01/11/2023 A

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MM : 397 Haloalkanes and haloarenes. Alcohol, phenols and ethers-02201 Time : 100 Min.

Chemistry

1. Sodium 5. Out of the following halogen derivatives,

acelylide choose the one which is having zero dipole
CH3 − CH2 − Br ⟶ P, P is moment.
(1) 1-Butene (1) Dichloromethane
(2) Butane (2) Chloroform
(3) 1-Butyne (3) Chloromethane
(4) 2-Butene (4) Tetrachloromethane

2. The compound which can be most easily 6. Given below are two statements: One is
protonated, is labelled as Assertion (A) and the other is
(1) labelled as Reason (R).
Assertion ( A) : 3° alkyl halide undergoes
(2) SN1 reaction very fast.
Reason ( R) : 3° carbocation has high
(3) stability.
(1) Both Assertion & Reason are true and
(4) the Reason is the correct explanation
of the Assertion
(2) Both Assertion & Reason are true but
3. Ethyl alcohol exhibits acidic nature on the Reason is not the correct
reaction with explanation of the Assertion
(1) Acidic K2 Cr2 O7 (3) Assertion is true statement but Reason
is false
(2) Sodium metal
(4) Both Assertion and Reason are false
(3) HCl
statements
(4) Concentrated H2 SO4

4. Major product of the given reaction is

(1)

(2)

(3)

(4)
7. Most acidic compound among the following 9. Identity the major product in the following
is reaction.
(1) C2 H5 OH
(2)

(1)

(2)
(3)

(3)
(4)

(4)

8. In the following reaction, the major product

(A) is

10.

Major product A is
(1)
(1)

(2)
(2)

(3) (3)

(4) (4)
11. 15. Major product obtained when phenol reacts
with Br2 /Water is
(1)

Which of the following reaction is suitable to

carry out the following conversion?
(1) Hydroboration – oxidation
(2) Oxymercuration – reduction
(3) Hydration of alkene
(2)
(4) Oxidation of alkene

12. The relative rate of SN2 reaction is maximum

in
(1) CH3 — X (3)
(2) CH3 — CH2 — X
(3)

(4)
(4)

13. Which among the following has highest 16. Which of the alcohol will give red colour in
dipole moment? Victor Meyer’s test?
(1) CH3 F (1) C2 H5 OH
(2) CH3 Cl (2)

(3) CH3 Br
(4) CH3 I
(3)

14. The major product obtained in the following

reaction is

(4)

(1) 2-methylpropene
(2) Butanal
(3) But-2-ene
(4) Acetone
17. 21. The compound which will react fastest with
Lucas reagent is
(1) CH3 – CH2 – OH
(2) CH2 = CH – CH2 – OH
The product is (3) CH3 OH
(1) (4)

(2)
22. Phenol on reaction with CO2 in presence of
NaOH following by acidic hydrolysis will give
(1) Picric acid
(2) Salicylaldehyde
(3) (3) Salicylic acid
(4) Benzoic acid

23.
(4)

Product (P) is
(1)
18. In the following reaction,
(i) Mg, ether

C6 H5 Br −−−−−−→ A , the product (A) is

(ii) C2 H5 OH
(2)
(1) C6 H6
(2) C6 H5 – C2 H5
(3) C6 H5 – OH
(3)
(4) C6 H5 OC2 H5

19. Phenol can be distinguished from

cyclohexanol by all reagents except
(1) NaOH (4)
(2) FeCl3
(3) Br2 /H2 O
(4) Na 24. ethanolic KOH
PCl 5

CH3 − CH2 − CH2 OH −

−→ A−−−−−→ B
Δ
20. Consider the following reactions (Major)
Identify B in the above scheme
(1) Propyne
Major product C is (2) Propene
(1) (3) Propanone
(4) Propanol

(2)
25. The decreasing order of boiling point of the
(3) following compounds is
(I) Butan-1-ol
(II) Tert-butyl alcohol
(III) diethyl ether
(4)
(1) II > I > III
(2) I > III > II
(3) I > II > III
(4) III > I > II
26. Major product of the following reaction is 29.

(1)

Product B is a/an
(1) Aldehyde
(2)
(2) Primary alcohol
(3) Carboxylic acid
(4) Secondary alcohol

(3) 30. Which one is least reactive towards SN1

reaction?
(1) CH3 – CI
(2) (CH3 )3 C – Cl
(4) (3) CH2 = CH – CH2 – CI
(4)

27. Which alcohol in reaction with Cu at 573 K 31. HI(conc.)

gives ketone as major product? CH3 OCH2 CH3 −−−−→ A + B. Product A and
(1) Excess, Δ
B are
(1) CH3 OH + CH3 CH2 I
(2) (2) CH3 I + CH3 CH2 OH
(3) CH3 OH + CH3 CH2 OH

(3) (4) CH3 I + CH3 CH2 I

32. Consider the following compounds,

(4)

28. In the following reaction, the major products

(A) is

The correct order of acidic strength is

(1) I > III > II
(1) (2) II > I > III
(3) II > III > I
(4) III > I > II

(2)

(3)

(4)
33. When phenol is treated with Br2 /CS2 at 0o C 37. The major product of the following chemical
then the major product obtained is reaction is :
(1)

(1)
(2)

(2)

(3)

(3)
(4)

38. Consider the following reaction

(4)

Products A and B are

(1) CH3 – I and (CH3 )3 C – OH
34. R – Br + AgF → R – F + AgBr (2) (CH3 )3 C – I and CH3 – OH
The above reaction is known as
(1) Finkelstein Reaction (3) CH3 – I and (CH3 )3 C – I
(2) Swarts Reaction (4)
(3) Fittig Reaction
(4) Dow’s Process

35. Which alcohol on reaction with copper at

300°C gives alkene as major product?
39. ( CH3 ) CBr + CH3 ONa → Product
(1) 3

Major product formed is

(1)
(2)

(2) (CH3 )3 C – OH
(3) (3) (CH3 )3 C – OCH3
(4) CH3 CH2 OH
(4)

36. Glycerol on heating with KHSO4 gives

(1)

(2)

(3)

(4)
40. Consider the following reaction sequence 42. The reaction of Lucas reagent is fastest with
(1) CH3 (CH2 )2 OH
(2) (CH3 )3 COH
(3) (CH3 )2 CHOH
Product C is (4) CH3 CH2 OH
(1)
43. Which alkyl halide will react fastest by SN1
mechanism?
(1)
(2)
(2)
(3)

(4)
(3)

44. Which of the following ether cannot be

prepared by Williamson’s synthesis?
(4) (1)
(2)
(3)
(4)

41. In the given reaction 45. Select an incorrect statement about the
following reaction.

the product P is
(1)
(1) It involves formation of carbocation
intermediate
(2) It involves ring expansion
(3) It involves hydride shift
(4) It is an example of E1 elimination

(2) 46. Select the chiral molecule among the

following
(1) CH3 — CHBr — CH3
(2) CH3 — CH2 — Br
(3) CH3 — CH2 — CHBr — CH3
(3) (4) CH3 — CH2 — CHBr — CH2 — CH3

47. In the reactions,

(4)

B and C are
(1) Benzene and propan-2-ol
(2) Phenol and propane
(3) Benzene and acetone
(4) Phenol and acetone
48. 50. How many stereoisomers does the molecule
CH2 = CH – CH2 – CH(Cl)CH3 have?
(1) 8
What are the products A and B? (2) 2
(1) (3) 4
(4) 6

(2) 51. Which of the following compounds will not

give Fehling’s test?
(1) H – CHO
(3) (2) CH3 CHO
(3)

(4) (4)

52. Structure of aspirin (Acetylsalicylic acid) is

(1)
49.

(2)

Product(major)
(1) (3)

(4)

(2)

53. Electrophile formed in Reimer–Tiemann

reaction is
(1) ⊕
CCl2

(2) ¯
¯¯¯
CCl2

(3) : CCl2

(3) (4) ⊝
CHCl2

(4)
54. 56. Consider the following reaction

Major product P is
(1)
The major product P is
(2)
(1)

(3)

(2) (4)

57. Match List I with List II and choose the

correct option.
(3) List I List II

a. Fittig reaction i.

Reimer-
b. Tiemann ii.
(4) reaction
Williamson
c. iii.
synthesis

Clemmensen
d. iv. R – X + R – O– Na+ →
reduction

55. (1) a(i), b(ii), c(iii), d(iv)

(2) a(iv), b(iii), c(ii), d(i)
(3) a(ii), b(i), c(iv), d(iii)
(4) a(iii), b(ii), c(i), d(iv)

The product P is 58. Major product of the given reaction is

(1)

(1)
(2)

(2)

(3)

(3)

(4) (4)
59. 61.

Product B will be
(1)
The products A and B are
(1)
(2)

(2)
(3)

(3)
(4)

(4)

62. 1º, 2º and 3º alcohols are passed over

copper at 573 K, the products respectively
are
60. Identify the most stable carbocation involved (1) Aldehyde, ketone and alkene
in following conversion (2) Aldehyde, ketone and carboxylic acid
(3) Aldehyde, ketone and aldehyde
(4) Ketone, alkene and ketone

(1) 63.

Product D is.
(2) (1) H5 C6 – NH – CH2 – CH3
(2) C6 H5 – CH2 – NH2
(3) C6 H5 – CH2 – OH
(4) C6 H5 NH – OH

(3) 64. Acetone

RCl + Nal ⟶ R + NaCl is known as
(1) Frankland reaction
(2) Finkelstein reaction
(3) Fittig reaction
(4) Ullmann reaction
(4)
65. 69. Which alkyl halide will react fastest with KI in
acetone?
(1) CH3 – Cl
(2)
gives ‘X’ as the major product when heated
with conc. H2 SO4 . ‘X’ is (3)
(1)
(4)

(2)
70. C — Cl bond has partial double bond
character in
(1) Vinyl chloride
(2) Chlorobenzene
(3)
(3) m-nitrochlorobenzene
(4) All of these

71. A : Ethyl alcohol is polar protic solvent.

(4)
R : Acetone is polar aprotic solvent.
(1) Both Assertion & Reason are true and
the reason is the correct explanation of
the assertion
(2) Both Assertion & Reason are true but
66. When ethyl chloride is reacted with AgNO2 the reason is not the correct
then major product formed is explanation of the assertion
(1) CH3 CH2 – O – N = O (3) Assertion is true statement but Reason
(2) CH3 CH2 – NO2 is false
(4) Both Assertion and Reason are false
(3) CH2 = CH2
statements
(4) CH3 CH3
72. CF3 − CH = CH2 + HBr → P;

67. Alkyl iodide is prepared from alkyl chloride The main product P is
by the reaction with NaI in dry acetone. This (1)
reaction is known as
(1) Swarts reaction
(2) Wurtz reaction
(3) Finkelstein reaction (2)
(4) Fittig reaction

68. Consider the following sequence of (3)

reactions

The product (B) is (4)

(1) C2 H5 CH = C = CH2
(2) C2 H5 C ≡ C – CH2 CH3
(3) C2 H5 C ≡ C – CH2 OH
(4) 73. Identify z in the following sequence of
reactions
PBr 3 Alc. KOH dil. H2 SO4

Ethanol −→
− x −−−−−→ y −−−−−→ z

(1) CH2 = CH2

(2) CH3 CH2 OH
(3) CH3 CH2 –O–CH2 CH3
(4) CH3 CH2 OSO3 H
74. Among the following, which one gives 78. The major product obtained on reaction of
turbidity immediately in Lucas test?
(1) CH3 CH2 CH2 OH
(2)
the compound by LiAlH4
followed by hydrolysis is
(1) CH3 CH2 CH2 CH2 OH
(3)
(2)

(3)
(4)

(4)
75. Example of pesticide is
(1) DDT
(2) NaClO3
(3) Na3 AsO4 79.

(4) Na2 SO4

76. Correct reactivity order of haloarene for the

reaction with NaOH is
(1) (1)

(2)
(2)

(3)

(3)

(4)

(4)

77. Which of the following is correct for following

compounds?

80.

(1)

(1) Structure I and II are diastereomers

(2) Structure II and III are enantiomers (2)
(3) Structure I and III are identical
(4) Both (2) & (3)
(3)

(4)
81. Phenol decolourises bromine water and 85. Consider the following reactions.
gives white precipitate by which reaction PCC

mechanism (i) CH3 CH2 – OH −

−→ product (A)]

Cu
(1) Electrophilic addition reaction (ii) CH3 CH2 CH2 – OH −−→ product (B)
(2) Nucleophilic addition reaction 573 K

(3) Electrophilic aromatic substitution Products A and B respectively are

(1) CH3 CHO and CH3 CH2 CHO
(4) Nucleophilic aromatic substitution
(2) CH3 CHO and CH3 COCH3
82. The most suitable solvent for SN2 reaction of (3)
alkyl halides is
(1) (CH3 )2 SO
(2) CS2 (4)
(3) C6 H6
(4) CH3 OH

83. Consider the following chemical reactions 86. Ethylene oxide when treated with phenyl
magnesium bromide followed by hydrolysis
yields
(1) Benzene
(2) Ethylene
(3) 2-ethylphenol
The major product P and Q respectively are (4) 2-phenylethanol
(1)
87. (i) PhMgBr ( excess)
COCl2 −−−−−−−−→ X; Major product X is
(2) ⊕
(ii) H3 O

(1)
(3)
(2)
(4)

(3)

84.
(4)

(1)
88.

(2) (B) as a major product is

(1)

(3) (2)

(4) (3)

(4)
89. Consider the following reaction sequence 94. The Wurtz-Fittig reactions involves
PBr 3 alc. KOH
(1) Two molecules of aryl halides
C2 H5 OH −→
− A−−−−→ B
(2) Two molecules of alkyl halides
B is (3) One molecule of each of alkyl halide
(1) CH2 = CH2 and aryl halide
(2) CH3 CH2 – O – CH2 CH3 (4) One molecule of each of aryl halide
(3) CH3 CH3 and phenol

(4) CH3 CH2 OH

95. A : NBS is a specific reagent for allylic
bromination.
90. Consider the reaction. R : Allylic bromination occurs through
(i) CH 3 MgCl / Dry ether carbocation intermediates.
( CH3 ) C = O −−−−−−−−−−−−−−→ A
2 (1) Both Assertion & Reason are true and
(ii) H2 O
the reason is the correct explanation of
Product A is the assertion
(1) (CH3 )2 CH2 (2) Both Assertion & Reason are true but
(2) (CH3 )2 CHOH the reason is not the correct
explanation of the assertion
(3) (CH3 )3 C – OH
(3) Assertion is true statement but Reason
(4) is false
(4) Both Assertion and Reason are false
statements

96. A : Alkyl halides are colourless when pure.

R : Alkyl bromide develops colour when
91. Which among the following alcohols do not exposed to light.
give iodoform test?
(1) Both Assertion & Reason are true and
(1) PhCH(OH)CH3 the reason is the correct explanation of
(2) PhCH(OH)CH2 CH3 the assertion
(3) CH3 – CH2 – OH (2) Both Assertion & Reason are true but
the reason is not the correct
(4) CH3 CH2 CH(OH)CH3 explanation of the assertion
(3) Assertion is true statement but Reason
92. A : Phenol does not react with NaHCO3 . is false
R : Phenol is weaker acid than H2 CO3 . (4) Both Assertion and Reason are false
(1) Both Assertion & Reason are true and statements
the reason is the correct explanation of
the assertion 97. A : Boiling point of chloroform is higher than
(2) Both Assertion & Reason are true but dichloromethane.
the reason is not the correct R : Chloroform is a polar molecule.
explanation of the assertion (1) Both Assertion & Reason are true and
(3) Assertion is true statement but Reason the reason is the correct explanation of
is false the assertion
(4) Both Assertion and Reason are false (2) Both Assertion & Reason are true but
statements the reason is not the correct
explanation of the assertion
93. A : White precipitate is obtained on treatment (3) Assertion is true statement but Reason
of phenol with bromine water. is false
R : –OH group attached to benzene ring is (4) Both Assertion and Reason are false
an electron donating group. statements
(1) Both Assertion & Reason are true and
the reason is the correct explanation of
the assertion
(2) Both Assertion & Reason are true but
the reason is not the correct
explanation of the assertion
(3) Assertion is true statement but Reason
is false
(4) Both Assertion and Reason are false
statements
98. A : (C6 H5 )3 CCl is rapidly hydrolysed by SN1 100. A : Methyl alcohol reacts with PhMgBr.
mechanism. R : Methyl alcohol contains acidic hydrogen.
R : (C6 H5 )3 CCl can form the stable (1) Both Assertion & Reason are true and
Carbocation by Ionization. the reason is the correct explanation of
(1) Both Assertion & Reason are true and the assertion
the reason is the correct explanation of (2) Both Assertion & Reason are true but
the assertion the reason is not the correct
(2) Both Assertion & Reason are true but explanation of the assertion
the reason is not the correct (3) Assertion is true statement but Reason
explanation of the assertion is false
(3) Assertion is true statement but Reason (4) Both Assertion and Reason are false
is false statements
(4) Both Assertion and Reason are false
statements

99. A : A meso compound does not show optical

activity.
R : Meso compound does not have chiral
centres.
(1) Both Assertion & Reason are true and
the reason is the correct explanation of
the assertion
(2) Both Assertion & Reason are true but
the reason is not the correct
explanation of the assertion
(3) Assertion is true statement but Reason
is false
(4) Both Assertion and Reason are false
statements