STEP-2

For JEE(Main) & State Engineering Entrance Exams

Assignment
codes are provided for Video solutions of selected solution.
G QR questions. Please Scan QR code to watch the
Questions to be discussed in Class.

Objective Type Questions (One option is correct) 4. Three-dimensional arrangements which can be
interconverted into one another due to rotation
[Nomenclature]
along a single bond are known as
The IUPAC name of the compound (1) Conformers
CH, (2) Tautomers
CH,
CH (3) Chain isomers
CH, (4) Positional isomers
CH, ÇH-
¢ CH 5 Which of the following compounds will have
CH, H cHs highest enolic content?

CH, CHa
(1) (2) CH,COCH,CHO
(1) 3-disopropyl-2,4-dimethylpentane
(2) 2, 4-dimethyl-3-disopropylbutane (3) CH,CHO (4) CH,COCH,
(3) 2, 4-dimethyl-3-3-bis(1-methylethyl) 6 Compound having molecular formula CsH,,0
pentane cannot show
(4) None of these (1) Tautomerism
Me (2) Position isomerism
(3) Metamerism
2. The IUPAC name of the compound (4) Functional isomerism
7 Which of the following compounds cannot have
Ét a r bond?
(1) 3-methyl-6-ethylcyclohexene (1) C,oHz,N (2) C,H2
2) 6-ethyl-3-methyl cyclohexene (3) CgoHCi,0 (4) CysHsoBr,0,
8 Which of the following contains chiral carbon?
(3) 3ethyl-6-methylcyclohexene
4) 6-methyl-3-ethyl cyclohexene (1) 1-Bromobutane (2) Butan-2-ol
(3) Propane (4) Propan-2-ol
[lsomerism] [Intermedlate, Electron Displacement in
3
Covalent Bond, Hyperconjugation]
The compounds and 9 Which willhave highest meltingpoint?
are
(1) (2)
(1) Chain isomers (2) Metamers
(S) Position isomers (4) Both (1) &(2) (4)
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 Differe!eonomat.

146 Organic Chemistry :Some Basic Principles (Main) & State

and Techniques JEE Engineering Entrance
free Exarns
10. Out of the given reactive 18. Correct stability order of the given
intermediates which
Wll be attracted towards the
(1) Carb0cation
magnetic field? is

CH,
radicals
(2) Carbanion
(1)
(3) Cartbon free radical
(4) Nitrene
11. Which of the following
CH, (CHH
species cannot behave
as electrophile? , >CHC>(CH),H
(2)
(1) BCI, (2) AICI,
(3) NH, CH,
(4) SO,
12. At conjugated position -
NO, imparts
(1) +M and +l effect (2) -M and
(3) +M and - effect (4) -M and +|
effect (9) CH-¢> (O-, >(CH)OH
effect CH,
13. Which of the
following groups will have
strongest electron-donating mesomeric effect?
(1) - (2) -N Me
Me
CH,
19*. Among the following, the most stable carbocatinn
(3)
H,C
14. Which ofthe following organic
molecules cannot (1) CH, -CH-CH, (2)
form hydrogen bond in pure state but can form
the same in water?
(1) (CH,CH,),NH (2) CH,CHO
(3) (4)
(3) CH,CH,COOH (4) CH,-C-NH, 20. Least stable carbocation among the following
15. Inthe given anion, -ve charge is delocalized on
ÇH,
H,C-Ç-CH, CH,
(1) One atom (2) Three atom (1)
(3) Four atom (4) Five atom
(2)
16. Resonance is not possible in

(1) (2) GH, (3) CH,-- CH, (4)

CH,
(3) NO, (4) BH,
21*. In which of the following molecules positve
17. The most stable free radical is charge is not delocalized because of resonance:
NH

(1) | (2) (1) (2)

"CH
H,RNH,
NH,
(3) (4 Me
(3)-Ñ
Me
Me
Me (4) NH,NH
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 (Main).& State
JEE
Engineering Entrance Exams Organic Chemistry: Some Basic Principles and Techniques 147
22 Which ofthe following reactions will not
generatea carbanion? 27. Most acidic species among the following is

(1) CH, -C- CH, (2) CH, -0-H

(1) NaOEt
Et-OH (3) CH,-C= C-H (4)
28. Which of the following is most acidic?
NH,.
(2)
NO,
NH, NH,
SbFk (1) (2)
(3)

(4) CH, -C=C-H

NaNH, NH
23. Strongest and weakest acids among the (3) CH,-0-H (4) H,N -NH,
following are 29*. Which of the following compounds will not
1. CH, - NO, dissolve in aqueous NaOH?
II. CH,-CHO
Il. CH, -F
(1) (2) OH
IV. CH,-CN
H OH
(1) land I| (2) IlIl and IV
(3) land I| (4) l and |l|
24. Correct order of acidic strength for the given (3) (4)
species.
OH

I. CH-CæGH [Aromaticity]
I. CH-CH CH, 30. Which of the following is the strongest base in
water?
lI. CH C=C-H
(2)
IV
H
(1) | >||> V>| | (2) || > IV >||>|
(3) II| >|> |V> || (4) |> I| >|V> | (3) (4)
25". Most acidic species among the following is
(1 (2 31. In which of the following, all electronic
effects namely inductive, mesomeric and
hyperconjugative effects are present?
(3) (4)

c0. Which of the following hydrocarbons is most

acidic? (1) (2) Hal CH,

(1) (2 CH,
(4)
(3) (4)

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148 Organic Chemistry : SomeBasic
Principles and Techniques JEE(Main) &State Engineering
32. Which of the Entrance E xams
following is correct order of dipoie (1) II|>|>|| (2) |> | >|
moment of o, m and p-methyl (3) || >| >| (4) ||> >|
CH, CH,
benzonitrile?
CH, 36. In which of the following homolytic
(1)
CN
takes place? bond fis ion
CN
(1) Alkaline hydrolysis of ethylchloride
CN
(2) Additión of HBr to double bond
CH, CH, CH, (3) Photochlorination of methane
CN (4) Nitration of benzene
(2
[Purification]
CN 37. Amixture containsfour solid organic,
CH,
CN
CH, CH, A, B, Cand D. On heating, only C Compounds
changest
solid to vapour state. The compound sfrom
(3) be separated from the mixture by (C) can
(1) Distillation
CN
CN (2) Kinetic resolution
CH, CH, CH, (3) Crystallization
CN (4) Sublimation
(4) 38. Which of the following reagents can be used to
CN separate benzoic acid from a mixture of Benznie
CN acid, Phenol, Benzaldehyde and Toluene?
33. Among the (1) aq. HCI (2) aq. NaHCo,
following, the correct order of
reactivity of chloride is (3) Diethyl ether (4) NaOH
C CI [Qualitative and Quantitative Analysis of
Organic Compounds]
39*. Which of the following compounds will give
negative Lassaigne's test for Nitrogen?
(1) |> ||> I|I| (2) I| > I| >| (1 NH,
(3) I| >|>| | (4) I| >I| >|
34*. Which of the following double bonds in the given
molecule is most reactive towards astrong (2)
protic acid?
Me A
(3)
-Me
B D
Me
(4) NO,
(1) A (2) B
(3) C (4) D 40. Which of the following compounds will 9ive
35. Which of the following represents the correct blood red colour while doing the Lassaigne s
order of stability of the given carbocations? test for N?
(1) (NH2),C=0 (2) H,N (CH,) SO,H
CH,
NH,

(3) C,H,SO,H (4)

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 Cloen

(Main)&State Engineering Entrance Exams

EE Organic Chemistry:Some Basic Principles and Techniques 149
Numerical Value Based Questions
50. Asample of 0.5 g of an organic compound was
The
How many the treated according to Kjeldahl's method.
of
following molecules can ml of
41 undergotautomerisation in the
presence of ammonia evolved was absorbed in 100
60
acid? 0.25 M H,SO,. The residual acid required
for neutralisation.
ml of0.5 M solution of NaOH
Find the percentage composition of nitrogen in
the compound.
51. During estimation of nitrogen present in an
organic Compound by Kjeldahl's method, the
ammonia evolved from 0.73g of the compound
neutralized 100 mL of 0.5 M H,SO,. If 0.73 g
Duma's
of this organic compound is used in
method, then x mL of nitrogen (N,)is collected
at 300 Kand623 mm of Ha pressure. The value
12. Total number of ketones (excluding of x/30 is
stereoisomer) with molecular formula CaH,,0 is (Aqueous tension at 300 K is 15 mm and
0.08 atm L
13. How many structural heterocyclic ethers of R
molecular formula GH,O are possible? molK

What is the index of hydrogen deficiency in the PREVIOUS YEARS QUESTIONS

molecule C.,H,,NO?
K How many of the tollowWing molecules will have Objective Type Questions
degree of unsaturation equal to three or greater [Nomenclature]
than three? 52. The IUPAC name of ethylidene chioride is
[JEE (Main)-2022]
(1) 1-Chloroethene
Ph
(2) 1-Chloroethyne
-a, La,
(3) 1,2-Dichloroethane
(4) 1, 1-Dichloroethane
53. The correct decreasing order of priority
Ph
of functional groups in naming an organic
Ph
compound as per IUPAC system of nomenclature
is (JEE (Main)-2022]
of
46. The number of possible geometrical isomers (1) -COOH >-CONH, >-COCI >-CHO
the following compound is (2) -SO,H >-COcl> -CONH, >-CN
CH= CH-CH= CH, (3) -COOR> -COC| > -NH, > C=0
(4) -COOH>-COOR>-CONH, > -COCI
54. What is the IUPAC name of the following
possible compound? [JEE (Main)-2019]
3 How many geometrical isomers are
for the following compound? QH, CH,
CH- CH= CH- CH,
H
CH; Br
CH,
Number of hyperconjugable hydrogens of (1) 3-Bromo-1, 2-dimethylbut-1-ene
propene is
49, On complete combustion of 2g of an organic (2) 4-Bromo-3-methylpent-2-ene
amount (3) 3-Bromo-3-methy-1,2- dimethylprop-1-ene
VUmpound gave 4.4g of CO, and some
composition
Orwater. What is the percentage compound? (4) 2-Bromo-3-methylpent-3-ene
y mass of carbon in the organic
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Corporate Office
 AlTArnnl ges and Moe

150 Organic Chemistry : Some Basic Principles and JEE(Main) & State Engineering
55. Choose the correct name for
Techniques
59. The correct IUPAC nomenclature
Entrance Exams
below, compound give
(JEE (Main)-2021]
following compound is:
[JEE (Main)f-o2r0231the
Br CH CH,
H,C CH,
COOH
(1)
(4E)-5-Bromo-hex-2-en-4-yne
(2)
(2E)-2-Bromo-hex-4-yn-2-ene (1) 2-Methyl-5-oxohexanoic acid
(3)
(2E)-2-Bromo-hex-2-en-4-yne (2) 2-Formyl-5-methylhexan-6-oic acid
(4)
(4E)-5-Bromo-hex-4-en-2-yne (3) 5-Methyl-2-oxohexan-6-oic acid
56. The IUPAC name for (4) 5-Formyl-2-methylhexanoic acid
the
following compound is
CHO [lsomerism]
CH 60*. In the following molecule,
H,C
COOH (JEE (Main)-2021]
(JEE (Main)-2020]
(1) 6-formyl-2-methyl-hex-3-enoic acid
(2) 2, 5-dimethyl-6-carboxy-hex-3-enal H H
(3) 2, 5-dimethyl-5-carboxy-hex-3-enal
(4) 2, Hybridisation of Carbon a, b and c respectively
5-dimethyl-6-0X0-hex-3-enoic acid
57. The IUPACname of the following are
compound is (1) sp°, sp, sp (2) sp', sp', sp
CH,
-OH
(3) sp', sp, sp (4) sp", sp,sp
61. Which one of the following pairs of isomers is
an example of metamerism?
Br [JEE (Main)-2021]
[JEE (Main)-2020] OH
(1) 3-Bromo-5-methylcyclopentane carboxylic
acid
(1) H,c, OH and H,C,
(2) 3-Bromo-5-methylcyclopentanoic acid
(3) 5-Bromo-3-methylcyclopentanoic acid
(4) 4-Bromo-2-methylcyclopentane carboxylic (2) CH,CH,CH,CH,CH, and H,c-¢-CH,
acid H,
58. The IUPAC name of the following compound is
OH

NH,
(3) c,H and H,Cg

O,N
CHO
[JEE (Main)-2020] (4)
(1) 4-amino-2-formyl-5-hydroxymethyl 62. Which of the following compounds will
nitrobenzene the maximum 'enol' content? Snow
(2) 5 -amino-4 - hydroxymethyl-2 (JEE (Main)-2019]
nitrobenzaldehyde (1)CH,COCH,CO0C,H,
(3) 3-amino-4-hydroxymethyl-5 (2) CH,CoCH,
nitrobenzaldehyde
(4) 2-nitro -4-hyd roxymethyl-5-amino (3) CH,COCH,COCH,
benzaldehyde (4) CH,COCH,CONH,
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JEE
Engineering Entrance Exams
(Main)& State Organic Chemistry: Some Basic Principles and Techniques 151
Assertion A: Enol form of 67*, Match List- with List-|l.
63
acetone [CH,COCH,) exists [JEE (Main)-2022]
in<0.19% quantity. However,
the enol form of acetyl acetone List-| D3
List-l
rCH,COCH,OCCH,] exists in (i) Spiro compound
approximately 15% quantity,. (A)
Reason R: Enol form of acetyl acetone is (iü) Aromatic compound
(B)
stabilized by intramolecular hydrogen bondina,
which is not possible in enol form of acetone. (ti) Non-planar
Choose the correct statement. heterocyclic
(JEE (Main)-2021] compound
(1) A is false but R is true (iv) Bicyclo compound
(2) Both Aand Rare true and R is the correct
explanation of A (A)- (I),(B) - (),(C) - (IV), (D) - (1)
(1)
(3) A is true but R is false (2) (A) -(V),(B) -(1),(C) - (), (D) - (1)
(4) Both A and R are true but R is not the (3) (A) -(I),(B) -(V),(C)- (), (D)- (1)
correct explanation of A
(4) (A) -(), (B) -(1), (C) -(1), (D)-(|)
BA Which willhave the highest enol content?
(JEE (Main)-2022]) (Intermediate, Electron Displacement in
Covalent Bond, Hyperconjucation]
68. The correct decreasingorder for acid strength
(1) (2) is [JEE (Main)-2019]
(1) FCH,COOH > NCCH,COOH>
NO,CH,COOH>CICH,COOH
(3) (4) (2) CNCH,cOOH >0,NCH,COOH>
FCH,COOH > CICH,C0OH
(3) NO,CH,COOH >NCCH,COOH >
65. Which one of the following molecules does not FCH,COOH> CICH,COOH
showstere0-isomerism? (JEE (Main)-2021|] (4) NO,CH,COOH> FCH,COOH >
(1) 4-Methylhex-1-ene
CNCH,COOH > CICH,COOH
(2) 3-Ethylhex-3-ene
69.
(3) 3,4-Dimethylhex-3-ene
(4) 3-Methylhex-1-ene
b6. In the following structures, which one is having
staggered conformation with maximum dihedral
angle? (JEE (Main)-2022]
(A) (B)
H. CH,
CH, CH
(1) (2)
H H
H CH,
(C) (D)
CH,
H CHsÇH, Among the given species the Resonance
stabilised carbocations are
(3) (JEE (Main)-2021]
(4)
H H (1) (C) and (D) only (2) (A), (B) and (C) only
CH, H (3) (A) and (B) only (4) (A), (B) and (D) only
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 , Magnetin
lectromaona
,

152 organic Chemistry : Some Basic Principles and JEE (Main) &State Engineering
Techniques
order of the
Entrance Exarma
70. Amange the following 75. The increasing
order of stability. cartbocations in decreasing
[JEE (Main)-2022]
the
a-hydrogen of following acidit
compoundsy ofisthe
TJEE (Main)-20201
A Phr
B Ph
(1) A>C>B (A) (B)
(2) A> B>C
(3) C > B>A (4) B>A>C
71. Which of the following
stable? carbocations is most OM
Me
OCH,
[JEE (Main)-2022]
(C) (D) NMe,
(1)
(1) (C) <(A) <(B) <(D)
OCHa (2) (B) <(C) <(A)<(D)
(2) (3) (A)<(C)<(D) <(B)
(3) H,CO. (4) (D) < (C) < (A) < (B)
76*. Which one among the following
(4) H,Co»
72. The correct order of stability for the
structures is not correct? resonating
following (JEE (Main)-2021)
alkoxides is [JEE (Main)-2020]
(1)

NO2 NO, (2)

(A) (B) (C)
(1) (B) > (A) >(C) (2) (C) >(B) >(A)
(3) (B) > (C) > (A) (4) (C) > (A) > (B) (3)
73. Arrange the following compounds in increasing
order ofC-OH bond length
[JEE (Main)-2020]
methanol, phenol, p-ethoxyphenol (4)
(1) phenol <p-ethoxyphenol < methanol
(2) methanol < phenol < p-ethoxyphenol 77. Among the following marked proton of which
(3) methanol < p-ethoxyphenol < phenol compound shows lowest pk, value.
(4) phenol < methanol <p-ethoxyphenol [JEE (Main)-2022]
74*. Arrange the following labelled hydrogens in
decreasing order of acidity
[JEE (Main)-2020] (1) HzC-COOH
NO, C=C-,
(2) H,C-C- CH,
H
-0 Coo CHg
(3)
(1) b>c>d>a
(2) b>a >c>d H
OH
(3) c> b>d>a
(4)
(4) c>b>a>d
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 Engineering Entrance Exams Techniques 153
(Main)& State ganic Chemistry:Some Basic Principles and
EE
two
Given below are statements : 81. Match LIST-| with LIST-II.
78.
Statement|:Hyperconjugationis a LIST-I
permanent LIST-I
effect.
Type of
StatementI|:Hyperconjugation in Isomeric pairs
ethyl cation isomers

IcH, -CH,) involves the overlapping of A. Propanamine and Metamers

H bond with empty 2p orbital of other N-Methylethanamine
carbon. B Hexan-2-one and ||. Positional
isomers
Choose the corect option. Hexan-3-one
[JEE (Main)-2021] Functional
(1) Both statement l and statement Il are true C.Ethanamide and
Hydroxyethanimine iSomers
(2) Statement I is incorrect but statement || is
true D.0-ntrophenol and IV. Tautomers
p-nitrophenol
(3) Statement I is Correct but statement || is
false
Choose the correct answer from the options
) Both statement I andstatement Ilare false given below. [JEE (Main)-2023]
To The most stable carbocation for the following (1) A-lI, B-I, C-IV, D-l|
[JEE (Main)-2023] (2) A-IV, B-IlI, C-I, D-I|
NHg NH2 NH, NH, (3) A-ll, B-llI, C-I, D-IV
(4) A-lI,B-IV, C-1, D-1|
[Aromaticity]
82. Which one of the following compounds is not
aromatic? [JEE (Main)-2021]
(1) a
(2) b (1) (2)

(3) d
(4) c
80. Which willundergo deprotonation most readily (4)
in basic medium [JEE (Main)-2023]
83. The increasing order of basicity of the following
Compounds is [JEE (Main)-2020]
Me0 OMe
b

OMe

(A) (8) (C) (D)

(1) conly
(2) aonly (1) (B) <(A) <(D) <(C)
(2) (D) <(A)<(B) <(C)
(3) Both a and c (3) (B) <(A) <(C) <(D)
(4) bonly (4) (A)<(B) <(C) <(D)
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 &Matter
-Blo Tinciples
i &D Waves
154 Organic Chemistry : Some Basic JEE (Main) & State Engineering

84*. The increasing order of the

Principles and Techniques
pk, of the following 87. Among the following, the aronmatic
Entrance Exarms
compound is [JEE (Main)-2019] are

(A) (B)
Compounds
(A)

(D)
CH,0 Choose the correct answer from
(B) the
options.
(1) (A), (B) and (C) only
(JEE (Mai nfo)-2021
l owing
(2) (B), (C) and (D) only
O,N, (3) (B) and (C) only
(C) (4) (A) and (B) only
88. Which of the folowing is most stable?
H H
[JEE (Main)-2022)
H,C
S
(D) (1) (2)

H H
(1) (B) <(D) < (A) <(C) (3) (4)
(2) (A) <(C) <(D) <(B) 89. Which of the following structures are aromatic
(3) (B) < (D) < (C)< (A) in nature?
(4) (C)< A)< (D) < (B)
[JEE (Main)-2022]
85. The decreasingorder of basicity of the following
amines is (JEE (Main)-2020]
NH, A C
NH,
(1) A, B, Cand D
(2) Only Aand B
() (I) (I) (IV) (3) Only Aand C
(1) (1) > () > () > (1V) (4) Only B, Cand D
(2) (I1) > (1) > (1V) > (|) 90*. Which of the following compounds is not
(3) (1) > (i) > (V) > ()
aromatic? [JEE (Main)-2022)
(4) (1I) > (1) > () > (V)
86. The increasing order of the pK, values of the (1)
following compounds is [JEE (Main)-2019]
OH OH OH OH
(2)

NO, OMe (3)

A B D

(1) D <A< C<B (2) B<C<D<A

(3) B< C <A<D (4) C<B<A<D (4)

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 State Engineering Entrance Exams Organic Chemistry:Some Basic Principles and Techniques 155
(Main) &
EE
two
Givenbeloware statements: one is labelled [Purification]
o Assertion A and, the other is labelled as
Reason R. 94. If dichloromethane (DCM) and water (H,0) are
Assertion A: Annulene, [8] Annulene and used for differential extraction, whichone of the
cis-[10]| Annulene, are respectively aromatic, following statements is correct?
not-aromatic and aromatic. [JEE (Main)-2019]
(1) DCM and H,0 will make turbid/colloidal
H mixture

(6]Annulene [8] Annulene cis-[10] Annulene (2) DCM and H,0 will be miscible clearly
Reason R: Planarity is one of the requirements (3) DCM and H,0 would stay as upper and
of aromatic systems. lower layer respectively in the separating
In the light of the above statements, choose
funnel (S.F.)
the most appropriate answer from the options (4) DCM and H,O would stay as lower and
given below. [JEE (Main)-2022] upper layer respectively in the S.F.
(1) Both A and R are correct and R is the 95. The correct match between items Iand || is
correct explanation of A Item-! Item-1|
(2) Both AandR are correct but R is NOT the (Mixture) (Separation
correct explanation of A method)
(3) A is Correct but R is not correct (P) Sublimation
(A) H,O:Sugar
(4) A is not correct but R is correct (Q) Recrystallization
(B) H,0:Aniline
92. Amongthe foliowingcompounds, the one which (C) H,0:Toluene (R) Steam distillation
shows highest dipole moment is
(S) Differential
[JEE (Main)-2023] extraction
(JEE (Main)-2019]
(1) (1) (A) ’ (R), (B) ’ (P), (C) ’ (S)
(2) (A)’ (S), (B) ’ (R),(C) ’> (P)
(3) (A)’ (Q), (B) -’ (R), (C)’ (P)
(2) (4) (A) ’ (Q), (B) ’ (R), (C)’ (S)
96. Given below are twO statements : one is
(3)
labelled as Assertion (A) and the other is
labelled as Reason (R). [JEE (Main)-2021]
Assertion (A) : A simple distillation can be
(4) used to separate a mixture of propanol and
propanone.

93. Given below are two statements : Reason (R):Two liquids with a difference of
more than 20°C in their boiling points can be
Statement I: Tropolone is an aromatic separated by simple distillations.
Compound and has 8 t electrons.
In the light of the above statements, choose the
Staternent Il : electrons of >C=0 group in
tropolone is involved in aromaticity. most appropriate answer from the options
given below.
Inthe light of the above statements choose the
Correct answer from the options given below: (1) (A) is false but (R) is true
[JEE (Main)-2023] (2) (A) is true but (R) is false
() Statement I is true but Statement |l is false (3) Both (A)and (R)are correct and (R) is the
1<) Statement I is false but Statement Il is true correct explanation of (A)
(3) Both Statement l andStatement ll are false (4) Both (A)and (R) are correct but (R) is not
(9) Both StatementIand Statement Il are true the correct explanation of (A)
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 156 Organic Chemistry : Some
97. Basic Principles and Techniques JEE (Main) & State Engineering
Which purification
boiling organic liguidtechnigue is used for hign
compound
101. Which technique among the Entrance Exams
near its boiling
(1) Reduced point)? [JEE (decomposeS
(Main)-2021]
pressure distillation
(2) Simple distillation
(3) Steam distillation
most appropriate in
separation
100 mg of p-nitrophenol and
(1) Steam distillation
fol owing,
of a
is
mid?xlure of
[JEEpicric(Maiacin)-20221
(4) Fractional distillation (2) 2-5 ft long column of silica gel
98.
Given below are two (3) Sublimation
State ment |:A statements:A
mixture of (4) Preparative TLC (Thin Layer
chloroform and aniline can be Chromatography)
separated by simple distillation. 102. Match List-Iwith List-I|.
Statement Il: When separating aniline from a
mixture of aniline and List-I [JEE
List-|
(Main)-2022
aniline boils belowitswater by steam distillation
boiling point. (Mixture)
In the light of the
above statements, choose
the most appropriate answer (A) Chloroform & (1)
(Purification
Process)
Steam distillation
given below. from the options
(1) Both statement | and
[JEE (Main)-2021] Aniline

(2) Both statement|and statement are false

|l (B) Benzoic acid & (1) Sublimation
(3) Statement Iis true but
statement || are true Naphthalene
(4) Statement l is false but
statement I| isfalse (C) Water &Aniline (1) Distillation
99 statement || is true
Given below are two statements: one is (D) Naphthalene & (IV)Crystallisation
as Assertion A and the labelled Sodium chloride
other is abelled as
Reason R. Choose the Correct answer
Assertion A:A mixture contains benzoic acid from the options given below:
and naphthalene. The pure benzoic acid can
be separated out by the use of benzene. (1) (A}-(V), (B-(I|1), (C-(), (D}()
Reason R: Benzoic acid is soluble in hot water. (2) (A)-(I), (B)-(), (C-(V). (D-(l)
In the light of the above (3) (A}(I), (B)-(V), (C)-(I1), (D-()
statements, choose
the most appropriate answer from the options
given below.
(4) (A-(), (B-(V), (C-(), (D}-(I1)
[JEE (Main)-2022] 103. Given below are two statements :
(1) Both A and R are true and Ris the correct
explanation of A Statement I: Retardation factor (R,) can be
(2) Both A and R are true but R is NOT the measured in meter/centimeter.
Correct explanation of A Statement Il: R, value of a compound remains
(3) A is true but R is false Constant in all solvents.
(4) A is false but R is true Choose the most appropriate answer from the
100*.Which of the following is structure of aseparating options given below. [JEE (Main)-2021]
funnel? [JEE (Main)-2022] (1)Statement Iis true but statement Il is false
(2) Both statement I andstatement Ilare true
(3) Both statement Iand statement ll are tals
(1) (2) (4) Statement l| is false but statement II iS truo
purification
104. In chromatography technique, the
of compound is independent of (Main)-2021]
[JEE
(1) Solubility of the compound
(3) (4) (2) Mobility or flow of solvent system
(8) Length of the column or TLC Plate
compound
(4) Physical state of the pure
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 &
EE(Main) State Engineering Entrance Exams genic Chemistry : Some BasicPrinciples and Techniques 157

Which
one ofthe following techniques is 108. Match items of columns-l and ||
used to spot Components of a mixture
not
separatedon thin layer chromatographic Column-! Column-4|
plate? [JEE (Main)-2022] (Mixture of (Separation
compounds) Technique)
(1)4 (Solid)
() Crystallization
(2)U.V.Light (A)H,0/ CH,CI,
Visualisation agent as a component of (OH (i) Differential
(3)V (B)
mobile phase solvent
extraction
(4) Spraying
of an appropriate reagent
below are two statements: One is labelled NO,
106. Given
Assertion A and the other is labelled as
(C)| KerOsene / (ii) |Column
ReasonR. chromatography
Naphthalene
Assertion A: Thinlayer chromatography is an (D) C,H,20,/ NaCl (iv)|Fractional
adsorption chromatography. Distillation

Reason R: Athin layer of silica gel is spread Correct match is [JEE (Main)-2023]
plate of suitable size in thin layer
Over a glass
chromatography which acts as an
adsorbent. (1) A-(i), B-(ii), C-(v), D-(i)
statements, choose the (2) A-(i), B-(iv), C-(i), D-(ii)
In the light of the above
correct answer from the options
given belo. (3) A-(), B-(ii), C-(i), D-(iv)
[JEE (Main)-2022] (4) A-(iiü), B-(iv), C-(ii), D-(i)
and R is the correct column chromatography
(1) BothAand R are true 109. From the figure of statements.
explanation of A. given below, identify incorrect
true but R is NOT the
(2) Both A and R are
Correct explanation of A
false
(3) A is true but R is
(4) A is false but R is true
[JEE (Main)-2023]
107. Match List-l with List-lI.
List-ll
List-l
(Separation
(Mixture) Technique)
Steam more polar than 'a' and b'
|A. CHCI, +C,H,NH, . distillation A. Compound 'c' is
least polar
Differential B. Compound 'a' is
comes out of the
column
||.
B. C,Ht C,H2 extraction C. Comound 'b'
before 'c' and after 'a'
Distillation spends more time in the
C. CH,NH, + H,0 D. Compound 'a'
Fractional column
D. Organic V. answer from the options
distillation Choose the correct [JEE (Main)-2023]
compound in given below
H,0 (1)A, Band Donly
(1) A- I,B-1.C-IV, D-II (2) A,Band C only
(2) A-IV,B-I.C-III, D-I! (3) Band Donly
only
(3) A- |I,B-IV, C-|, D-I| (4) B, C and D
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 CUrrent, Floa netism, Maon
158 Organic Chemistry ; Some Basic JEE(Main) & State Engineering
Principles and Technique
114. Given beloW are two statements:
Entrance Exams
[Detection and Estimation)
110. Match List- with Statement I: In 'Lassaigne's Test.
List-ll: nitrogen and sulphur are presentin both when
List
compound, sodium thiocyanate is an
formed.organic
List-ll
Test/Reagents/ Species detected Statement Il: If both nitrogen and
Observation(s)
(a) Lassaigne's Test (i)
present in an organic compound,
excess of sodium used in sodium
sultphhuren
are
the
Carbon
(b) Cu(ll) oxide (i) Sulphur
decomp0se the sodium
give NaCN and Na,S. thiocyanate fusiformoned
wil
to
(c) Silver nitrate (i) N, S, P, and
In the light of the above
(d) The sodium
halogen the most appropriate answer from statements, choose
the
fusion extract
(iv) Halogen Specifically given below: options
(JEE (Main)-2022]
4) Both Statement Iand
gives black Correct
Statement Il 2ro
precipitate with (2) Both
acetic acid and
Statement Iand Statement ll aro
incorrect
lead acetate
(3) Statement l is correct but Statement Il is
The correct match is
[JEE (Main)-2021] incorrect
(1) (a)-(ii). (b)-(i), (c)-(iv), (d)-(i) (4) Statement Iis incorrect but Statement Il
(2) (a)-(i). (b)-(v), (C)-(ii), (d-(i) is correct
(3) (a)-(i), (b)-(), (c-(i), (d-(iv) 115. The formula of the purple colour formed in
(4) (a)-(i), (b)-(1), (c)-(iv), (d)-(ii) Laissaigne's test for sulphur using sodium
111. Which one of the following set of nitroprusside is [JEE (Main)-2022]
elements can
be detected using sodium fusion extract? (1) NaFe[Fe(CN)]
[JEE (Main)-2021] (2) Na[Cr(NH),(NCS)]
(1) Phosphorous,Oxygen, Nitrogen,Halogens (3) Na,[Fe(CN),(NO)]
(2) Nitrogen, Phosphorous, Carbon, Sulfur (4) Na,[Fe(CN),(NOS)
(3) Sulfur, Nitrogen, Phosphorous, Halogens 116*. Kjeldahl's method cannot be used to
(4) Halogens, Nitrogen, Oxygen, Sulfur estimate nitrogen for which of the following
Compounds? [JEE (Main)-2020]
112. Which of the following compound is added to
the sodium extract before addition of silver (1) CH,CH-C=N
nitrate for testing of halogens?
[JEE (Main)-2021] (2) NH, &-NH,
(1) Hydrochloric acid (3) C,H,N0,
(2) Sodium hydroxide (4) CaH,NH,
(3) Ammonia 117. In Carius method of estimation of halogen,
(4) Nitric acid 0.172 g of an organic compound showeu
113. During halogen test, sodium fusion extract is presence of 0.08gof bromine. Which of these
boiled with concentrated HNO, to is the correct structure of the compound?
[JEE (Main)-2020]
[JEE (Main)-2022]
(1) Remove unreacted sodium NH NH,
Bi
(2) Decompose cyanide or sulphide of sodium
(2)
(3) Extract halogen from organic compound
Br Br
(4) Maintain the pH of extract
(3) H,C- Br (4) H,C- CH, -Br
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 Engineeringi Entrance Exams Techniques 159
(Main)&<State Organic Chemistry Some Basic Principles and
JEE
Nitrogen can estimated
be by Kjeldahl's method 123. Match List-! with List-|.
118. which offthe following compound?
for List-l List-ll
(JEE (Main)-2021] Element detected Reagent
used/Product
formed
(2) Na,[Fe(CN),NOJ
(1) A. Nitrogen |.
N=NCI CH, - NH,
B.Sulphur II.AgNO,

(3)
(4) C. Phosphorus L.Fe,[Fe(CN)s
NO, D. Halogen IV (NH,),MoO,
119In Carius method, halogen containing organic Choose the correct answer from the options
compoundis heated with fuming nitric acid in given below: [JEE (Main)-2023]
the presence of [JEE (Main)-2021] (1) A’ II; B’ I;C’ IV; D’ ||
(1) HNO, (2) Cuso, (2) A ’ Il; B’ IV; C ’ 1; D’ ||
(3) BaSO, (3) A’ IV; B ’ Il; C ’1; D’ | |
(4) AgNO, (4) A’ I1; B ’ 1; C’ V;D’ I||
120. 120 g of an organic compound that contains
only carbon and hydrogen gives 330 g of Co, Numerical Value Based Questions
and270 g of water on complete combustion. [lsomerism]
The percentage of carbon and hydrogen, 124. The total number ofC-Csigma bond/s in
respectively are [JEE (Main)-2022] (Round off
mesityl oxide (CHo) is
(1) 25 and 75 (2) 40 and60 to the Nearest Integer). (JEE (Main)-2021]
(3) 60 and 40 (4) 75 and 25 125. The number of acyclic structural isomers
(including geometrical isomers) for pentene are
121. In Carius method of estimation [JEE (Main)-2021]
of halogen, 0.45 g of an organic 126. Observe structures ofthe following compounds
compound gave 0.36 g of AgBr.
CI NH,
Find out the percentage of D
OH OH
bromine in the compound. H,N
(Molar masses : AgBr = 188 g mol;
Br =80 g mol) (JEE (Main)-2022]
(1) 34.04% (2) 40.04%
(3) 36.03% (4) 38.04% OH

122. 116 g of a substance upon dissociation reaction,

yields 7.5 gof hydrogen, 60g of oxygen and The total number of structures/compounds
48.5gof carbon. Given that the atomic masses which possess asymmetric carbon atoms is
of H, Oand Care 1, 16 and 12, respectively. [JEE (Main)-2022]
Ihe data agrees with how many formulae of 127.The number of sp hybridised carbons in an
the following? [JEE (Main)-2022] acyclic neutral compound with molecular
formula C,H,N is
(1) CH,COOH [JEE (Main)-2022]
(2) HCHO 128. The dihedral angle in staggered form of
(3) CH,00CH, Newman projection of 1, 1, 1-Trichloro ethane
is degree. (Round off to the Nearest
(4) CH,CHO Integer) (JEE (Main)-2021]
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 Dblin- . ter
Oordin Sses of
JEE(Main) & State Engineering
160 Organic Chemistry :Some Rasic
Principles and Techniques
[Detention and Estimationl
Entrance Exams
129*. The [Purification] 133. In an
estimation of bromine by
Carius
separation of two coloured
substances was done by paper 1.6 g of an organic Compound gave method
chromatography.
travelled by
The distances
solvent
substance Aand substance front,B
AgBr. The mass percentage of
compound is
(Atomic mass, Ag = 108, Br= 80
bromin188go
e in the
g mor
from the baseline are 3.25 cm, 2.08 cm and
1.05 cm, respectively. The ratio of R, values of 1JEE (Main)-20201
Ato B is 134. The number of moles of CuO, that wWil
be
niitrogenutlizined a
[JEE (Main)-2022] in Dumas methodfor estimating
130".Using provided information in the following
the sample of 57.5 gof N,N
paper chromatogram [JEE (Main)-2021] is
dim[JEEethylam(Maiinopen) n-2t021)ana
x 10. (Nearest integer)

135. In Carius methodfor estimation of

gave0.1hal88gogens,of AgBr0.is2
Solvent front
Be gof an organic compound
The percentage of bromine in the
5 cm
T2 cm (Nearest integer) compound
A JAtomic mass : Ag= 108, Br= 801
2 cm
[JEE (Main)-2021])
136. In the sulphur estimation, 0.471 goff an
Base line compound gave 1.44 organiThec
gof barium sulfate.
Spot
percentage of sulphur in the compound is
Fig: Paper chromatography for compounds A %. (Nearest integer)
and B.
(Atomic Mass of B= 137 u)
The calculated R, value of A x 101,
[JEE (Main)-2021)
131.Following chromatogram was developed by 137.The transformation occurring in
adsorption of compound 'A'on a 6cm TLC glass Duma's method is given below.
plate. Retardation factor of the compound 'A'
x 10. [JEE (Main)-2023] C,H;N +(2x +Cuo
0.5 cm -- Solvent Front
XCO, +
Compound A --
The value of y is (Integer answer)
>3.5 cm [JEE (Main)-2021]
138. In Duma's method of estimation of nitrogen,
1t 0.5 cm
0.1840 gof an organic compound gave 30 mL
of nitrogen collected at 287 K and 758 mm of
132. Three organic compounds A, B and C were Hg pressure. The percentage compositionor
allowed to run in thin layer chromatography nitrogen in the compound is
using hexane and gave the following result (Round off to the nearest Integer)
(see figure). The R, value of the most polar (Given : Aqueous tension at 287 K= 14 mmo
Compound is x10 (JEE (Main)-2023] (JEE (Main)-2021]
Hgl
139. When 0.15 g of an organic Compound was
A analyzed using Carius method for estimationu
The
bromine, 0.2397 gof AgBr was obtained.
compound
8 cm
percentage of bromine in the organic
is
(Nearest integer)
l2 cm [Atomic mass : Silver =108, Bromine=80]
(JEE(Main)-2021
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c Inductir
Engineering Entrance Exams Organic Chemistry: Some Basic Principles and Techniques 161
(Main)&State
JEE
fan organic compound was analysed by
g ofa
146. In the estimation of bromine, 0.5 g of an organic
140. 0.8
Kjeldahl's, method fortthe estimation of nitrogen. Compound gave 0.40 g of silver bromide. The
percentage of nitrogen in the compound percentage of bromine in the given compound
Ifthe
was
found to be 42%, then mL of1 % (nearest integer)
would have been neutralized by the
MH,SO, (Relative atomic masses of Ag and Br are 108
ammonia evolved duringthe analysis.
[JEE (Main)-2021] uand 80 u, respectively).
[JEE (Main)-2022]
organic compound is subjected to
An
141. chlorination 147. The complete combustion of 0.492 g of an
to
get compound Ausing 5.0 g of
chlorine. Whent 0.5g of compound Ais reacted organic compound containing 'C, 'H' and 'O'
gives 0.793 g of CO, and 0.,442 g of H,o.
with AgNO, [Carius Method], the percentage of The percentage of oxygen composition in the
is
chlorine in compound A
when it forms
of AgCI. (Round off to the Nearest organic compound is [nearest integer]
0.3849 [JEE (Main)-2022]
Integer) 148. Kjeldahl's method was used for the estimation
(Atomic massesS of Ag and CI are 107.87 and
35.5 respectively) [JEE (Main)-2021] of nitrogen in an organic compound. The
ammoniaevolved from 0.55 g of the compound
12 A0.166 g sample of an organic compound was neutralised 12.5 mL of 1. M H,SO, solution.
digested with conc. H,SO, and then distilled
with NaOH. The ammonia gas evolved was
The percentage of nitrogen in the compound
is (Nearest integer)
Dassed through 50.0 mL of 0.5 N H,SO,. [JEE (Main)-2022]
The used acid required 30.0 mL of 0.25 N
NaOH for complete neutralisation. The mass 149. While estimating the nitrogen present in an
percentage of nitrogen in the organic compound organiC compound by Kjeldahl's method,
[JEE (Main)-2022] the ammonia evolved fromn 0.25 g of the
compound neutralized 2.5 mL of 2 M H,SO,.
143. 0.2 gof an organic compound
The percentage of nitrogen present in organic
was subjected to estimation of Compound is (JEE (Main)-2022]
nitrogen by Duma's method in
which volume of N, evolved (at 150. A sample of 0.125 g of an organic compound
STP) was found to be 22.400.mL whenanalysed by Duma's method yields 22.78
The percentage of nitrogen in the compound is mL of nitrogen gas collected over KOH solution
[nearest integer] at 280 K and 759 mm Hg. The percentage of
(Given : Molar mass of N, is 28 g mol", Molar nitrogen in the given organic compound is
volume of N, at STP: 22.4L) (Nearest integer)
[JEE (Main)-2022] Given:
144. On complete combustion 0.30 g of an organic (a) The vapour pressure of water
Compound gave 0.20 g of carbon dioxide and of 280 K is 14.2 mm Hg.
0.10g of water. The percentage of carbon in (b) R= 0.082 L atm K molr
the given organic compound is
[JEE (Main)-2022]
(Nearest Integer) [JEE (Main)-2022]
145.Gniorine
0.25 gave 0.40
g of an organic compound containing
gof silver chloride in Carius
151. In sulphur estimation, 0.471 g of an organic
compound gave 1.4439.g of barium sulphate.
estimation, The percentage of chlorine present The percentage of sulphur in the compound is
in the (Nearest integer)
compound is . [in nearest integer]
(Gven : Molar mass of Ag is 108 g mol and (Given: Atomic mass Ba: 137 u, S: 32 u,
that of CI is 35.5 a molr') [JEE (Main)-2022 O:16 u) [JEE (Main)-2023]

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