Session: 2023-24 Total Questions: 341

CHEMISTRY

10.HALOALKANES AND HALOARENES

Single Correct Answer Type

1. Among the following the one that gives positive iodoform test upon reaction with I and NaOH is
a) CH CH CH(OH)CH CH
b) C H CH CH OH
H C − CH − CH OH
c) |
CH
d) PhCHOHCH
2. Vicinal and geminal dihalides can be distinguished by:
a) KOH(𝑎𝑞. ) b) KOH(alc.) c) Zn dust d) None of these
3. An alkyl halide may be converted into an alcohol by:
a) Addition b) Substitution c) Dehydrohalogenation d) Elimination
4. Dehydrohalogenation in haloalkanes produces:
a) A single bond b) A double bond c) A triple bond d) Fragmentation
5. Chlorination of CS gives:
a) CCl b) CS Cl c) CH d) CHCl
6. Methylene chloride on hydrolysis yields:
a) HCHO b) CH CHO c) CHCl d) CH COCl
7. The greater the ionic character of the carbon metal bond:
a) The more reactive is the organometallic compound
b) The less reactive is the organometallic compound
c) Both are correct
d) None of the above is correct
8. For the reaction,
C H OH + H𝑋 ⎯⎯ C H 𝑋, the order of reactivity is:
a) HI > 𝐻𝐶𝑙 > 𝐻𝐵𝑟 b) HI > 𝐻𝐵𝑟 > 𝐻𝐶𝑙 c) HCl > 𝐻𝐵𝑟 > 𝐻𝐼 d) HBr > 𝐻𝐼 > 𝐻𝐶𝑙
9. The order of reactivities of methyl halides in the formation of Grignard reagent is
a) CH I > 𝐶H Br > 𝐶H Cl b) CH Cl > 𝐶H Br > 𝐶H I
c) CH Br > 𝐶H Cl > 𝐶H I d) CH Br > 𝐶H I > 𝐶H Cl
10. The antiseptic character of iodoform is due to:
a) Its poisonous nature
b) Unpleasant smell
c) Liberation of free iodine
d) None of the above
11. On treating a mixture of two alkyl halides with sodium metal in dry ether, 2-methyl propane was obtained.
The alkyl halides are
a) 2-chloropropane and chloromethane b) 2-chloropropane and chloroethane
c) Chloromethane and chloroethane d) Chloromethane and 1-chloropropane
12. The IUPAC name of the compound, (CH ) CHCH CH Br is:
a) 2-methyl-3-bromopropane

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 b) 1-bromopentane
c) 2-methyl-4-bromobutane
d) 1-bromo-3-methylbutane
13. The given reaction is an example of,
C H Br + KCN(𝑎𝑞. ) ⟶ C H CN + KBr:
a) Elimination
b) Nucleophilic substitution
c) Electrophilic substitution
d) Redox change
14. Which one of the following compound reacts with chlorobenzene to produce DDT?
a) Acetaldehyde b) Nitrobenzene
c) 𝑚-chloroacetaldehyde d) Trichloroacetaldehyde
15. Preparation of alkyl halides in laboratory is least preferred by:
a) Halide exchange
b) Direct halogenation of alkanes
c) Treatment of alcohols
d) Addition of hydrogen halides to alkenes
16. Which one of the following pairs is the strongest pesticide?
a) Chloroform and benzene hexachloride b) DDT and 666
c) 666 and ether d) isocyanides and alcohol
17. Iodoform gives a precipitate with AgNO on heating but chloroform does not because:
a) Iodoform is ionic
b) Chloroform is covalent
c) C—I bond in iodoform is weak and C—Cl bond in chloroform is strong
d) None of the above
18. Which reagent is useful in increasing the carbon chain of an alkyl halide?
a) HCN b) KCN c) NH CN d) AgCN
19. Chloroform on reaction with conc. HNO gives an insecticide and war gas known as:
a) Chloropicrin b) Nitromethane c) Picric acid d) Acetylene
20. Aryl halides are less reactive towards electrophiles than alkyl halides due to:
a) Resonance
b) Stability of carbonium ions
c) High boiling point
d) None of the above
21. Carbon tetrachloride reacts with steam at 500℃ to give:
a) COCl b) CHCl c) Both (a) and (b) d) None of these
22. Chloroform on reaction with acetone yields:
a) Insecticide b) Hypnotic agent c) Analgesic d) Isocyanide
23. In Wurtz reaction alkyl halide reacts with
a) Sodium in ether b) Sodium in dry ether c) Sodium only d) Alkyl halide in ether
24. When iodoform is heated with silver powder it forms:
a) Acetylene b) Ethylene c) Methane d) Ethane
25. 1,3-dibromopropane reacts with metallic zinc to form:
a) Propene b) Cyclopropane c) Propane d) Hexane
26. In the reaction sequence

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 Compound ‘X ’ is
a) Chlorobenzene b) Benzene c) Toluene d) Biphenyl methane
27. Which is used as a general anaesthetic in place of diethyl ether?
a) CF —CHClBr b) CF —CHCl c) CF —CHBr d) None of these
28. Which of the following ketones will not respond to iodoform test?
a) Methyl isopropyl ketone b) Ethyl isopropyl ketone
c) Dimethyl ketone d) 2-hexanone
29. Propyl iodide and isopropyl iodide are:
a) Functional isomers b) Chain isomers c) Metamers d) Position isomers
30. 𝑋 + KCN ⟶ CH CN ⎯⎯⎯⎯⎯⎯ /
CH CH NH ,
What is (X)?
a) CH CH Cl b) CH Cl c) CH CH CH Cl d) (CH ) CHCl
31. 2-chlorobutane obtained by chlorination of butane, will be:
a) 𝑚𝑒𝑠𝑜-form b) Racemic form c) 𝑑-form d) 𝑙-form
32. Reaction of alkyl halides with aromatic compounds in presence of anhy. AlCl is known as
a) Friedel-Craft’s reaction b) Hofmann degradation
c) Kolbe’s synthesis d) Beckmann rearrangement
33. Which of the following statements is incorrect regarding benzyl chloride?
a) It gives white precipitate with alcoholic AgNO
b) It is an aromatic compound with substitution in the side chain
c) It undergoes nucleophilic substitution reaction
d) It is less reactive than vinyl chloride
34. Which of the following compounds is not formed in iodoform reaction of acetone?
a) CH COCH I b) ICH COCH I c) CH COCHI d) CH COCI
35. Of the isomeric hexanes, the isomers that give the minimum and maximum number of monochloro
derivatives are respectively
a) 3-methylpentane and 2, 3-dimethylbutane b) 2, 3-dimethylbutane and n-hexane
c) 2, 2-dimethylbutane and 2-methylpentane d) 2, 3-dimethylbutane and 2-methypentane
36. 1, 2-dibromo cyclohexane on dehydrogenation gives
d) None of these
a) b) c)

37. Ethyl ortho formate is formed by heating ………… with sodium ethoxide.
a) CHCl b) C H OH c) HCOOH d) CH CHO
38. Chloroform is kept in dark coloured bottles because:
a) It is inflammable
b) It gives a peroxide
c) It undergoes rapid chlorination
d) It is oxidized to poisonous phosgene
39. Which of the following will not respond to iodoform test?
a) Ethyl alcohol b) Propanol-2 c) Propanol-1 d) Ethanal
40. At higher temperature, iodoform reaction is given by:
a) CH COOCH b) CH COOC H c) C H COOCH d) CH COOC H
41. Molecular formula of chloropicrin is
a) CHCl NO b) CCl NO c) CCl NO d) CCl NO
42. Which one of the following is not true for the hydrolysis of t-butyl bromide with aqueous NaOH?
a) Reaction occurs through the 𝑆 1 mechanism.
b) The intermediate formed is a carbocation.
c) Rate of the reaction doubles when the concentration of alkali is doubled.
d) Rate of the reaction doubles when the concentration of t-butyl bromide is doubled.
43. CHCl reacts with conc. HNO to give
a) CCl NO b) CH NO c) CH CN d) CH CH NO
44. The correct order of melting and boiling points of the primary (1 ͦ), secondary(2 ͦ) and tertiary (3 ͦ) alkyl
halides is:
a) 𝑃 > 𝑆 > 𝑇 b) 𝑇 > 𝑆 > 𝑃 c) 𝑆 > 𝑇 > 𝑃 d) 𝑇 > 𝑃 > 𝑆
45. Ethyl alcohol gives ethyl chloride on treatment with:
a) NaCl b) SOCl c) Cl d) KCl
46. 20% aqueous solution of sodium chloride containing ethyl alcohol on electrolysis gives:
a) Ethyl chloride b) Chloral c) Acetaldehyde d) Chloroform
47. Which of the following statements about benzyl chloride is incorrect?
a) It is less reactive than alkyl halides
b) It can be oxidised to benzaldehyde by boiling with copper nitrate solution
c) It is a lachrymatory liquid and answers Beilstein’s test
d) It gives a white precipitate with alcoholic silver nitrate
48. The S 1 reactivity of ethyl chloride is:
a) More or less equal to that of benzyl chloride
b) Less than that of benzyl chloride
c) More or less equal to that of chlorobenzene
d) Less than that of chlorobenzene
49. Which of the following will not give iodoform test?
a) Isopropyl alcohol
b) Ethanol
c) Ethanal
d) Benzyl alcohol
50. Elimination of HBr from 2-bromobutane results in the formation of:
a) Equimolar mixture of 1- and 2- butene
b) Predominantly 2-butene
c) Predominantly 1- butene
d) Predominantly 2-butyne
51. 1,2-dibromoethane is added to prevent deposition of lead metal in :
a) Water pipes
b) Petrol engines
c) Electric heaters
d) Metal working lathe machines
52. For the reaction,

a) CH —CH=CH— CH predominates

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 b) CH =CH—CH —CH predominates
c) Both are formed in equal amounts
d) The product ratio is dependent on the halogen X
53. Grignard reagent is prepared by the reaction between:
a) Zinc and alkyl halide
b) Magnesium and alkyl halide
c) Magnesium and alkane
d) Magnesium and aromatic hydrocarbon
54. In the following swquence of reactions

the end product (𝐶) is:

a) Acetaldehyde b) Ethyl alcohol c) Acetone d) Methane
55. The IUPAC name of the compound,
CH COCH—CHCOOH is:
⃒ ⃒
Cl Br
a) 2-bromo-3-chloro-4-oxopentanoic acid
b) 3-chloro-2-bromo-4-oxopentanoic acid
c) 4-carboxybromo-3-chloro-2-butanone
d) None of the above
56. Which of the following is primary halide?
a) Isopropyl halide b) Sec-butyl halide c) Tert-butyl halide d) Neo-hexyl chloride
57.

Compound A is

a) b) c) d)

58. Which of the following do not form Grignard reagent?

a) CH F b) CH Cl c) CH Br d) CH I
59. The structure of the major product formed in the following reaction is

a) b)
 c) d)

60. Butane nitrile may be prepared by heating:

a) Propyl alcohol with KCN
b) Butyl alcohol with KCN
c) Butyl chloride with KCN
d) Propyl chloride with KCN
61. Consider the following reaction,

Identify the structure of the major product ‘X ‘:

a)

b)

c)

d)

62. A mixture of 1-chloropropane and 2-chloropropane when treated with alcoholic KOH, it gives:
a) 1-propene
b) 2-propene
c) Isopropylene
d) A mixture of 1-propene and 2-propene
63. In Wurtz reaction of alkyl halides with sodium, the reactivity order of these halides is:
a) 𝑅I > 𝑅Br > 𝑅Cl b) 𝑅Cl > 𝑅Br > 𝑅I c) 𝑅Br > 𝑅I > 𝑅Cl d) None of these
64. A mixture of sodium acetate and sodalime is heated and the product treated with excess of chlorine in
presence of bright sunlight. The product is:
a) CH COOH b) CH BrCOOH c) CCl d) CH Cl
65. 1-chlorobutane on reaction with alcoholic KOH gives:
a) 1-butene b) 1-butanol c) 2-butene d) 2-butanol
66. Which halide does not get hydrolysed by sodium hydroxide?
a) Vinyl chloride b) Methyl Chloride c) Ethyl chloride d) Isopropyl chloride
67. Iodoform test is not given by
a) 2-pentanone b) Ethanol c) Ethanal d) 3-pentanone
68. The alkyl halides that can be made by free radical halogenation of alkanes are
a) 𝑅Cland 𝑅Br but not 𝑅F 𝑜𝑟 𝑅I b) 𝑅F, 𝑅Cland 𝑅Brbut not RI
c) 𝑅F, 𝑅Cl, 𝑅B𝑟, 𝑅I d) 𝑅F, 𝑅CI 𝑎𝑛𝑑 𝑅Ibut not 𝑅Br
69. Non-sticking frying pans are coated with:
a) Ethylene
b) Styrene
c) Tetrafluoroethylene (Teflon )
d) Chlorofluoro methane
70. Ethyl chloride on heating with AgCN forms a compound X. The functional isomer of X is
a) C H NC b) C H NH c) C H CN d) None of these
71. Chlorine is most reactive towards NaOH in:
 a) CH Cl b) CH =CHCl c) C H Cl d) C H CH Cl
72. The chemical formula of ‘tear gas’ is
a) COCl b) CO c) Cl d) CCl NO
73. The order of polarity of CH I, CH Br and CH Cl molecules follows the order:
a) CH Br > CH Cl > CH I
b) CH I>CH Br > CH Cl
c) CH Cl > CH Br > CH I
d) CH Cl > CH I>CH Br
74. Chloroform gives a trichloro derivative of an alcohol on reaction with
a) conc. nitric acid b) aq. alkali
c) acetone and alkali d) a primary amine and an alkali
75. In order to convert aniline into chlorobenzene the reagent used is
a) NaNO /HCl, CuCl b) Cl /CCl c) Cl /AlCl d) CuCl
76. Number of monochloro derivatives obtained when 𝑛𝑒𝑜 −pentane is chlorinated, is
a) One b) Two c) Three d) Four
77. Which of the following will not form a yellow precipitate on heating with an alkaline solution of iodine?
a) CH CH(OH)CH b) CH CH CH(OH)CH c) CH OH d) CH CH OH
78. CaOCl + H O → Ca(OH) + 𝑋
𝑋 + CH CHO → 𝑌
𝑌 + Ca(OH) → CHCl .
What is ‘Y’?
a) CH CH(OH) b) CH Cl c) CCl CHO d) CCl COCH
79. Reaction of 𝑡𝑟𝑎𝑛𝑠-2-phenyl-1-bromocyclopentane on reaction with alcoholic KOH produces
a) 4-phenylcyclopentene b) 2-phenylcyclopentene
c) 1-phenylcyclopentene d) 3-phenylcyclopentene
80. In order to get ethanethiol from C H Br, the reagent used is:
a) Na S b) NaHS c) KCNS d) K S
81. Solvent used in dry-cleaning of clothes is:
a) Alcohol b) Acetone c) Carbon tetrachloride d) freon
82. Correct order of reactivity for halides is:
a) Vinyl chloride > allyl chloride > propyl chloride
b) Propyl chloride > vinyl chloride > allyl chloride
c) Allyl chloride > propyl chloride > vinyl chloride
d) None of the above
83. The substance employed as tear gas is:
a) Westron b) Chloropicrin c) Chloretone d) None of these
84. One of the following that cannot undergo dehydrohalogenation is
a) 𝑖𝑠𝑜-propyl bromide b) ethanol c) Ethyl bromide d) None of the above
85. The starting material for the preparation of CHI is:
a) C H OH b) CH OH c) C H CHO d) HCHO
86. Optically active compound is:
a) 2-chloropropane b) 2-chlorobutane c) 3-chloropentane d) None of these
87. CCl is insoluble in water because:
a) Water is non-polar
b) CCl is non-polar
c) Water and CCl are polar
d) None of the above
88. Which one is most reactive towards S 1 reactions?
a) C H CH(C H )Br b) C H CH(CH )Br c) C H C(CH )(C H )Br d) C H CH Br
89. Which of the following applies in the reaction,
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 .
CH CHBrCH CH ⎯⎯⎯⎯⎯⎯
(i)CH CH = CHCH (major product)
(ii) CH = CHCH CH (minor product)
a) Markownikoff’s rule b) Saytzeff’s rule c) Kharasch effect d) Hofmann’s rule
90. The following compound on hydrolysis in aqueous acetone will give

a) Mixture of (K) and (L) b) Mixture of (K) and (M)

c) Only (M) d) Only (K)
91. The metal used for the de-bromination reaction of 1, 2-dibromoethane.
a) Na b) Zn c) Mg d) Li
92. Reaction of t-butyl bromide with sodium methoxide produces
a) Isobutane
b) Isobutylene
c) Sodium t-butoxide
d) t-butylmethyl ether
93. CH Br + KCN(alc. ) → 𝑋
⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯ 𝑌

What is Y in the series?

a) CH CN b) C H CN c) C H NH d) CH NH
94. If methyl iodide and ethyl iodide are mixed in equal proportions, and the mixture is treated with metallic
sodium in presence of dry ether, the number of possible products formed is:
a) 2 b) 3 c) 1 d) 4
95. An alkyl iodide on standing darkens, due to:
a) Hydrolysis
b) Conversion into ether
c) Liberation of iodine
d) Formation of alkanes
96. X compound reacts with Na to give CH3 CH2CH2 CH3 , then compound X is
a) CH CH OH
b) CH CH − Cl
 c) CH − CH
d) CH CH CH CH OH
97. Maximum number of molecules of CH I that can react with a molecule of CH NH are
a) 3 b) 4 c) 2 d) 1
98. The CCl and CHCl can be distinguished by the action of:
a) 𝑅NH + KOH alc. b) 𝑅CN + KOH alc. c) Hydrolysis d) Burning in air
99. Alkyl halides reacts with dialkyl lithium cuprate to give:
a) Alkenes b) Alkyl Cu halide c) Alkanes d) Alkenyl halide
100. Which responds to the iodoform test?
a) Butanol b) Butan-1-al c) Butanone-2 d) 3-pentanone
101. In the reaction sequence,
⨁
C H Cl + KCN ⎯⎯⎯⎯⎯⎯ 𝑋 ⎯⎯⎯ 𝑌
△
What is the molecular formula of Y?
a) C H O b) C H N c) C H O d) C H O
102. Which one of the following forms propane nitrile as the major product?
a) Ethyl bromide + alcoholic KCN b) Propyl bromide + alcoholic KCN
c) Propyl bromide + alcoholic AgCN d) Ethyl bromide + alcoholic AgCN
103. The compound 𝐴 forms 𝐵 with sodium metal and again 𝐴 forms 𝐶 with PCl , but 𝐵 and 𝐶 form diethyl
ether. Therefore 𝐴, 𝐵 and 𝐶 are:
a) C H OH, C H ONa, C H b) C H OH, C H Cl, C H ONa c) C H OH, C H Cl, C H Cld) C H OH, C H Cl, C H ONa
104. For the carbylamine reaction we need hot alcoholic KOH and:
a) Any amine and chloroform
b) Chloroform and silver powder
c) A primary amine and an alkyl halide
d) Any monoalkyl amine and trichloro methane
105. Ethyl bromide reacts with lead-sodium alloy to form:
a) Tetraethyl lead b) Tetraethyl bromide c) Both (a) and (b) d) None of these
106. The number of possible enantiomeric pairs that can be produced during mono-chlorination of 2-methyl
butane is
a) 3 b) 4 c) 1 d) 2
107. Alkyl halides on treatment with a suspension of Ag O moist in ether gives:
a) Alkanol b) Alkanal c) Alkanes d) Alkoxy alkane
108. The conversion of ethyl chloride into diethyl ether takes place by
a) Williamson’s synthesis b) Perkin’s reaction
c) Wurtz reaction d) Grignard reaction
109. Which process does not occur during formation of CHCl from C H OH and bleaching powder?
a) Hydrolysis b) Oxidation c) Elimination d) Chlorination
110. Which of the following does not answer iodoform test?
a) 𝑛-butyl alcohol b) Acetophenone c) Acetaldehyde d) Ethylmethyl ketone
111. Methyl bromide is not used:
a) As an insecticide
b) As disinfectant
c) For dyeing clothes
d) As disinfectant for young fruit trees
112. Which compound on reaction with ethyl magnesium bromide and water will form 2-methyl-2-butanol?
a) CH COCH b) CH COOCH c) CH CH CHO d) C H COCH
113. Alkyl halides are less soluble in water because
a) they ionise in water b) they do not form H-bonds with water
c) they are highly viscous d) they have very strongC − 𝑋 bond

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114. Hexachloroethane is also called
a) Artificial sweetner b) Artificial camphor c) Artificial polymer d) None of these
115. Isobutyl magnesium bromide with dry ether and absolute alcohol gives:

a)

b)

c)

d)

116. Strong reducing agent converts CHCl into:

a) C H b) C H c) C H d) CH
117. Which of the following are arranged in decreasing order of dipole moment:
a) CH Cl, CH Br, CH F b) CH Cl, CH F, CH Br c) CH Br, CH Cl,CH F d) CH Br, CH F, CH Cl
118. Fluorobenzene (C H F) can be synthesised in the laboratory
a) By heating phenol with HF and KF
b) From aniline by diazotisation followed by heating the diazonium salt with HBF
c) By direct fluorination of benzene withF gas
d) By reacting bromobenzene with NaF solution
119. 1-chlorobutane on reaction with alcoholic potash gives
a) but-1-ene b) butan-1-ol c) but-2-ene d) butan-2-ol
120. On warming with silver powder, chloroform is converted into
a) Acetylene b) Hexachloroethane
c) 1, 1, 2, 2-tetrachloroethane d) Ethylene
121. What is the product A in the following?

a) b)

c) Both (a) and (b) d) None of the above

122. Identify (Z) in the following reaction series,

CH —CH CH =CH
a) CH —CH —CN b) c) ⃒ ⃒ d) ⃒ ⃒
Br CN Br CN
123. How many structures of F is possible?

a) 2 b) 5 c) 6 d) 3
124. PVC plastics are produced by the polymerization of:
a) Vinyl acetate b) Allyl chloride c) Vinyl chloride d) Ethene
125. Ethylene dichloride can be prepared by the reaction of HCl and :
a) Ethane b) Ethylene c) Acetylene d) Ethylene glycol
126. Polymer of chloroethylene is:
 a) PVC b) Teflon c) Nylon d) Terylene
127. Most readily hydrolysed halides is:
a) C H Cl b) (C H ) CHCl c) C H CH Cl d) (C H ) CCl
128. What is the product of the reaction of 1, 3-butadiene with Br ?
a) 1, 4-dibromo butene b) 1, 2- dibromo butene
c) 3, 4- dibromo butene d) 2, 3- dibromo-2-butene
129. Chlorobenzene gives aniline with
a) NH /Cu 0 b) NH /H SO c) NaNH d) None of the above
130. In the following compound, least number of monochlorination is possible

a) CH CH CH CH CH b)

c) d)

131. 2, 2-dichloro propane on hydrolysis yields

a) Acetone b) 2, 2-propane diol
c) Isopropyl alcohol d) Acetaldehyde
132. The product of vinyl chloride and HCl is a
a) 𝑔𝑒𝑚 chloride b) Ethylidene chloride
c) 1, 1 dichloroethane d) All of the above are correct
133. Among the following, the molecule with the highest dipole moment is:
a) CH Cl b) CH Cl c) CHCl d) CCl
134. CO on reaction with C H MgBr and H O gives:
a) Ethane b) Propionic acid c) Acetic acid d) None of these
135. Methyl chloride reacts with silver acetate to yield:
a) Acetic acid b) Methyl acetate c) Acetyl chloride d) Acetaldehyde
136. A compound 𝐴 of formula C H Cl on reaction with alkali can give 𝐵 of formula C H O or 𝐶 of formula
C H . 𝐵on oxidation gave a compound of the formula C H O . 𝐶with dilute
H SO containing H ion gave 𝐷 of formula C H O, which with bromine and NaOH gave the sodium salt
of C H O . Then 𝐴 is:
a) CH CH CHCl
b) CH CCl CH
c) CH ClCH CH Cl
d) CH CHClCH Cl
137. Compounds formed, when methyl amine is heated with chloroform in the presence of KOH is:
a) CH —C≡N b) CH N ≡C c) CH — N ≡C d) CH NHCH
138. Tertiary butyl alcohol gives tertiary butyl chloride on treatment with
a) Conc. HCl/anhy. ZnCl b) KCN c) NaOCl d) Cl
139. The reaction of toluene with Cl in presence of FeCl gives predominantly
a) Benzoyl chloride b) Benzyl chloride
c) o-and p-chlorotoluene d) m-chlorotoluene
140. Which one of the following compounds when heated with KOH and a primary amine gives carbylamine
test?
a) CHCl b) CH Cl c) CH OH d) CH CN
141. In the following reaction:
 a) C H CH OCH C H b) C H CH OH c) C H CH d) C H CH CH C H
142. For a given alkyl group, the densities/b. p./m. p. are in the order:
a) 𝑅I < 𝑅Br < 𝑅Cl b) 𝑅I < 𝑅Cl < 𝑅Br c) 𝑅Br < 𝑅I < 𝑅Cl d) 𝑅Cl < 𝑅Br < 𝑅I
143. Carbylamine test is performed by heating alc. KOH with:
a) CHCl and Ag
b) Trihalogenated methane and primary amine
c) CH Cl and C H NH
d) 𝑅CN and 𝑅NH
144. Which of these compounds is synthesised by chloral?
a) DDT b) BHC c) Chloroform d) Michlers ketones
145. Iodoform can be prepared from all except:
a) Isopropyl alcohol b) 3-methyl -2-butanone c) Isobutyl alcohol d) Ethyl methyl ketone
146. When vinyl chloride is passed through alcoholic KOH solution:
a) It dissolves b) It forms vinyl alcohol c) It forms acetylene d) It has no action
147. Following compounds are given:
(i) CH CH OH (ii) CH COCH

Which of the above compound(s), on being warmed with iodine solution and NaOH, will give iodoform?
a) (i),(iii) and (iv) b) Only (ii) c) (i), (ii) and (iii) d) (i) and (ii)
148. DDT is obtained by the reaction of chlorobenzene with
a) Chloral b) Chloroform c) Dichloromethane d) Acetaldehyde
149. The reaction products of the reaction between C H NH , CHCl and KOH are:
a) C H NC + KCl
b) C H OH + NH Cl + H O
c) C H Cl + NH Cl + KCl
d) C H CN + KCl
150. In the reaction,
CH C ≡CNa + (CH ) CHCl ⟶
the product formed is:
a) 4-methyl-2-pentyne b) Propyne c) Propyne and propene d) None of these
151. Which one of the following chlorohydrocarbons readily undergoes solvolysis?

a) CH = CHCl b)

c) d)

152. Grignard reagent with hydrogen cyanide gives:

a) Aldehyde b) Ketone c) Both (a) and (b) d) None of these
153. What happens if CCl is treated with AgNO ?
a) A white ppt. of AgCl will form b) NO will be evolved
c) CCl will dissolve in AgNO d) Nothing will happen
154. Among the following which one has weakest carbon-halogen bond?
a) Benzyl bromide b) Bromobenzene c) Vinyl bromide d) Benzyl chloride
155. Of the five isomeric hexanes, the isomer which can give two monochlorinated compounds is
a) 2-methylpentane b) 2,2-dimethylbutane c) 2, 3-dimethylbutane d) n-hexane
156. Which of the following compounds gives trichloromethane on distilling with bleaching powder?
 a) Methanal b) Phenol c) Ethanol d) Methanol
157. Sodium ethoxide reacts with ethyl iodide to yield:
a) CH CH b) C H OCH c) C H OC H d) None of these
158. CH Br + KCN (alc. ) → 𝑋 ⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯ 𝑌, what is Y in the series?
/
a) CH CN b) C H CN c) C H NH d) CH NH
159. Identify A and B in the following reactions
.
𝐴 ⎯⎯⎯⎯⎯⎯⎯ C H OH ⎯⎯⎯⎯⎯ 𝐵
∆
a) 𝐴 = C H , 𝐵 = C H b) 𝐴 = C H Cl, 𝐵 = C H
c) 𝐴 = C H , 𝐵 = C H Cl d) 𝐴 = C H Cl, 𝐵 = C H Cl
160. The reagent used in the conversion of 1-butanol to 1-bromobutane is:
a) CHBr b) Br c) CH Br d) P + Br
161. t-butyl chloride preferably undergo hydrolysis by
a) S 1 mechanism
b) S 2 mechanism
c) Any of (a) and (b)
d) None of the above
162. Which statement is wrong about chloroform?
a) Chloroform is used as anaesthetic
b) Chloroform has distorted tetrahedral shape
c) Chloroform is used as a solvent
d) Chloroform has 𝑠𝑝 -hybridised carbon atom
163. When CCl is boiled with KOH, the product formed is:
a) Formic acid b) Methyl alcohol c) Formaldehyde d) Carbon dioxide
164. Which set of reagents will produce freon(CCl F ) ?
a) C + F + Cl ⟶ b) CH Cl + F ⟶ c) CCl + HF ⎯⎯ d) CCl + F ⟶
165. Which of the following will not give positive iodoform test?
a) CH CH CHOHCH b) CH CH CH COCH c) CH CH COCH CH d) CH COC H
166. Which of the following does not react with benzene in presence of anhydrous AlCl ?
a) C H Cl b) C H CH Cl c) CH Cl d) C H CH CH CH Cl
167. Iodoform is obtained when ethanol is heatd with
a) KI and aq. KOH b) I and aq. KOH c) I /aq. KI d) HI and HIO
168. 𝑛-propyl bromide reacts with ethanolic KOH to form:
a) Propane b) Propene c) Propyne d) Propyl alcohol
169. Which of the following statements regarding the S 1 reaction shown by alkyl halide is not correct?
a) The added nucleophile plays no kinetic role in S 1 reaction.
b) The S 1 reaction involves the inversion of configuration of the optically active substrate.
c) The S 1 reaction on the chiral starting material ends up with racemization of the product.
d) The more stable the carbocation intermediate the faster the S 1 reaction.
170. Pick up the correct statement about alkyl halides:
a) They show H-bonding.
b) They are soluble in water.
c) They are soluble in organic solvents.
d) They do not contain any polar bond.
171. The product of reaction between alcoholic silver nitrite with ethyl bromide is
a) Ethene b) Ethane c) Ethyl nitrile d) Nitro ethane
172. 1-phenyl, 2-chloropropane on treating with alc. KOH gives mainly:
a) 1-phenylpropene
b) 2-phenylpropene

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 c) 1-phenylpropan-2-ol
d) 1-phenylpropan-1-ol
173. In the reaction,

The major product A is

H3CO

a) b) c) d)
Cl

174. (CH ) CMgCl on reaction with D O gives:

a) (CH ) CD b) (CH ) OD c) (CD ) CD d) (CD ) OD
175. Grignard reagent shows addition on:
a) b) —C≡N c) d) All of these
176. When tetrahydrafuran is treated with excess HI, the product formed is
a) 1, 4-diiodobutane b) 1, 4-butanediol
c) 2-iodotetrahydrofuran d) 4-iodo-1-butanol
177. Lodoform can be used in medicine as:
a) Anaesthetic b) Antiseptic c) Analgesic d) Antifebrin
178. A mixture of two organic compounds was treated with sodium metal in ether solution. Isobutane was
obtained as a product. The two chlorine compounds are:
a) Methyl chloride and propyl chloride
b) Methyl chloride and ethyl chloride
c) Isopropyl chloride and methyl chloride
d) Isopropyl chloride and ethyl chloride
179. Wurtz’s reaction involves the reduction of alkyl halide with
a) Zn/HCl b) HI c) Zn/Cu couple d) Na in ether
180. In the following sequences of reactions;
( .)
CH CH CH Br ⎯⎯⎯⎯⎯ (𝐴) ⎯⎯
( .)
(𝐵) ⎯⎯⎯⎯⎯ (𝐶) the end product (𝐶)is :
a) Propene
b) Propyne
c) Propan-l-ol
d) Propan-2-ol
181. When CHCl is boiled with NaOH, it gives
a) Formic acid b) Trihydroxy methane
c) Acetylene d) Sodium formate
182. Which of the following compounds has the highest boiling point ?
a) CH CH CH Cl b) CH CH CH CH Cl
c) CH CH(CH )CH Cl d) (CH ) CCl
183. Which one is liquid at room temperature?
a) CH Cl b) C H Cl c) CH Br d) C H Br
184. The organic chloro compound, which shows complete stereochemical inversion during an 𝑆 2 reaction is
a) (C H ) CHCl b) (CH ) CCl c) (CH ) CHCl d) CH Cl
185. The best method for the conversion of an alcohol into an alkyl chloride is by treating the alcohol with
a) PCl b) PCl
c) SOCl in presence of pyridine d) dry HCl in the presence of anhydrous ZnCl
186. Which compound is used in cooling?
a) CHCl b) CCl c) CF d) CCl F
187. Which is finally produced when acetylene reacts with HCl?
a) CH =CHCl b) CH CHCl c) ClCH=CHCl d) None of these
188. The reaction,

shows:
a) Reduction
b) Oxidation
c) Neutralisation
d) Nucleophilic substitution
189. Which of the following alkyl halide is used as methylating agent?
a) C H Cl b) C H Br c) C H I d) CH I
190. The products of reaction of alcoholic silver nitrite with ethyl bromide are:
a) Ethane b) Ethene c) Ethyl alcohol d) Nitroethane
191. Which is most reactive for S 2 reactions?
a) CH I b) C H I c) C H I d) C H I
192. The product obtained on treatment of ethyl chloride with potassium cyanide is reduced by sodium and
alcohol to give:
a) Propyl amine b) Ethyl amine c) Diethyl amine d) Acetic acid
193. The molecular formula of the chlorinated acetone formed in the distillation of acetone with bleaching
powder is:
a) CH COCl b) CCl OCl c) CH ClCOOH d) CCl COCH
194. Compound ‘A’ reacts with alcoholic KOH to yield compound ‘B’ which on ozonolysis followed by reaction
with Zn/H O gives methanal and propanal. Compound ‘A’ is
a) 1-propanol b) 1-butanol c) 1-chlorobutane d) 1-chloropentane
195. Phenol is heated with CHCl and alcoholic KOH when salicylaldehyde is produced. The reaction is known
as:
a) Rosenmund’s reaction
b) Reimer-Tiemann reaction
c) Friedel-Craft’s reaction
d) Sommelet reaction
196. Which of the following can be used as local anaesthetic?
a) CHCl b) C H with O c) C H Cl d) C H OH
197. Which of the following is not inflammable?
a) CHCl b) Benzene
c) Toluene d) Carbon tetrachloride
198. Which of the following does not answer iodoform test?
a) N-butyl alcohol b) Sec-butyl alcohol c) Acetophenone d) Acetaldehyde
199. Grignard reagent is not prepared in aqueous medium but prepared in either medium, because
a) the reagent is highly reactive in ether b) the reagent does not react with water
c) the reagent becomes inactive in water d) the reagent reacts with water
200. The reaction in which phenol differs from alcohol is
a) It undergoes esterification with carboxylic acid b) It reacts with ammonia
c) It forms yellow crystals of iodoform d) It liberates H with Na metal
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201. Which compound is used as helminthicide for elimination of hook worms?
a) CH b) CHCl c) C H Cl d) CCl
202. In the preparation of chlorobenzene from aniline, the most suitable reagent is
a) Chlorine in the presence of ultraviolet light b) Chlorine in the presence of AlCl
c) Nitrous acid followed by heating with Cu Cl d) HCl and Cu Cl
203. Methyl magnesium iodide on treatment with D O furnishes a hydrocarbon, alongwith Mg(OD)I. The
hydrocarbon is:
a) CH D b) CH CH D c) CH d) None of these
204. A Grignard reagent is prepared by reacting magnesium with:
a) Methyl amine b) Diethyl ether c) Ethyl iodide d) Ethyl alcohol
205. Identify A and B in the following reaction
C H Cl ⎯⎯ C H OH ⎯⎯ C H Cl
a) A= aqueous KOH; B= AgOH b) A= alcoholic KOH/ ∆; B=aqueous NaOH
c) A= aqueous NaOH; B= AgNO d) 𝐴 = AgNO ; 𝐵 = KNO
206. A yellow precipitate is obtained when aqueous AgNO is added to a solution of the compound:
a) CCl CHO b) CHI c) CHCl d) C H CH Cl
207. Which statement is correct?
a) C H Br reacts with alcoholic KOH to form C H OH
b) C H Br when treated with metallic sodium gives ethane
c) C H Br when treated with sodium ethoxide forms diethyl ether
d) C H Br with AgCN forms ethyl cyanide
208. Phosgene is a common name for:
a) CO and PH b) Phosphoryl chloride c) Carbonyl chloride d) Carbon tetrachloride
209. The alkyl halide which does not give white precipitate with alcoholic AgNO solution is:
a) Ethyl chloride b) Allyl chloride c) Isopropyl chloride d) Vinyl chloride
210. An alkyl halide reacts with equivalent amount of NH to give:
a) Amide b) Cyanide c) Amine d) None of these
211. The combination which produces 𝑡-butyl alcohol when treated with Grignard reagent:
a) CH MgBr + CH COCH
b) C H MgBr + CH COCH
c) CH MgBr + (CH ) CHOH
d) CH MgBr + (CH ) COH
212. Methyl chloride on treatment with potassium cyanide followed by hydrolysis yields:
a) HCOOH b) CH COOH c) CH CN d) CH COOK
213. 9.65 C of electric current is passed through fused anhydrous magnesium chloride. The magnesium metal
thus, obtained is completely converted into a Grignard reagent. The number of moles of the Grignard
reagent obtained is
a) 5 × 10 b) 1 × 10 c) 5 × 10 d) 1 × 10
214. A bromoalkane ‘X’ reacts with magnesium in dry ether to form compound ‘Y’. The reaction of ‘Y’ with
methanal followed by hydrolysis yield an alcohol having molecular formula C H O. The compound ‘X’ is
a) Bromoethane b) Bromomethane c) 1-bromopropane d) 2-bromopropane
215. C H Br ⎯ (𝐴) ⎯⎯⎯⎯⎯⎯⎯ (𝐵)
The compound (𝐵) in above reaction is:
a) Ethylene chloride b) Acetic acid c) Propionic acid d) Ethyl cyanide
216. A salt solution is treated with chloroform drops and is shaken with chlorine water. Chloroform layer
becomes violet, solution contains:
a) NO b) NO c) Br d) I
217. Which of the following is least reactive in a nucleophilic substitution reaction?
a) (CH ) CCl b) CH =CHCl c) CH CH Cl d) CH =CHCH Cl

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218. Ethylidine dichloride (CH CHCl ) can be prepared by the addition of hydrogen chloride on:
a) C H b) C H c) C H d) All of these
219. Which of the following statements is true?
a) Allyl chloride is more reactive than vinyl chloride
b) Vinyl chloride is as reactive as allyl chloride
c) Vinyl chloride is more reactive than allyl chloride
d) Both of them are more reactive than chlorobenzene
220. An alkyl halide (RX) reacts with Na to from 4, 5-diethyloctane. Compound RX is
a) CH (CH ) Br b) CH (CH ) CH(Br)CH CH
c) CH (CH ) CH(Br)CH d) CH (CH ) Br
221. PCl reacts with propanone, to give:
a) Gem dichloride b) Vic dichloride c) Propanal d) Propane chloride
222. Which is not present in Grignard reagent?
a) Carboxylic radical represented by COOH
b) Magnesium represented by Mg
c) Alkyl radical represented by 𝑅
d) Halide radical represented by X
223. Alkyl iodide reacts with NaCN to give alkyl cyanide and small amount of alkyl isocyanide. Formation of
these two products is due to the
a) ionic character of NaCN b) nucleophilic character of CN
c) ambidentate character of CN d) Electrophilic character of CN
224. Which of the following gives iodoform test?
a) CH − CH (OH)
b) C H CHO
c) (CH OH)
d) None of the above
225. C H Br can be obtained in the laboratory by the action of ethyl alcohol with:
a) KBr b) NH Br c) Br d) KBr and conc. H SO
226. Predict the product,

a) b) c) d)

227. Trichloro acetone reacts with lime water to form:

a) CH CHO b) CHCl c) CH Cl d) CH OH
228. When 32.25 g of ethyl chloride is subjected to dehydrohalogenation reaction the yield of the alkene
formed is 50%. The mass of the product formed is (atomic mass of chlorine is 35.5)
a) 14 g b) 28 g c) 64.5 g d) 7 g
229. Which one of the following possess highest m.pt. ?
a) Chlorobenzene b) o-dichlorobenzene c) m- dichlorobenzene d) p- dichlorobenzene
230. Which of the compounds when brominated turns to 𝑚𝑒𝑠𝑜 2, 3-dibromobutane?
a) 𝐶𝑖𝑠-2-butene b) 𝐼𝑠𝑜-butane c) Butane d) 𝑇𝑟𝑎𝑛𝑠-2-butene
231. Iodoform can be obtained on warming NaOH and iodine with
O
a) CH − CH − CH(OH)CH b) ∥
(CH ) CH − C − C H
 CH − C − OCH
c) ∥ d) (CH ) CCH OH
O
232. 1-chlorobutane on reaction with alcoholic potash gives
a) 1-butene b) 1-butanol c) 2-butene d) 2-butanol
233. S 1 reaction is favoured by:
a) Non-polar solvents
b) More no. of alkyl group on the carbon atom attached to the halogen atom
c) Small groups on the carbon attached to the halogen atom
d) None of the above
234. What mass of isobutylene is obtained from 37 g of tertiary butyl alcohol by heating with 20% H SO at
363 K, if the yield is 65%?
a) 16 g b) 18.2 g c) 20 g d) 22 g
235. Tertiary alkyl halides are practically inert to substitution by S 2 mechanism because of
a) Steric hindrance b) Inductive effect c) Instability d) Insolubility
236. Identify the set of reagents/reaction conditions ‘𝑋’ and ‘𝑌’ in the following set of transformations:
CH CH CH Br Product (CH ) CHBr
𝑋= dilute NaOH 𝑎𝑞. ; 20℃
a)
𝑌= HBr/acetic acid; 20℃
𝑋=conc., alc. NaOH; 80℃
b)
𝑌= HBr/acetic acid; 20℃
𝑋= dilute aqueous NaOH; 20℃
c)
𝑌= Br /CHCl ; 0℃
𝑋= conc., alc. NaOH; 80℃
d)
𝑌=Br /CHCl ; 0℃
237. In the dichlorination reaction of propane, mixture of products are obtained. How many isomers the
mixture contains?
a) 2 b) 3 c) 4 d) 5
238. The number of stereoisomers of compound
CH — CH = CH— CHBr— CH would be:
a) 3 b) 6 c) 2 d) 4
239. The industrial preparation of chloroform employs acetone and:
a) Sodium chloride b) Chlorine gas c) Calcium hypochlorite d) Phosgene
240. 𝑅𝑋 + 𝐴 → 𝑅𝑁𝐶
A is
a) AgCN b) KCN c) NaCN d) HCN
241. On mixing a certain alkane with chlorine and irradiating it with ultraviolet light, it forms only one
monochloroalkane.
a) Propane b) Pentane c) 𝐼𝑠𝑜-pentane d) 𝑁𝑒𝑜-pentane
242. Formation of alkane by the action of Zn on alkyl halide is called:
a) Wurtz reaction b) Kolbe’s reaction c) Cannizzaro’s reaction d) Frankland’s reaction
243. Chloretone used as a drug is prepared by the reaction of acetone with:
a) Chlorine b) Ethyl chloride c) Chloroform d) Ethylene dichloride
244. Which is gem dihalide?
a) CH ∙ CHBr b) CH Br ∙ CH Br c) CH ∙ CHBr ∙ CH Br d) None of these
245. Which of the following is a Grignard reagent?
a) Ammoniacal solution ofAgNO
b) Ethereal solution of C H MgCl
c) Alcoholic solution of KOH

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 d) Aqueous solution of caustic soda
246. The product formed on reaction of ethyl alcohol with bleaching powder is
a) CHCl b) CCl CHO c) CH COCH d) CH CHO
247. Chloral is:
a) CCl CHO b) CCl ∙ CO ∙ CH c) CCl ∙ CO ∙ CCl d) CCl ∙ CH OH
248. Which of the following compounds undergo 𝐸 reactions more easily?
(CH ) C ∙ CH CH
a) ⃒
Br
b) CH (CH ) CH Cl
c) CH (CH ) CH I
I
d) ⃒
(CH ) — C— CH CH
249. Decomposition of benzene diazonium chloride by using Cu Cl /HCl to form chlorobenzene is
a) Raschig’s reaction b) Sandmeyer’s reaction
c) Kolbe’s reaction d) Cannizaro’s reaction
250. Isobutyl chloride and butyl chloride are:
a) Position isomers b) Chain isomers c) Functional isomers d) Metamers
251. CH Br + Nu → CH − Nu + Br
The decreasing order of the rate of the above reaction with nucleophiles (Nu ) 𝐴 to 𝐷 is [Nu =
(𝐴)PhO , (𝐵)AcO , (𝐶)HO , (𝐷)CH O ]
a) D > C > A < B b) D > C > B > A c) A > B > C > D d) B > D > C > A
252. The reaction described below is:

a) S 1 b) S 2 c) S 1 d) S 2
253. Identify ‘Z ’ in the following reaction series,

Mixture of
a)

b)

c)

d)

254. Which of the following when heated with KOH and primary amine gives carbylamine test?
a) CHCl b) CH Cl c) CH OH d) CCl
255. The reagent used for dehalogenation of 1,2-dichloropropane is:
a) Zn dust b) Zn—Hg c) Na d) Zn—Cu couple
256. CH NH reacts with CH Mg𝑋 to give:
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 a) Acetone b) Alcohol c) Methane d) Ethane
257. Which of the following haloalkanes is most reactive?
a) 1-chloropropane b) 1-bromopropane c) 2-chloropropane d) 2-bromopropane
258. Iodoform is formed when ethanol is heated with:
a) Potassium iodide and sodium hydroxide
b) Iodine and aqueous potassium hydroxide
c) Chloroform and iodine
d) Iodine and potassium iodide
259. Tertiary alkyl halides are practically inert to S 2 mechanism because of:
a) Insolubility b) Instability c) Inductive effect d) Steric hinderance
260.

The final product, is

Cl

Br
a) b) c) d)

261. Carbon tetrachloride on treatment with Fe/H O gives:

a) Chloromethane b) Methane c) Chloroform d) Methylene chloride
262. Which group is displaced by a halogen group?
a) Hydroxyl (OH) group
b) Aldehyde (—CHO) group
c) Nitro (—NO ) group
d) Keto (C=O) group
263. A small amount of alcohol is usually added to CHCl bottles because:
a) It retards the anaesthetic property of CHCl
b) It retards the oxidation of CHCl to phosgene
c) It converts any phosgene formed to harmless ethyl carbonate
d) Both (b) and (c)
264. Which one is correct?
a) Freon-14 is CF ; Freon-13 is CF Cl;Freon-12 is CF Cl and Freon-11 is CFCl
b) Freons are chlorofluorocarbons
c) Freons are used as refrigerants
d) All of the above
265. The reactivity order of alkyl halides depends upon:
a) Nature of alkyl group only
b) Nature of halogen atom only
c) Nature of both alkyl group and halogen atom
d) None of the above
266. p-nitrobromobenzene can be converted to p-nitroaniline by using NaNH . The reaction proceeds through
the intermediate named
a) Carbocation b) Carbanion c) Benzyne d) Dianion
267. Reagent not used to prepare an alkyl halide from an alcohol is:
a) HCl + ZnCl b) NaCl c) PCl d) SOCl
268. The catalyst used in the preparation of an alkyl chloride by the action of dry HCl on an alcohol is
a) anhy. AlCl b) FeCl c) anhy. ZnCl d) Cu
269. Following is the substitution reaction in which –CN replaces –Cl.
∆
R − Cl + KCN ⎯⎯⎯ R − CN + KCl
alcoholic
To obtain propanenitrile, R – Cl should be
a) Chloroethane b) 1-chloropropane c) Chloromethane d) 2-chloropropane
270. CH Br + OH → CH OH + Br reaction proceeds by S 2 mechanism. Its rate is dependent on the
concentration of
a) CH Br, OH b) CH Br only c) OH only d) CH Br, CH OH
271. If chloroform is left open in air in presence of sun-rays:
a) Explosion takes place
b) Poisonous phosgene gas is formed
c) Polymerization takes place
d) No reaction takes place
272. Westrosol is:
a) Acetylene tetrachloride
b) Acetylene dichloride
c) Trichloroethyne
d) 1,1,2-trichloroethene
273. The compound formed on heating chlorobenzene with chloral in the presence of concentrated sulphuric
acid is
a) Gammexane b) DDT c) Freon d) Hexachloroethane
274. The C—Mg bond in CH CH MgBr is:
a) Ionic b) Non-polar covalent c) Polar covalent d) Hydrogen
275. In S 1 reaction, the first step involves the formation of:
a) Free radical b) Carbanion c) Carbocation d) Final product
276. The alkyl group of Grignard reagent acts as:
a) Free radical b) Carbonium ion c) Carbanion d) None of these
277. Methyl ketone is identified by
a) Iodoform test b) Fehling solution c) Tollen’s reagent d) Schiff’s reagent
278. Product on monobromination of this compound is

a) b)

O
H O
N H
H3C CH3 N
H3C CH3
c) d)

Br
Br
279. Which of the following is added to chloroform to slow down its aerial oxidation in presence of light?
a) Carbonyl chloride b) Ethyl alcohol c) Sodium hydroxide d) Nitric acid
280. When a solution of AgNO is added to pure CCl :
 a) A pale yellow precipitate is formed
b) Curdy white precipitate is formed
c) No precipitate is formed
d) None of the above
281. A compound containing two —OH groups attached with one carbon atom is unstable but which one of the
following is stable?
d) None of these
a) b) c)

282. Westron is:

a) CHCl=CHCl b) CHCl ∙ CHCl c) CH Cl—CH Cl d) None of these
283. Monohalogen derivative of alkanes with alcoholic KOH gives:
a) Alkane
b) Alkene
c) Alkyne
d) Alicyclic hydrocarbon
284. The reaction 𝑅Cl + NaI ⎯⎯⎯⎯⎯ 𝑅— I + NaCl is known as:
a) Wurtz reaction b) Fittig reaction c) Frankland’s reaction d) Finkelstein’s reaction
285. The hydrogen atom in chloroform is:
a) Acidic b) Basic c) Neutral d) None of these
286. The major product of the following reaction is

a) b) c) d)

287. Ethyl bromide and isopropyl chloride can be distinguished by:

a) Alcoholic AgNO
b) Comparing their colours
c) Burning the compound on spatula
d) Aqueous KOH solution
288. In the following sequence of reactions
C H Br ⎯⎯⎯⎯⎯ 𝑋 ⎯⎯⎯⎯⎯⎯ 𝑌; 𝑌 is
a) n-propyl amine b) Isopropylamine c) Ethylamine d) ethylmethyl amine
289. Which alkyl halide is preferentially hydrolysed by S 1 mechanism?
a) CH Cl b) CH CH Cl c) CH CH CH Cl d) (CH ) C ∙ Cl
290. Treatment of ammonia with excess of ethyl chloride will yield:
a) Diethyl amine
b) Ethane
c) Tetraethyl ammonium chloride
d) Methyl amine
291. In a group of isomeric alkyl halides, the order of boiling points is
a) primary < secondary < tertiary b) primary > secondary < tertiary
c) primary < secondary > tertiary d) primary > secondary > tertiary
292. Ethylene dichloride and ethylidene chloride are isomeric compounds. Identify the statement which is not
applicable to both of them?
a) React with alcoholic potash
b) React with aqueous potash and give the same products
c) Are dihalides
d) Answer Beilstein’s test
293. The Mg—Br bond inCH CH MgBr is:
a) Ionic b) Non-polar c) Covalent d) None of these
294. Chloroform is slowly oxidised by air in the presence of light and air to form
a) Formyl chloride b) Trichloro methanol c) Phosgene d) Formaldehyde
295. Among the following the one that gives positive iodoform test upon reaction with I and NaOH is:
a) CH CH CH(OH)CH CH
b) C H CH CH OH

c)

d) PhCHOHCH
296. 2-bromopentane is heated with potassium ethoxide in ethanol. The major product is:
a) 𝑡𝑟𝑎𝑛𝑠-pent-2-ene b) 2-ethoxy pentane c) pent-1-ene d) 𝑐𝑖𝑠-pent-2-ene
297. Bottles containing C H I and C H CH I lost their original labels. They were labelled 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 HNO and then some AgNO solution was added. Substance B gave a yellow
precipitate. Which one of the following statements is true for this experiment?
a) A was C H I b) A was C H CH I
c) B was C H I d) Addition of HNO was unnecessary
298. 2CHCl + O → 2COCl + 2HCl
In the above reaction X stands for:
a) An oxidant b) A reductant c) Light and air d) None of these
299. Identify the product (A) in following reaction series,
/ [ ]
CH CN ⎯⎯⎯⎯⎯⎯⎯ (X ) ⎯⎯ (Y )

a) CH CHO b) CH CONH c) CH COOH d) CH —CH —NHOH

300. Isocyanide test is used to detect:
a) Primary alcohols b) Primary amines c) Secondary amines d) Secondary alcohols
301. Which would be obtained by boiling CHCl with caustic soda?
a) CH COONa b) HCOONa c) Na C O d) CH OH
302. In the following sequences of reactions:
( .) /
CH CH CH I ⎯⎯⎯⎯⎯ (A) (B) ⎯⎯⎯⎯⎯⎯⎯⎯ (C)
the end product (C ) is:
a) Alkene b) Alkanol c) Alkyne d) Alkyl amine
303. Which of the following compound give yellow precipitate with I and NaOH?

a) CH OH b) CH CH CH OH c) C H OC H d) CH CH OH
304. In the reaction of phenol with CHCl andaqueous NaOH at 70℃, the electrophile attacking the ring is:
a) CHCl b) CHCl c) CCl d) COCl
305. The product formed in the reaction of H𝑋 with (CH ) C=CH is:
P a g e |23
 a) (CH ) C𝑋CH b) (CH ) CH ∙ CH 𝑋 c) (CH ) CHCH d) (CH ) C𝑋CH 𝑋
306. The molecular formula of diphenyl methane is

CH2 is C13H12

How many structural isomers are possible when one of the hydrogen is replaced by a chlorine atom?
a) 6 b) 4 c) 8 d) 7
307. For the preparation of p-nitroiodobenzene from p-nitroaniline, the best method is
a) NaNO /HCl followed by KI b) NaNO /HCl followed by CuCN
c) LiAlH followed by I d) NaBH followed by I
308. Iodoform test is not given by
a) HCHO b) CH CHO c) CH COCH d) C H OH
309. Fires result from the combustion of alkali metals can be extinguished by:
a) CCl b) Sand c) Water d) Kerosene
310. The reactivities of methyl chloride (A ) propyl chloride (B ) and chlorobenzene (C ) are in the order :
a) 𝐴 > 𝐵 > 𝐶 b) 𝐶 > 𝐵 > 𝐴 c) 𝐴 > 𝐶 > 𝐵 d) 𝐵 > 𝐴 > 𝐶
311. A sample of chloroform before being used as an anaesthetic is tested by:
a) AgNO solution
b) AgNO solution after boiling with alc. KOH
c) Fehling’s solution
d) Ammoniacal Cu Cl
312. Ethylene dichloride can be prepared by adding HCl to:
a) Ethane b) Ethylene c) Acetylene d) Ethylene glycol
313. Which of the following can be obtained by halide exchange method?
a) CH Cl b) C H Cl c) CH I d) CH Br
314. Grignard reagent undergoes:
a) Nucleophilic substitution
b) Nucleophilic addition
c) Both (a) and (b)
d) None of the above
315. Ethylene on treatment with chlorine gives:
a) Ethylene dichloride
b) Ethylene chlorohydrin
c) CH
d) C H
316. Ethylidene dichloride on treatment with 𝑎𝑞. KOH gives:
CH OH c) HCHO d) CHO
a) CH CHO b) ⃒ ⃒
CH OH CHO
317. The bad smelling substance formed by the action of alcoholic caustic potash on chloroform and aniline is:
a) Phenyl isocyanide b) Nitrobenzene c) Acetylene d) Chlorobenzene
318. In the reaction,
∆
2𝐴 + dry oxide ⎯⎯ ether + 2Ag𝑋
𝐴 is a/an
a) Primary alcohol b) Acid c) Alkyl halide d) Alcohol
319. Ethyl alcohol is used as a preservative for chloroform because it
a) Prevents aerial oxidation of chloroform b) Prevents decomposition of chloroform
d) Removes phosgene by converting it to ethyl
c) Decomposes phosgene to CO and Cl
carbonate
320. Anhydrous HCl gas, on passing through ethyl alcohol, in presence of anhy. ZnCl gives:
 a) Ethane b) Ethyl chloride c) Ethene d) CCl
321. Which one of the isomers of cyclohexane hexachloride is strong pesticide?
a) 𝛼 b) 𝛽 c) 𝛾 d) 𝛿
322. Which one of the following does not give iodoform?
O

a) C CH3
b) CH OH

c) CH CH OH d)

323. The IUPAC name of the compound ,

a) 1,3-dibromo-3-methylbutane
b) 3-methyl-1,2-bromobutane
c) 3-methyl-1,3-bromopropane
d) None of the above
324. Ethyl iodide on treatment with alcoholic potash gives:
a) Ethyl alcohol b) Ethane c) Acetylene d) Ethylene
325. Chloroform is used as an:
a) Antiseptic b) Anaesthetic c) Insecticide d) Antipyretic
326. Chlorination of toluene in presence of light and heat followed by treatment with aqueous NaOH gives
a) o-cresol b) p-cresol
c) mixture of o-cresol and p-cresol d) 1, 3, 5-trihydroxy toluene
327. 1, 2-dibromoethane reacts with alcoholic KOH to yield a product X. The hybridisation state of the carbons
present in X respectively, are
a) 𝑠𝑝, 𝑠𝑝 b) 𝑠𝑝 , 𝑠𝑝 c) 𝑠𝑝 , 𝑠𝑝 d) 𝑠𝑝 , 𝑠𝑝
328. The phosphorus pentachloride reacts with ethanol to give:
a) Ethyl chloride b) Ethylene chloride c) Ethylidene chloride d) None of these
329. Elimination of bromine from 2-bromobutane results in the formation of
a) Predominantly 2-butyne b) Predominantly 1-butene
c) Predominantly 2-butene d) Equimolar mixture of 1 and 2-butene
330. The compound formed in carbylamine test is:
a) C H —C≡N b) c) CH —O—C≡N d) CH —N=C=O
331. Best method of preparing alkyl chloride is
a) 𝑅OH + SOCl ⟶ b) 𝑅OH + PCl ⟶
.
c) 𝑅OH + PCl ⟶ d) 𝑅OH + HCl ⎯⎯⎯⎯⎯⎯⎯⎯
332. CH =CHCl reacts with HCl to form:
a) CH Cl—CH Cl b) CH — CHCl c) CH =CHCl ∙ HCl d) None of these
333. In dihalogen derivatives if two halogen atoms are attached to the same carbon atom, the compound is
called:
a) Gem dihalide b) Vicinal dihalide c) Both (a) and (b) d) None of these
334. Vapour density of an organic compound is 23.0. It contains 52.17% of carbon and 13% of hydrogen. The
compound gives iodoform test. The compound is:
a) Ethanol b) Dimethyl ether c) Acetone d) Methanal
335. An alkyl halide reacts with alcoholic ammonia in a sealed tube, the product formed will be
a) A primary amine b) A secondary amine
c) A tertiary amine d) A mixture of all the three
336. Chloropicrin is obtained by the reaction of
 a) Steam on carbon tetrachloride b) Nitric acid on chlorobenzene
c) Chlorine on picric acid d) Nitric acid on chloroform
337. Which of the following solvent may be used instead of ether in the preparation of Grignard reagent?
a) THF b) C H OCH c) C H N(CH ) d) All are correct
338. Chloroform on reduction with Zn and HCl (alc.) gives:
a) Formic acid b) Chloretone c) Chloropicrin d) Methylene dichloride
339. Identify X and Y in the following sequence
C H Br ⎯⎯⎯ product ⎯⎯⎯ C H NH
a) 𝑋 = KCN, 𝑌 = LiAlH b) 𝑋 = KCN, 𝑌=H O
c) 𝑋 = CH Cl, 𝑌 = AlCl /HCl d) 𝑋 = CH NH , 𝑌 = HNO
340. In alkyl nitrites the oxygen of —O—N=O group is linked with carbon. An alkyl nitrite is:
a) An ester b) A nitro compound c) An amide d) A nitrile
341. In the chemical reactions,

The compounds ‘A’ and ‘B’ respectively are

a) Nitrobenzene and fluorobenzene
b) Phenol and benzene
c) Benzene diazonium chloride and fluorobenzene
d) Nitrobenzene and chlorobenzene
342. Chloroform, when kept open, is oxidised to
a) CO b) COCl c) CO , Cl d) None of these
343. 𝑋 ⎯⎯⎯⎯⎯ Y Yellow or white ppt.

Which of the following cannot be X?

N2+Cl-

a) b) (CH ) CHCl c) d)
Session: 2023-24 Total Questions: 341

CHEMISTRY

10.HALOALKANES AND HALOARENES

: ANSWER KEY :
1) d 2) a 3) b 4) b 161) a 162) d 163) d 164) c
5) a 6) a 7) a 8) b 165) c 166) a 167) b 168) b
9) a 10) c 11) a 12) d 169) b 170) c 171) d 172) a
13) b 14) d 15) b 16) b 173) a 174) a 175) d 176) a
17) c 18) b 19) a 20) a 177) b 178) c 179) d 180) d
21) a 22) b 23) b 24) a 181) d 182) b 183) d 184) d
25) b 26) b 27) a 28) b 185) c 186) d 187) b 188) d
29) d 30) b 31) b 32) a 189) d 190) d 191) a 192) a
33) d 34) b 35) d 36) b 193) d 194) c 195) b 196) c
37) a 38) d 39) c 40) b 197) d 198) a 199) d 200) c
41) d 42) c 43) a 44) a 201) d 202) c 203) a 204) c
45) b 46) d 47) a 48) b 205) a 206) b 207) c 208) c
49) d 50) b 51) b 52) a 209) d 210) c 211) a 212) b
53) b 54) b 55) a 56) d 213) c 214) c 215) c 216) d
57) a 58) a 59) d 60) d 217) b 218) c 219) a 220) b
61) b 62) a 63) a 64) c 221) a 222) a 223) c 224) a
65) a 66) a 67) d 68) a 225) d 226) a 227) b 228) d
69) c 70) c 71) d 72) d 229) d 230) d 231) a 232) a
73) c 74) c 75) a 76) a 233) b 234) b 235) a 236) b
77) c 78) c 79) d 80) b 237) c 238) d 239) c 240) a
81) c 82) c 83) b 84) b 241) d 242) d 243) c 244) a
85) a 86) b 87) b 88) c 245) b 246) a 247) a 248) d
89) b 90) a 91) b 92) b 249) b 250) b 251) a 252) b
93) c 94) b 95) c 96) b 253) b 254) a 255) a 256) c
97) a 98) a 99) c 100) c 257) d 258) b 259) d 260) a
101) a 102) a 103) a 104) d 261) c 262) a 263) d 264) d
105) a 106) d 107) d 108) a 265) c 266) c 267) b 268) c
109) c 110) a 111) c 112) a 269) a 270) a 271) b 272) d
113) b 114) b 115) d 116) d 273) b 274) c 275) c 276) c
117) b 118) b 119) a 120) a 277) a 278) b 279) b 280) c
121) a 122) b 123) d 124) c 281) c 282) b 283) b 284) d
125) d 126) a 127) d 128) a 285) a 286) a 287) a 288) d
129) a 130) d 131) a 132) d 289) d 290) c 291) d 292) b
133) a 134) b 135) b 136) a 293) a 294) c 295) d 296) a
137) b 138) a 139) c 140) a 297) a 298) c 299) c 300) b
141) c 142) d 143) b 144) a 301) b 302) c 303) d 304) c
145) c 146) c 147) c 148) a 305) a 306) b 307) a 308) a
149) a 150) a 151) d 152) a 309) a 310) a 311) b 312) d
153) d 154) a 155) c 156) c 313) c 314) c 315) a 316) a
157) c 158) c 159) d 160) d 317) a 318) c 319) d 320) b
P a g e |27
321) c 322) b 323) a 324) d
325) b 326) c 327) a 328) a
329) c 330) b 331) a 332) b
333) a 334) a 335) d 336) d
337) d 338) d 339) a 340) a
341) c 342) b 343) a

P a g e |28
Session: 2023-24 Total Questions: 341

CHEMISTRY

10.HALOALKANES AND HALOARENES

: HINTS AND SOLUTIONS :

1 (d) |
For positive iodoform test, alcohol molecule must 𝐶𝐻
have 𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻 + 2𝑁𝑎𝐶𝑙
CH − CH − group. |
| 𝐶𝐻
OH 13 (b)
Ph − CH − CH ⎯⎯⎯⎯⎯⎯⎯ CHI + Ph − COO Br is replaced by a nucleophile CN .
| 15 (b)
OH A mixture of halides is formed.
2 (a) 16 (b)
( .) DDT and 666 (C H Cl or benzene hexachloride)
CH ClCH Cl ⎯⎯⎯⎯⎯ CH OHCH OH is the pair of strongest pesticides.
,
( .) 17 (c)
CH CHCl ⎯⎯⎯⎯⎯ CH CHO
Thus, decomposition of CHI occurs.
3 (b) 18 (b)
( .) CH 𝑋 + KCN ⟶ CH CN
𝑅 — 𝑋 ⎯⎯⎯⎯⎯ 𝑅 — OH
19 (a)
4 (b)
( .) CHCl + HNO
CH CH Cl ⎯⎯⎯⎯⎯ CH = CH + HCl ⟶ CCl ∙ NO + H O ∙ CCl
5 (a) ∙ NO is called chloropicrin.
CS + 2Cl ⟶ CCl + 2S 20 (a)
6 (a) Aryl halides show resonance in their structure.
CH Cl ⎯ CH (OH) ⎯⎯ HCHO 21 (a)
CCl + H O(v) ⟶ COCl + 2HCl
8 (b)
23 (b)
HI reacts with C H OH even in absence of Zn𝑋 .
In Wurtz reaction alkyl halide react with sodium
Larger is bond length, more is reactivity.
in dry ether to produce alkane having double
9 (a)
number of carbon atoms as in alkyl halide.
Among alkyl halides, iodides are least stable,
hence these form Grignard reagent easily. Hence, 2𝑅 − 𝑋 + 2Na ⎯⎯⎯⎯⎯ 𝑅 − 𝑅 + 2Na𝑋
the correct order of reactivity in formation of alkyl halide alkane
Grignard reagent is 24 (a)
CH I > 𝐶H Br > 𝐶H Cl CH I + 6Ag + I HC ⟶ C H + 6Ag𝑋
10 (c) 26 (b)
The I has antiseptic nature. This is the preparation method of DDT (dichloro
11 (a) diphenyl trichloroethane).
This is Wurtz reaction. 2-chloropropane and
chloromethane reacts in presence of dry ether t
form 2-methyl propane.
𝐶𝐻 𝐶𝑙 + 2𝑁𝑎 + 𝐶𝑙 − 𝐶𝐻 − 𝐶ℎ ⎯⎯
P a g e |29
 27 (a)
CF CHClBr, 𝑖. 𝑒. , haloethane is less hazardous and rapid
28 (b)
All the except ethyl isopropyl ketone gives
iodoform test in this question.

29 (d)
CH CH CH I and CH CHICH ; note the position of
iodine.

30 (b)
𝑅Cl + KCN → 𝑅CN + KCl
alkylalkyl
chloride cyanide

/
CH Cl + KCN → CH CN ⎯⎯⎯⎯⎯⎯ CH CH NH
methyl methyl ethyl amine
chloride cyanide (Primary amine)
31 (b)
An optically inactive compound forming optically
active compound during a reaction always gives
racemic mixture.
32 (a)
Vinyl chloride(CH = CH . Cl), on the other hand,
Friedel-Craft reaction : In this reaction alkyl
halides react with aromatic compounds in is less reactive than benzyl chloride due to
presence of AlCl or FeCl to form alkyl
substituted aromatic compounds. resonance.

33 (d)
Benzyl chloride is very reactive. It readily gives
white precipitate with alcoholic AgNO at room
temperature. It also readily undergoes
nucleophilic substitution. Its structure is as
follows

34 (b)
O O
∥ ∥
CH − C − CH ⎯⎯ CH − C − CH I + OH
O O
∥ ∥
CH − C − CH I ⎯⎯ CH − C − CHI + OH
 O O
∥ ∥
CH − C − CHI ⎯⎯ CH − C − CI + OH
𝐶𝐻 − 𝐶 − 𝐶𝑙 ⎯ 𝐶𝐻 − 𝐶 = 𝑂 + 𝐶𝐻𝐼
|
𝑂
35 (d)
The possible isomers of hexane are

2-methyl pentane

[5 monochloro derivatives (maximum) are

possible]
37 (a)
CHCl + 3C H ONa → CH(OC H ) + 3NaCl

2,3-dimethyl butane Ethy ortho formate

Out of these structure (iii) and (i) have 38 (d)

respectively minimum and maximum number of 1
2CHCl + O
monochloro derivatives 2
For structure(iii) ⟶ COCl
+ H O; COCl 𝑖. 𝑒. , phosgene is poisonous gas.
39 (c)
Iodoform test is given by only those compounds
which conatain either
CH C = O or CH CH − OH group
| |
(a) CH CH − OH (b) CH CH − OH
(b) Cl
| |
H CH
[Only 2 monochloro derivatives (minimum) are ethyl alcohol propanol-2
possible] (c) CH CH CH OH (c) CH − C = O
For structure (i). Propanol-1 |
H
ethanal
Hence, propanal-1 due to absence of above given
groups, does not give positive iodoform test.
40 (b)
At higher temperature, esters undergoes
hydrolysis to give alcohol and acid. In (b) ethyl
alcohol is formed which respond for positive
iodoform test.
𝑅𝐶𝑂𝑂𝑅′ ⎯ 𝑅′OH + 𝑅COOH
41 (d)
CHCl + HNO → CCl NO + H O
Chloroform nitric acid chloropicrin
Thus, the molecular formula of chloropicrin is
 CCl NO .
42 (c)
The reaction between 𝑡𝑒𝑟𝑡-butyl bromide and
hydroxide ion yields 𝑡𝑒𝑟𝑡-butyl alcohol and
follows the first order kinetics. The rate of
reaction depends upon the concentration of only (i) 𝑖𝑠𝑜-propyl alcohol, ethanol ad ethanal all have
one reactant, which is tertiary butyl bromide. CH CO or CHOH group, therefore they give
iodoform test.
(ii) Benzyl alcohol does not have
CH CO − or CHOH group,
|
CH
Therefore, it does not give iodoform test.
50 (b)
43 (a) Follow Saytzeff’s rule.
Chloroform reacts with conc. HNO to give 51 (b)
chloropicrin which is used as tear gas. The lead deposited is exhaused out in the form of
∆ PbBr .
CHCl + HNO ⎯⎯ CCl NO + H O 53 (b)
chloropicrin
44 (a) 𝑅𝑋 +Mg ⎯⎯ 𝑅Mg𝑋
More is the branching in molecule, lesser is 54 (b)
surface area, lower is attraction, lower is b.p. CH Br + KCN ⎯⎯ CH CN ⎯ CH COOH
45 (b)
C H OH + SOCl ⟶ C H Cl + SO + HCl ⎯⎯⎯ CH CH OH
46 (d) (𝐴)(𝐵)(𝐶)
Cl formed at anode reacts with C H OH in 56 (d)
presence of NaOH (formed in reaction ) to give (CH ) CCH CH Cl; halogen is attached on 1 ͦ
haloform reaction. carbon.
47 (a) 57 (a)
Benzyl chloride is more reactive than alkyl
halides. Benzyl carbocation is stabilised by
resonance hence, benzyl chloride easily gives
nucleophilic substitution reaction.
48 (b)
S 1 order. As-CCl group is 𝑚𝑒𝑡𝑎 -directing.
Benzyl > Allyl > 3 ͦ > 2 ͦ > 1 ͦ > Phenyl halide. 58 (a)
49 (d) 𝑅MgF are unstable compounds.
Iodoform test is given by compounds which have 59 (d)
CH CO or CH CHOH group.
H
|
(a)H C − C − CH (b)CH CH OH
| ethyl alcohol
OH Chloride is an 1° aliphatic carbon which is
Iso-propyl alcohol substituted easier in comparison to iodide which
O is arylic and more stable due to delocalisation
∥ hence, difficult to substitute.
(c) CH − C − H
ethanal
 double bond character due to resonance.

Vinyl chloride
Thus, it is very difficult to break C-Cl bond. Hence,
vinyl chloride not get hydrolysed by NaOH.
60 (d)
67 (d)
CH CH CH Cl + KCN ⟶ CH CH CH CN + KCl
Iodoform test is given by compounds which have
61 (b) (CH − CO −) group or CH − CH − group.
Br is less reactive and more selective and thus,
|
formation of 3 ͦ free radical will be the major
OH
product.
Hence, 2-pentanone, CH CHO and C H OH give
62 (a)
the test. But 3-pentanone does not give iodoform
( .)
CH CH CH Cl ⎯⎯⎯⎯⎯ CH CH=CH test. Actually, iodoform test can be used to
( .) distinguish methyl ketones from ketones.
CH CHClCH ⎯⎯⎯⎯⎯ CH CH=CH
63 (a)
Larger is C—𝑋 bond length; more is reactivity.
64 (c)
CH COONa + NaOH ⟶ CH + Na CO
↓Cl
CCl
66 (a)
In vinyl chloride, the C-Cl bond acquires some
68 (a)
RCl and RBr can be prepared by free radical halogenation of alkanes while RF and RI cannot be prepared.
With F , the reaction is not only explosive but also brings cleavage of C-C bonds while with I the reaction
is too slow to be of any practical value.
70 (c) CH3
C H Cl + AgCN → C H NC + AgCl
H3C C CH3
(𝑋)
Functional isomer of 𝑋 is C H CN.
CH3
71 (d)
∵It contains only one type of hydrogens.
Benzyl carbonium ion is most stable and thus, its
∴ It will give only ony monochloro derivative
chloride is most reactive.
72 (d)
Tear gas is chloropicrin. It is obtained by the
reaction of chloroform with nitric acid.
CHCl + HNO → CCl NO + H O
chloropicric 77 (c)
73 (c) An organic compound forms yellow precipitate of
C—Cl bond is more polar due to more iodoform with I in presence of alkali, if it has
electronegativity difference. CH CO − group directly or it has
76 (a) |
The number of monochloro derivatives of a CH − CHOH
compound depends upon the type of hydrogen 78 (c)
present in the compound. The structure of 𝑛𝑒𝑜- CaOCl + H O → Ca(OH) + Cl
pentane is (X)
CH CHO + Cl → CCl CHO
(X) (Y)
2CCl CHO + Ca(OH) → 2CHCl + (HCOO) Ca
 (Y)
79 (d)

90 (a)
The product (K) is formed through simple
Anti-elimination, means –H and the –Br both substitution while major product (L) is formed
departing group must be present at dihedral angle through H shift 𝑣𝑖𝑎 S 1 reaction and methoxy
of 180° (anti). group stabilizes the carbocation intermediate of
80 (b) product (L).
CH CH 3 CH 3 3
C H Br + NaHS ⟶ C H SH + NaBr
H C O
H2O + acetone
82 (c) 3 NO 2

Allyl carbonium shows resonance and thus, allyl H Cl CH 3

chloride is more reactive. Vinyl chloride shows CH CH3 CH 3 3

resonance and thus, less reactive. H C O 3 NO 2

83 (b) OH CH
H 3

CCl NO is chloropicrin used as tear gas. (K) minor prodduct

+
CH CH
84 (b)
CH3 3 3

H C O
Ethanol cannot undergo dehydrohalogenation as 3 NO 2

it does not contain any halogen. OH H CH 3

(L) major product
85 (a)
91 (b)
By haloform reaction.
Zinc is used for debromination of dibromoalkane
86 (b)
to give alkene.
CH — CHCH CH has one asymmetric carbon
CH2 Br CH2
atom. + Zn Alcohol + ZnBr2
⃒ CH
CH2 Br 2
Cl
92 (b)
87 (b)
CH
CCl is non-polar; H O is polar.
|
88 (c)
CH − C − Br + CH ONa ⟶
Most stable carbocation formation by halide
| sodium
shows more reactivity for S reactions.
CH
t-butyl bromide
methanol
CH
|
89 (b) CH − C = CH + CH OH + NaBr
Alkyl halides on heating with alcoholic KOH give 2-methyl propene methanol
dehydrogenation reaction to yield alkene. If in methoxide (isobutylene)
reaction, more than one alkenes are formed, then 93 (c)
. /
according to Saytzeff, the most highly substituted CH Br ⎯⎯⎯⎯⎯ CH CN ⎯⎯⎯⎯⎯⎯⎯⎯ CH CH NH
alkene is the major product.
(X) (Y)
95 (c)
Liberated iodine is absorbed by iodides to darken
their colour.
96 (b)
 This is Wurtz reaction. In this reaction two 4C H Br + 4Na – Pb ⟶ (C H ) Pb + 4NaBr
molecules of alkyl halide react with each other to 106 (d)
form alkane having double the number of carbon
atoms.
2CH CH Cl + 2Na ⎯⎯⎯⎯⎯⎯⎯
(𝑋)
Its monochloro derivatives are follows
ethyl chloride
CH CH CH CH + 2NaCl
butane
97 (a)
CH NH ⎯⎯⎯⎯⎯ (CH ) NH ⎯⎯⎯ (CH ) N

⎯⎯ (CH ) N I
Hence, three molecules of CH I is used.
98 (a) It will exist as enantiomers pair 𝑑 and 𝑙-forms
CHCl will give positive carbylamine reaction.
99 (c)
This is corey house synthesis:
𝑅 CuLi + 𝑅 𝑋 ⟶ 𝑅𝑅 + 𝑅Cu + Li𝑋
100 (c)
When a carbonyl compound having the structure no asymmetric C atom
CH − CO − 𝑅is reacted with a halogen in the Cl
presence of NaOH, KOH, Na CO or K CO solution, |
haloform is obtained. Thus, butanone-2 gives +ve (iii) 𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻
iodoform test. |
/ 𝐶𝐻
CH − CH − C − CH ⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯ It will exist as enantiomeric pair (𝑑-and 𝑙- forms)
( )
∥
O
2-butanone
O No asymmetric carbon atom
∥ Hence, only two enantiomeric pairs will be
CHI + CH − CH − C − ONa obtained by the monochlorination of 2-
iodoform methylbutane.
101 (a) 107 (d)
C H Cl + KCN ⎯⎯⎯⎯⎯⎯ C H CN + KCl 𝑅𝑋+ Ag O( ) ⟶ 𝑅 ∙ O ∙ 𝑅 +2Ag𝑋
(X) 108 (a)
, Williamson’s synthesis
C H CN ⎯⎯⎯⎯⎯⎯⎯⎯ C H COOH + NH
∆ C H ONa + ClC H → C H OC H + NaCl
(𝑌)or (C H O ) diethyl ether
So, the molecular formula of the Y is C H O . 109 (c)
102 (a) CaOCl + H O ⟶ Ca(OH) + Cl (Hydrolysis)
When ethyl bromide reacts with alcoholic KCN, Cl + C H OH ⟶ CH CHO (Oxidation)
propane nitrile is obtained as main product. CH CHO + Cl ⟶ CCl CHO (Substitution)
C H Br + Alc. KCN → C H CN CCl CHO + Ca(OH) ⟶ CHCl +
propane nitrile
(HCOO) Ca (Hydrolysis)
104 (d)
110 (a)
Carbylamine reaction is characteristic reaction for
Iodoform test is given by the compounds
primary amine and chloroform.
containing either
105 (a)
|
 CH CO − roup or CH CHOH group. 𝛼 and 𝜔-dihalogen derivative of an alkane on
The structures of the given compounds are as treatment with Mg or Zn or Na gives cycloalkane.
1. CH CH CH CH OH 122 (b)
( .)
2. CH COC H C H I ⎯⎯⎯⎯⎯ C H CH BrCH Br
CH BrCH Br ⎯ CH CNCH CN
3. CH CHO 123 (d)
4. CH COC H

∴ 𝑛 butyl alcohol does not give iodoform test

because it does not possess the

CH CO − or CH CHOH group.

111 (c)
It is not a colouring material.
113 (b) In [F] order of quantity of alkene 2 > 1> 3
Alkyl halides are less soluble in water. They are These on addition with Br /CCl to give their
polar but fail to form H-bonds with water. addition products which have C H Br as
114 (b) molecular formula.
Hexachloroethane is also called artificial (1)CH − CH − CH − CH
camphor. Its structure is | |
Cl Cl Br Br
| | Br
Cl − C − C − Cl |
| | (2)CH − CH − CH − CH
Cl Cl |
115 (d) Br
(3)BrH C − CH − CH − CH
(CH ) CHCH MgBr + HOC H ⎯⎯ |
Br
(4)BrH C − CH − CHBr − CH
(5)CH Br − CH − CH − CH Br
117 (b)
125 (d)
Dipole moment of CH Cl is more than CH F due to
larger C—𝑋 bond. Also electronegativity of Br CH OHCH OH CH ClCH Cl
being less than F and Cl and thus inspite of larger 127 (d)
C—𝑋 bond dipole moment of CH Br is lowest. Tertiary carbonium is most stable.
119 (a) 128 (a)
. CH = CH − CH = CH + Br ⟶
CH − CH − CH − CH − Cl ⎯⎯⎯⎯⎯ CH − CH
∆ 1,3-butadiene
− CH = CH + HCl (i)CH = CH − CH − CH
1-chlorobutane | |
butene-1 Br Br
120 (a) 3,4-dibromo butane
△
2CHCl + 6Ag ⎯⎯⎯ CH ≡ CH + 6AgCl (ii) CH − CH = CH − CH
121 (a) | |
Br Br
1,4-dibromo-2-butene
1,4-adduct is more stable than the 1,2-adduct.
130 (d) | |
Write chlorination reaction for all of them to find CH − C − CH ⎯⎯⎯⎯⎯⎯⎯⎯ CH − C − CH
which gives of the maximum number of | |
monochlorination product. Cl OH
(a) CH CH CH CH CH + Cl ⎯⎯⎯ 2,2-dichloro propane unstable
Cl ⎯⎯⎯⎯ CH − C − CH
|
∥
ClCH − (CH ) CH + CH − CH − (CH )
O
CH + CH − CH − CH − CH − CH
acetone
|
132 (d)
Cl
CH = CHCl + HCl → CH − CHCl
∴ Total 3 monochlorinated products are formed. ethylidene chloride
sor
(b) CH − CH − CH − CH + Cl ⎯⎯⎯ 1, 1 dichloroethane
| 133 (a)
CH μ = 0; μ = 1.0 D; μ = 1.6 D, μ
Cl = 1.86 D
| 134 (b)
ClCH − CH − CH − CH + CH − C − CH O=C=O + C H OMgBr ⟶
| |
CH CH
−CH + CH − CH − CH − CH Cl
| 135 (b)
CH CH COOAg + CH Cl ⟶ CH COOCH + AgCl
∴ Total 3 monochlorinated products are formed. 136 (a)
CH
|
(c) CH − C − H + Cl ⎯⎯⎯⎯
|
CH
CH CH Cl
| |
CH − C − Cl + CH −C − H
| | Since, 𝐵 and 𝐷 are different thus, 𝐵 is CH CH CHO
CH CH and so 𝐴 is CH CH CHCl .
∴ Total 3 monochlorinated products are formed. 138 (a)
CH Tertiary alcohols readily react with Lucas reagent
| (ZnCl /conc. HCl) to give white turbidity due to
the formation of halide.
(d)CH − C − CH + Cl ⎯⎯⎯⎯
|
CH
CH
|
140 (a)
CH − C − CH Cl
Carbylamine test is a characteristic test of
|
aliphatic and aromatic primary amines. In this
CH
test, amine is heated with chloroform and
∴ Only one monochlorinated products formed.
alcoholic potash when a bad smelling isocyanide
(carbylamine) is formed.
131 (a)
Cl OH
 156 (c)
Ethanol on reaction with bleaching powder, gives
chloroform (trichloromethane).
CaOCl + H O → Ca(OH) + Cl
142 (d) C H OH + Cl → CH CHO + 2HCl
The density order is: CH CHO + 3Cl → CCl . CHO + 3HCl
Iodine > Bromide > Chloride > Fluoride.
2CCl . CHO + Ca(OH) ⎯⎯⎯⎯⎯ 2CHCl
Higher is the molecular weight, more is b.p, m.p.
+ (HCOO) Ca
143 (b)
chloroform
4C H Br + 4Na – Pb ⟶ (C H ) Pb + 4NaBr
157 (c)
147 (c)
C H ONa + C H I
Follow iodoform test.
⟶ C H OC H
148 (a)
+ NaI; Williamson s synthesis.
Chloral + Chlorobenzene → DDT
158 (c)
150 (a)
CH Br + KCN(alc. )
CH C≡CNa+(CH ) CHCl ⟶CH C≡CCH(CH ) +
NaCl ⟶ CH CN ⎯⎯⎯⎯⎯⎯⎯⎯⎯ CH CH NH
151 (d)
Solvolysis of haloalkanes follows first order ethylamine
kinetics. During this process an intermediate 159 (d)
carbocation is formed. Therefore, the Ethyl chloride can be converted into ethanol
halohydrocarbon which gives more stable either by its alkaline hydrolysis or by its reaction
carbocation undergoes solvolysis readily. with moist AgOH.
153 (d) .
CCl is a covalent compound, therefore, it does not C H Cl ⎯⎯⎯⎯⎯⎯ C H OH ⎯⎯⎯⎯ C H Cl
∆
ionise to give Cl ions hence, it does not give (𝐴) (𝐵)
white ppt. of AgCl when treated with 160 (d)
AgNO soution. There is no reaction to evolve CH CH CH CH OH ⎯⎯⎯ CH CH CH CH Br
NO . CCl will form a separate layer as it is 161 (a)
immiscible with water. Tertiary halide preferentially undergoS 1
154 (a) substitution as they can give stable carbocation.
𝐶 − 𝑋 bond in benzyl bromide is much weaker CH
than in vinyl bromide and bromobenzene since |
the benzyl cation left after the removal of the
bromide ion is stabilized by resonance. Further, C- H C − C − Cl ⎯⎯⎯⎯ (H C) C ⎯⎯⎯ (H C) COH
Br is weaker than C-Cl bond. Therefore, | carbocation t-butyl alcohol
C H CH Br has the weakest C-X bond. CH
155 (c) t-butyl chloride
162 (d)
5. 2-methylpentane ⎯⎯⎯ five types of
In CHCl , carbon is 𝑠𝑝 -hybridised.
monochlorinated compounds
163 (d)
CCl + KOH(𝑎𝑞. )⟶ C(OH) ⟶ CO + 2H O
6. 3-methylpentane ⎯⎯⎯ four types of
164 (c)
monochlorinated compounds
CCl + 2HF ⎯⎯ CCl F + 2HCl
7. 2, 2-dimethylbutane ⎯⎯⎯ three types …… 165 (c)
Iodoform test is positive for compounds which
8. 2, 3-dimethylbutane ⎯⎯⎯ two types …. have O

∥
9. 𝑛-hexane ⎯⎯⎯ three types ….
CH − C
 group or 2° alcohol group. 𝑅 + 𝑂𝐻 ⎯⎯ 𝑅𝑂𝐻
H 170 (c)
| Alkyl halides are soluble in organic solvents.
(a) CH − CH − C − CH 171 (d)
| C H Br + AgNO (alc. ) → C H NO + AgBr
OH nitro ethane
has 2° alcoholic group 173 (a)
O This reaction follows benzyne mechanism.
∥
(b)CH − CH − CH − C − CH
hasCH CO − group
O
∥
(d) CH − C − C H
has CH CO − group 175 (d)
∴ Compounds in choice (a), (b) and (d) give Grignard reagent give nucleophilic addition (of
positive iodoform test. 𝑅 ) at +ve centre.
O 176 (a)
∥ Tetrahydrofuran when treated with excess HI,
CH − CH − C − CH − CH give 1, 4-diiodobutane.
∵ This compound doesn’t have CH CO − or 2°
alcoholic group.
∴ It does not give positive iodoform test.
166 (a) 177 (b)
In C H Cl,Cl is firmly attached to C H nucleus. I possesses antiseptic nature.
167 (b) 179 (d)
For iodoform reaction, we need an oxidising agent Wurtz’s reaction involves the reduction of alkyl
halide with Na in ether.
which is provided by only , 𝑖. 𝑒. , IO ion. 181 (d)
CHCl + 4NaOH → HCOONa + 3NaCl + 2H O
Hypoiodide ion first oxidises (aq) sodium formate
182 (b)
CH CH OH → CH CHO Straight chain alkyl halides have greater boiling
point than their isomers. Therefore,
and then brings about iodination of
CH CH CH CH Cl has highest boiling point.
CH CHO to I C . CHO. Alkaline hydrolysis of 183 (d)
CH Cl, C H ClandCH Brare gases at room temperature
Cl CHO then gives CHl . The other three reagents 184 (d)
Nucleophilic substitution bimolecular (S 2)
do not contain any oxidising species and hence, prefers less sterically hindered site to attack.
Lesser the steric hindrance better the
fail to give iodoform test.
S 2 reaction. So, ease of reaction is 1° > 2° >
169 (b) 3° . S 2 involves inversion of configuration
Statement (b) is not correct regarding the S 1 stereochemically (Walden inversion)
reaction for alkyl halide because in S 1 reaction
no inversion takes place. The removal of X and the
attachment of OH will take place from the same
side.
𝑅 − 𝑋 ⎯⎯⎯ 𝑅 + 𝑋 185 (c)
The best method for the conversion of an alcohol
 into an alkyl chloride is by treating the alcohol 200 (c)
with SOCl in the presence of pyridine. Iodoform test is given by those compounds which
𝑅OH + SOCl → 𝑅Cl + HCl + SO has
The other products being gases escape leaving CH − C − C/H or CH − CH − units.
behind pure alkyl halide. ∥ |
186 (d) O OH
Freon, CCl F is used in cooling.
187 (b) Hence, this test is not given by phenol
CH≡CH + 2HCl ⟶ CH CHCl (C H − OH).
188 (d) 201 (d)
Cl is replaced by OH , 𝑖.𝑒., nucleophilic CCl is used as medicine in this form.
substitution. 202 (c)
189 (d)
𝑅𝑋 are called alkylating agent. CH 𝑋 is
methylating agent; C H 𝑋 is ethylating agent.
191 (a)
Methyl iodide is more reactive for nucleophilic
substitution of II order.
(Diazotization)
192 (a)
/
204 (c)
C H Cl ⎯ C H CN ⎯⎯⎯⎯⎯⎯⎯ C H CH NH C H I + Mg ⟶ C H MgI
193 (d) 205 (a)
.
CH COCH CH COCCl C H Cl ⎯⎯⎯⎯⎯⎯ C H OH ⎯⎯⎯⎯ C H Cl
194 (c) 206 (b)
1-chlorobutane gives butene-1 on reaction with Due to less stable nature of CHI .
alc. KOH (dehydrohalogenation) which on 207 (c)
ozonolysis yields methanal and propanal. The C H Br + C H ONa ⟶ C H OC H ; also in
reaction is as follows (a) C H is formed; in (b) C H is formed, in
(d) C H NC is formed.
208 (c)
Phosgene is COCl .
210 (c)
𝑅— 𝑋 + NH ⟶ 𝑅NH
212 (b)
CH 𝑋 + KCN ⟶ CH CN ⎯ CH COOH; —CN
group hydrolyses to —COOH.
213 (c)
MgCl → Mg + 2Cl
197 (d) Mg + 2e → Mg (at cathode)
Carbon tetrachloride is not inflammable. It is 2F 1 mol

used as fire-proof agent under the name ‘pyrene’. ∵ 2F(2 × 96500 C)deposits Mg = 1 mol
198 (a)
1 × 9.65
𝑛-butyl alcohol (CH CH CH CH OH) does not ∴ 9.65 C charge will deposit Mg =
give iodoform test because it does not possess the 2 × 96500
= 5 × 10 mol
CH CO − or CH CHOH group.
199 (d) 𝑅Br + Mg ⎯⎯⎯⎯⎯⎯ 𝑅MgBr
Grignard reagents are highly reactive and react Grignard reagent

with any source of proton to give hydrocarbons. It In order to prepare Grignard reagent, one mole of
is therefore necessary to avoid even traces of Mg is used per mole of reagent obtained. Thus, by
moisture from a grignard reagent. 5 × 10 mol mg ,5 × 10 mole of Grignard
 reagent is obtained. |
215 (c) OH
C H CN(𝐴) on hydrolysis gives C H COOH. 225 (d)
216 (d) KBr and conc. H SO gives HBr , which reacts with
2Nal + Cl ⟶ NaCl + I C H OH to give C H Br.
I + CHCl ⟶ Violet 227 (b)
218 (c) CCl COCH + Ca(OH) ⟶ CHCl + (CH COO) Ca
CH≡CH ⎯ CH CHCl 228 (d)
219 (a) C H Cl ⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯ C H
Allyl carbonium shows resonance and thus, allyl (24+5+35.5) (24+4)
chloride is more reactive. Vinyl chloride shows 64.5 g of C H Cl forms=28 gC H
resonance and thus, less reactive. ∴ 32.25 g of C H Cl will form= × 32.25
.
220 (b) = 14 g C H
Since, the alkyl halide RX gives 4, 5-diethyloctane, yield of alkene = 50% of 14 g
when reacts with Na, it must be 50
CH (CH ) CH(Br)CH CH . = × 14 = 7g
100
2CH CH CH CH − Br ⎯⎯⎯⎯⎯⎯ 229 (d)
𝑝- dichlorobenzene molecule has symmetrical
|
structure. It can fit well in its crystal lattice. The
CH CH
intermolecular forces of attraction are strong.
CH CH CH CH
Hence, it possesses highest melting point.
| |
231 (a)
CH (CH ) CH − CH − (CH ) − CH
The compound containing
The reaction is known as Wurtz reaction.
O OH
221 (a)
∥ |
CH COCH + PCl ⟶ CH CCl CH + POCl
CH − C − and − CH − CH
222 (a)
groups on heating with sodium hypoiodite (NaOI)
Grignard reagent is𝑅Mg𝑋.
or I with aq. NaOH or aq. Na CO gives yellow ppt.
223 (c)
of iodoform and the reaction is known as
CN (cyanide) is an ambidenate ligand, 𝑖. 𝑒., it can
iodoform.
donate electrons to the alkyl iodide either by
H C − CH − CH − CH + OI ⟶
using carbon or by using nitrogen.
|
OH
O
∥
CH − CH − C − CH + I + H O
O
In principle, the reaction can occur either through ∥
carbon or nitrogen. But in practice, the reaction CH − CH − C − CH + OI ⟶
mainly occurs through carbon as carbon behave O
like a strong nucleophile. ∥
224 (a) CH − CH − C − CI + OH
The iodoform test is given by compounds which O
have ∥
O OH CH CH − C − CI + HONa
∥ | O
CH − C − or CH − CH − group. ∥
In this given compounds only CH CH OH gives CH − CH − C − ONa + CHI
positive iodoform test as it has iodoform
CH − CH − group.
232 (a)
Alkyl halides in presence of strong alcoholic alkali
give elimination reaction.

CH − CH − CH
| |
Cl Cl
1,3-dichloro propane
234 (b) 238 (d)
Two optical and two geometrical.
(CH ) COH ⎯⎯⎯ (CH ) C = CH
. . . . 239 (c)
∵ % yield = 65 Industrial preparation of CHCl is carried out by
∴ Real yield = × 37 × = 18.2 g the action of bleaching powder over acetone.
240 (a)
235 (a)
𝑅𝑋 + AgCN → 𝑅NC + Ag𝑋
In S 2 reaction, nucleophile and alkyl halide
alkyl isocyanide
react in one step. When alkyl halide reacts with silver cyanide,
isocyanides are obtained. It is due to nucleophilic
substitution in presence of Ag .
241 (d)
Neo-pentane gives only one monochloro
derivative.
CH CH
Thus, tertiary carbon is under steric hindrance
| |
thus reaction does not take place until (C-Br)
bond breaks CH − C − CH + Cl ⎯⎯⎯ CH − C − CH Cl
| |
CH CH
242 (d)
𝑅— 𝑋+ Zn ⟶ 𝑅— 𝑅 + Zn𝑋 ; if Zn is used in place
of Na, the reaction is called Frankland’s reaction.
Which is the 𝑆 1reaction. 244 (a)
236 (b) A gem dihalide possesses two halogens on same
carbon atom.
245 (b)
𝑅 —Mg𝑋 are obtained as ethereal solution.
246 (a)
Chloroform (CHCl ) is formed on reaction of
Acc. To Markownikoff’s rule.
ethyl alcohol with bleaching powder. The reaction
NaOH(𝑎𝑞. )will lead to the formation of
is complex and takes place in the following steps
CH CH CH OH; in
(i) CaOCl + H O → Ca(OH) + Cl
(d) CH CHBrCH Brwill be formed.
237 (c) bleaching
There are four isomers obtained.
powder
CH − CH − CH + Cl ⟶
CH − CH − CHCl + 2HCl (ii) CH CH OH + Cl → CH CHO + 2HCl
(1,1,dichloro propane)
oxidation step

(iii) CH CHO + 3Cl → CCl CHO + 3HCl

 chloral 𝑅 — OH + PCl ⟶ 𝑅Cl + POCl + HCl
chlorination step 265 (c)
𝑅— I > 𝑅— Br > 𝑅— Cl > 𝑅— F; reactivity order
due to halogen atom.
3 ͦ > 2 ͦ > 1 ͦ; reactivity order due to alkyl group.
(iv) 266 (c)
Aryl halides in presence of strong base likeNaNH
247 (a) , gives nucleophilic substitution reaction through
Chloral is commercial name of CCl CHO. benzyne intermediate.
248 (d)
C—I bond is broken easily as well as ease of
reaction is 𝑡-alkyl halide >𝑠-alkyl halide >
𝑝-alkyl halide.
249 (b)
N2+Cl- Cl
267 (b)
Rest all replace —OH by —Cl.
Cu2Cl2/HCl + N2 268 (c)
benzene chlorobenzene -OH group is converted into –Cl group by SOCl or
diazonium anhydrous ZnCl /conc. HCl or HCl etc.
chloride 269 (a)
This reaction is known as Sandmeyer’s reaction. C H Cl + KCN → C H CN + KCl
250 (b) Chloroethanealcoholic propanenitrile
(CH ) CHCH ClandCH CH CH CH Cl; only chain 270 (a)
is different. CH Br + OH → CH OH + Br
251 (a) This reaction proceeds by S 2 mechanism.
Nucleophilicity order is ; Rate ∝ [substrate][nucleophile]
Rate ∝ [CH Br][OH ]
271 (b)
1
2CHCl + O ⟶ COCl + H O;
2
COCl , 𝑖. 𝑒. , phosgene is poisonous gas.
272 (d)
254 (a)
Westrosol is formed during addition of Cl on
CHCl + 𝑅NH + 3KOH
CH≡CH followed with action of lime. It is a very
⟶ 𝑅NC + 3KCl + 3H O
good solvent.
255 (a) CH≡CH + 2Cl ⟶ CHCl CHCl
Zn dust removes 𝑋 from molecule.
⎯⎯ CHCl = CCl
257 (d)
Order of reactivity of alkyl halide 274 (c)
iodide > bromide > chloride > fluoride and C—Mg bond is covalent but polar.
tertiary > secondary > primary 275 (c)
258 (b) 𝑅𝑋 ⟶ R + 𝑋 ; 𝑅 + OH ⟶ 𝑅OH
( .)
𝑅 — 𝑋 ⎯⎯⎯⎯⎯ 𝑅 — OH 277 (a)
259 (d) 10. Iodoform test is done to detect presence
Reactivity of 𝑡-alkyl halides to show S 2 of CH CO group in organic compounds.
mechanism is least due to steric hinderance. 11. Fehling solution identifies aldehydes.
261 (c)
/ ( ) 12. Tollen’s reagent identifies aldehydes.
CCl + [H] ⎯⎯⎯⎯⎯⎯ CHCl
262 (a)
 13. Schiff’s reagent identifies aldehydes.

Methyl ketone is CH − C − 𝑅.

O
287 (a)
∥ C H Br gives yellow ppt. of AgBr whereas,
(CH ) CHCl gives white ppt. if AgCl.
∵ It has CH − C group. It is tested by using
288 (d)
iodoform test.
C H Br ⎯⎯⎯ C H NC ⎯⎯⎯⎯⎯⎯⎯ C H NH. CH
The compound having CH CO group give yellow (X) (Y)
ppt. on reaction with I and aqueous alkali. Ethyl isocyanide ethyl methyl amine
289 (d)
278 (b)
S 1 order is TH > SH > PH.
290 (c)
C H Cl + NH ⟶ (C H ) N Cl
292 (b)
CH CHCl gives aldehyde; CH ClCH Cl gives
glycol.
294 (c)
Chloroform is oxidised by air in the presence of
light to form phosgene or carbonyl chloride which
It is electrophilic substitution, so electrophile is poisonous gas.
must be attacked on o/p-position due to higher 1
CHCl + O ⎯⎯⎯⎯⎯ COCl + HCl
electron density on this position. In this ring, the 2
Chloroform phosgene
attached –NH- group will have high electron
295 (d)
density due to resonance and 𝑜𝑟𝑡ℎ𝑜 position is
( .)
blocked, so electrophile is attached on 𝑝𝑎𝑟𝑎 𝑅 — 𝑋 ⎯⎯⎯⎯⎯ 𝑅 — OH
position. 296 (a)
280 (c) CH CHBrCH CH CH ⎯⎯⎯⎯ CH CH=CHCH CH
CCl is covalent compound. α-,β- elimination gives 𝑡𝑟𝑎𝑛𝑠-isomers as main
282 (b) product.
Westrosol is formed during addition of Cl on 298 (c)
CH≡CH followed with action of lime. It is a very Oxidation of CHCl occurs in air and light.
good solvent. 301 (b)
CH≡CH + 2Cl ⟶ CHCl CHCl
CHCl ⎯⎯⎯ HCOONa + 3NaCl + 2H O
⎯⎯ CHCl = CCl 303 (d)
283 (b) Ethyl alcohol gives positive iodoform test (𝑖. 𝑒. ,
Elimination reaction. yellow ppt. with I and NaOH).
286 (a) CH CH OH + 4I + 6NaOH →
PhS - is a strong nucleophile and dimethyl CHI ↓ + 5NaI + CH COONa + 3H O
yellow
formamide (DMF) is a highly polar aprotic
304 (c)
solvent. Condition indicates that nucleophilic
Reimer-Tiemann reaction.
substitution (S 2) takes place at 2°benzylic place,
305 (a)
stereochemically, it involves inversion of
configuration. (CH ) CH=CH (CH ) C𝑋 ∙ CH ;
 Follow Markownikoff’s rule. CH =CH + Cl ⟶ CH ClCH Cl
306 (b) 316 (a)
The molecular formula of diphenyl methane ( .)
CH CHCl ⎯⎯⎯⎯⎯ CH CHO
shows four isomers in form of monochloro
317 (a)
derivatives.
C H NH + CHCl + 3KOH ⟶
C H NC + 3KCl + 3H O
318 (c)
Monochloro derivatives An alkyl halide on heating with dry silver oxide
gives ether.
∆
2𝑅 − 𝑋 + Ag O ⎯⎯⎯ 𝑅 − O − 𝑅 + 2AgX
alkyl halide dry ether
319 (d)
Ethyl alcohol converts phosgene to ethyl
carbonate.
COCl + 2C H OH → (C H O) CO + 2HCl
phosgene ethyl carbonate
320 (b)
C H OH + HCl ⎯⎯ C H Cl
321 (c)
𝛾-isomer of cyclohexane hexachloride is strong
pesticide. It is also known as lindane.

307 (a)
𝑝-nitroiodobenzene can be prepared from 𝑝-
nitroaniline as follows
NO2 NO2 NO2

NaNO2/HCl Kl

322 (b)
NH2 N2Cl I
Methyl alcohol (CH OH) does not give iodoform
p-nitro-iodobenzene test.
308 (a) 324 (d)
Iodoform test is given by those compounds which Elimination of HCl by alc. KOH.
have – CH CO group or on oxidation yields this 325 (b)
group. HCHO does not give this test. Vapours of chloroform on inhaling causes
309 (a) unconsciousness.
CCl is ire extinguisher used under the name pyrene327 (a)
310 (a) Alkyl halides give elimination reaction with
Among the primary halides reactivity order is alcoholic KOH and yield an alkene or alkyne (from
CH 𝑋 > C H 𝑋 > C H 𝑋, also chlorobenzene is dihalides) 𝑒. 𝑔 . ,
less reactive due to resonance.
311 (b)
A white ppt. of AgCl is obtained if CHCl is impure.
312 (d) 1,2-dibromo ethane acetylene
Hence, product has both 𝑠𝑝-hybridised carbon.
CH OHCH OH CH ClCH Cl
328 (a)
313 (c)
C H OH + PCl ⟶ C H Cl + POCl + HCl
Only iodides and fluorides are obtained.
329 (c)
315 (a)
 / ( .)
CHCl ⎯⎯⎯⎯⎯⎯⎯ CH Cl
339 (a)
Ethyl bromide on treating with KCN, gives ethyl
cyanide, which on reduction gives propyl amine.

Stability of I>II hence, I is predominant.

330 (b)
C H NH + CHCl + 3KOH
340 (a)
⟶ C H NC + 3KCl + 3H O
The compounds of oxyacids in which H-atom of —
331 (a) OH group is replaced by an alkyl group are called
𝑅OH + SOCl → 𝑅Cl + SO ↑ + HCl ↑ inorganic esters.
∵ SO and HCl are gaseous by-products and can R —𝑋 + K — O — N=O⟶𝑅—O—N=O + K𝑋
be removed easily to get pure alkyl halide. 342 (b)
∴ It is best method for preparation of alkl halide. Chloroform is oxidised to a poisonous gas,
332 (b) phosgene (COCl ) by atmospheric oxidation.
CH =CHCl + HCl ⟶CH CH Cl CHCl + O → COCl + HCl
335 (d) 343 (a)
When an alkyl halide reacts with alcoholic
𝑋 ⎯⎯⎯⎯ yellow or white ppt.
ammonia in a sealed tube then a mixture of
primary, secondary and tertiary amine is formed.
𝑅𝑋 + NH → 𝑅NH + H𝑋
𝑝𝑟𝑖-amine
𝑅NH + 𝑋𝑅 → 𝑅 NH + H𝑋
𝑠𝑒𝑐-amine The above reaction is not give by
𝑅 NH + H𝑋 → 𝑅 N + 𝐻𝑋 because in bromobenzene, halogen is directly
𝑡𝑒𝑟-amine attached with the benzene ring.
336 (d)
Chloroform on reaction with nitric acid give
chloropicrin (nitro chloroform) according to
following reaction
CHCl + HNO → C(NO )Cl + H O
nitrochloroform
(chloropicrin)
337 (d)
𝑅Mg𝑋 is soluble in each.
338 (d)
Session: 2023-24 Total Questions: 341

CHEMISTRY

10.HALOALKANES AND HALOARENES

Matrix-Match Type

This section contain(s) 0 question(s). Each question contains Statements given in 2 columns which have to be
matched. Statements (A, B, C, D) in columns I have to be matched with Statements (p, q, r, s) in columns II.

1. Match the following. The correct match is

Column-I Column- II

(A) C H Cl, moistAg O (1) CH CH ONO

(B) C H Cl, aqueous ethanolic AgCN (2) C H

(C) C H Cl,aqueous ethanolic AgNO (3) CH CH OH

(D) C H Cl, ethanolic KOH (4) CH CH NC

(5) C H

CODES :

A B C D

a) 5 3 4 1

b) 1 2 3 4

c) 3 4 1 2

d) 4 1 2 5

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Session: 2023-24 Total Questions: 341

CHEMISTRY

10.HALOALKANES AND HALOARENES

: ANSWER KEY :
1) c

P a g e |48
Session: 2023-24 Total Questions: 341

CHEMISTRY

10.HALOALKANES AND HALOARENES

: HINTS AND SOLUTIONS :

1 (c)
Reactants Products
A. C H Cl , moist Ag O (iii)CH CH OH
B. C H Cl , aqueous (iv)CH CH NC
ethanolic AgCN
C. C H Cl , aqueous (i) CH CH ONO
ethanolic AgNO
D. C H Cl , ethanolic (ii) C H
KOH

P a g e |49
Session: 2023-24 Total Questions: 341

CHEMISTRY

10.HALOALKANES AND HALOARENES

Matrix-Match Type

This section contain(s) 0 question(s). Each question contains Statements given in 2 columns which have to be
matched. Statements (A, B, C, D) in columns I have to be matched with Statements (p, q, r, s) in columns II.

1. Match the following. The correct match is

Column-I Column- II

(A) C H Cl, moistAg O (1) CH CH ONO

(B) C H Cl, aqueous ethanolic AgCN (2) C H

(C) C H Cl,aqueous ethanolic AgNO (3) CH CH OH

(D) C H Cl, ethanolic KOH (4) CH CH NC

(5) C H

CODES :

A B C D

a) 5 3 4 1

b) 1 2 3 4

c) 3 4 1 2

d) 4 1 2 5

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Session: 2023-24 Total Questions: 341

CHEMISTRY

10.HALOALKANES AND HALOARENES

: ANSWER KEY :
1) c

P a g e |51
Session: 2023-24 Total Questions: 341

CHEMISTRY

10.HALOALKANES AND HALOARENES

: HINTS AND SOLUTIONS :

1 (c)
Reactants Products
A. C H Cl , moist Ag O (iii)CH CH OH
B. C H Cl , aqueous (iv)CH CH NC
ethanolic AgCN
C. C H Cl , aqueous (i) CH CH ONO
ethanolic AgNO
D. C H Cl , ethanolic (ii) C H
KOH

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