HALOALKANE AND HALO ARENES - 2025

Board Questions

10.2 Nomenclature 11. Write the structure of the following

compound :
VSA (1 mark) 1, 4-dibromobut-2-ene
1. Draw the structure of 2-bromopentane. 12. Write the structure of the
following compound :
2-(2-Bromophenyl)butane
2. Write the IUPAC name of
13. Give IUPAC name of the following organic
CH3 CH CH2 CH CH2
compound :
Cl CH3CH C CH CH3
3. Write the IUPAC name of CH3 Br
CH3
14. Write the structure of the following compound :
CH3CH CH C CH3 2-(2-chlorophenyl)-1-iodooctane
15. Write the structure of the following
Br
compound :
4. Write the IUPAC name of 1-bromo-4-sec-butyl-2-methylbenzene
(CH3)2CHCH(Cl)CH3.
5. Write the IUPAC name of the following 16. Write the structure of the compound :
compound : 4-tert-butyl-3-iodoheptane
CH3 17. Write the IUPAC name of the following
compound :
CH3 C CH CH3
CH3
CH3 Cl
H3 C C CH2Cl
6. Write the IUPAC name of the following
compound : CH3
CH3 CH CH2 CH CH3 18. Write the structure of the compound 1-chloro-
4-ethylcyclohexane.
Br C 19. Write the IUPAC name of the following
7. Write IUPAC name of the following : compound :
CH3 C C CH2OH CH3CH CH CH3
CH3 Br Cl Br
20. State the IUPAC name of the following
8. Give the IUPAC name of the following compound :
compound : H3C H
H
CH2 C CH2Br H H Br
CH3 21. Write the IUPAC name of ClCH2C CCH2Br.
9. Write the IUPAC name of the following
compound : SA I (2 marks)
(CH3)3CCH2Br
22. Write the IUPAC names of the following
10. Write the IUPAC name of the following compounds :
compound : (i) CH2 CHCH2Br (ii) (CCl3)3CCl
CH2 CHCH2Br
SA II (3 marks) 32. Complete the following chemical equation :
Peroxide
23. Give the IUPAC names of the following CH3CH2CH CH2 + HBr ...
compounds :
(i) CH3 CH CH2 CH3
SA I (2 marks)
Br 33. Draw the structure of major monohalo product
Br
in each of the following reactions :
(ii) (i)
Br
(iii) CH2 CH CH2 Cl
(ii)
10.4 Methods of Preparation
VSA (1 mark) 34. Write the mechanism of the following reaction :
24. How do you convert : CH3CH2OH CH3CH2Br + H2O
Propene to 1-iodopropane ?
25. Write the major products in the following : 35. Complete the following reaction equations :
CH2 CH3
Br2, UV light (i) OH + SOCl2
O2N CH2OH
(ii) + HCl
26. Write the structure of the major product in the OH
following reaction :
36. Complete the following reaction equations :
CH3
(i) + HI
27. A hydrocarbon C5H12 gives only one
(ii) CH3CH2CH CH2 + HBr
monochlorination product. Identify the
hydrocarbon. (Delhi 2013C)
37. Complete the following reaction equation :
28. Draw the structure of major monohalogen
(i) C6H5N2Cl + KI
product formed in the following reaction :
CH3 (ii)
+ HI

29. Draw the structure of major monohalogen

SA II (3 marks)
product in the following reaction :
Heat 38. Compute the following reaction equations:
+ Br2 CH3
Light
(i) + HI
30. Draw the structure of major monohalo product
in the following reaction :
Fe (ii) H
2
+ HBr
H H
31. What happens when bromine attacks (iii) CH3CH2CH CH2 + HBr
CH2 CH CH2 C CH?
39. Complete the equation for the following CH3 CH2 CH Cl , which is more reactive
reactions : CH3
(i) towards SN1 reaction and why?
48. Write the structure of an isomer of compound
C4H9Br which is most reactive towards SN1
CH3
reaction.
(ii) + HI
49. Which would undergo SN2 reaction faster in
the following pair and why?
(iii) OH + SOCl2 CH3
CH3 CH2 Br and CH3 C CH3
10.5 Physical Properties Br
VSA (1 mark)
40. Give reason : 50. Which would undergo SN1 reaction faster in
n-Butyl bromide has higher boiling point than the following pair :
t-butyl bromide.
41. Why are alkyl halides insoluble in water?

42. Why does p-dichlorobenzene have a higher

m.p. than its o- and m-isomers?
51. Which would undergo SN2 reaction faster in
the following pair and why?
43. Explain the following : CH3 CH2 Br and CH3 CH2 I
Alkyl halides, though polar, are immiscible
with water.
52. Identify the chiral molecule in the following
44. Answer the following : pair :
Haloalkanes easily dissolve in organic solvents,
why?
45. Out of ethyl bromide and ethyl chloride which
53. Which halogen compound in each of the
has higher boiling point and why?
following pairs will react faster in SN2 reaction :
(i) CH3Br or CH3I
SA I (2 marks) (ii) (CH3)3CCl or CH3Cl
46. Explain why
(i) the dipole moment of chlorobenzene is 54. What happens when CH3 Br is treated with
lower than that of cyclohexyl chloride? KCN?
55. What happens when ethyl chloride is treated
with aqueous KOH?
(ii) alkyl halides, though polar, are immiscible
with water? 56. Why is (±)-butan-2-ol is optically inactive?

10.6 Chemical Reactions 57. Which compound in the following pair

undergoes faster SN1 reaction?
VSA (1 mark)
Cl
47. Out of CH3 CH CH2 Cl and and
CH3
58. How may methyl bromide be preferentially 70. How do you convert?
converted to methyl isocyanide? (i) Chlorobenzene to biphenyl
59. Account for the following : (ii) 2-bromobutane to but-2-ene
Grignard’s reagents should be prepared under
anhydrous conditions. 71. Write the major product(s) in the following :
Na
(i) 2CH3 CH CH3 Dry ether
60. Predict the order of reactivity of four isomeric
bromobutanes in SN1 reaction. Cl
AgCN
61. Predict the order of reactivity of the (ii) CH3 CH2 Br
following compounds in SN1 reaction. 72. Give reasons:
C6H5CH2Br, C6H5C(CH3)(C6H5)Br, (i) Racemic mixture is optically inactive.
C6H5CH(C6H5)Br, C6H5CH(CH3)Br (ii) The presence of nitro group (—NO2)
at o/p positions increases the reactivity
62. Give a chemical test of distinguish between of haloarenes towards nucleophilic
C2H5Br and C6H5Br. substitution reactions. (2/3, Delhi 2015)
63. Which will react faster in SN2 displacement, 73. Write the structure of the major product in
1-bromopentane or 2-bromopentane and why? each of the following reactions :
(i)
64. Which will react faster in SN1 displacement
reaction :
1-Bromobutane or 2-bromobutane and why?
(ii)
65. A solution of KOH hydrolyses
CH3CHClCH2CH3 and CH3CH2CH2CH2Cl.
Which one of these is more easily hydrolysed? 74. (i) Why is butan-1-ol optically inactive but
butan-2-ol is optically active?
(ii) Although chlorine is an electron
66. Explain the following reactions with an
withdrawing group, yet it is ortho-,
example :
para-directing in electrophilic aromatic
Friedel-Crafts reaction.
substitution reactions. Why?
67. Why is the following occur :
Chloroform is stored in closed dark coloured
75. (i) Which alkyl halide from the following pair
bottles completely filled so that air is kept out. is chiral and undergoes faster SN2 reaction?

68. Explain why in the pair, (CH3)3CCl and CH3Cl (a) (b)
will react faster in SN2 reaction with OH– ?
(ii) Out of SN1 and SN2, which reaction occurs
with
SA I (2 marks) (a) inversion of configuration
(b) racemisation?
69. Give reasons :
(i) C Cl bond length in chlorobenzene 76. Write chemical equations when
is shorter than C Cl bond length in (i) ethyl chloride is treated with aqueous
CH3 Cl. KOH.
(ii) SN1 reactions are accompanied by (ii) chlorobenzene is treated with CH3COCl
racemization in optically active alkyl halides. in presence of anhydrous AlCl3.
Haloalkanes and Haloarenes

77. (i) Which alkyl halide from the following (i) Benzyl chloride to benzyl alcohol,
pairs would you expect to react more (ii) Methyl magnesium bromide to
rapidly by an SN2 mechanism and why? methylpropan-2-ol.
CH3 CH2 CH CH3 87. Which compound in the following couple will
Br react faster in SN2 displacement and why?
(i) 1-Bromopentane or 2-bromopentane
CH3 CH2 CH2 CH2 Br (ii) 1-Bromo-2-methylbutane or
(ii) Racemisation occurs in SN1 reactions.
2-bromo-2-methylbutane.
Why?
78. Write chemical equations when
88. (a) Why is sulphuric acid not used during
(i) methyl chloride is treated with AgNO2.
the reaction of alcohols with KI in the
(ii) bromobenzene is treated with CH3Cl in
conversion of an alcohol to the alkyl
the presence of anhydrous AlCl3.
iodide?
(b) Why are haloarenes less reactive than
79. What are ambident nucleophiles? Explain with haloalkanes towards nucleophilic
an example. substitution reactions?
80. Chlorobenzene is extremely less reactive 89. How would you account for the following :
towards a nucleophilic substitution reaction. (i) Grignard reagents are prepared strictly
Give two reasons for the same. under anhydrous conditions ?
81. Account for the following: Cl
(i) The C Cl bond length in chlorobenzene
(ii) undergoes faster SN1
is shorter than that in CH3 Cl.
(ii) Chloroform is stored in closed dark brown reaction than Cl ?
bottles.
82. Give reasons for the following :
(i) Ethyl iodide undergoes SN2 reaction faster 90. Which one in the following pairs of substances
than ethyl bromide. undergoes SN2 substitution reaction faster and
(ii) C X bond length in halobenzene why?
is smaller than C X bond length in (i) CH2Cl or Cl
CH3 X.
83. Haloalkanes undergo nucleophilic substitution I Cl
(ii) or
whereas haloarenes undergo electrophilic
substitution. Explain.
91. Which one in the following pairs undergoes
84. Answer the following :
SN1 substitution reaction faster and why?
(i) What is known as a racemic mixture? Give
an example. Cl
(ii) Of the two bromoderivatives, C6H5CH(CH3)Br Cl
C
and C6H5CH(C6H5)Br, which one is more (i) or
reactive in SN1 substitution reaction and
Cl
why? Cl
85. Write the mechanism of the following reaction : (ii) or
EtOH, H2O
n-BuBr + KCN n-BuCN
92. Suggest a possible reason for the following
observations :
86. How are the following conversions carried (i) The order of reactivity of haloalkanes is
out? RI > RCl > RBr.
(ii) Neopentyl chloride (CH3)3CCH2Cl does (i) What is meant by chirality of a compound?
not follow SN2 mechanism. Give an example.
(ii) Which one of the following compounds is
93. Give reasons for the following observations : more easily hydrolysed by KOH and why?
(i) Haloarenes are less reactive than haloalkanes CH3CHClCH2CH3 or CH3CH2CH2Cl
towards nucleophilic substitution reactions. (iii) Which one undergoes SN2 substitution
(ii) The treatment of alkyl chloride with reaction faster and why?
aqueous KOH leads to the formation of I or Cl
alcohol but in the presence of alcoholic
KOH, alkene is the major product.
100. Rearrange the compounds of each of the
94. (i) Why is it that haloalkanes are more reactive following sets in order of reactivity towards
than haloarenes towards nucleophiles. SN2 displacement:
(ii) Which one of the following reacts faster in (i) 2-Bromo-2-methylbutane,
an SN1 reaction and why? 1-Bromopentane, 2-Bromopentane
Cl (ii) 1-Bromo-3-methylbutane, 2-Bromo-2-
Cl methylbutane,3-bromo-2-methylbutane
or (iii) 1-Bromobutane, 1-Bromo-2, 2-dimethyl
propane, 1-Bromo-2-methylbutane
95. (i) Why are haloalkanes more reactive towards
nucleophilic substitution reactions than
haloarenes? 101. (a) Write a chemical test to distinguish
(ii) Which one of the following two substances between :
undergoes SN1 reaction faster and why? (i) Chlorobenzene and benzyl chloride
Cl (ii) Chloroform and carbon tetrachloride
(b) Why is methyl chloride hydrolysed more
or Cl easily than chlorobenzene? (Delhi 2011C)
102. Differentiate between SN1 and SN2 mechanisms
96. Discuss the mechanism of SN1 reaction of
and give examples.
haloalkanes.
97. What is Saytzeff rule? Illustrate with suitable 10.7 Polyhalogen Compounds
example.
98. Give one example of each of the following
VSA (1 mark)
reactions : 103. State one use each of DDT and iodoform.
(i) Wurtz reaction
(ii) Wurtz-Fittig reaction. 104. Write the balanced equation for the following:
(i) When chloroform is oxidised by air.
SA II (3 marks)
(ii) Chloroform reacts with chlorine.
99. Answer the following questions: