-I with an appropriate structure from List-II and select the correct answer using the code
given below the lists. [JEE(Advanced) 2014]
P R + R'O
–CO2↑
Q
R + R'O → R + X + carbonyl compound ↑
O –CO2↑
O
R O R'
(Peroxyester) R
RCO2 + R'O →
–CO
R + X + carbonyl compound ↑
2
S RCO2 + R'O → R + R'O

–CO2↑
List-I List-II
O
(P) Pathway P (1) C6H5CH2 O O CH3
O
(Q) Pathway Q (2) C6H5 O O CH3
O CH3
(R) Pathway R (3) C6H5CH2 O O CH3
CH2C6H5
O CH3
(S) Pathway S (4) C6H5 O O CH3
C6H5
Code :
P Q R S
(A) 1 3 4 2
(B) 2 4 3 1
(C) 4 1 2 3
(D) 3 2 1 4
3
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®
ORGANIC CHEMISTRY
ACID DERIVATIVE
1. Considering the reaction sequence given below, the correct statement(s) is(are) [JEE(Advanced) 2022]
O
 ⊕
1. N K
1. Br2, red phosphorous O

COOH
H3C COOH P 2. NaOH Q +
2. H2O
3. H3O + COOH
(A) P can be reduced to a primary alcohol using NaBH4.

(B) Treating P with conc. NH4OH solution followed by acidification gives Q.
(C) Treating Q with a solution of NaNO2 in aq. HCl liberates N2.
(D) P is more acidic than CH3CH2COOH.
1

®
ORGANIC CHEMISTRY
AMINE DERIVATIVE
1. In the following reactions, P, Q, R, and S are the major products. [JEE(Advanced) 2023]
(i) Mg, dry ether
P
(ii) H2O
Cl
(i) Mg, dry ether
(ii) CO2, dry ether
+ Q
(iii) H3O
Cl (iv) NaOH
(i) Mg, dry ether
(ii) CH3CHO, then H2O
R
(iii) CrO3
Cl
(i) ethanolic NaCN
(ii) H2/Ni
S
(iii) CHCl3/KOH, ∆
Cl (iv) LiAlH4, then H2O
The correct statement about P, Q, R, and S is
(A) P is a primary alcohol with four carbons.
(B) Q undergoes Kolbe’s electrolysis to give an eight-carbon product.
(C) R has six carbons and it undergoes Cannizzaro reaction.
(D) S is a primary amine with six carbons.
2. Consider the following reaction sequence,
NO2
P R HO
Q S 2 T
H3C
U
COOH
the correct option(s) is(are) [JEE(Advanced) 2022]

(A) P = H2/Pd, ethanol R = NaNO2/HCl U = 1. H3PO2
2. KMnO4 - KOH, heat
⊕ 
N2 Cl
(B) P = Sn/HCl R = HNO2 S=
H3C
⊕ 
N2 Cl OH
(C) S = T= U= 1. CH3CH2OH
H3C H3C
2. KMnO4 - KOH, heat
NO2 OH
(D) Q = R = H2/Pd, ethanol T=
HOOC H 3C
1
3. The reaction of Q with PhSNa yields an organic compound (major product) that gives positive Carius test
on treatment with Na2O2 followed by addition of BaCl2. The correct option(s) for Q is (are).
O2N MeS
F O2N
(A) O2N (B) I (C) Br (D) Cl
NO2O2N O2N MeS
4. Scheme 1 and 2 describe the conversion of P to Q and R to S, respectively. Scheme 3 describes the
synthesis of T from Q and S. The total number of Br atoms in a molecule of T is ________.
Scheme 1 :
(i) Br2 (excess), H2O
NH 2
(ii) NaNO 2 , HCl, 273 K
(iii) CuCN/KCN
Q
(iv) H 3 O+, ∆ (major)
P (v) SOCl 2 , pyridine
Scheme 2 :
(i) Oleum
(ii) NaOH, ∆
S
(iii) H + (major)
(iv) Br2 , CS2 273 K
R
Scheme 3 :
(i) NaOH
S T
(ii) Q (major)
5. Aniline reacts with mixed acid (conc. HNO3 and conc. H2SO4) at 288 K to give P (51%), Q (47%) and
R (2%). The major product(s) the following reaction sequence is (are) :- [JEE(Advanced) 2018]
1) Ac2O, pyridine 1) Sn/HCl
2) Br2, CH3CO2H 2) Br2/H2O (excess)
R S
3) H3O
+
3) NaNO2, HCl/273-278K major product(s)
4) NaNO2, HCl/273-278K 4) H3PO2
5) EtOH, ∆
Br Br Br Br
(A) Br (B) Br (C) (D)
Br Br Br Br Br Br
Br Br Br
6. The major product of the following reaction is [JEE(Advanced) 2017]
OH
i) NaNO2, HCl, 0°C
ii) aq. NaOH
NH2
–
O Na+ OH OH
N=N OH
(A) (B) (C) (D)
N=N Cl
N2Cl
2

®
7. The product(s) of the following reaction sequence is(are) [JEE(Advanced) 2016]
NH2
(i) Acetic anhydride/pyridine
(ii) KBrO3 / HBr
+
(iii) H3O , heat
(iv) NaNO2 / HCl, 273-278 K
(v) Cu/HBr
Br
Br
(A) (B)
Br Br
Br
Br Br Br
Br Br
(C) (D)
Br
8. The major product of the reaction is : [JEE(Advanced) 2015]
H3C CO2H
NaNO2.aqueous HCl
0º C
CH3 NH2
H3C CO2H
H3C NH2
(A) (B)
CH3 OH CH3 OH
H3C CO2H H3C NH2

(C) (D)
CH3 OH CH3 OH
9. In the following reactions, the major product W is : [JEE(Advanced) 2015]
OH
NH2 , NaOH
NaNO2, HCl
0º C
V W
OH
N=N OH
(A) N=N
(B)
HO
OH
(C)
N=N (D) N=N
3
10. In the reaction shown below, the major product(s) formed is / are : [JEE(Advanced) 2014]
NH2
NH2  → product(s)

acetic anhydride
CH 2 Cl2
O
H
N CH3
O
(A) + CH3COOH
NH2
O
NH2
(B) H + CH3COOH
N CH3
O O
H
N CH3
O
(C) H + H2O
N CH3
O O
⊕ 
NH3CH3COO
(D) H
N CH3
O O
4
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®
ORGANIC CHEMISTRY
BIOMOLECULES
1. A disaccharide X cannot be oxidised by bromine water. The acid hydrolysis of X leads to a
laevorotatory solution. The disaccharide X is [JEE(Advanced) 2023]
CH2OH CH2OH
H O H O H
H
(A) OH H H HO
OH O
CH2OH
H OH OH H
CH2OH CH2OH
H O O H
H
OH H
(B) H OH H
HOH2C O OH
H OH H OH
CH2OH CH2OH
O O
OH H OH
H O H
(C) OH H OH H
H H H
H OH H OH
CH2OH CH2OH
H O H H O H
H H
(D) OH H O H HO
OH OH
H OH OH H
2. Treatment of D-glucose with aqueous NaOH results in a mixture of monosaccharides, which are
CHO CHO CHO

HO H OH HO H
H
HO H HO H HO H
(A) H OH HO H HO H
H OH , H O and H OH
CH2OH CH2OH CH2OH
CH2OH CHO CHO

O HO H HO H
HO H H OH HO H
(B)
H OH H OH HO H
H OH , H OH and H OH
CH2OH CH2OH CH2OH
1
CHO CH2OH CHO
H OH O HO H
HO H HO H HO H
(C) H OH H OH H OH
H O , H OH and H OH
CH2OH CH2OH CH2OH
CHO CHO CHO

H OH H OH HO H
HO H HO H HO H
(D) HO H H OH H OH
H OH , H OH and H OH
CH2OH CH2O CH2OH
3. The structure of a peptide is given below
NH2
HO
O
H
N OH
H2N N
O H O
CO2H
If the absolute values of the net charge of the peptide at pH = 2, pH = 6, and pH = 11 are z1 , z 2 and
z3 , respectively, then what is z1 + z 2 + z3 ? [JEE(Advanced) 2020]
4. Which of the following statement(s) is(are) true ? [JEE(Advanced) 2019]
(A) Oxidation of glucose with bromine water gives glutamic acid
(B) The two six-membered cyclic hemiacetal forms of D-(+)-glucose are called anomers
(C) Hydrolysis of sucrose gives dextrorotatory glucose and laevorotatory fructose
(D) Monosaccharides cannot be hydrolysed to give polyhydroxy aldehydes and ketones
5. Choose the correct option(s) from the following [JEE(Advanced) 2019]
(A) Natural rubber is polyisoprene containing trans alkene units
(B) Nylon-6 has amide linkages
(C) Cellulose has only α-D-glucose units that are joined by glycosidic linkages
(D) Teflon prepared by heating tetrafluoroethene in presence of a persulphate catalyst at high pressure
2
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®
6. The Fischer presentation of D-glucose is given below.
CHO
H OH
HO H
H OH
H OH
CH2OH
D-glucose
The correct structure(s) of β-L-glucopyranose is (are) :- [JEE(Advanced) 2018]
H
H
O
O CH2OH
CH2OH HO OH
HO OH
(A) (B)
H H
H H H H
H HO
OH OH
OH H
CH2OH H
O O
H CH2OH
H OH HO H
(C) (D)
HO H H OH
OH HO H HO
H H OH H
7. The structure of D-(+)-glucose is
CHO
H OH
HO H
H OH
H OH
CH2OH
The structure of L(–)-glucose is [JEE(Advanced) 2015]
CHO CHO CHO CHO
HO H H OH HO H HO H
H OH HO H HO H HO H
(A) HO H (B) H OH (C) H OH (D) HO H
HO H HO H HO H H OH
CH2OH CH2OH CH2OH CH2OH
3
8. The total number of distinct naturally occurring amino acids obtained by complete acidic hydrolysis of
the peptide shown below is [JEE(Advanced) 2014]
O
H H H
O O O O N
N N N
N N N
H
N CH2 O O CH2 O
H H
O
4

®
ORGANIC CHEMISTRY
POLYMER
1. In the following reactions, P, Q, R and S are the major products. [JEE(Advanced) 2023]
(i)KMnO 4 ,KOH,∆

(ii)H O⊕
→P
3
H3CH2C
MeOOC COCI

(i)NaOH,H 2O
(ii)H O⊕
→Q
3
O
⊕
(i)H3O ,∆
COOMe 
(ii)H 2CrO 4
→R
CN
Br

(i)Mg, dry ether
(ii)CO , then H O⊕
→S
2 3
O (iii)Aammoniacal AgNO3 ,H3O⊕
The correct statement (s) about P, Q, R, and S is (are)
(A) P and Q are monomers of polymers dacron and glyptal, respectively.
(B) P, Q, and R are dicarboxylic acids.
(C) Compounds Q and R are the same.
(D) R does not undergo aldol condensation and S does not undergo Cannizzaro reaction.
2. Among the following, the correct statement(s) about polymers is(are) [JEE(Advanced) 2022]
(A) The polymerization of chloroprene gives natural rubber.
(B) Teflon is prepared from tetrafluoroethene by heating it with persulphate catalyst at high pressures.
(C) PVC are thermoplastic polymers.
(D) Ethene at 350-570 K temperature and 1000-2000 atm pressure in the presence of a peroxide initiator
yields high density polythene.
3. On complete hydrogenation, natural rubber produces [JEE(Advanced) 2016]
(A) ethylene-propylene copolymer
(B) vulcanised rubber
(C) polypropylene
(D) polybutylene
1
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ORGANIC CHEMISTRY
MISCELLANEOUS
1. Match the compounds in LIST-I with the observation in LIST-II, and choose the correct option.
LIST-I LIST-II
(I) Aniline (P) Sodium fusion extract of the compound on
boiling with FeSO4, followed by acidification
with conc. H2SO4, gives Prussian blue color.
(II) o-Cresol (Q) Sodium fusion extract of the compound on
treatment with sodium nitroprusside gives blood
red color.
(III) Cysteine (R) Addition of the compound to a saturated solution
of NaHCO3 results in effervescence.
(IV) Coprolactam (S) The compound reacts with bromine water to give
a white precipitate.
(T) Treating the compound with neutral FeCl3
solution produces violet color.
(A) I → P, Q; II → S; III → Q, R; IV → P (B) I → P ; II → R, S; III → R; IV → Q, S
(C) I → Q, S; II → P, T; III → P; IV → S (D) I → P, S; II → T; III → Q, R; IV → P
2. The maximum number of possible isomers (including stereoisomers) which may be formed on
mono-bromination of 1-methylcyclohex-1-ene using Br2 and UV light is ______. [JEE(Advanced) 2021]
3. The reaction sequence(s) that would lead to o-xylene as the major product is (are) [JEE(Advanced) 2021]
1. NaNO2/HCl
Me 273 K 1. Mg, CO2, H3O+
NH2 2. CuCN Me 2. SOCl2
(A) 3. DIBAL-H (B) 3. H2, Pd-BaSO4
then H3O+ Br 4. Zn-Hg, HCl
4. N2H4, KOH
heat
1. i. BH3
Me 1. O3, Zn/H2O
ii. H2O2, NaOH
(C) (D) 2. N2H4, KOH, heat
2. PBr3
3. Zn, dil. HCl
4. Correct option(s) for the following sequence of reactions is(are) [JEE(Advanced) 2021]
V
Br2 1. Q CHCl3 S
PhCH3 P R foul smelling
light 2. H2, Pd/C KOH
i. KMnO4
KOH, heat
ii. H3O+
1. NH3 W
T U
2. heat
(A) Q = KNO2, W = LiAlH4 (B) R = benzenamine, V = KCN
(C) Q = AgNO2, R = phenylmethanamine (D) W = LiAlH4, V = AgCN
1
5. Fusion of MnO2 with KOH in presence of O2 produces a salt W. Alkaline solution of W upon eletrolytic
oxidation yields another salt X. The manganese containing ions present in W and X, respectively, are
Y and Z. Correct statement(s) is (are) [JEE(Advanced) 2019]
(A) Y is diamagnetic in nature while Z is paramagnetic
(B) Both Y and Z are coloured and have tetrahedral shape
(C) In both Y and Z , π-bonding occurs between p-orbitals of oxygen and d-orbitals of manganese.
(D) In aqueous acidic solution, Y undergoes disproportionation reaction to give Z and MnO2.
6. Consider the following reactions (unbalanced)
Zn + hot conc. H2SO4 → G + R + X
Zn + conc. NaOH → T + Q
G + H2S + NH4OH → Z (a precipitate) + X + Y
Choose the correct option(s). [JEE(Advanced) 2019]
(A) The oxidation state of Zn in T is +1
(B) Bond order of Q is 1 in its ground state
(C) Z is dirty white in colour
(D) R is a V-shaped molecule
Paragraph "X"
Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3/CuCl followed by reaction with
Ac2O/NaOAc gives compound X as the major product. Compound X upon reaction with
Br2/Na2CO3, followed by heating at 473 K with moist KOH furnishes Y as the major product. Reaction of
X with H2/Pd-C, followed by H3PO4 treatment gives Z as the major product.
(There are two questions based on PARAGRAPH "X", the question given below is one of them)
7. The compound Y is :- [JEE(Advanced) 2018]
OH Br
COBr Br COBr
(A) (B) (C) (D)
HO O Br
Paragraph "X"
Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3/CuCl followed by reaction with
Ac2O/NaOAc gives compound X as the major product. Compound X upon reaction with Br2/Na2CO3,
followed by heating at 473 K with moist KOH furnishes Y as the major product. Reaction of X with
H2/Pd-C, followed by H3PO4 treatment gives Z as the major product.
(There are two question based on PARAGARAPH "X", the question given below is one of them)
8. The compound Z is :-
OH
(A) (B) (C) (D)

O O O
2
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®
Paragraph "A"
An organic acid P (C11H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol to
produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products.
P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes
another set of reactions to produce S. [JEE(Advanced) 2018]
(1) H2/Pd-C
(2) NH3/∆ (1) H2/Pd-C (1) HCl
(3) Br2/NaOH (2) SOCl2 (2) Mg/Et2O
S S Q R
(4) CHCl3,KOH, ∆ (3) MeMgBr, CdCl2 (3) CO2(dry ice)
(5) H2/Pd-C (4) NaBH4 (4) H3O+
(There are two questions based on PARAGRAPH "A", the question given below is one of them)
9. The compound R is
HO2C
(A) CO2H (B)
CO2H CO2H
(C) (D)
Paragraph "A"
An organic acid P (C11H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol to
produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products.
P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes another
set of reactions to produce S.
(1) H2/Pd-C
(2) NH3/∆ (1) H2/Pd-C (1) HCl
(3) Br2/NaOH (2) SOCl2 (2) Mg/Et2O
S S Q R
(4) CHCl3,KOH, ∆ (3) MeMgBr, CdCl2 (3) CO2(dry ice)
(5) H2/Pd-C (4) NaBH4 (4) H3O+
(There are two questions based on PARAGRAPH "A", the question given below is one of them)
10. The compound S is
H
(A) (B) (C) NH2 (D) N
NH2 HN
3
11. The desired product X can be prepared by reacting the major product of the reactions in LIST-I with one
or more appropriate reagents in LIST-II. [JEE(Advanced) 2018]
(given, order of migratory aptitude: aryl > alkyl > hydrogen)
O
Ph
OH
Ph
Me
X
LIST-I LIST-II
Ph
HO
P. Me + H2SO4 1. l2, NaOH
Ph
OH
Me
Ph
H2N
Q. H + HNO2 2. [Ag(NH3)2]OH
Ph
OH
Me
Ph
HO
R. Ph + H2SO4 3. Fehling solution
Me
OH
Me
Ph
Br
S. H + AgNO3 4. HCHO, NaOH
Ph
OH
Me
5. NaOBr
The correct option is
(A) P → 1; Q → 2,3; R → 1,4; S → 2,4 (B) P → 1,5; Q → 3,4; R → 4,5; S → 3
(C) P → 1,5; Q → 3,4; R → 5; S → 2,4 (D) P → 1,5; Q → 2,3; R → 1,5; S → 2,3
12. LIST-I contains reactions and LIST-II contains major products. [JEE(Advanced) 2018]
LIST-I LIST-II
ONa +
Br 
→
P. 1. OH
Q. OMe + HBr 
→ 2. Br
R. Br + NaOMe 
→ 3. OMe
S. ONa + MeBr 
→ 4.
O
5.
Match each reaction in LIST-I with one or more product in LIST-II and choose the correct option.
(A) P → 1,5; Q → 2; R → 3; S → 4 (B) P → 1,4; Q → 2; R → 4; S → 3
(C) P → 1,4; Q → 1,2; R → 3,4; S → 4 (D) P → 4,5; Q → 4; R → 4; S → 3,4
4
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®
Answer Q.13, Q.14 and Q.15 by appropriately matching the information given in the three columns
of the following table. [JEE(Advanced) 2017]
Columns 1, 2 and 3 contains starting materials, reaction conditions, and type of reactions,
respectively.
Column-1 Column-2 Column-3
(I) Toluene (i) NaOH/Br2 (P) Condensation
(II) Acetophenone (ii) Br2 / hv (Q) Carboxylation
(III) Banzaldehyde (iii) (CH3CO)2O/CH3COOK (R) Substitution
(IV) Phenol (iv) NaOH/CO2 (S) Haloform
13. For the synthesis of benzoic acid, the only CORRECT combination is
(A) (III) (iv) (R) (B) (IV) (ii) (P) (C) (I) (iv) (Q) (D) (II) (i) (S)
14. The only CORRECT combination in which the reaction proceeds through radical mechanism is
(A) (I) (ii) (R) (B) (II) (iii) (R) (C) (III) (ii) (P) (D) (IV) (i) (Q)
15. The only CORRECT combination that gives two different carboxylic acids is
(A) (IV) (iii) (Q) (B) (III) (iii) (P) (C) (II) (iv) (R) (D) (I) (i) (S)
16. Compound P and R upon ozonolysis produce Q and S, respectively. The molecular formula of Q and S is
C8H8O. Q undergoes Cannizzaro reaction but not haloform reaction, whereas S undergoes haloform
reaction but not Cannizzaro reaction. [JEE(Advanced) 2017]
(i) P Q (ii) R S
(C8H8O) (C8H8O)
The option(s) with suitable combination of P and R, respectively, is(are)
(A) and
(B) and
(C) and
(D) and
2–
17. Among [Ni(CO)4], [NiCl4] , [Co(NH3)4Cl2]Cl, Na3[CoF6], Na2O2 and CsO2, the total number of
paramagnetic compounds is - [JEE(Advanced) 2016]
(A) 2 (B) 3 (C) 4 (D) 5
–
18. In dilute aqueous H2SO4 , the complex diaquodioxalatoferrate(II) is oxidized by MnO4 . For this reaction,
+ –
the ratio of the rate of change of [H ] to the rate of change of [MnO4 ] is - [JEE(Advanced) 2015]
5
Paragraph for Question No. 19 and 20
Schemes 1 and 2 describe sequential transformation of alkynes M and N. Consider only the major
products formed in each step for both the schemes. [JEE(Advanced) 2014]
1.1.NaNH (excess)
NaNH22(excess)
2.2.CH
CH33CH
CH22II (1
(1 equivalent)
equivalent)
H X Scheme-1
HO 3.3.CH
CH33II (equivalent)
(1 equivalent)
M 4.4.HH22, ,(Lindlar
(Lindlar catalyst)
catalyst)
1. NaNH
NaNH22(2(2equivalent)
equivalent)
OH
2.
Br
H ⊕
Y Scheme-2
3. H33OO⊕(Mild)
3. H (Mild)
N 4. H
H22, Pd/C
5. CrO33
5. CrO
19. The product X is -

HH3CO
3CO
H
H
(A) (B)
H
H
H
H H
H CO
HH33CO
H
H
CH3CH
CH 3CH22O
(C) (D)
H
H
CHCH
CH 3CH 2O
H
H H
H 3 2O
20. The correct statement with respect to prodcut Y is -

(A) It gives a positive Tollens test and is a functional isomer of X
(B) It gives a positive Tollens test and is a geometrical isomer of X
(C) It gives a positive Iodoform test and is a functional isomer of X
(D) It gives a positive Iodoform test and is a geometrical isomer of X
21. Match the four starting materials (P , Q, R, S) given in List I with the corresponding reaction scheme
(I, II, III, IV) provided in List - II and select the correct answer using the code given below in lists.
List - I List – II [JEE(Advanced) 2014]
(P) H H (1) Scheme I
– +
(i) KMnO4, HO, heat (ii) H, H2O
(iii) SOCl2 (iv) NH3
? C7H6N2O3
OH
(Q) (2) Scheme II

OH
(i) Sn/HCl (ii) CH3COCl (iii) conc.H2SO4
(iv) HNO3 (v) dil.H2SO4, heat (vi) HO–
? C6H6N2O2
6
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®
NO2
(R) (3) Scheme III
(i) red hot iron, 873 K (ii) fuming HNO3, H2SO4, heat
(iii) H2S.NH3 (iv) NaNO2, H2SO4 (v) hydrolysis
? C6H5NO3
NO2
(S) (4) Scheme IV

CH3
(i) conc. H2SO4, 60ºC
(ii) conc. HNO3, conc. H2SO4 (iii) dil. H2SO4, heat
? C6H5NO4
Code :
P Q R S
(A) 1 4 2 3
(B) 3 1 4 2
(C) 3 4 2 1
(D) 4 1 3 2

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 JEE Advanced Chemistry 10 Years Topicwise Questions with Solutions

2. The IUPAC name(s) of the following compound is(are) [JEE(Advanced) 2017]

(A) P – iii, Q – iv, R – ii, S – i (B) P – i, Q – ii, R – iii, S – iv

the correct statement is

(D) The reaction is exothermic with ∆H° = – 25 kcal mol .

NH2 H3C N CH3

NH2 H3C N CH3 O2N NO2 O2N NO2

Choose the correct statement(s).

I and II and III

The correct order of their boiling point is [JEE(Advanced) 2014]

8. In the following monobromination reaction, the number of possible chiral products is

9. For 'invert sugar', the correct statement(s) is (are)

1. Na, liquid NH3

4. The major product formed in the following reaction is [JEE(Advanced) 2021]

Question Stem for Q.5 and Q.6

NaNH2 red hot iron

x g and y g are mass of R and U, respectively.

(B) H 3C NaOH, CaO, ∆

Cl Zn, dil. HCl

10. The major product U in the following reactions is : [JEE(Advanced) 2015]

The correct statement about S is

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

Zn/Hg, HCl SOCl

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

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

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

(i) NaNO2 + HCl/0–5ºC

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

Paragraph for Question No. 11 & 12

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

Paragraph For Q.14 & Q.15

(P) (-)-1-Bromo-2-ethylpentane aq. NaOH (1) Inversion of configuration

(Q) (-)-2-Bromopentane aq. NaOH (2) Retention of configuration

(R) (-)-3-Bromo-3-methylhexane aq. NaOH (3) Mixture of enantiomers

(S) (4) Mixture of structural isomers

(5) Mixture of diastereomers

2. Consider the following reaction. [JEE(Advanced) 2022]

[Given : Atomic mass of H = 1, C = 12, N = 14, O = 16, S = 32, Cl = 35]

(I) Br (II) (III) (IV)

(A) I and II follow SN2 mechanism

PhCH 2 CHO 

The correct statement(s) about P, Q, R, and S is(are)

(C) R is (D) S is H3C

(major) (major) (major)

CH3 H3C Br CH3 H3C Br

4. The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is (are) [JEE(Advanced) 2018]

NaOBr NH3 , ∆ Br 2 /KOH Br 2 (3 equiv)

6. Positive Tollen's test is observed for [JEE(Advanced) 2016]

(i) HCHO (excess) / NaOH, heat

(i) EtMgBr, H2O

12. The major compound Y is :

S RCO2 + R'O → R + R'O

1. Br2, red phosphorous O

(A) P can be reduced to a primary alcohol using NaBH4.

the correct option(s) is(are) [JEE(Advanced) 2022]

H3C CO2H H3C NH2

NH2  → product(s)

CHO CHO CHO

CH2OH CH2OH CH2OH

CH2OH CHO CHO

CH2OH CH2OH CH2OH

CHO CHO CHO

CH2OH CH2O CH2OH