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JEE Advanced-2022
Selected Question for Revision | Organic Chemistry-I
1. Which of the following hydrocarbons has the lowest dipole moment ?
(A) cis-2-butene (B) 2-butyne (C) 1-butyne (D) H2 C  CH  C  CH
2. The compound formed in the positive test for nitrogen with the Lassaigne solution of an organic
compound is :
(A) Fe 4 [Fe  CN 6 ]3 (B) Fe4 [Fe  CN 5 NOS]
(C) Fe(CN)3 (D) Na 3[Fe(CN)6 ]

3. An organic compound having molecular mass 60 is found to contain C = 20%, H = 6.67% and
N = 46.67% while rest is oxygen. On heating it gives NH3 along with a solid residue. The solid residue give
violet colour with alkaline copper sulphate solution. The compound is :
(A) CH3NCO (B) CH3CONH2 (C) (NH2)2CO (D) CH3CH2CONH2
4. The correct stability order of the following resonance structure is :
 –  – –  – 
(I) H 2C  N  N (II) H2 C N  N (III) H2 C N  N (IV) H2 C N  N

(A) (I) > (II) > (IV) > (III) (B) (I) > (III) > (II) > (IV)
(C) (II) > (I) > (III) > (IV) (D) (III) > (I) > (IV) > (II)

5. The most polar compound among the following is :

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

6. 29.5 mg of an organic compound containing nitrogen was digested according to Kjeldahl’s method and
the evolved ammonia was absorbed in 20 mL of 0.1 M HCl solution. The excess of the acid required 15
mL of 0.1 M NaOH solution for complete neutralization. The percentage of nitrogen in the compound is :
(A) 59.0 (B) 47.4 (C) 23.7 (D) 29.5
7. 1.4 g of an organic compound was digested according to Kjeldahl's method and the ammonia evolved
was absorbed in 60 mL of M/10 H2SO 4 solution. The excess sulphuric acid required 20 mL of
M /10 NaOH solution for neutralization. The percentage of nitrogen in the compound is :
(A) 3 (B) 5 (C) 10 (D) 24
8. Match the organic compounds in Column-I with the Lassaigne's test results in Column-II appropriately :

Column-I Column-II

1 Aniline (p) Red color with FeCl3

2 Benzene sulfonic acid (q) Violet colour with nitroprusside

3 Thiourea (r) Blue color with hot and acidic solution of FeSO4

(A) [1-q] [2-p] [3-r] (B) [1-r] [2-q] [3-p] (C) [1-q] [2-r] [3-p] (D) [1-r] [2-p] [3-q]

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9. Which compound exhibits maximum dipole moment among the following ?

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

10. Sodium extract is heated with concentrated HNO3 before testing for halogens because :

(A) Silver halides are totally insoluble in nitric acid

(B) Ag 2S and AgCN are soluble in acidic medium

(C) S2  and CN  , if present, are decomposed by conc. HNO3 and hence do not interfere in the test

(D) Ag reacts faster with halides in acidic medium

11. Which of the following molecules is least resonance stabilized ?

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

12. Which of the following compounds will be suitable for Kjeldahl’s method for nitrogen estimation ?

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

13. Which compound(s) out of the following is/are not aromatic ?

(A) (B), (C) and (D) (B) (C) and (D) (C) (A) and (C) (D) (B)
14. In the following skew conformatioin of ethane, H  C  C  H dihedral angle is :

(A) 120° (B) 149° (C) 58° (D) 151°

15. The IUPAC name for the following compound is :

(A) 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
(B) 3,5-dimethyl-4-propylhept-1-en-6-yne
(C) 3,5-dimethyl-4-propylhept-6-en-1-yne
(D) 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne

16. Which of the following has the shortest C  Cl bond ?

(A) Cl  CH  CH2 (B) Cl  CH  CH  OCH 3

(C) Cl  CH  CH  NO2 (D) Cl  CH  CH  CH3

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17. The predominant intermolecular forces present in ethyl acetate, a liquid, are :
(A) London dispersion, dipole-dipole and hydrogen bonding
(B) London dispersion and dipole-dipole
(C) Dipole-Dipole and hydrogen bonding
(D) Hydrogen bonding and London dispersion

18. Glycerol is separated in soap industries by:

(A) Differential extraction (B) Steam distillation
(C) Distillation under reduced pressure (D) Fractional distillation
*19. Keto-enol tautomerism is observed in :
O O
|| ||
(A) C 6 H5  C  H (B) C6H5  C  CH3
O O O
|| || ||
(C) C 6 H5  C  C 6 H5 (D) C6H5  C  CH2  C  CH3

20. Polarisation of electrons in acrolein may be written as :


O O
 ||  ||
(A) H2 C  CH  C  H (B) H2 C  CH  C  H


O O
  ||  ||
(C) H2 C  CH  C  H (D) H2 C  CH  C  H
21. The enolic form of acetone contains :
(A) 9 sigma bonds, 1 pi bond and 2 lone pairs
(B) 8 sigma bonds, 2 pi bonds and 2 lone pairs
(C) 10 sigma bonds, 1 pi bonds and 1 lone pair
(D) 9 sigma bonds, 2 pi bonds and 1 lone pair
22. 2, 3, 4-trichloropentane has three asymmetric carbon atoms. (True/False)
23. The kind of delocalisation involving sigma bond orbitals is called________.
*24. Tautomerism is exhibited by :

(A) (B)

(C) (D)

25. The optically active tartaric acid is named as D  ( ) -tartaric acid because it has a positive :
(A) optical rotation and is derived from D-glucose
(B) pH in organic solvent
(C) optical rotation and is derived from D  (  ) -glyceraldehyde
(D) optical rotation when substituted by deuterium
*26. The IUPAC name(s) of the following compound is(are) :

(A) 4-chlorotoluene
(B) 4-methylchlorobenzene
(C) 1-chloro-4-methylbenzene
(D) 1-methyl-4-chlorobenzene

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*27. In the Newman’s projection for 2, 2-dimethylbutane X and Y can respectively be :

(A) H and H (B) H and C2H5 (C) C2H5 and H (D) CH3 and CH3

28. Explain, why o-hydroxybenzaldehyde is a liquid at room temperature while p- hydroxybenzaldehyde is a

high melting solid ?
29. Statement I : p –hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid.
Statement II : o-hydroxybenzoic acid has intramolecular hydrogen bonding.
(A) Statement-I is True, Statement-II is True and Statement-II is a correct explanation for
Statement-I.
(B) Statement-I is True, Statement-II is True and Statement-II is NOT a correct explanation for
Statement-I.
(C) Statement-I is True, Statement-II is False.
(D) Statement-I is False, Statement-II is True.
30. obs   x
i i

Where  i is the dipole moment of stable conformer and x i is the mole fraction of that conformer.

(a) Write stable conformer for Z  CH 2  CH 2  Z in Newman’s projection. If solution  1.0 D and
mole fraction of anti form = 0.82, find gauche.
(b) Write most stable meso conformer of (CHDY )2. If (i) Y  CH3 about C2  C3 rotation and
(ii) Y  OH about C 1  C2 rotation.

31. The IUPAC name of C6H5COCl is :

(A) benzoyl chloride (B) benzene chloro ketone
(C) benzene carbonyl chloride (D) chloro phenyl ketone
*32. The correct statements concerning the structures E, F and G is/are :

(A) E, F and G are resonance structures

(B) E, F and E, G are tautomers
(C) F and G are geometrical isomers
(D) F and G are diastereomers

*33. The correct statements about the compound given below is :

(A) the compound is optically active
(B) the compound possesses centre of symmetry
(C) the compound possesses plane of symmetry
(D) the compound possesses axis of symmetry

34. Hyperconjugation involves overlap of the following orbitals :

(A)  (B) p (C) pp (D) 

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*35. The correct statements about the compound H 3C(HO)HC  CH  CH  CH(OH)CH3 (X ) is/are :
(A) the total number of stereoisomers possible for X is 6
(B) the total number of diastereomers possible for X is 3
(C) if the stereochemistry about the double bond in X is trans, the number of enantiomer possible for
X is 4
(D) if the stereochemistry about the double bond in X is cis, the number of enantiomers possible for
X is 2
36. Give the total number of cyclic structural as well as stereoisomers possible for a compound with the
molecular formula C5H10 .

37. In the following carbocation; H/CH3 that is most likely to migrate to the positively charged carbon is :
H H
1
| 3 | 4 5
H3 C  C2  C  C  C H3
| | |
OH H CH3
(A) CH3 at C  4 (B) H at C  4 (C) CH3 at C  2 (D) H at C  2
38. The total number of cyclic structural as well as stereo isomers possible for a compound with the
molecular formula C5H10 is :

*39. Amongst the given options, the compounds in which all the atoms are in one plane in all possible
conformations is :

(A) (B)

(C) H 2C  C  O (D) H 2C  C  CH2

40. The total number of contributing structures showing hyperconjugation (involving C-H bonds) for the
following carbocation is _______________ .

*41. Which of the given statements about N, O, P and Q with respect to M is correct ?

(M) (N) (O) (P) (Q)

(A) M and N are non-mirror image stereoisomers
(B) M and O are identical
(C) M and P are enantiomers
(D) M and Q are identical

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*42. Which of the following molecules, in pure form, is (are) unstable at room temperature ?

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

*43. The correct combination of names of isomeric alcohols with molecular formula C4 H10 O is/are :
(A) tert-butanol and 2-methylpropan-2-ol
(B) tert-butanol and 1, 1-dimethylethan-1-ol
(C) n-butanol and butan-1-ol
(D) iso-butyl alcohol and 2-methylpropan-1-ol
44. The total numbers of stable conformers with non-zero dipole moment for the following compound
is________.

45. Among the following, the number of aromatic compound(s) is _________.

46. For the given compound X, the total number of optically active stereoisomers is _________.

47. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the
molecular formula C4 H8O is________.

48. Bottles containing C6H5I and C6 H5CH2I lost their original labels. They were labeled A and B for testing.
A and B were separately taken in a test tube and boiled with NaOH solution. The end solution in each
tube was made acidic with dilute HNO3 and then some AgNO 3 solution was added. Substance B gave a
yellow precipitate. Which one of the following statements is true for this experiment ?
(A) A was C6H5I
(B) B was C6H5CH 2I
(C) B was C6H5I
(D) Addition of HNO3 was unnecessary

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49. The structure of the major product formed in the following reaction is :

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

50. Compound (A ), C8H 9Br, gives a white precipitate when warmed with alcoholic AgNO 3. Oxidation of (A)
gives an acid (B), C8H6O 4 . (B) easily forms anhydride on heating. Identify the compound (A).

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

51. Which of the following will most readily give the dehydrohalogenation product ?

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

52. The major product of the following reaction is :

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

53. The major product of the following reaction is :

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

*54. Which of the following compounds reacts with ethylmagnesium bromide and also decolourizes bromine
water solution :

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

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55. The major product of the following reaction is :

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

56. The major products A and B for the following reactions are, respectively:

(A) (B)

(C) (D)
57. The number of chiral centres present in [B] is ____________.

58. Show by chemical equations only, how would you prepare the following from the indicated starting
materials? Specify the reagents in each step of the synthesis.
(i) Chloroform from carbon disulphide
(ii) Hexachloroethane (C2Cl6) from calcium carbide.

59. The reaction condition that leads to the best yield of C2H5Cl are :
UV light dark
(A) C2H6 (excess)  Cl2  (B) C2H6  Cl 2 (excess) 
room temp.

UV light UV light
(C) C2H6  Cl2 (excess)  (D) C2H6  Cl2 
60. Identify the major product in the following reaction.
H
AlcKOH HBr
C6H5  CH2 CH3  ? 
?

Br

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61. Complete the following, giving the structures of the principal organic products :

62. Chlorobenzene can be prepared by reacting aniline with

(A) hydrochloric acid
(B) cuprous chloride
(C) chlorine in presence of anhydrous aluminium chloride
(D) nitrous acid followed by heating with cuprous chloride
63. Choose the correct options(s) for the following set of reactions

(A) (B)

(C) (D)

64. Which of the following reactions produce(s) propane as a major product?

(A) (B)

(C) (D)

65. Tertiary alkyl halides are practically inert to substitution by SN2 mechanism because of :
(A) insolubility (B) instability
(C) inductive effect (D) steric hindrance

66. Consider the following bromides :

The correct order of S N1 reactivity is :

(A) A>B>C (B) B>C>A (C) B>A>C (D) C>B>A

67. An unknown alcohol is treated with the "Lucas reagent" to determine whether the alcohol is primary,
secondary or tertiary. Which alcohol reacts fastest and by what mechanism ?
(A) Isopropyl alcohol by SN2 (B) Secondary alcohol by SN1
(C) Tertiary alcohol by SN1 (D) Secondary alcohol by SN2

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68. The increasing order of the reactivity of the following halides for the S N1 reaction is :
I. CH3 CHCH2CH3 II. CH3CH2CH2Cl III. p - H 3CO  C6H 4  CH 2Cl
|
Cl
(A) I < III < II (B) II < III < I (C) III < II < I (D) II < I < III

69. Which of the following, upon treatment with tert - BuONa followed by addition of bromine water, fails to
decolourise the colour of bromine ?

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

70. The major product obtained in the following reaction is:

(A) (  )  C6 H5CH (t-BuO) CH2C6 H5 (B) ( )  C6 H5CH (t-BuO)CH2 C6 H5

(C) (  )  C6 H5CH (t-BuO) CH2C6 H5 (D) C6H5CH  CHC6H5

71. The major product of the following reaction is:

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

72. The increasing order of nucleophilicity of the following nucleophiles is:
(a) CH3CO2 (b) H 2O (c) CH3SO3 (d) OH
(A) (b) < (c) < (d) < (a) (B) (d) < (a) < (c) < (b)
(C) (b) < (c) < (a) < (d) (D) (a) < (d) < (c) < (b)

73. Increasing order of reactivity of the following compounds for S N1 substitution is:

(A) (B) < (C) < (D) < (A) (B) (B) < (C) < (A) < (D)
(C) (A) < (B) < (D) < (C) (D) (B) < (A) < (D) < (C)

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74. Increasing rate of S N1 reaction in the following compounds is:

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

(A) (A) < (B) < (D) < (C) (B) (B) < (A) < (C) < (D)
(C) (B) < (A) < (D) < (C) (D) (A) < (B) < (C) < (D)
75. The increasing order of reactivity of the following compounds towards aromatic electrophilic substitution
reaction is :

(A) A<B<C<D (B) B<C<A<D (C) D<A<C<B (D) D<B<A<C

76. Consider the following reactions :

(i)

(ii)

(iii)

(iv)

Which of these reactions are possible?

(A) (i) and (iv) (B) (ii), (iii) and (iv) (C) (ii) and (iv) (D) (i) and (ii)
77. For the following reactions

where,

ks
k s and k e are, respectively, the rate constants for substitution and elimination, and   , the correct
ke

option is:
(A) B   A and k e (B)  K e (A) (B)  A   B and k e (B)  K e (A)

(C)  A   B and k e (A )  K e (B) (D) B   A and k e (A )  K e (B)

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78. Which of the following reactions will not produce a racemic product?
O
HBr
 HCN
(A) CH3CH2CH  CH2 
 (B) CH3  C CH2CH3  

CH3
| HCl
(C) CH3 C  CH  CH2  (D)
|
H

79. The major product in the following reaction is:

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

80. Which of these will produce the highest yield in Friedel Crafts reaction?

(A) (B)

(C) (D)

81. The major product of the following reaction is :

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

82. Consider the following reactions:

2 4 concH SO alcKOH
(a) (CH3 )3 CCH(OH)CH3  
 (b) (CH3 )2 CHCH(Br)CH3 

 
3 3 (CH ) COO K 
(c) (CH3 )2 CHCH(Br)CH3 
 (d) (CH3 )2 C CH 2  CHO 

|
OH
Which of these reactions will not produce Saytzeff product?
(A) (a), (c) and (d) (B) (d) only
(C) (c) only (D) (b) and (d)

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83. The major products A and B in the following reactions are:

(A)

(B)

(C)

(D)

84. The major product in the following reaction is:

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

85. The decreasing order of reactivity of the following compounds towards nucleophilic substitution (S N 2) is:

(A) (II) > (III) > (I) > (IV) (B) (IV) > (II) > (III) > (I)
(C) (III) > (II) > (IV) > (I) (D) (II) > (III) > (IV) > (I)

86. The total number of monohalogenated organic products in the following (including stereoisomers)
reaction is __________ .
(i) H /Ni/
2
A 
(Simplest optically active alkene) (ii) X 2 /

87. The mechanism of S N1 reaction is given as:

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

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

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88. The major product formed in the following reaction is:

HBr
CH3CH  CHCH CH3  2  

(A) CH3CH  Br  CH2CH  CH 3  (B) CH3CH2CH2C Br   CH3 2

2

(C) CH3CH2CH  Br  CH  CH3  (D) Br  CH2  CH  CH 3 

2 3 2

89. The major product [R] in the following sequence of reactions is:

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

90. Which of the following compounds will form the precipitate with aq. AgNO3 solution most readily?

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

91. The decreasing order of reactivity of the following organic molecules towards AgNO3 solution is:

(A) (B) > (A) > (C) > (D) (B) (A) > (B) > (C) > (D)
(C) (A) > (B) > (D) > (C) (D) (C) > (D) > (A) > (B)
92. Consider the reaction sequence given below:

Which of the following statements is true:

(A) Doubling the concentration of base will double the rate of both the reactions
(B) Changing the base from OH to 
OR will have no effect on reaction (2)
(C) Changing the concentration of base will have no effect on reaction (1)
(D) Changing the concentration of base will have no effect on reaction (2)

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93. The major product of the following reaction is:

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

94. The increasing order of the boiling points of the major products A, B and C of the following reactions will
be :

(A) C<A<B (B) B<C<A (C) A<C<B (D) A<B<C

95. The major product of the following reaction is:

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

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

Br Br
| |
(A) CH3  CH2 C  CH  CH3 (B) CH3CH2 CH  CH  CH 2

F
|
(C) CH3CH2CH  C  F (D) CH3  CH  CH  CH  CH3
|
CH
3

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97. The major products of the following reactions are:

CH3
| (i) KOtBu/
CH3 CH CH  CH3  
(ii) O3 /H2 O2
|
OSO2CH3

(A) (B)

(C) (D)

98. The major product obtained from the following reaction is:

(A)

(B)

(C)

(D)

99. A solution of (+)-2-chloro-2-phenylethane in toluene racemises slowly in the presence of small amount of
SbCl5, due to the formation of :
(A) carbanion (B) carbene (C) free-radical (D) carbocation

100. Explain briefly the formation of products giving the structures of the intermediates.

(i)

(ii)

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101. An SN2 reaction at an asymmetric carbon of a compound always gives :

(A) an enantiomer of the substrate (B) a product with opposite optical rotation
(C) a mixture of diastereomers (D) a single stereoisomer

102. Which one of the following will most readily be dehydrated in acidic condition ?

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

H 2 4 Br / CCl
103. [F]  C4 H8Br2
/ H2O 
5 such products
are possible
How many structures of F is(are) possible?
(A) 2 (B) 5 (C) 6 (D) 3
104. The following compound on hydrolysis in aqueous acetone will give :

(K)

(L)

(M)

It mainly gives :
(A) K and L (B) only K (C) L and M (D) only M

105. Give reasons for the following :

(i)

(ii)

(iii) 7-Bromo-1,3,5-cycloheptatriene exists as an ionic compound, while 5-bromo-1,3-cyclopentadiene

does not ionize even in presence of Ag+ ion. Explain.
106. Match the following:

Column I Column II

CH3  CHBr  CD3 on treatment with alc. KOH gives

(A) P E1 reaction
CH2  CH  CD3 as a major product

(B) Ph  CHBr  CH 3 reacts faster than Ph  CHBr  CD3 Q E2 reaction

Ph  CH2  CH2Br on treatment with C2H5 OD / C2H5 O

(C) R E1cB reaction
gives Ph-CD = CH2 as the major product

(D) PhCH2CH2Br and PhCD2CH2Br react with same rate S. First order reaction

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107. The major product of the following reaction is :

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

108. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using

alcoholic KOH is :

109. The major product of the following reaction is :

(A) (B)

(C) (D)

110. KI in acetone, undergoes S N 2 reaction with each of P, Q, R and S. The rates of the reaction vary as :

(A) P>Q>R>S (B) S>P>R>Q (C) P>R>Q>S (D) R>P>S>Q

111. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is(are) :

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

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

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113. For the following compounds, the correct statement(s) with respect to nucleophilic substitution reactions
is(are) :

(A) I and III follow SN 1 mechanism

(B) I and II follow SN 2 mechanism
(C) Compound IV undergoes inversion of configuration
(D) The order of reactivity for I, III & IV is IV > I > III

114. In the reaction scheme shown below, Q, R and S are the major products.

The correct structure of

(A) S is (B) Q is

(C) R is (D) S is

115. Which of the following plots is(are) correct for the given reaction?
( [P]0 is the initial concentration of P)

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

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116. In the following reaction, compound Q is obtained from compound P via an ionic intermediate.

What is the degree of unsaturation of Q?

117. The predominant form of histamine present in human blood is (pK a Histidine = 6.0) :

(A) (B)

(C) (D)

118. The peptide that gives positive ceric ammonium nitrate and carbylamines tests is:
(A) Lys - Asp (B) Ser – Lys (C) Asp - Gln (D) Gln – Asp

119. Fructose and glucose can be distinguished by:

(A) Seliwanoff’s test (B) Benedict’s test
(C) Barfoed’s test (D) Fehling’s test

120. The increasing order of pKa of the following amino acids in aqueous solution is : Gly Asp Lys Arg
(A) Gly < Asp < Arg < Lys (B) Asp < Gly < Lys < Arg
(C) Asp < Gly < Arg < Lys (D) Arg < Lys < Gly < Asp
121. Among the following compounds most basic amino acid is :
(A) Asparagine (B) Lysine (C) Histidine (D) Serine

122. The correct structure of histidine in a strongly acidic solution (pH  2) is :

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

123. The correct match between Item I and Item II is :
Item-I Item-II
(a) Ester test (P) Tyr
(b) Carbylamine test (Q) Asp
(c) Phthalein dye test (R) Ser
(S) Lys
(A) (a)-(Q); (b)-(S); (c) (P) (B) (a)-(R); (b)-(S); (c) (Q)
(C) (a)-(R); (b)-(Q); (c) (P) (D) (a)-(Q); (b)-(S); (c) (R)
124. In the following compounds, the decreasing order of basic strength will be :
(A) (C2H5 )2 NH  NH3  C2H5 NH2 (B) NH3  C2H5 NH2  (C2H5 )2 NH

(C) (C2H5 )2 NH  C2H5 NH2  NH3 (D) C2H5 NH2  NH3  (C2H5 )2 NH

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125. The increasing order of the pK b of the following compound is:

(i) (ii)

(iii) (iv)

(A) (ii) < (iv) < (i) < (iii) (B) (ii) < (iv) < (iii) < (i)
(C) (i) < (iii) < (iv) < (ii) (D) (iii) < (i) < (iv) < (ii)

126. Which amongst the following is the strongest acid ?

(A) CHI3 (B) CHBr 3 (C) CHCl 3 (D) CH(CN)3

127. The increasing order of the pKa values of the following compounds is :

(A) B<C<D<A (B) C<B<A<D (C) D<A<C<B (D) B<C<A<D

128. The correct decreasing order for acid strength is :

(A) NO 2CH 2COOH  NCCH2COOH  FCH2COOH  ClCH2COOH
(B) NO 2CH 2COOH  FCH2COOH  CNCH2COOH  ClCH2COOH
(C) CNCH2COOH  O2NCH 2COOH  FCH2COOH  ClCH2COOH

(D) FCH2COOH  NCCH2COOH  NO2CH2COOH  ClCH2COOH

129. Arrange the following amines in the decreasing order of basicity :

(A) I > II > III (B) III > II > I (C) I > III > II (D) III > I > II

130. The increasing basicity order of the following compounds is :

CH2CH3
|
(A) CH 3CH 2CH 2 (B) CH3CH2 NH
CH3 CH3
| |
(C) H3C  N  CH3 (D) Ph  N  H
(A) (A) < (B) < (D) < (C) (B) (A) < (B) < (C) < (D)
(C) (D) < (C) < (A) < (B) (D) (D) < (C) < (B) < (A)

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131. In the following compound,

The favorable site/s for protonation is/are :

(A) (b), (c) and (d) (B) (a) (C) (a) and (e) (D) (a) and (d)

132. The major product in the following reaction is:

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

133. A, B and C are three biomolecules. The results of the tests performed on them are given below:

Molisch’s Test Barfoed Test Biuret Test

A Positive Negative Negative
B Positive Positive Negative
C Negative Negative Positive
A, B and C are respectively:
(A) A = Lactose, B = Glucose, C = Alanine
(B) A = Lactose, B = Fructose, C = Alanine
(C) A = Glucose, B = Fructose, C = Albumin
(D) A = Lactose, B = Glucose, C = Albumin
134. A chemist has 4 samples of artificial sweetener A, B, C and D. To identify these samples, he performed
certain experiments and noted the following observations:
(i) A and D both form blue-violet colour with ninhydrin.
(ii) Lassaigne extract of C gives positive AgNO3 test and negative Fe4 [Fe(CN)6 ]3 test

(iii) Lassaigne extract of B and D gives positive sodium nitroprusside test.

Based on these observations which option is correct?
(A) A : Saccharin; B : Alitame; C : Sucralose; D : Aspartame
(B) A : Aspartame; B = Alitame; C : Saccharin; D : Sucralose
(C) A : Aspartame; B : Saccharin; C : Sucralose; D : Alitame
(D) A : Alitame; B = Saccharin; C : Aspartame; D : Sucralose
135. The decreasing order of basicity of the following amines is:

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

(A) (III) > (II) > (I) > (IV) (B) (II) > (III) > (IV) > (I)
(C) (III) > (I) > (II) > (IV) (D) (I) > (III) > (IV) > (II)

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136. The increasing order of basicity for the following intermediates is (from weak to strong)

(A) (v) < (iii) < (ii) < (iv) < (i) (B) (iii) < (iv) < (ii) < (i) < (v)
(C) (iii) < (i) < (ii) < (iv) < (v) (D) (v) < (i) < (iv) < (ii) < (iii)
137. A solution of m-chloroaniline, m-chlorophenol and m-chlorobenzoic acid in ethyl acetate was extracted
initially with a saturated solution of NaHCO3 to give fraction A. The left over organic phase was extracted
with dilute NaOH solution to give fraction B. The final organic layer was labelled as fraction C. Fractions
A, B and C, contain respectively:
(A) m-chlorobenzoic acid, m-chlorophenol and m-chloroaniline
(B) m-chlorophenol, m-chlorobenzoic acid and m-chloroaniline
(C) m-chlorobenzoic acid, m-chloroaniline and m-chlorophenol, m-chloroaniline
(D) m-chlorobenzoic acid and m-chlorophenol
138. The increasing order of pK b for the following compounds will be:

(A) (C) < (A) < (B) (B) (A) < (B) < (C) (C) (B) < (C) < (A) (D) (B) < (A) < (C)
139. Which one of the following compounds possesses the most acidic hydrogen ?

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

140. The increasing order of the acidity of the   hydrogen of the following compounds is:

(A) (D) < (C) < (A) < (B) (B) (B) < (C) < (A) < (D)
(C) (C) < (A) < (B) < (D) (D) (A) < (C) < (D) < (B)
141. The increasing order of basicity of the following compounds is:
(A) (D) < (A) < (B) < (C)
(B) (B) < (A) < (D) < (C)
(C) (A) < (B) < (C) < (D)
(D) (B) < (A) < (C) < (D)
142. Arrange the following labeled hydrogens in decreasing order of acidity:

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

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143. The increasing order of pK b values of the following compounds is:

(A) II < I < III < IV (B) I < II < IV < III (C) II < IV < III < I (D) I < II < III < IV

144. The total number of basic groups in the following form of lysine is

145. The structure of a peptide is given below.

If the absolute values of the net charge of the peptide at pH = 2, pH = 6 and pH = 11 are
| z1 |,| z2 | and | z3 | respectively, then what is | z1 |  | z2 |  |z 3 | ?

146. With respect to the compounds I-V, choose the correct statement(s).

(A) The acidity of compound I is due to delocalization in the conjugate base

(B) The conjugate base of compound IV is aromatic
(C) Compound II becomes more acidic, when it has a  NO2 substituent

(D) The acidity of compounds follows the order I > IV > V > II > III
147. Consider the following four compound I, II, III and IV.

Choose the correct statement(s).

(A) The order of basicity is II > I > III > IV
(B) The magnitude of pK b difference I and II is more than that between III and IV
(C) Resonance effect is more in III than in IV
(D) Steric effect makes compound IV more basic than III

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148. What is the product formed when acetylene reacts with hypochlorous acid ?
(A) CH3COCl (B) ClCH2CHO (C) Cl2CHCHO (D) ClCHCOOH
149. Which of these will not react with acetylene ?
(A) NaOH (B) Amm. AgNO3 (C) Na (D) HCl
150. Reaction of one molecule of HBr with one molecule of 1, 3-butadiene at 40C gives predominantly :

(A) 3-Bromobutene under kinetically controlled conditions

(B) 1-Bromo-2-butene under thermodynamically controlled conditions
(C) 3-Bromobutene under thermodynamically controlled conditions
(D) 1-Bromo-2-butene under kinetically controlled conditions
151. Toluene is nitrated and the resulting product is reduced with tin and hydrochloric acid. The product so
obtained is diazotized and then heated with cuprous bromide. The reaction mixture so formed contains :
(A) mixture of o- and p-bromotoluenes (B) mixture of o- and p-dibromobenzenes
(C) mixture of o- and p-bromoanilines (D) mixture of o- and m-bromotoluenes
152. The hydrocarbon which can react with sodium in liquid ammonia is :
(A) CH3 CH 2CH2C  CCH2CH2 CH3 (B) CH3 CH 2C  CH
(C) CH3 CH  CHCH3 (D) CH 3CH2C  CCH2CH3
153. When 2-butyne is treated with H 2 / Lindlar's catalyst, compound X is produced as the major product and
when treated with Na /liq. NH3 it produces Y as the major product. Which of the following statements is
correct ?
(A) X will have higher dipole moment and higher boiling point than Y.
(B) Y will have higher dipole moment and higher boiling point than X.
(C) X will have lower dipole moment and lower boiling point than Y.
(D) Y will have higher dipole moment and lower boiling point than X.
154. The increasing order of nitration of the following compounds is :

(A) (b) < (a) < (c) < (d) (B) (a) < (b) < (c) < (d)
(C) (b) < (a) < (d) < (c) (D) (a) < (b) < (d) < (c)
155. The major product of the following reaction is :
I. KOH alc.
CH3CH2 CH  CH2  
II. NaNH2 in liq. NH3
| |
Br Br
(A) CH 3CH 2C  CH (B) CH 3CH  C  CH 2
(C) CH3CH2 CH  CH2 (D) CH3CH  CHCH2NH2
| |
NH2 NH2
156. In the following sequence of reactions the maximum number of atoms present in molecule ‘C’ in one
plane is________.
Red hot3 CH Cl (1eq.)
A 
 B  C. (A is a lowest molecular weight alkyne)

Cu tube Anhydrous AlCl 3

157. The number of sp2 hybrid orbitals in a molecule of benzene is :

(A) 24 (B) 6 (C) 12 (D) 18

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158. The correct order of heat of combustion for following alkadienes is :

(a) (b) (c)

(A) (b) < (c) < (a) (B) (a) < (b) < (c) (C) (a) < (c) < (b) (D) (c) < (b) < (a)
159. The compound with highest boiling point is :
(A) 2-methyl butane (B) n-pentane
(C) 2, 2-dimethyl propane (D) n-hexane

160. Following statements are true, under some specific conditions. Write the condition for each subquestion
in not more than two sentences:
(i) 2-methyl propene can be converted into isobutyl bromide by hydrogen bromide.
(ii) Ethyne and its derivatives will give white precipitate with ammonical silver nitrate
solution.
161. The highest boiling point is expected for :
(A) iso-butane (B) n-octane
(C) 2, 2, 3, 3-tetramethyl butane (D) n-butane
*162. Only two isomeric monochloro derivatives are possible for :
(A) n-butane (B) 2, 4-dimethyl pentane
(C) benzene (D) 2-methyl propane
163. The number of structural and configurational isomers of a bromo compound, C5H9Br, formed by the
addition of HBr to 2-pentyne respectively, are :
(A) 1 and 2 (B) 2 and 4 (C) 4 and 2 (D) 2 and 1
164. Which one of the following has the smallest heat of hydrogenation per mole ?
(A) 1-butene (B) trans-2-butene
(C) cis-2-butene (D) 1, 3-butadiene
165. Give the structures of A & B (explanation are not required)
(i) A (C 4H 8 ) which adds on HBr in the presence and in the absence of peroxide to give same
product.
(ii) B(C 4H 8 ) which when treated with H 2O/ H2SO4 gives C4 H10O, which cannot be resolved into
optical isomers.

166. When gas A is passed through dry KOH at low temperature, a deep red coloured compound B and a gas
C are obtained. The gas A, on reaction with but-2-ene, followed by treatment with Zn / H2O yields
acetaldehyde. Identify A, B and C.
167. An organic compound E (C5H8 ) on hydrogenation gives compound F(C5H12). Compound E on ozonolysis
gives formaldehyde and 2-keto propanal. Deduce the structure of compound E.
168. 1, 3-butadiene with bromine in molar ratio of 1 : 1 generate predominantly________.
169. Complete the following reactions with appropriate reagents :

(A)

(B)

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170. In the presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti-Markownikoff’s
addition to alkenes because :
(A) both are highly ionic
(B) one is oxidizing and the other is reducing
(C) one of the steps is endothermic in both the cases
(D) all the steps are exothermic in both the cases

171. The reaction of propene with HOCl proceeds via the addition of :
(A) H in the first step (B) Cl  in the first step
(C) OH  in the first step (D) Cl  and OH  in single step

172. Hydrogenation of the given compound in the presence of poisoned palladium catalyst gives :

(A) an optically active compound (B) an optically inactive compound

(C) a racemic mixture (D) a diastereomeric mixture
For Question No. 173 to 174
(A) Statement1 is True, Statement 2 is True; Statement2 is a correct explanation for Statement1
(B) Statement  1 is True, Statement 2 is True; Statement  2 is NOT a correct explanation for Statement 1
(C) Statement  1 is True, Statement  2 is False
(D) Statement  1 is False, Statement  2 is True

173. Statement I : Addition of bromine to trans-2-butene yields meso-2, 3-dibromo butane.

Statement II : Addition of bromine to an alkene is an electrophilic addition.

174. Statement I : Dimethyl sulphide is commonly used for the reduction of an ozonide of an alkene to get the
carbonyl compound.
Statement II : It reduces the ozonide giving water soluble dimethyl sulphoxide and excess of it
evaporates.
175. 1-bromo-3-chlorocyclobutane when treated with two equivalents of Na, in the presence of ether which of
the following will be formed ?

(A) (B)

(C) (D)

176. Monomer A of a polymer on ozonolysis yields two moles of HCHO and one mole of CH3COCHO.
(a) Deduce the structure of A
(b) Write the structure of all cis form of polymer of compound A
177. 2-methylbutane on reacting with bromine in the presence of sunlight gives mainly :
(A) 1-bromo-2-methylbutane (B) 2-bromo-2-methylbutane
(C) 2-bromo-3-methylbutane (D) 1-bromo-3-methylbutane

178. Reaction of one molecule of HBr with one molecule of 1,3-butadiene at 40°C gives predominantly :
(A) 3-bromobutene under kinetically controlled conditions
(B) 1-bromo-2-butene under thermodynamically controlled conditions
(C) 3-bromobutene under thermodynamically controlled conditions
(D) 1-bromo-2-butene under kinetically controlled conditions

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179. Of the five isomeric hexanes, the isomer which can give only two monochlorinated compounds is :
(A) n-hexane (B) 2, 3-dimethylbutane
(C) 2,2-dimethylbutane (D) 2-methylpentane

Fractional distillation
180. (isomeric products) C5H11Cl 
 M (isomeric products).

What are N and M ?

(A) 6, 6 (B) 6, 4 (C) 4, 4 (D) 3, 3
181. HBr reacts with CH 2  CH  OCH3 under anhydrous conditions at room temperature to give :
(A) CH3CHO and CH 3Br (B) BrCH2CHO and CH3OH
(C) BrCH2  CH 2  OCH3 (D) H 3C  CHBr  OCH3

182. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula
C4 H6 is :
183. The maximum number of isomers (including stereoisomers) that are possible on mono-chlorination of the
following compound, CH3CH2CH (CH3 )CH2CH3 is :
184. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown in the
figure.

I. II. III.

The correct order of their boiling points is :

(A) I > II > III (B) III > II > I
(C) II > III > I (D) III > I > II
185. The reactivity of compound Z with different halogens under appropriate conditions is given below

The observed pattern of electrophilic substitution can be explained by :

(A) the steric effect of the halogen
(B) the steric effect of the tert-butyl group
(C) the electronic effect of the phenolic group
(D) the electronic effect of the tert-butyl group
*186. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is (are) :

(A) (B)

(C) (D)

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187. In the following reaction, the major product is :

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

188.

product of above reaction is :

(A) (B)

(C) (D)

189. How many isomeric optically active dibromo products are formed on bromination of compound given
below ?

190. Among the following reaction(s), which gives(give) tert-butyl benzene as the major product ?

(A) (B)

(C) (D)

191. The correct statement(s) for the following addition reactions is(are) :

(A) (M and O) and (N and P) are two pairs of enantiomers

(B) O and P are identical molecules
(C) Bromination proceeds through trans-addition in both the reactions
(D) (M and O) and (N and P) are two pairs of diastereomers

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192. Which of the following compounds will not undergo Friedel Craft’s reaction with benzene ?

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

193. Choose the correct option(s) that give(s) an aromatic compound as the major product :

(A) (B)

(C) (D)

194. Total number of hydroxyl groups present in a molecule of the major product P is________.

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JEE Advanced-2022
Answers to Selected Question for Revision | Organic Chemistry-I
IOC
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15

B A C B A C C B B C A D A B B

16 17 18 19 20 21 22 23 24 25 26 27

C B C BD D A T Hyperconjugation ACD C AC BD

28. Intramolecular H-bond in o-hydroxy benzaldehyde. 29. D

30. (a) 5.55D (b) 31. A

32. BCD 33. AD 34. B 35. AD 36. 7 37. D 38. 7

39. BC 40. 6 41. ABC 42. BC 43. ACD 44. 3 45. 5
46. 7 47. 10

HCOC
48 49 50 51 52 53 54 55 56 57 58 59 60 61 62

B D A C D C AC D B 4 A D

63 64

BC BD

Organic Chemistry
65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80

D B C D C D C C D B C C B C B D

81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96

B C C C D 8 D B B D A C A B C C

97 98 99 100 101 102 103 104 105 106 107 108 109

D A D D A D A [A-Q] [B-Q] [C-R] [D-P, S] A 5 A

110 111 112 113 114 115 116

B BD 5 ABC BD A 18

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Biomolecule
117 118 119 120 121 122 123 124 125 126 127 128 129 130

B D A B B A A C A D D A D C

131 132 133 134 135 136 137 138 139 140 141 142 143 144

A B D C A A A D A A B D B 2

145 146 147

5 ABC CD

Hydrocarbons
148 149 150 151 152 153 154 155 156 157 158

C A B A B A D A 13 D B

159. D 160. (i) HBr/peroxide (ii) Due to acidic nature of terminal alkyne.
161. B 162. AD 163. B 164. B
165. (i) (A) CH3CH = CHCH3 (ii) (B) (CH3 )2 C = CH2 166. (A) O3 , (B) KO3 , (C) O2

167. (CH3 )2 CH- CH = CH2 168. 1, 4-dibromo-2-butene

169. (a)

(b)

R  (CH3 )2 CHCH2

170. C 171. B 172. B 173. B 174. A

175. D 176. CH2 = C(CH3 )CH = CH2 177. B 178. B 179. B

180. B 181. D 182. 4 183. 8 184. B

185. ABC 186. BD 187. D 188. 5 189. BCD
190. CD 191. B 192. CD 193. 6

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