Anic Chemistry PDF - Watermark

Chapter 21
Organic Chemistry:
Some Basic Principles and Techniques
1. The IUPAC name of neopentane is [AIEEE-2009] complete neutralisation. The percentage of nitrogen
in the compound is [AIEEE-2010]
(1) 2, 2-dimethylpropane
(1) 29.5 (2) 59.0
(2) 2-methylpropane
(3) 47.4 (4) 23.7
(3) 2, 2-dimethylbutane
6. The non-aromatic compound among the following is
(4) 2-methylbutane
[AIEEE-2011]
2. Arrange the carbanions, (CH 3 ) 3 C , CCl3 ,
(1) (2)
(CH3)2 CH , C6H5 CH2 , in order of their decreasing
stability [AIEEE-2009]
(3) (4)
(1) (CH3)2 CH > CCl3 > C6H5 CH2 > (CH3)3 C
S
7. The order of stability of the following carbocations
(2) CCl3 > C6H5 CH2 > (CH3)2 CH > (CH3)3 C

CH2
(3) (CH3)3 C > (CH3)2 CH > C6H5 CH2 > CCl3

CH2 = CH – CH2; CH3 – CH2 – CH2; is
(4) C6H5 CH2 > CCl3 > (CH3)3 C > (CH3)2 CH I II III
3. The alkene that exhibits geometrical isomerism is [JEE (Main)-2013]
[AIEEE-2009]
(1) III > II > I (2) II > III > I
(1) 2 - methyl propene
(3) I > II > III (4) III > I > II
(2) 2 - butene
8. A gaseous hydrocarbon gives upon combustion
(3) 2 - methyl - 2 - butene 0.72 g of water and 3.08 g of CO2. The empirical
(4) Propene formula of the hydrocarbon is [JEE (Main)-2013]
4. The correct order of increasing basicity of the given (1) C2H4 (2) C3H4
conjugate bases (R = CH3) is [AIEEE-2010] (3) C6H5 (4) C7H8
9. For the estimation of nitrogen, 1.4 g of an organic
(1) RCOO HC { C NH2 R
compound was digested by Kjeldahl method and
the evolved ammonia was absorbed in 60 mL of
(2) RCOO HC { C R NH2
M
sulphuric acid. The unreacted acid required 20
(3) R HC { C RCOO NH2 10
M
(4) RCOO NH2 HC { C R mL of sodium hydroxide for complete
10
5. 29.5 mg of an organic compound containing neutralization. The percentage of nitrogen in the
nitrogen was digested according to Kjeldahl's compound is [JEE (Main)-2014]
method and the evolved ammonia was absorbed in (1) 6% (2) 10%
20 mL of 0.1 M HCl solution. The excess of the
(3) 3% (4) 5%
acid required 15 mL of 0.1 M NaOH solution for
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10. In Carius method of estimation of halogens, 250 (4) NO2CH2COOH > FCH2COOH >
mg of an organic compound gave 141 mg of AgBr.
CNCH2COOH > CICH2COOH
The percentage of bromine in the compound is (At.
mass Ag = 108; Br = 80) [JEE (Main)-2015] 16. The increasing basicity order of the following
compounds is [JEE (Main)-2019]
(1) 24 (2) 36
(3) 48 (4) 60 CH2CH3
11. The distillation technique most suited for separating (A) CH3CH2NH2 (B) CH3CH2NH
glycerol from spent-lye in the soap industry is
[JEE (Main)-2016] CH3 CH3
(1) Fractional distillation (C) H3C – N – CH3 (D) Ph – N – H
(2) Steam distillation
(1) (D) < (C) < (B) < (A)
(3) Distillation under reduced pressure
(2) (A) < (B) < (C) < (D)
(4) Simple distillation
(3) (A) < (B) < (D) < (C)
12. W hich of the following molecules is least
(4) (D) < (C) < (A) < (B)
resonance stabilized? [JEE (Main)-2017]
17. If dichloromethane (DCM) and water (H2O) are used
for differential extraction, which one of the following
(1) (2) statements is correct? [JEE (Main)-2019]
N
(1) DCM and H2O will make turbid/colloidal mixture
O
(2) DCM and H2O will be miscible clearly
(3) (4) (3) DCM and H2O would stay as upper and lower
layer respectively in the separating funnel (S.F.)
O
13. Which of the following compounds will be suitable (4) DCM and H2O would stay as lower and upper
for Kjeldahl's method for nitrogen estimation? layer respectively in the S.F.
[JEE (Main)-2018]
18. W hat is the IUPAC name of the following
compound?
NH2
(1) (2)
N H
H
+ –
NO2 N Cl
2 Br
(3) (4)
[JEE (Main)-2019]
14. Which amongst the following is the strongest acid?
(1) 3-Bromo-1, 2-dimethylbut-1-ene
[JEE (Main)-2019]
(2) 4-Bromo-3-methylpent-2-ene
(1) CHBr3 (2) CH(CN)3
(3) 3-Bromo-3-methyl-1, 2- dimethylprop-1-ene
(3) CHI3 (4) CHCI3
(4) 2-Bromo-3-methylpent-3-ene
15. The correct decreasing order for acid strength is
19. The correct match between items I and II is
[JEE (Main)-2019]
Item-I (Mixture) Item-II
(1) FCH2COOH > NCCH2COOH >
(Separation method)
NO2CH2COOH > CICH2COOH
(A) H2O : Sugar (P) Sublimation
(2) CNCH2COOH > O2NCH2COOH>
(B) H2O : Aniline (Q) Recrystallization
FCH2COOH > CICH2COOH
(C) H2O : Toluene (R) Steam distillation
(3) NO2CH2COOH > NCCH2COOH >
(S) Differential extraction
FCH2COOH > CICH2COOH
[JEE (Main)-2019]
CHEMISTRY ARCHIVE - JEE (Main)
(1) (A) o (R), (B) o (P), (C) o (S) 25. The correct IUPAC name of the following compound
is [JEE (Main)-2019]
(2) (A) o (S), (B) o (R), (C) o (P)
(3) (A) o (Q), (B) o (R), (C) o (P) NO 2
(4) (A) o (Q), (B) o (R), (C) o (S)
20. An organic compound is estimated through Dumas
method and was found to evolve 6 moles of
CO2, 4 moles of H2O and 1 mole of nitrogen gas. Cl
The formula of the compound is [JEE (Main)-2019] CH3
(1) C6H8N2 (2) C12H8N
(1) 3-chloro-4-methyl-1-nitrobenzene
(3) C6H8N (4) C12H8N2
(2) 5-chloro-4-methyl-1-nitrobenzene
21. In the following compound,
(3) 2-methyl-5-nitro-1-chlorobenzene
NH2 a
d (4) 2-chloro-1-methyl-4-nitrobenzene
N
Nb
26. The increasing order of the pKb of the following
e N
H
N
c compound is
the favourable site/s for protonation is/are F

S
[JEE (Main)-2019]
(A)
N N
(1) (a) (2) (b), (c) and (d)
H H
(3) (a) and (d) (4) (a) and (e)
22. The correct order for acid strength of compounds CH3O
S
CH {{ CH, CH3 — C {{ CH and CH2 == CH2 (B)
N N
is as follows [JEE (Main)-2019]
H H
(1) CH3 — C {{ CH > CH {{ CH > CH2 == CH2
O2N
(2) CH3 — C {{ CH > CH2 == CH2 > HC {{ CH S
(3) CH {{ CH > CH2 == CH2 > CH3 — C {{ CH (C)
N N
(4) HC {{ CH > CH3 — C {{ CH > CH2 == CH2 H H
23. The IUPAC name of the following compound is
H3C
S
C H 3 OH (D)
N N
H 3C – CH – CH – CH 2 – COOH H H
[JEE (Main)-2019] [JEE (Main)-2019]
(1) 3-Hydroxy-4-methylpentanoic acid (1) (B) < (D) < (A) < (C) (2) (A) < (C) < (D) < (B)
(3) (B) < (D) < (C) < (A) (4) (C) < (A) < (D) < (B)
(2) 4-Methyl-3-hydroxypentanoic acid
27. The IUPAC name for the following compound is
(3) 2-Methyl-3-hydroxypentan-5-oic acid
(4) 4,4-Dimethyl-3-hydroxybutanoic acid CH3
24. Which of the following compounds will show the H3C CH
maximum ‘enol’ content? [JEE (Main)-2019]
(1) CH3COCH2COOC2H5 (2) CH3COCH3 CH3
CH2
(3) CH3COCH2COCH3 (4) CH3COCH2CONH2
[JEE (Main)-2019] 33. The increasing order of basicity for the following
(1) 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene intermediates is (from weak to strong)
CH 3
(2) 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne
–
(3) 3,5-dimethyl-4-propylhept-1-en-6-yne H3C C– H2C CH CH2
(4) 3,5-dimethyl-4-propylhept-6-en-1-yne CH 3
28. In chromatography, which of the following (i) (ii)
statements is INCORRECT for Rf ? – – –
HC C CH 3 CN [JEE (Main)-2020]
[JEE (Main)-2019] (iii) (iv) (v)
(1) The value of Rf cannot be more than one. (1) (v) < (i) < (iv) < (ii) < (iii)
(2) Higher Rf value means higher adsorption. (2) (iii) < (iv) < (ii) < (i) < (v)
(3) Rf value is dependent on the mobile phase. (3) (v) < (iii) < (ii) < (iv) < (i)
(4) R f value depends on the type of (4) (iii) < (i) < (ii) < (iv) < (v)
chromatography.
34. Which of the following has the shortest C – Cl
29. The correct order of stability for the following
bond? [JEE (Main)-2020]
alkoxides is
– – (1) Cl – CH = CH – NO2
O O –
O (2) Cl – CH = CH2
O2N (3) Cl – CH = CH – CH3
NO 2 NO2
(4) Cl – CH = CH – OCH3
(A) (B) (C) 35. In Carius method of estimation of halogen, 0.172 g
[JEE (Main)-2020] of an organic compound showed presence of 0.08
(1) (B) > (A) > (C) (2) (C) > (B) > (A) g of bromine. Which of these is the correct
structure of the compound? [JEE (Main)-2020]
(3) (B) > (C) > (A) (4) (C) > (A) > (B)
30. Arrange the following compounds in increasing order NH2 NH 2
of C – OH bond length [JEE (Main)-2020] Br
methanol, phenol, p-ethoxyphenol (1) (2)
(1) phenol < p-ethoxyphenol < methanol Br Br
(2) methanol < phenol < p-ethoxyphenol (3) H3C – Br (4) H3C – CH2 – Br
(3) methanol < p-ethoxyphenol < phenol 36. The IUPAC name for the following compound is
(4) phenol < methanol < p-ethoxyphenol
CHO
31. A flask contains a mixture of isohexane and CH3
3-methylpentane. One of the liquids boils at 63°C H3 C
while the other boils at 60°C. What is the best COOH
way to separate the two liquids and which one will [JEE (Main)-2020]
be distilled out first? [JEE (Main)-2020] (1) 6-formyl-2-methyl-hex-3-enoic acid
(1) Simple distillation, isohexane
(2) 2, 5-dimethyl-6-carboxy-hex-3-enal
(2) Fractional distillation, isohexane
(3) 2, 5-dimethyl-5-carboxy-hex-3-enal
(3) Simple distillation, 3-methylpentane
(4) 2, 5-dimethyl-6-oxo-hex-3-enoic acid
(4) Fractional distillation, 3-methylpentane
37. Arrange the following labelled hydrogens in
32. Kjeldahl’s method cannot be used to estimate
decreasing order of acidity
nitrogen for which of the following compounds?
[JEE (Main)-2020] NO2 C{ C– H a
O
(1) CH3CH2–C{N (2) NH2–C–NH 2
d H –O COO H b
(3) C6H5NO2 (4) C6H5NH2 O– H C
[JEE (Main)-2020] [JEE (Main)-2020]

(1) b > c > d > a (2) b > a > c > d (1) (C) < (A) < (B) < (D)
(3) c > b > d > a (4) c > b > a > d (2) (B) < (C) < (A) < (D)
38. Which one of the following compounds possesses (3) (A) < (C) < (D) < (B)
the most acidic hydrogen? [JEE (Main)-2020]
(4) (D) < (C) < (A) < (B)
O 42. Among the following compounds geometrical
(1) isomerism is exhibited by [JEE (Main)-2020]
H 3C CH3
(2) H3C – C { C – H CHCl CH2

N{C C{ N
(3)
H H (1) (2)
O O
(4) MeO Cl
H OMe
O OMe
39. The IUPAC name of the following compound is
CH 3 O CHCl
C – OH
(3) (4)
Br CH3
[JEE (Main)-2020]
(1) 3-Bromo-5-methylcyclopentane carboxylic acid
(2) 3-Bromo-5-methylcyclopentanoic acid 43. The increasing order of pKb values of the following
(3) 5-Bromo-3-methylcyclopentanoic acid compounds is
N(CH 3)2 N(CH 3)2 NHCH 3 NHCH 3
(4) 4-Bromo-2-methylcyclopentane carboxylic acid
40. Among the following compounds, which one has
the shortest C – Cl bond? [JEE (Main)-2020] CN OH
OCH 3
Cl I II III IV
HC Cl
(1) (2) CH [JEE (Main)-2020]
CH 2
CH2 (1) I < II < IV < III (2) I < II < III < IV
H 3C (3) II < I < III < IV (4) II < IV < III < I
(3) H3C – Cl (4) H 3C Cl 44. W hich of the following compounds shows
CH 3 geometrical isomerism? [JEE (Main)-2020]
41. The increasing order of the acidity of the (1) 2-methylpent-1-ene
D-hydrogen of the following compounds is (2) 4-methylpent-1-ene
O O O (3) 2-methylpent-2-ene
(4) 4-methylpent-2-ene
Ph Ph
(A) (B) 45. The IUPAC name of the following compound is
OH
O O
NH 2
OMe NMe2
O2N
(C) (D)
CHO
[JEE (Main)-2020] (1) IV > III > II > I

(1) 4-amino-2-formyl-5-hydroxymethyl nitrobenzene (2) II > III > IV > I
(2) 5-amino-4-hydroxymethyl-2-nitrobenzaldehyde
(3) I > II > III > IV
(3) 3-amino-4-hydroxymethyl-5-nitrobenzaldehyde
(4) III > II > I > IV
(4) 2-nitro-4-hydroxymethyl-5-amino benzaldehyde
51. Given below are two statements:
46. In an estimation of bromine by Carius method,
1.6 g of an organic compound gave 1.88 g of Statement I : o-Nitrophenol is steam volatile due to
AgBr. The mass percentage of bromine in the intramolecular hydrogen bonding.
compound is _______.
Statement II : o-Nitrophenol has high melting due
(Atomic mass, Ag = 108, Br = 80 g mol–1)
to hydrogen bonding.
[JEE (Main)-2020]
In the light of the above statements, choose the
47. Which one of the following compounds is non-
most appropriate answer from the options given
aromatic? [JEE (Main)-2021]
below: [JEE (Main)-2021]
(1) Both statement I and statement II are true
(1) (2)
O (2) Statement I is false but statement II is true
(3) (4) (3) Statement I is true but statement II is false

(4) Both statement I and statement II are false
48. Using the provided information in the following paper
chromatogram : 52. Which of the following is ‘a’ FALSE statement?
[JEE (Main)-2021]
(1) Carius method is used for the estimation of
Solvent front
nitrogen in an organic compound
B
2 cm (2) Phosphoric acid produced on oxidation of
5 cm
A
phosphorus present in an organic compound is
2 cm precipitated as Mg2P2O7 by adding magnesia
mixture
Base line (3) Kjeldahl’s method is used for the estimation of

Spot
nitrogen in an organic compound
Fig : Paper chromatography for compounds A and B. (4) Carius tube is used in the estimation of
The calculated Rf value of A ______ × 10–1. sulphur in an organic compound
[JEE (Main)-2021] 53. Given below are two statements:
49. Which of the following compound is added to the Statement I : A mixture of chloroform and aniline
sodium extract before addition of silver nitrate for can be separated by simple distillation.
testing of halogens? [JEE (Main)-2021] Statement II : When separating aniline from a
(1) Hydrochloric acid (2) Sodium hydroxide mixture of aniline and water by steam distillation
aniline boils below its boiling point.
(3) Ammonia (4) Nitric acid
50. The correct order of acid character of the following
compounds is : [JEE (Main)-2021] most appropriate answer from the options given
below : [JEE (Main)-2021]
OH COOH COOH COOH
(3) Statement I is true but statement II is false
NO 2 CH3
I II III IV (4) Statement I is false but statement II is true
54. In chromatography technique, the purification of 58. Match List-I with List-II :
compound is independent of [JEE (Main)-2021]
List-I List-II
(1) Solubility of the compound
Test/Reagents/ Species detected
(2) Mobility or flow of solvent system
Observation(s)
(3) Length of the column or TLC plate
(a) Lassaigne’s Test (i) Carbon
(4) Physical state of the pure compound
(b) Cu(II) oxide (ii) Sulphur
55. Assertion A : Enol form of acetone [CH3COCH3]
(c) Silver nitrate (iii) N, S, P, and halogen
exists in < 0.1% quantity. However, the enol form
of acetyl acetone [CH3COCH2OCCH3] exists in (d) The sodium fusion (iv) Halogen Specifically
approximately 15% quantity. extract gives black
Reason R : Enol form of acetyl acetone is precipitate with acetic
stabilized by intramolecular hydrogen bonding,
which is not possible in enol form of acetone. acid and lead acetate
Choose the correct statement : [JEE (Main)-2021] The correct match is: [JEE (Main)-2021]
(1) A is false but R is true (1) (a)-(iii), (b)-(i), (c)-(iv), (d)-(ii)
(2) Both A and R are true and R is the correct (2) (a)-(i), (b)-(iv), (c)-(iii), (d)-(ii)
explanation of A (3) (a)-(iii), (b)-(i), (c)-(ii), (d)-(iv)
(3) A is true but R is false (4) (a)-(i), (b)-(ii), (c)-(iv), (d)-(iii)
(4) Both A and R are true but R is not the correct 59. In Duma’s method of estimation of nitrogen,
explanation of A 0.1840 g of an organic compound gave 30 mL of
56. Among the following, the aromatic compounds are: nitrogen collected at 287 K and 758 mm of Hg
pressure. The percentage composition of nitrogen
in the compound is ___________.
(A) CH2 (B)
(Round off to the nearest Integer).
[Given : Aqueous tension at 287 K = 14 mm of Hg]
(C) (D) [JEE (Main)-2021]
– +
60. Given below are two statements :
Choose the correct answer from the following
Statement I : Retardation factor (R f) can be
options : [JEE (Main)-2021]
measured in meter/centimeter.
(1) (A), (B) and (C) only
Statement II : Rf value of a compound remains
(2) (B), (C) and (D) only constant in all solvents.
(3) (B) and (C) only Choose the most appropriate answer from the
(4) (A) and (B) only options given below : [JEE (Main)-2021]
57. Statement I : Sodium hydride can be used as an (1) Statement I is true but statement II is false
oxidising agent. (2) Both statement I and statement II are true
Statement II : The lone pair of electrons on (3) Both statement I and statement II are false
nitrogen in pyridine makes it basic.
(4) Statement I is false but statement II is true
Choose the CORRECT answer from the options
61. Which of the following is an aromatic compound?
given below: [JEE (Main)-2021]
[JEE (Main)-2021]
(3) Statement I is false but statement II is true (1) (2)
(4) Statement I is true but statement II is false
Among the given species the Resonance stabilised

carbocations are : [JEE (Main)-2021]
(3) (4)
(1) (C) and (D) only (2) (A), (B) and (C) only
62. Nitrogen can be estimated by Kjeldahl’s method for
which of the following compound? (3) (A) and (B) only (4) (A), (B) and (D) only
[JEE (Main)-2021] 67. Which one of the following pairs of isomers is an

example of metamerism? [JEE (Main)-2021]
OH
(1) (2)
+ –
N { N Cl CH2 – NH 2 OH and H 5C6
(1) H5C6
CH3
(3) (4) (2) CH 3 CH 2CH 2 CH 2 CH 3 and H 3 C C CH3
N NO 2 CH3
63. The total number of C – C sigma bond/s in mesityl
oxide (C 6H 10 O) is ______. (Round off to the O
Nearest Integer). [JEE (Main)-2021]
(3) C6H5 and H5C6 H
64. Compound with molecular formula C3H6O can show
[JEE (Main)-2021] O
(1) Positional isomerism
(2) Both positional isomerism and metamerism O O
(4) and
(3) Metamerism
(4) Functional group isomerism 68. In Carius method, halogen containing organic
65. In the following molecule, compound is heated with fuming nitric acid in the
presence of [JEE (Main)-2021]
a
H 3C (1) HNO3 (2) CuSO4
b
c
C=C– O
(3) BaSO4 (4) AgNO3
H H
69. W hen 0.15 g of an organic compound was
Hybridisation of Carbon a, b and c respectively are : analyzed using Carius method for estimation of
[JEE (Main)-2021] bromine, 0.2397 g of AgBr was obtained. The
(1) sp3, sp, sp (2) sp3, sp2, sp2 percentage of bromine in the organic compound is
_______. (Nearest integer) [JEE (Main)-2021]
(3) sp3, sp, sp2 (4) sp3, sp2, sp
ª Atomic mass :º
66. + + «Silver = 108 »
CH2 CH 2 « »
«¬Bromine = 80 »¼
H
70. Which purification technique is used for high boiling

H organic liquid compound (decomposes near its
boiling point)? [JEE (Main)-2021]
(A) (B )
+ + (1) Reduced pressure distillation
CH2 CH
(2) Simple distillation
(3) Steam distillation
O
(4) Fractional distillation
(C) (D )
71. Which one of the following compounds does not (1) (D) > (C) > (B) > (A)
exhibit resonance? [JEE (Main)-2021] (2) (C) > (B) > (A) > (D)
(1) CH3CH2OCH = CH2 (3) (A) > (B) > (C) > (D)
CH2OH (4) (C) > (D) > (A) > (B)
(2) 76. Which among the following is the strongest acid ?
[JEE (Main)-2021]
(3) CH3CH2CH2CONH2
(4) CH3CH2CH = CHCH2NH2 (1) (2)
72. Which one of the following molecules does not
show stereo isomerism? [JEE (Main)-2021]
(1) 4-Methylhex-1-ene (3) CH3CH2CH2CH3 (4)
(2) 3-Ethylhex-3-ene
77. 0.8 g of an organic compound was analysed by
(3) 3,4-Dimethylhex-3-ene Kjeldahl’s method for the estimation of nitrogen. If
(4) 3-Methylhex-1-ene the percentage of nitrogen in the compound was
found to be 42%, then _______ mL of 1 M H2SO4
73. The number of acyclic structural isomers (including would have been neutralized by the ammonia
geometrical isomers) for pentene are ______. evolved during the analysis. [JEE (Main)-2021]
[JEE (Main)-2021] 78. Given below are two statements
74. W hich one among the following resonating Statement I : Aniline is less basic than
structures is not correct? [JEE (Main)-2021] acetamide.
Statement II : In aniline, the lone pair of electrons
O
N on nitrogen atom is delocalised
(1) over benzene ring due to
O resonance and hence less available
to a proton
O Choose the most appropriate option
N
(2) [JEE (Main)-2021]
O
(1) Statement I is false but statement II is true.
(2) Both statement I and statement II are false.
O
N (3) Statement I is true but statement II is false.
(3)
O (4) Both statement I and statement II are true.
O +
N CH 2
(4)
O
79. + + +
75. The correct decreasing order of densities of the CH2 = CH CH3 – CH 2 HC { C
following compounds is : [JEE (Main)-2021] A B C D
Cl Br
Cl The correct order of stability of given carbocation is
[JEE (Main)-2021]
Cl Cl (1) C > A > D > B (2) D > B > C > A

(A) (B) (C) ( D)
(3) A > C > B > D (4) D > B > A > C
80. Staggered and eclipsed conformers of ethane are

[JEE (Main)-2021] O
H
(1) (2)
(1) Rotamers (2) Mirror images —
(3) Polymers (4) Enantiomers

81. An organic compound is subjected to chlorination
to get compound A using 5.0 g of chlorine. When
(3) (4)
0.5 g of compound A is reacted with AgNO3 [Carius +
Method], the percentage of chlorine in compound
A is ______ when it forms 0.3849 g of AgCl. 86. In the sulphur estimation, 0.471 g of an organic
(Round off to the Nearest Integer) compound gave 1.44 g of barium sulfate. The
(Atomic masses of Ag and Cl are 107.87 and 35.5 percentage of sulphur in the compound is
respectively) ______%. (Nearest integer)
(Atomic Mass of B = 137 u) [JEE (Main)-2021]
[JEE (Main)-2021]
87. The number of moles of CuO, that will be utilized
82. Given below are two statements :
in Dumas method for estimating nitrogen in a
Statement I : Hyperconjugation is a permanent sample of 57.5 g of N,N-dimethylaminopentane is
effect. ______ × 10–2. (Nearest integer)
Statement II : Hyperconjugation in ethyl cation [JEE (Main)-2021]
§ ·
88. In Carius method for estimation of halogens, 0.2 g
¨© CH3 – CH2 ¸¹ involves the overlapping of
of an organic compound gave 0.188 g of AgBr. The
C – H1s bond with empty 2p orbital of other percentage of bromine in the compound is _____.
sp2
(Nearest integer)
carbon.
[Atomic mass : Ag = 108, Br = 80]
Choose the correct option: [JEE (Main)-2021]
[JEE (Main)-2021]
89. Given below are two statements : one is labelled
(2) Statement I is incorrect but statement II is true as Assertion (A) and the other is labelled as
(3) Statement I is correct but statement II is false Reason (R).
(4) Both statement I and statement II are false Assertion (A) : A simple distillation can be used
to separate a mixture of propanol
83. Which one of the following set of elements can be and propanone.
detected using sodium fusion extract?
Reason (R) : Two liquids with a difference of
[JEE (Main)-2021] more than 20°C in their boiling
(1) Phosphorous, Oxygen, Nitrogen, Halogens points can be separated by
simple distillations.
(2) Nitrogen, Phosphorous, Carbon, Sulfur
(3) Sulfur, Nitrogen, Phosphorous, Halogens
most appropriate answer from the options given
(4) Halogens, Nitrogen, Oxygen, Sulfur below : [JEE (Main)-2021]
84. The dihedral angle in staggered form of Newman (1) (A) is false but (R) is true
projection of 1, 1, 1-Trichloro ethane is _____
(2) (A) is true but (R) is false
degree. (Round off to the Nearest Integer).
(3) Both (A) and (R) are correct and (R) is the
[JEE (Main)-2021] correct explanation of (A)
85. Which one of the following compounds is not (4) Both (A) and (R) are correct but (R) is not the
aromatic? [JEE (Main)-2021] correct explanation of (A)
90. Choose the correct name for compound given 94. A 0.166 g sample of an organic compound was
below: [JEE (Main)-2021] digested with conc. H2SO4 and then distilled with
NaOH. The ammonia gas evolved was passed
through 50.0 mL of 0.5 N H2SO4. The used acid
Br
required 30.0 mL of 0.25 N NaOH for complete
neutralisation. The mass percentage of nitrogen in
the organic compound is ________.
(1) (4E)-5-Bromo-hex-2-en-4-yne [JEE (Main)-2022]
(2) (2E)-2-Bromo-hex-4-yn-2-ene 95. 120 g of an organic compound that contains only
(3) (2E)-2-Bromo-hex-2-en-4-yne carbon and hydrogen gives 330 g of CO2 and 270
(4) (4E)-5-Bromo-hex-4-en-2-yne g of water on complete combustion. The
percentage of carbon and hydrogen, respectively
91. Arrange the following conformational isomers of
n-butane in order of their increasing potential are [JEE (Main)-2022]
energy [JEE (Main)-2021] (1) 25 and 75 (2) 40 and 60
CH3 CH3 CH3 H (3) 60 and 40 (4) 75 and 25
H H CH3 H CH3 H
H
96. Arrange the following carbocations in decreasing
HH H H
H H HH H
H
H3C CH3 order of stability. [JEE (Main)-2022]
CH 3
I II III IV
(1) II < IV < III < I
(2) I < III < IV < II
(3) II < III < IV < I
(4) I < IV < III < II
92. The transformation occurring in Duma’s method is (1) A > C > B (2) A > B > C
given below [JEE (Main)-2021] (3) C > B > A (4) C > A > B
97. 0.2 g of an organic compound was subjected to

§ y·
C2H7N ¨ 2x ¸ CuO
© 2¹ estimation of nitrogen by Duma’s method in which
volume of N2 evolved (at STP) was found to be
y z § y· 22.400 mL. The percentage of nitrogen in the
o xCO2 H2O N2 ¨ 2x ¸ Cu
2 2 © 2 ¹ compound is _____. [nearest integer]
The value of y is _____. (Integer answer) (Given : Molar mass of N2 is 28 g mol–1, Molar volume
93. Which one of the following compounds is aromatic of N2 at STP : 22.4L) [JEE (Main)-2022]
in nature? [JEE (Main)-2021] 98. In the following structures, which one is having
staggered conformation with maximum dihedral
angle? [JEE (Main)-2022]
(1) (2)
CH3
+ (1) (2)
(3) (4)
In the light of the above statements, choose the most

appropriate answer from the options given below:
[JEE (Main)-2022]
(3) (4) (1) Both Statement I and Statement II are
correct.
(2) Both Statement I and Statement II are
99. The IUPAC name of ethylidene chloride is: incorrect.
[JEE (Main)-2022] (3) Statement I is correct but Statement II is
(1) 1-Chloroethene (2) 1-Chloroethyne incorrect.
(3) 1, 2-Dichloroethane (4) 1, 1-Dichloroethane (4) Statement I is incorrect but Statement II is

correct.
100. Given below are two statements: one is labelled as
103. Which will have the highest enol content?
Assertion A and the other is labelled as Reason
R. [JEE (Main)-2022]
Assertion A: A mixture contains benzoic acid and

naphthalene. The pure benzoic acid can be separated
out by the use of benzene.
(1) (2)
Reason R: Benzoic acid is soluble in hot water.
In the light of the above statements, choose the most
appropriate answer from the options given below.
[JEE (Main)-2022]
(1) Both A and R are true and R is the correct
explanation of A. (3) (4)
(2) Both A and R are true but R is NOT the
correct explanation of A.
(3) A is true but R is false.
104. On complete combustion 0.30 g of an organic
(4) A is false but R is true.
compound gave 0.20 g of carbon dioxide and
101. During halogen test, sodium fusion extract is
0.10 g of water. The percentage of carbon in the
boiled with concentrated HNO3 to
given organic compound is ______.
[JEE (Main)-2022]
(Nearest Integer) [JEE (Main)-2022]
(1) remove unreacted sodium
(2) decompose cyanide or sulphide of sodium 105. Which of the following is structure of a separating
funnel? [JEE (Main)-2022]
(3) extract halogen from organic compound
(4) maintain the pH of extract.
102. Given below are two statements:
Statement I: In ‘Lassaigne’s Test’, when both nitrogen (1) (2)

and sulphur are present in an organic compound,
sodium thiocyanate is formed.
Statement II: If both nitrogen and sulphur are present

in an organic compound, then the excess of sodium
used in sodium fusion will decompose the sodium (3) (4)
thiocyanate formed to give NaCN and Na2S.
106. Which of the following is most stable? 111. The formula of the purple colour formed in
Laissaigne’s test for sulphur using sodium
[JEE (Main)-2022]
nitroprusside is [JEE (Main)-2022]
(1) NaFe[Fe(CN)6] (2) Na[Cr(NH3)2(NCS)4]
(3) Na2[Fe(CN)5(NO)] (4) Na4[Fe(CN)5(NOS)]
(1) (2)
112. In the estimation of bromine, 0.5 g of an organic
compound gave 0.40 g of silver bromide. The
percentage of bromine in the given compound is
(3) (4) _____% (nearest integer)
(Relative atomic masses of Ag and Br are 108 u and

107. 116 g of a substance upon dissociation reaction, 80 u, respectively). [JEE (Main)-2022]
yields 7.5 g of hydrogen, 60 g of oxygen and 48.5 113. The complete combustion of 0.492 g of an organic
g of carbon. Given that the atomic masses of H, compound containing ‘C’, ‘H’ and ‘O’ gives 0.793
O and C are 1, 16 and 12, respectively. The data g of CO2 and 0.442 g of H2O. The percentage of
agrees with how many formulae of the following? oxygen composition in the organic compound
_______. [JEE (Main)-2022] is_____.[nearest integer] [JEE (Main)-2022]
(1) CH3COOH (2) HCHO 114. Kjeldahl’s method was used for the estimation of
nitrogen in an organic compound. The ammonia
(3) CH3OOCH3 (4) CH3CHO
evolved from 0.55 g of the compound neutralised
108. 0.25 g of an organic compound containing chlorine 12.5 mL of 1 M H2SO4 solution. The percentage of
gave 0.40 g of silver chloride in Carius estimation. nitrogen in the compound is _____. (Nearest
The percentage of chlorine present in the integer) [JEE (Main)-2022]
compound is ______. [in nearest integer]
115. Observe structures of the following compounds
(Given : Molar mass of Ag is 108 g mol–1 and that of
Cl is 35.5 g mol–1) [JEE (Main)-2022]
109. Which one of the following techniques is not used
to spot components of a mixture separated on thin
layer chromatographic plate? [JEE (Main)-2022]
The total number of structures/compounds which
(1) I2 (Solid) possess asymmetric carbon atoms is _____.
(2) U.V. Light [JEE (Main)-2022]
(3) Visualisation agent as a component of mobile 116. W hich of the following carbocations is most
phase stable? [JEE (Main)-2022]
(4) Spraying of an appropriate reagent
110. Which of the following structures are aromatic in (1)
nature? [JEE (Main)-2022]
(2)
(3)
(1) A, B, C and D (2) Only A and B

(4)
(3) Only A and C (4) Only B, C and D
117. While estimating the nitrogen present in an organic 123. Given below are two statements: one is labelled as
compound by Kjeldahl’s method, the ammonia
evolved from 0.25 g of the compound neutralized Assertion A and, the other is labelled as Reason R.
2.5 mL of 2 M H2SO4. The percentage of nitrogen Assertion A: [6] Annulene, [8] Annulene and
present in organic compound is ________.
cis-[10] Annulene, are respectively aromatic,
[JEE (Main)-2022] not-aromatic and aromatic.
118. The number of sp3 hybridised carbons
in an acyclic
neutral compound with molecular formula C4H5N is
________. [JEE (Main)-2022]
119. The separation of two coloured substances was done
by paper chromatography. The distances travelled
by solvent front, substance A and substance B from Reason R: Planarity is one, of the requirements of
the base line are 3.25 cm, 2.08 cm and 1.05 cm,
respectively. The ratio of Rf values of A to B is_____. aromatic systems.
[JEE (Main)-2022] In the light of the above statements, choose the most
120. Which technique among the following, is most appropriate answer from the options given below.
appropriate in separation of a mixture of 100 mg of [JEE (Main)-2022]
p-nitrophenol and picric acid?
(1) Both A and R are correct and R is the correct
[JEE (Main)-2022] explanation of A
(1) Steam distillation (2) Both A and R are correct but R is NOT the
(2) 2-5 ft long column of silica gel correct explanation of A
(3) Sublimation (3) A is correct but R is not correct
(4) Preparative TLC (Thin Layer Chromatography) (4) A is not correct but R is correct
121. Which of the following compounds is not aromatic? 124. In Carius method of estimation of halogen, 0.45 g of
[JEE (Main)-2022] an organic compound gave 0.36 g of AgBr. Find out
the percentage of bromine in the compound.
(1) (2) (Molar masses: AgBr = 188 g mol–1; Br = 80 g mol–1)

[JEE (Main)-2022]
(1) 34.04% (2) 40.04%
(3) 36.03% (4) 38.04%

(3) (4)
125. Match List-I with List-II
122. The correct decreasing order of priority of functional List-I List-II
groups in naming an organic compound as per
IUPAC system of nomenclature is (Mixture) (Purification Process)
[JEE (Main)-2022] (A) Chloroform & Aniline (I) Steam distillation
(1) COOH ! CONH2 ! COCl ! CHO (B) Benzoic acid & (II) Sublimation
Napthalene
(2) SO3H ! COCl ! CONH2 ! CN
(C) Water & Aniline (III) Distillation
(3) (D) Napthalene & Sodium (IV) Crystallisation
chloride
(4) COOH ! COOR ! CONH2 ! COCl
Choose the correct answer from the options given

below:
[JEE (Main)-2022] (3) (4)
(1) (A)-(IV), (B)-(III), (C)-(I), (D)-(II)
(2) (A)-(III), (B)-(I), (C)-(IV), (D)-(II)
128. Given below are two statements: One is labelled
(3) (A)-(III), (B)-(IV), (C)-(II), (D)-(I)
as Assertion A and the other is labelled as
(4) (A)-(III), (B)-(IV), (C)-(I), (D)-(II) Reason R.
126. Match List - I with List - II Assertion A: Thin layer chromatography is an
List-I List-II adsorption chromatography.
Reason R: A thin layer of silica gel is spread over a

(A) (i) Spiro compound glass plate of suitable size in thin layer
chromatography which acts as an adsorbent.
(B) (ii) Aromatic In the light of the above statements, choose the
correct answer from the options given below
compound [JEE (Main)-2022]
(1) Both A and R are true and R is the correct
(C) (iii) Non-planar explanation of A.
(2) Both A and R are true but R is NOT the
Heterocyclic
correct explanation of A
compound (3) A is true but R is false
(4) A is false but R is true
(D) (iv) Bicyclo compound 129. A sample of 0.125 g of an organic compound
when analysed by Duma’s method yields 22.78
[JEE (Main)-2022]
mL of nitrogen gas collected over KOH solution at
(1) (A) - (II), (B) - (I), (C) - (IV), (D) - (III)
280 K and 759 mm Hg. The percentage of nitrogen
(2) (A) - (IV), (B) - (III), (C) - (I), (D) - (II)
in the given organic compound is____.(Nearest
(3) (A) - (III), (B) - (IV), (C) - (I), (D) - (II)
integer)
(4) (A) - (IV), (B) - (III), (C) - (II), (D) - (I)
Given :
127. Among the following marked proton of which
compound shows lowest pKa value (a) The vapour pressure of water of 280 K is 14.2 mm
[JEE (Main)-2022] Hg.
(b) R = 0.082 L atm K-1 mol-1

(1) (2) [JEE (Main)-2022]

Chapter 21
Organic Chemistry:
Some Basic Principles and Techniques
1. Answer (1) structures. n-propyl carbocation (II) is least stable
as it is stabilised by +I and +H effects of ethyl
CH3 group.
1 2 3
CH3 – C – CH3 8. Answer (4)
CH3 § y· y
CxHy ¨ x ¸ O2 o xCO2 H2O
© 4 ¹ 2
IUPAC name : 2, 2-dimethylpropane
2. Answer (2) 3.08
Number of moles of CO2 0.07; x 0.07
44
CCl3 > C6H5 CH2 > (CH3)2 CH > (CH3)3 C
3. Answer (2) 0.72
Number of moles of H2O 0.04; y 0.08
18
CH3 CH3 CH3 H
C C and C C x : y = 7 : 8.
H H H CH3 Therefore, empirical formula of hydrocarbon is C7H8
cis-2-Butene trans-2-Butene
9. Answer (2)
4. Answer (1) As per question
Θ
R COO HC { CΘ NH2 R Normality Volume
o
increasing basic strength N
H2SO4 60mL
As sp3 C is less electronegative than sp3 N alkyl 5
N
carbanion R is more basic than NH . However
Θ NaOH 20mL
2 10
sp hybridized carbon is more electronegative than
Θ Θ (ngeq )H2SO4 (ngeq )NaOH (ngeq )NH3
sp3 N. Hence NH2 is more basic than HC { C
5. Answer (4) 1 60 1 20
u u (ngeq )NH3
5 1000 10 1000
1.4 NV
%N 6 1
W (ngeq )NH3
500 500
1.4 u 0.1u (20 15)
29.5 u103 5 1
(ngeq )NH3
700 500 100
23.7
29.5
1
6. Answer (2) (nmol )N (nmol )NH3 (ngeq )NH3
100
= 4Se–, non-planar = non-aromatic 14

(Mass)N 0.14 g
100
7. Answer (4)
Benzyl carbocation (III) is more stable than allyl 0.14
Percentage of "N" u100 = 10%
carbocation (I) as it has more number of resonating 1.4
10. Answer (1) CHBr3 and CHI3 are less stable as their conjugate
Percentage of Br bases are stabilised by inductive effect of halogens.
Weight of AgBr Mol. mass of Br Conjugate base of CHCl3 involves back bonding
= Mol. mass of AgBr u Weight of O.C. u 100 between 2p and 3p orbitals.
15. Answer (3)
141 80
= u u100 The acidic strength of the given compounds is
188 250
= 24% decided on the basis of (–I) effect of the
substituents of carboxylic acids. Higher the (–I)
11. Answer (3)
effect of substituent, higher will be the acidic
As glycerol decomposes before reaching its boiling
strength. The decreasing order of (–I) effect of the
point under 1 atm pressure. So, in order to prevent
given substituents is NO2 > CN > F > Cl.
its deomposition, it is distilled under reduced
pressure. Therefore, correct decreasing order of acidic
12. Answer (2) strength
However, all molecules given in options are O2NCH2COOH > NCCH2COOH > FCH2COOH >
stabilised by resonance but compound given in ClCH2COOH
option (2) is least resonance stabilised (other three 16. Answer (4)
are aromatic)
pKb values from NCERT
–
O O (A) EtNH2 3.29
(B) (Et2)NH 3.00
(C) Me3N 4.22
(D) Ph – NH – Me 4.7
13. Answer (2) So, order of basic strength
Kjeldahl method is not applicable for compounds (B) > (A) > (C) > (D)
containing nitrogen in nitro, and azo groups and 17. Answer (4)
nitrogen in ring, as N of these compounds does
Density of dichloromethane is greater than water.
not change to ammonium sulphate under these
So, DCM would be the lower layer and
conditions. Hence only aniline can be used for
water will form the upper layer in the separating
estimation of nitrogen by Kjeldahl’s method.
funnel.
14. Answer (2)
18. Answer (2)
Of the given compounds CH(CN) 3 is strongest
_
acid because
CH(CN)its conjugate
+ base is stabilised by
H + C(CN)
3 3 1
resonance
2
(–) N H 3 4 H
NC
{
C
C–C{N C=C=N Br
C 5
CN N{
4-Bromo-3-methylpent-2-ene
N
C 19. Answer (4)
C–C{N H2O : Sugar – Recrystallisation.
C
N{ Sugar is purified by this method.
H2O : Aniline – Separation by steam distillation.
N
{
C 20. Answer (1)

–
C–C{N Mol of CO2 = 6 so mol of C is = 6

C
C Mol of H2O = 4 so mol of H is = 8
N (–) Mol of N2 = 1 so mol of N is = 2
Formula C6H8N2
21. Answer (2) 26. Answer (1)

The lone pair which is participating in resonance EWG attached to benzene ring will reduce the
and aromaticity will not be a favourable site for basic strength and increase pK b while EDG
protonation. decreases pKb.
Correct order of pKb
d : NH 2 a
N (C) > (A) > (D) > (B)
: Nb
e N
N
c
27. Answer (3)
H
lone pair of N atom b, c and d is not the part of CH 3

aromaticity. 1 2 3 4
H 2C==CH—CH—CH—CH—C {{CH
5 6 7
22. Answer (4)

CH 3 CH 2
Order of acidic strength is
CH 2
CH {{ CH > CH3 — C {{ CH > CH2 == CH2
sp hybridised sp hybridised sp2 hybridised CH 3
carbon carbon and + I carbon

3, 5-dimethyl-4-propylhept-1-en-6-yne
(more effect of —CH3 (less
28. Answer (2)
electronegative) electronegative)
Froth floatation is a method of concentration and it
23. Answer (1)
was discovered by a washer women.
IUPAC name
29. Answer (2)

4 2
5 1 OH
3
3-Hydroxy-4-methyl NO2 NO2
pentanoic acid O2N
OH O
– – O–
O O
24. Answer (3) (A) (B) (C)
Enol content v acidity of active methelene hydrogens.
Stability order C > B > A
O O 30. Answer (1)
CH3 – C – CH – C – CH3 C-OH bond length in methanol, phenol and
p-ethoxyphenol is least in phenol due to resonance
H } Most acidic
Hydrogen and maximum in methanol due to lack of
resonance whereas it will have some intermediate
Maximum enol content value in p-ethoxyphenol.
25. Answer (4) ? correct increasing order is
phenol < p-ethoxyphenol < methanol
NO 2
31. Answer (2)
4
3 Two volatile liquids having their boiling points close
to each other can be separated by fractional
1 2 Cl distillation. Out of the two given liquids, isohexane
CH 3 has lower boiling point and hence will distill out
first.
All Groups attached are to be treated as 32. Answer (3)
substituents and lowest set of locant rule is
Kjeldahl’s method is not applicable to compounds
followed.
containing nitrogen in nitro, azo groups and
2-Chloro-1-methyl-4-nitrobenzene nitrogen present in ring (pyridine).

Order of basic strength
In CH2 == CH – Cl due to resonance, C – Cl bond
H3C CH3
C > CH3 > CH2=CH–CH2 > C CH > C N acquires partial double bond character and has
CH3
(iv) (ii) (iii) (v)
shortest bond length among given species.
(i)
41. Answer (4)
? Order of basicity is : i > iv > ii > iii > v
34. Answer (1) O O O
> >
O Ph
Ph
:
Cl – CH = CH – N
O Active
methylene
due to strong – R effect of – NO2 group, partial (highly acidic)
double bond character between C and Cl
increases.
O O
35. Answer (1) >
Given 0.172 g organic compound showed presence OMe NMe2
of 0.08g Bromine or 172 g organic compound will
show 80 g Bromine which matches, exactly with Lower – M effect as
option (1) compared to —C— group
NH2 O
Contain 80g Bromine 42. Answer (4)

M.W. = 172
H Cl Cl H
Br
36. Answer (4) C C
6 shows
CHO and G.l.
CH3
CH3 CH3
5 3
H 3C 2
4
COOH 43. Answer (1)
1
2, 5-dimethyl-6-oxo-hex-3-enoic acid. N(CH3)2 N(CH3)2 NHCH3 NHCH3

37. Answer (1)
b>c>d>a
CN OH
38. Answer (4)
OCH3
Compound with most acidic hydrogen among the I II III IV
given compounds is
+R effect (–I effect (–I effect
O O and –I effect of –CN of –OH
of OCH3 group) group)
MeO H OMe
O OMe – OCH3 group increases electron density of ring at
39. Answer (4) O and P position making (I) most basic.
CH3 O NHCH3
2 C – OH is least basic due to – I effect of – CN
3
1
CN
Br 4 group at meta position.
4-Bromo-2-methylcyclopentane carboxylic acid. Since – I effect of – CN > – I effect of – OH group
Hence correct basic strength will follow the order 48. Answer (4)
I > II > IV > III Retardation factor (Rf)
1 Distance moved by the

Basic strength v pK value
b substance from base line
=
Order of Kb value Distance moved by the
I < II < IV < III solvent from base line
44. Answer (4)
2
H
=
5
= 0.4
4-methylpent-2-ene
= 4 × 10–1
H
49. Answer (4)
H The sodium fusion extract is acidified with nitric
acid and then treated with silver nitrate.
H geometrical
isomers 50. Answer (2)
H H
Trans Cis Acidic strength
45. Answer (2)
OH
4 NH2
3
5
> > >
6
O2 N 2 1
CHO
5-amino-4-hydroxymethyl-2-nitrobenzaldehyde
46. Answer (50) –I, –R +I, +R
Mass of organic compound = 1.6 gm

Since carboxylic acids are more acidic than
Mass of AgBr = 1.88 gm phenols.
1.88 –I and – R effect increase the acidic strength
Moles of Br = Moles of AgBr = = 0.01 where as +I and +R effect decrease the acidic
188
strength of carboxylic acids.
Mass of Br = 0.01 × 80 = 0.80 gm
51. Answer (3)
0.80 u 100
% of Br = = 50% O – O
½
1.60 N H Has intramolecular hydrogen
47. Answer (2) bonding and steam volatile
¾
O
Melting point is not affected
¿
by intramolecular hydrogen
O- Nitrophenol bonding
Aromatic
O
So the correct option should be (3)
Non-aromatic 52. Answer (1)
Carius method is used for the estimation for
3
sp hybridized halogens and sulphur in organic compound.
53. Answer (2)
Aromatic x Mixture of chloroform and aniline can be
separated by simple distillation as these two
liquids have sufficient difference in boiling point.
Aromatic
Chloroform (b.p. 334 K), aniline (b.p. 457 K)
x In steam distillation, if one of the substances 58. Answer (1)

is water and the other, a water insoluble Lassaigne’s test is used in qualitative detection of
substance (like aniline) then the mixture will N, S, P and halogens.
boil close to but below 373 K. (a) o (iii)
54. Answer (4) Cu(II) oxide is used for the estimation of carbon.
In chromatography technique, the purification of (b) o (i)
compound is independent of physical state of the Silver nitrate is used for detecting halogens in
pure compound. organic compounds (Carius Method)
55. Answer (2) (c) o (iv)
Sodium fusion extract when treated with acetic acid
and lead acetate gives black precipitate if sulphur
is present.
O OH
CH3 — C — CH3 CH3 — C S2– Pb2 o PbS
black
CH2 (d) o (ii)

(< 0.1%)
O O 59. Answer (19)
CH3 — C — CH2 — C — CH3 Pressure due to nitrogen = 758 – 14 = 744 mm Hg
Using ideal gas equation : PV = nRT
H
O O 744 u 30
nN2
CH 3 — C 760 u 1000 u 0.082 u 287
CH3
Intramolecular n N 2 ×28
H-bonding % of nitrogen = u 100
0.184
( 15% )
744 u 30 u 28 u 100
= 760 u 1000 u 0.082 u 287 u 0.184
Acetyl acetone in enol form have intramolecular
= 18.99 %
H-bonding, which is absent in acetone.
| 19%
56. Answer (3)
Conditions for aromaticity are 60. Answer (3)
(i) Planarity Retardation factor (Rf) is the ratio of distance

moved by the substance from the base line to the
(ii) Complete delocalisation of the S electrons in distance moved by the solvent from the base line.
the ring So, it is dimensionless. The distance moved by the
(iii) Presence of (4n + 2)S electrons in the ring substance is due to adsorption of the substance
where n is an integer (n = 0, 1, 2....). on the stationary phase. It does not depend on the
nature of solvent. But the distance moved by the
Compounds B and C are aromatic
solvent will change with the nature of solvent.
Compound A is non-aromatic Therefore, Rf will vary with the change in solvent.
Compound D is anti-aromatic So, both the statements are false.
x NaH is a strong H–
(hydride) donor. Hence A compound which has (4n + 2)S electrons
cannot be used as an oxidising agent. completely delocalised over the cyclic ring is
aromatic.
x Pyridine
N
In Pyridine, lone pair of ‘N’ is localised, makes it n = 1 (Aromatic)

basic.
62. Answer (2)

Kjeldahl’s method can’t be used for compounds + H
CH
containing nitro or azo groups.
Also for compounds containing nitrogen in ring,
O O
Kjeldahl’s method can’t be used.
(e.g. for pyridine or quinoline) Empty P-orbital and S bond P-orbital are not in
same phase to overlap. Hence no conjugation
? Compound gives nitrogen estimation 67. Answer (4)
Metamers have a common functional group and
CH2NH 2 differ in the type of alkyl groups attached to the
functional group
through Kjeldahl’s method.
O O
63. Answer (5)
and are metamers
Structure of mesityl oxide is
O 68. Answer (4)
Halide ion reacts with silver nitrate to give silver
halide precipitate.
Number of C–C sigma bonds = 5
C3H6O (degree of unsaturation = 1) Atomic mass of Br u m1
% of Br = u 100
O O molecular mass of AgBr u m
|| ||
CH3 – CH2 – C – H CH3 – C – CH3 m = mass of organic compound taken
m1 = mass of AgBr obtained.
Functional group isomerism.
65. Answer (2) 80 u 0.2397
? % of Br u 100
188 u 0.15
a
H 3C = 68
b
c
C=C– O 70. Answer (1)
H H Reduced pressure distillation technique is used to
a – sp
3 purify the liquid which decomposes near its boiling
b – sp
2 point.
2
c – sp 71. Answer (4)
66. Answer (3)
+
CH2
+
CH2 CH3 – CH2 – CH = CH – CH2 – NH2
+ (Resonance is not possible in this compound)
CH2
72. Answer (2)
+ *
CH2 (i)
No Resonance
4-methylhex-1-ene has chiral centre

(ii) 76. Answer (1)

Cyclopentadiene is the strongest acid as its
conjugate base is aromatic.
3-ethylhex-3-ene cannot show geometerical
isomerism +
+ H
(iii)
(–)
Aromatic
3, 4–dimethylhex –3-ene can show
geometerical isomerism 77. Answer (12)
wt of N in given organic compound
(iv) *
0.8 u 42
= 0.336 g
100
3-methylhex-1-ene has Chiral centre moles of N = moles of NH3

73. Answer (6) = 0.024
C5H10 ' N1V1 = N2V2
C=C–C–C–C (NH3) (H2SO4)
C – C = C – C – C + geometrical isomer V
0.024 = 2 × 1 ×
1000
C C C C CC C C
| | V = 12
C C 78. Answer (1)
C C C C Total 6 isomers are possible
| NH2 O O
C
74. Answer (1)
CH3 NH2 CH3 NH2
O
N As lone pair of ‘N’ in amide is in conjugation with
carbonyl that is strong electron.
O Withdrawing group, so aniline is more basic than
acetamide.
C – C double bond S electrons move towards –NO2
In aniline, lone pair is less available for protonation.
O 79. Answer (3)
group, so the structure N is Order of stability of carbocation is
O +
CH2
incorrect.
+ + +
> CH3CH2 > CH2 = CH > CH { C
75. Answer (1)
The density of the given organic compounds is A C B D
decided by their molecular mass and polarity. Resonance +ve charge +ve charge +ve charge
3 2
Higher the molecular mass and higher the polarity, on sp on sp on sp
higher will be the density. hybridized hybridized hybridized
carbon carbon carbon
? Correct order of densities is
Br Cl
80. Answer (1)
Cl
Staggered and eclipsed conformers are formed
> > > because of C–C bond rotation. So they are known
Cl Cl as Rotamers.
(D) (C) (B) (A)
81. Answer (19) 87. Answer (1125)

The chemical formula of N,N-dimethylaminopentane
0.3849
Number of moles of AgCl = is C7H17N (Molar mass = 115)
143.37
= 2.684 ×10–3 mol 57.5

Number of moles of C7H17N taken = = 0.5
115
% of chlorine in the compound A is
2.684 u 10–3 u 35.5 § 17 ·

C7H17N ¨ 14 ¸ CuO
u 100 © 2 ¹
0.5
= 19.0564% 17 1 § 17 ·
o 7CO2 H2O N2 ¨ 14 ¸ Cu
82. Answer (3) 2 2 © 2 ¹
Hyperconjugation, inductive and mesomeric effect For 0.5 moles of C7H17N, number of moles of CuO
are permanent electronic effect.
1§ 17 ·
In CH3 CH2 required = ¨ 14 ¸ = 45 = 1125 × 10–2
2© 2 ¹ 4
Overlapping of C – H1s bond with empty 2p 88. Answer (40)
sp 3
orbital of other carbon takes place. Mass of organic compound = 0.2 gm

83. Answer (3) Mass of AgBr = 0.188
Lassaigne’s test – Sodium fusion extract 0.188 u 80
p Mass of Br = = 0.08 gm
188
Used for detection of N, S, X, P
0.08 u 100
X = halogen Percentage of Br in the compound =
0.2
84. Answer (60)
= 40%
dihedral angle is 60°
89. Answer (3)
85. Answer (3)
x Simple distillation can be used to separate a
Non plan ar and number of S mixture of propanol and propanone.
electrons are not equal to Huckel’s x Two liquid with difference in B.P. around 20°C
rule [(4n + 2)S electrons]. Hence it can be separated by simple distillation.
is non-arom atic
x B.P. of propanol is 370 K.
86. Answer (42) B.P. of acetone is 329 K.
SO24
90. Answer (3)
Organic compound o o BaSO4 p
Na O BaCl 2 2 2
Heat
(containing sulphur) 2 1
Br
233 gram of BaSO4 contains 32 gram of sulphur 1 E
1.44 u 32 2
1.44 gram of BaSO4 contains gram of H
233
sulphur
First prioritise the groups according to CIP rule
Percentage of sulphur in the organic compound
It is (2E)-2-Bromo-hex-2-en-4-yne
weight of sulphur 91. Answer (2)
= weight of organic compound u 100
Energy in increasing order is,
1.44 u 32 Anti < Gauche < Partially Eclipsed < Eclipsed

u 100 | 42%
233 u 0.471 I < III < IV < II
92. Answer (7) Mass of H2O = 270 g
§ y· 270
C2H7N ¨ 2x ¸ CuO o
© 2 ¹ Moles of H2O = = 15
18
y z § y· ...(i) Mass of hydrogen = 15 × 2 = 30 gm

xCO2 H2O N2 ¨ 2x ¸ Cu
2 2 © 2¹
30 u 100
Percentage of H = = 25%
§ y· 120
Cx HyNz ¨ 2x ¸ CuO o
© 2¹ 96. Answer (Bonus)
y z § y· The given carbocations are

xCO2 H2O N2 ¨ 2x ¸ Cu ...(ii)
2 2 © 2¹
Comparing (i) and (ii) we get,
x=2
y= 7
z=1
Carbocation (A) is stabilised by hyperconjugation
93. Answer (2)
due to 4 D hydrogen atoms. Carbocation (C) is also
Compounds that are planar and that have (4n + 2)
Se– are aromatic. stabilised by hyperconjugation due to 4 D hydrogen
atoms but destabilised by –I effect of O-atom.
Carbocation (B) is most stable as it is stabilised by
Se– = 6 follows Huckel’s rule = aromatic resonance.
is non-aromatic in nature
94. Answer (63)
30 u 0.25
Millimoles of used acid = ? Correct decreasing order of stability is
2
Millimoles of NH3 = 30 × 0.25 = 7.5 B>A>C
Mass% of nitrogen = None of the given options is correct.
97. Answer (14)
7.5
u 10 3 u 14 u 100 63%
0.166 Mass of organic compound = 0.2 g
95. Answer (4) Volume of N2 gas evolved at STP = 22.4 mL
Mass of organic compound = 120 g
22.4 u 103 u 28
Mass of CO2 = 330 g Mass of N2 gas evolved
22.4
330 = 0.028 g
Moles of CO2 = = 7.5
44
Percentage of nitrogen in the compound
Mass of carbon = 7.5 × 12 = 90 gm
0.028 u 100
90 u 100 14%
0.2
Percentage of C = = 75%
120
It is the staggered conformation with maximum

dihedral angle.
99. Answer (4)
Ethylidene chloride is CH 3 – CHCl2, its IUPAC
name is 1,1-Dichloromethane.
100. Answer (4)
1,3-cyclohexadiene is most stable because it is a
Since, both benzoic acid and naphthalene will
neutral molecule. All others are intermediates and
dissolve in benzene. Hence assertion is wrong.
hence less stable.
Benzoic acid is almost insoluble in cold water but
107. Answer (2)
soluble in hot water. Hence Reason is true
Element Mass% Moles% Relative
101. Answer (2)
During test for halogen, if nitrogen or sulphur is also moles
present in the compound, then sodium fusion H 6.46 6.46 2
extract is first boiled with concentrated nitric acid to
O 51.72 3.23 1
decompose cyanide or sulphide of sodium formed
during Lassaigne’s test. C 41.81 3.48 1
102. Answer (1)
? Empirical formula = COH2
NaSCN + 2Na o NaCN + Na2S
103. Answer (3) The empirical formula goes with acetic acid
CH3COOH and formaldehyde HCHO.
Thus data agrees with 2 formulae.

108. Answer (40)
Mass of organic compound = 0.25 g
Mass of AgCl = 0.40 g
104. Answer (18) 35.5 u (mass of AgCl)

% Cl u 100
143.5 u (mass of organic compound)
12 0.20
C% u u 100
44 0.30 35.5 u 0.40 u 100
143.5 u 0.25
200
= 18.18 | 18
11 39.581
40
105. Answer (1) % Cl = 40 %
The diagram in option (1) clearly represents 109. Answer (3)
separating funnel which is used to separate two
The function of mobile phase is to carry the
immiscible liquids.
components present on TLC.
110. Answer (2) 116. Answer (4)
are aromatic as they are
cyclic, planar and has 4n + 2 S e– (n = 1)

111. Answer (4)
S2– + [Fe(CN)5NO)]2– o [Fe(CN)5(NOS)]4– 117. Answer (56)
NH3 gas is neutralized by 2.5 mL of 2 M H2SO4
Purple
112. Answer (34) ? Moles of NH3 neutralized = 25 × 2 × 2 millimole
= 10×10–3 moles
188 g AgBr has 80 g of Br
? Weight of N present in compound will be
80
? 0.4 g AgBr u 0.4 = 10 × 10–3 × 14
188
= 0.14 g
% of Br in given organic compound
? % of ‘N’ in compound
80 u 0.4
= u 100 0.14
188 u 0.5 = u 100
0.25
| 34%
= 56%
113. Answer (46)
118. Answer (1)
CxHy Oz O2 o CO2 H2O C4H5N
0.793 §H X N·

weight of carbon u 12 0.216 g DBE = C 1 ¨ ¸
44 © 2 ¹
0.442
u2 0.05 g § 5 1·
weight of hydrogen
18 = 4 1 ¨ ¸ 52 3
© 2 ¹
weight of oxygen = 0.492 – (0.216 + 0.05) 3 double bond equivalent are present in compound
= 0.226 g
0.226
% by mass of oxygen in compound u 100
0.492 Only 1 sp3 hybridised carbon is there
46% (Keeping compound as acyclic)

114. Answer (64) 119. Answer (2)
1.4 u N u V Distance travelled by the substance

Rf
% N = Massof organic compound Distance travelled by the solvent front
1.4 u 2 u 12.5 2.08

63.63% 64 (R f )A
0.55 3.25
115. Answer (3) 1.05

(R f )B
3.25
(Rf )A
2
(R f )B
120. Answer (4) (C) Water & Aniline (I) Steam distillation
Thin layer chromatography is a technique used to
(D) Napthalene (II) Sublimation (only
isolate non-volatile mixtures.
& Sodium chloride naphthalene has
Hence, mixture of p-nitrophenol and Picric acid is
separated by TLC. the tendency for
121. Answer (3) sublimation)
126. Answer (3)
is a non-planar compound,
(A) = Non-planar
hence it is not aromatic. Heterocyclic

122. Answer (2)
compound
The order of decreasing priority for functional group is
–COOH > –SO3H > – COOR > –COCl > – CONH2 > (B) = Bicyclo compound
–CN > –CHO > > –NH2
(C) = Spiro compound
Hence correct order is
–SO3H > –COCl > –CONH2 > –CN
123. Answer (4) (D) = Aromatic compound
[6] Annulene is aromatic because it is planar. 127. Answer (3)

[8] Annulene and [10] Annulene are both not
aromatic because they are not planar. So, Assertion
(A) is not correct.
Reason (R) is correct because planarity is one of

the requirements of aromatic system.
124. Answer (1)
188 g of AgBr = 80 g of Br
80
0.36 g of AgBr = u 0.36
188
% of Br in given organic compound
80 u 0.36
= u 100
188 u 0.45
= 34.04 %
125. Answer (4)
The correct match is
(A) Chloroform (III) Simple distillation
& Aniline
(B) Benzoic acid & (IV) Crystallisation
Napthalene (Sublimation is
not used as both
sublime heating)
The conjugate base of compound (C) is stabilized 129. Answer (22)
by extended conjugation. Hence the indicated Pactual = 759 – 14.2 = 744.8 mmHg
proton of compound C is most acidic i.e. will have 744.8 u 22.78
nN2
lowest pKa. 760 u 0.0821u 280 u 1000
128. Answer (1) = 0.000971 mol
Thin layer chromatography is an adsorption Mass of N2 = 0.02719 gm

chromatography. A thin layer of silica gel is spread Percentage of nitrogen
over a glass plate of suitable size and act as an
0.0271
adsorbent. = u 100 21.75 22
0.125


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Chapter 21

(2) DCM and H2O will be miscible clearly

the favourable site/s for protonation is/are F

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

(2) H3C – C { C – H CHCl CH2

[JEE (Main)-2020] (1) IV > III > II > I

(3) (4) (3) Statement I is true but statement II is false

Base line (3) Kjeldahl’s method is used for the estimation of

[JEE (Main)-2021] 53. Given below are two statements:

(1) A is false but R is true (1) (a)-(iii), (b)-(i), (c)-(iv), (d)-(ii)

(4) Statement I is true but statement II is false

Among the given species the Resonance stabilised

[JEE (Main)-2021] 67. Which one of the following pairs of isomers is an

70. Which purification technique is used for high boiling

Cl Cl (1) C > A > D > B (2) D > B > C > A

80. Staggered and eclipsed conformers of ethane are

(3) Polymers (4) Enantiomers

97. 0.2 g of an organic compound was subjected to

In the light of the above statements, choose the most

(3) 1, 2-Dichloroethane (4) 1, 1-Dichloroethane (4) Statement I is incorrect but Statement II is

Assertion A: A mixture contains benzoic acid and

102. Given below are two statements:

Statement I: In ‘Lassaigne’s Test’, when both nitrogen (1) (2)

Statement II: If both nitrogen and sulphur are present

(Relative atomic masses of Ag and Br are 108 u and

(1) A, B, C and D (2) Only A and B

(1) (2) (Molar masses: AgBr = 188 g mol–1; Br = 80 g mol–1)

(3) 36.03% (4) 38.04%

[JEE (Main)-2022] (A) Chloroform & Aniline (I) Steam distillation

(3) (D) Napthalene & Sodium (IV) Crystallisation

Choose the correct answer from the options given

Reason R: A thin layer of silica gel is spread over a

(b) R = 0.082 L atm K-1 mol-1

= 4Se–, non-planar = non-aromatic 14

C 20. Answer (1)

C–C{N Mol of CO2 = 6 so mol of C is = 6

21. Answer (2) 26. Answer (1)

lone pair of N atom b, c and d is not the part of CH 3

22. Answer (4)

carbon carbon and + I carbon

29. Answer (2)

33. Answer (3) 40. Answer (2)

Contain 80g Bromine 42. Answer (4)

2, 5-dimethyl-6-oxo-hex-3-enoic acid. N(CH3)2 N(CH3)2 NHCH3 NHCH3

1 Distance moved by the

Mass of organic compound = 1.6 gm

x In steam distillation, if one of the substances 58. Answer (1)

CH2 (d) o (ii)

(i) Planarity Retardation factor (Rf) is the ratio of distance

In Pyridine, lone pair of ‘N’ is localised, makes it n = 1 (Aromatic)

62. Answer (2)

66. Answer (3)

4-methylhex-1-ene has chiral centre

(ii) 76. Answer (1)

3-methylhex-1-ene has Chiral centre moles of N = moles of NH3

81. Answer (19) 87. Answer (1125)

= 2.684 ×10–3 mol 57.5

2.684 u 10–3 u 35.5 § 17 ·

orbital of other carbon takes place. Mass of organic compound = 0.2 gm

1.44 u 32 Anti < Gauche < Partially Eclipsed < Eclipsed

92. Answer (7) Mass of H2O = 270 g

y z § y· ...(i) Mass of hydrogen = 15 × 2 = 30 gm

y z § y· The given carbocations are

0.793 §H X N·

46% (Keeping compound as acyclic)