UNIT

3 HALOALKANES AND HALOARENES

Exercise 1: NCERT Based Topic-wise MCQs

7.0 INTRODUCTION
1. Haloarenes contain halogen atom(s) attached to hybridised carbon atom. NCERT/Page-289 / N-159
3 2
(a) 𝑠𝑝 (b) 𝑠𝑝 (c) 𝑠𝑝 (d) both (a) and (b)

7.1 CLASSIFICATION
2. When two halogen atoms are attached to same carbon atom then it is: NCERT/Page-292 / N-162
(a) vic-dihalide (b) gem-dihalide (c) 𝛼, 𝜔-halide (d) 𝛼, 𝛽-halide

3. Which of the following halide is 2∘ ? NCERT/Page-290 / N-160

(a) Isopropyl chloride (b) Isobutyl chloride (c) 𝑛-Propyl chloride (d) 𝑛-Butyl chloride

4. Which one of the following is not an allylic halide? NCERT Page N-160
(a) 4-Bromopent-2-ene (b) 3-Bromo-2-methylbut-1-ene
(c) 1-Bromobut-2-ene (d) 4-Bromobut-1-ene

7.2 CLASSIFICATION
5. The IUPAC name of the compound shown below is NCERT Page-291 / N-161

(a) 2-bromo-6-chlorocyclohex-1-ene (b) 6-bromo-2-chlorocyclohexene

(c) 3-bromo-1-chlorocyclohexene (d) 1-bromo-3-chlorocyclohexene
6. A compound is formed by substitution of two chlorine for two hydrogens in propane. The number of
possible isomeric compounds is NCERT Page N-164
(a) 4 (b) 3 (c) 5 (d) 2

7. IUPAC name of (CH3 )3 CCl is NCERT Page-291 / N-161

(a) 3-Chlorobutane (b) 2-Chloro-2-methylpropane
(c) 𝑡-butyl chloride (d) 𝑛-butyl chloride
8. IUPAC name of CH3 CH2 C(Br) = CH − Cl is NCERT PAGE N- 162
(a) 2-bromo-1-chlorobutene (b) 1-chloro-2-bromobutene
(c) 3-chloro-2-bromobutene (d) None of the above

9. Phosgene is a common name for NCERT PAGE N- 187

(a) phosphoryl chloride (b) thionyl chloride
(c) carbon dioxide and phosphine (d) carbonyl chloride

7.3 NATURE OF C-X BOND

10. The main difference in C − X bond of a haloalkane and a haloarene is NCERT Page-312/N-182
a) haloalkanes are less reactive than haloarenes due to difficulty is C − X cleavage in haloalkanes.
b) in haloalkanes the C attached to halagen in C − X bond is 𝑠𝑝3 hybridised while in haloarenes it is 𝑠𝑝2
hybridised.
c) C − X bond in haloalkanes is shorter than haloarenes.
d) C − X bond in haloarenes acquires a double bond character due to higher electronegativity of X than
haloalkanes.
11. C − Cl bond of chlorobenzene in comparison to C − Cl bond in methyl chloride is NCERT Page-312 / N-182
(a) Longer and weaker (b) Shorter and weaker
(c) Shorter and stronger (d) Longer and stronger

7.4 METHODS OF PREPARATION OF HALOALKANES

12. Halogenation of alkanes is NCERT PAGE N- 164
(a) a reductive process (b) an oxidative process
(c) an isothermal process (d) an endothermal process

13. Ethylene dichloride can be prepared by adding HCl to NCERT Page 𝐍 − 𝟏𝟔𝟓
(a) ethane (b) ethylene (c) acetylene (d) ethylene glycol

14. The best method for the conversion of an alcohol into an alkyl chloride is by treating the alcohol with
(a) PCl5 NCERT Page-294 / N-164
(b) dry HCl in the presence of anhydrous ZnCl2
(c) SOCl2 in presence of pyridine
(d) none of these

15. Conant-Finkelstein reaction for the preparation of alkyl iodide is based upon the fact that
NCERT Page-295/N-165
(a) sodium iodide is soluble in methanol, while sodium chloride is insoluble in methanol
(b) sodium iodide is soluble in methanol, while NaCl and NaBr are insoluble in methanol
(c) sodium iodide is insoluble in methanol, while NaCl and NaBr are soluble
(d) the three halogens differ considerably in their electronegativity

16. Ethyl alcohol reacts with thionyl chloride in the presence of pyridine to give NCERT Page-294 / N-164
 (a) CH3 CH2 Cl + H2 O + SO2 (b) CH3 CH2 Cl + HCl
(c) CH3 CH2 Cl + HCl + SO2 (d) CH3 CH2 Cl + SO2 + Cl2

17. Hydrocarbon (CH3 )3 CH undergoes reaction with Br2 and Cl2 in the presence of sunlight, if the reaction
with Cl is highly reactive and that with Br is highly selective so no.of possible products respectively is (are)
(a) 2,2 (b) 2,1 (c) 1,2 (d) 1,1

7.5 PREPARATION OF HALOARENES

18. In the preparation of chlorobenzene from aniline, the most suitable reagent is NCERT Page-296 / N-166
(a) chlorine in the presence of ultraviolet light
(b) chlorine in the presence of AlCl3
(c) nitrous acid followed by heating with Cu2 Cl2
(d) HCl and Cu2 Cl2

19. Aryl halides can not be prepared by the reaction of aryl alcohols with PCl3 , PCl5 or SOCl2 because
(a) phenols are highly stable compounds. NCERT Page N-164
(b) carbon-oxygen bond in phenols has a partial double bond character.
(c) carbon-oxygen bond is highly polar
(d) all of these

20. Which of the following is the best method for synthesis of 1-bromo-3-chlorobenzene?

(a) NCERT Page-296 / N-166

(b)

(c)

(d)

7.6 PHYSICAL PROPERTIES

21. The decreasing order of boiling points of alkyl halides is NCERT Page-298 / N-168
(a) RF > RCl > RBr > RI (b) RBr > RCl > RI > RF
(c) RI > RBr > RCl > RF (d) RCl > RF > RI > RBr
22. Which of the following is liquid at room temperature (b.p. is shown against it)? NCERT Page N-168
(a) CH3 I 42∘ C (b) CH3 Br 3∘ C (c) C2 H5 Cl12∘ C (d) CH3 F − 78∘ C

23. Which of the following are gases at room temperature? NCERT Page N-168
(a) CH3 Cl (b) C4 H9 Cl (c) C5 H10 Br (d) C3 H7 I

24. Which of the following isomer has the highest melting point: [CBSE Sample Paper 2021-22]
(a) 1,2-dichlorobenzene NCERT Page-299 / N-168
(b) 1,3-dichlorobenzene
(c) 1,4-dichlorobenzene
(d) all isomers have same melting points

7.7 CHEMICAL REACTIONS

25. Which one is most reactive towards SN 1 reaction? NCERT Page-304 / N-174
(a) C6 H5 CH(C6 H5 )Br (b) C6 H5 CH(CH3 )Br
(c) C6 H5 C(CH3 )(C6 H5 )Br (d) C6 H5 CH2 Br

26. A Grignard reagent may be made by reacting magnesium with NCERT Page-310 / N-180
(a) Methyl amine (b) Diethyl ether
(c) Ethyl iodide (d) Ethyl alcohol

27. In 𝑆𝑁 1 reaction, the recemization takes place. It is due to NCERT Page-309 / N-179
(a) inversion of configuration (b) retention of configuration
(c) conversion of configuration (d) Both (a) and (b)

28. The order of reactivities of the following alkyl halides for a SN 2 reaction is NCERT Page-304 / N-174
(a) RF > RCl > RBr > RI (b) RF > RBr > RCl > RI
(c) RCl > RBr > RF > RI (d) RI > RBr > RCl > RF

29. Which among MeX, RCH2 X, R 2 CHX and R 3 CX is most reactive towards SN 2 reaction?
(a) MeX (b) RCH2 X NCERT/ Page-304 / N-174
(c) R 2 CHX (d) R 3 CX

30. Isopropyl chloride undergoes hydrolysis by NCERT Page-304 / N-174

(a) SN 1 mechanism (b) SN 2 mechanism
(c) SN 1 and SN 2 mechanisms (d) Neither SN 1 nor SN 2 mechanism

31. Tertiary alkyl halides are practically inert to substitution by SN 2 mechanism because of
(a) steric hindrance (b) inductive effect NCERT Page-302 / N-172
(c) instability (d) insolubility
32. Which of the following is an optically active compound? NCERT Page-307 / N-177
(a) 1-Butanol (b) 1-Propanol
(c) 2-Chlorobutane (d) 4-Hydroxyheptane

33. The mechanism of 𝑆𝑁 1 reaction is given as: NCERT Page N-179

Y⊖
R − X ⟶ R⊕ X ⊖ ⟶ R⊕ ∥ X ⊖ ⟶ R − Y + X ⊖
Ion pair Solvent
Separated ion
pair
A student writes general characteristics based on the given mechanism as :
(1) The reaction is favoured by weak nucleophiles.
(2) 𝑅 ⊕ . would be easily formed if the substituents are bulky.
(3) The reaction is accompanied by racemization.
(4) The reaction is favoured by non-polar solvents.
Which observations are correct?
(a) (1) and (2) (b) (1) and (3) (c) (1), (2) and (3) (d) (2) and (4)

34. The process of separation of a racemic modification into 𝑑-and ℓ-enantiomers is called
(a) Resolution (b) Dehydration (c) Revolution (d) Dehydrohalogenation

35. The major product in the reaction

(a) t-Butyl ethyl ether (b) 2,2-Dimethyl butane
(c) 2-Methyl pent-1-ene (d) 2-Methyl prop-1-ene

36. Racemic compound has NCERT Page-307 / N-177

(a) equimolar mixture of enantiomers (b) 1:1 mixture of enantiomer and diastereomer
(c) 1:1 mixture of diastereomers (d) 1:2 mixture of enantiomers

37. An organic molecule necessarily shows optical activity if it NCERT Page-307 / N-177
(a) contains asymmetric carbon atoms (b) is non-polar
(c) is non-superimposable on its mirror image (d) is superimposable on its mirror image

38. Mg reacts with RBr best in NCERT Page-310 / N-180

(a) C2 H5 OC2 H5 (b) C6 H5 OCH3 (c) C6 H5 N(CH3 )2 (d) Equally in all the three

39. 2-Bromopentane is heated with potassium ethoxide in ethanol. The major product obtained is
(a) 2-ethoxypentane (b) pentene-1 NCERT Page-310 / N-180
(c) trans-2-pentene (d) cis-pentene-2

40. An alkyl halide reacts with metallic sodium in dry ether. The reaction is known as : NCERT Page-311
(a) Frankland's reaction (b) Sandmeyer's reaction
(c) Wurtz reaction (d) Kolbe's reaction
41. When 2-Bromobutane reacts with alcoholic KOH, the reaction is called NCERT Page N-310
(a) halogenation (b) chlorination
(c) hydrogenation (d) dehydrohalogenation

42. An alkyl halide by formation of its Grignard reagent and heating with water yields propane. What is the
original alkyl halide? NCERT Page-311 / N-181
(a) Methyl iodide (b) Ethyl iodide
(c) Ethyl bromide (d) Propyl bromide

43. An organic compound A(C4 H9 Cl) on reaction with Na/ diethyl ether gives a hydrocarbon which on
monochlorination gives only one chloro derivative, then A is NCERT Page N-186
(a) tert-butyl chloride (b) sec-butyl chloride
(c) isobutyl chloride (d) 𝑛-butyl chloride

44. The major product of the following reaction is NCERT Page-309 & 311 / N-179 & 181

(a) (b) (c) (d)

45. NCERT Page-311 / N-180 & 181

(a) (b)

(c) (d) None of these.

46. A dihalogen derivative ' 𝑋 ' of a hydrocarbon with three carbon atoms reacts with alcoholic KOH and
produces another hydrocarbon which forms a red precipitate with ammoniacal Cu2 Cl2 ,′ 𝑋 ′ gives an
aldehyde on reaction with aqueous KOH. The compound ' 𝑋 ' is NCERT Page N-166 & 180
(a) 1,3-Dichloropropane (b) 1,2-Dichloropropane
(c) 2,2-Dichloropropane (d) 1,1-Dichloropropane

47. The major product (P) in the reaction

[Ph is −C6 H5 ] is [NCERT Page 𝐍 − 𝟏𝟔𝟓
 (a) (b)

(c) (d)

48. . What is true about the stereochemistry of the products

formed in this reaction? NCERT Page N-178
(a) Racemised product (b) Inverted product
(c) Retained product (d) More inverted than retained

49. Ammonolysis of Alkyl halides followed by the treatment with NaOH solution can be used to prepare
primary, secondary and tertiary amines. The purpose of NaOH in the reaction is NCERT Page N-182
(a) To remove basic impurities (b) To activate NH3 used in the reaction
(c) To remove acidic impurities (d) To increase the reactivity of alkyl halide

50. Chlorobenzene reacts with Mg in dry ether to give a compound (A) which further reacts with ethanol to
yield NCERT Page-311 / N-181
(a) Phenol (b) Benzene (c) Ethylbenzene (d) Phenyl ether

51. Benzene reacts with 𝑛-propyl chloride in the presence of anhydrous AlCl3 to give NCERT Page-315/N-185
(a) 3-Propyl-1-chlorobenzene (b) n-Propylbenzene
(c) No reaction (d) Isopropylbenzene

52. The major product in the following reaction is: NCERT Page-309 / N-179

(a) (b) (c) (d)

53. Which one of following is most reactive towards nucleophilic substitution reaction? NCERT-304/N-174
(a) CH2 = CH − Cl (b) C6 H5 Cl (c) CH3 CH = CH − Cl (d) ClCH2 − CH = CH2
54. CH3 − CH2 − CHCl − CH3 obtained by chlorination of n-butane, will be NCERT Page N-164
(a) 𝑙-form (b) 𝑑-form (c) Meso form (d) Racemic mixture

55. number of possible enantiomeric pairs that can be produced during monochlorination of 2 -methylbutane
is
(a) 2 (b) 3 (c) 4 (d) 1

56. Consider the following bromides: NCERT Page-304 / N-174

The correct order of SN 1 reactivity is

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

57. Consider the reactions Page-310 / N-180

C2 H5 OH
(i) (CH3 )2 CH − CH2 Br → (CH3 )2 CH − CH2 OC2 H5 + HBr
C 2 H 5 O−
(ii) (CH3 )2 CH − CH2 Br → (CH3 )2 CH − CH2 OC2 H5 + Br −
The mechanisms of reactions (i) and (ii) are respectively:
(a) SN 1 and SN 2 (b) SN 1 and SN 1
(c) SN 2 and SN 2 (d) SN 2 and SN 1

58. For which solvent rate of SN 2 will be maximum?

(a) Benzene (b) 100%H2 O (c) 100% acetone (d) 75%H2 O + 25% acetone

59. Increasing order of reactivity of the following compounds for SN 1 substitution is: NCERT Page N-174

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

60. Which of the following compounds will show retention in configuration on nucleophilic substitution by
OH − ion? NCERT Page N-178
61.
The best way to convert CH3 F into CH3 OH is NCERT Page-295 / N-165
(a) A (b) B (c) Both are same (d) None

62. The decreasing order of reactivity towards dehydrohalogenation (𝐸1 ) reaction of the following
compounds is: NCERT Page N-180

(a) D > B > C > A

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

63. Arrange the following in increasing order of reactivity towards nitration

(A) p-xylene
(B) bromobenzene
(C) mesitylene
(D) nitrobenzene
(E) benzene
Choose the correct answer from the options given below:
(a) C < D < E < A < B (b) D < B < E < A < C
(c) D < C < E < A < B (d) C < D < E < B < A

64. Order of reactivity in SN 1 reaction is NCERT Page-304 / N-174

(a) 4 > 3 > 2 > 1 (b) 2 > 1 > 4 > 3

(c) 2 > 4 > 1 > 3 (d) 2 > 4 > 3 > 1

65. The major product of the following reaction is: NCERT PAGE N-169
66. The major product of the following reaction is NCERT Page-309 / N-169

67. The correct order of the following compounds showing increasing tendency towards nucleophilic
substitution reaction is : NCERT Page N-174

(a) (iv) < (iii) < (ii) < (i) (b) (iv) < (i) < (ii) < (iii)
(c) (iv) < (i) < (iii) < (ii) (d) (i) < (ii) < (iii) < (iv)
(a) Br2 ⋅Fe
68. Product ' A ' of following sequence of reactions is Ethylbenzene Ethylbenzene → 'A' (Major product)
(b) Cl2 ,Δ
(c)alc. KOH
NCERT Page N-166 & 179

69. Which of the following reaction will go faster when concentration of attacking nucleophile is increased?
Page-303 / N-173
70. Which reagents are required for 1 step conversion of chlorobenzene to toluene? NCERT Page-311/N-181
(a) CH3 Cl/AlCl3 (b) CH3 Cl, Na, Dry ether [CBSE Sample Paper 2021-22]
(c) CH3 Cl/Fe dark (d) NaNO2 /HCl/0 − 5∘ C

7.8 POLYHALOGEN COMPOUNDS

71. CF𝑥 Cl𝑦 [where 𝑥 + 𝑦 = 4]. These compounds are not used because NCERT Page-188
(a) these are fluorocarbons (b) these are difficult to synthesise
(c) they deplete ozone layer (d) None of the these
72. Which of the following is used in fire extinguishers NCERT Page-317 / N-187
(a) CH4 (b) CHCl3 (c) CH2 Cl2 (d) CCl4

73. Solvent which is used in the synthesis of chlorofluorocarbons NCERT Page 𝐍 − 𝟏𝟖𝟖
(a) iodoform (b) chloroform
(c) carbon tetrachloride (d) methylene chloride

74. Uses of dichloromethane is NCERT Page-311 / N-187

(a) paint remover (b) solvent in drugs manufacturing
(c) metal cleansing and finishing solvent (d) All of the above

75. Haloforms are trihalogen derivatives of NCERT Page N-187

(a) Ethane (b) Methane (c) Propane (d) Benzene

76. Which of the following has highest chlorine content ? NCERT Page N-187
(a) Chloral (b) DDT (c) Pyrene (d) Gammexane

77. Which of the following are the harmful effects of methylene chloride? NCERT Page N-187
(a) Impaired hearing and vision (b) Dizziness, nausea and tingling
(c) Skin burning (d) All of these
78. If chloroform is left open in air in the presence of sunlight, it gives NCERT/ Page-317 / N-187
(a) carbon tetrachloride (b) carbonyl chloride
(c) mustard gas (d) lewisite

79. Full name of DDT is NCERT Page-318 / N-188

(a) 1,1,1-trichloro-2, 2-bis(p-chlorophenyl) ethane
(b) 1,1-dichloro-2, 2-diphenyl trimethylethane
(c) 1,1-dichloro-2, 2-diphenyl trichloroethane
(d) None of these

80. Which one is correct? NCERT Page-318 / N-188

(a) Freon-14 is CF4 , Freon- 13 is CF3 Cl, Freon- 12 is CF2 Cl2 and Freon- 11 is CFCl3 .
(b) Freons are chloroflurocarbons.
(c) Freons are used as refrigerants.
(d) All the above.

81. A small amount of the alcohol is usually added to CHCl3 bottles because NCERT Page N-187
(a) it retards the anasthetic property of CHCl3
(b) it retards the oxidation of CHCl3 to phosgene
(c) it converts any phosgene formed to harmless ethyl carbonate
(d) both (b) and (c)

82. When CCl4 is boiled with KOH, the product formed is

(a) formic acid (b) methyl alcohol
(c) formaldehyde (d) carbon dioxide

83. An organic compound 𝑋 when exposed to sunlight and air, slowly decomposes into a poisonous gas 𝑌 and
HCl. To prevent from decomposition 𝑋 is stored in dark brown coloured bottle and in 1% ethyl alcohol.
This retards the decomposition and converts 𝑌 into harmless 𝑍. Identify 𝑋, 𝑌 and 𝑍. NCERT Page N-187
(a) CCl4 , COCl2 , C2 H5 CO3 (b) CHCl3 , COCl2 , (C2 H5 )2 CO3
(c) CCl4 , CO2 , (C2 H5 )2 CO3 (d) CHCl3 , COCl2 , C2 H5 CO3
 Exercise 2: NCERT Exemplar & Past Years NEET
NCERT EXEMPLAR QUESTIONS
1. The order of reactivity of following alcohols with halogen acids is NCERT Page-304 / N-174

(A) CH3 CH2 − CH2 − OH

(B) CH3 CH2 − CH − OH

CH3

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

2. Which of the following alcohols will yield the corresponding alkyl chloride on reaction with concentrated
HCl at room temperature? NCERT Page N-165
(a) CH3 CH2 − CH2 − OH

3. Identify the compound Y in the following reaction. NCERT Page-296 / N-166

4. Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para halo compounds.
The reaction is NCERT/Page-314 / N-184
(a) electrophilic elimination reaction
(b) electrophilic substitution reaction
(c) free radical addition reaction
(d) nucleophilic substitution reaction

5. Which of the following is halogen exchange reactions? NCERT Page N-165

(a) RX + NaI → RI + NaX

(b)

(c)

(d)

6. Which reagent will you use for the following reaction?

CH3 CH2 CH2 CH3 → CH3 CH2 CH2 CH2 Cl + CH3 CH2 CHClCH3 NCERT Page N-165
(a) Cl2 /UV light (b) NaCl + H2 SO4
(c) Cl2 gas in dark (d) Cl2 gas in the presence of iron in dark

7. Arrange the following compounds in the increasing order of their densities.

(a) (i) < (ii) < (iii) < (iv) (b) (i) < (iii) < (iv) < (ii)
(c) (iv) < (iii) < (ii) < (i) (d) (ii) < (iv) < (iii) < (i)

8. Arrange the following compounds in increasing order of their boiling points. NCERT Page-298 / N-168

(i) (ii) CH3 CH2 CH2 CH2 Br (iii)

(a) (ii) < (i) < (iii) (b) (i) < (ii) < (iii) (c). (iii) < (i) < (ii) (d) (iii) < (ii) < (i)

9. In which of the following molecules carbon atom marked with asterisk (*) is asymmetric? NCERT -306/N-
176
 (a) (i), (ii), (iii) and (iv) (b) (i), (ii) and (iii)
(c) (ii), (iii) and (iv) (d) (i), (iii) and (iv)

10. Which of the following structures is enantiomeric with the molecule (A) given below? NCERT -306/N-176

11. Which of the following is an example of vic-dihalide? NCERT Page-295/N-165

(a) Dichloromethane (b) 1,2-dichloroethane
(c) Ethylidene chloride (d) Allyl chloride
12. The position of Br in the compound CH3 CH = CHC(Br) (CH3 )2 can be classified as NCERT N-160
(a) allyl (b) aryl (c) vinyl (d) secondary
13. Chlorobenzene is formed by reaction of chlorine with benzene in the presence of AlCl3 . Which of the
following species attacks the benzene ring in this reaction?
(a) Cl− (b) Cl+ (c) AlCl3 (d) [AlCl4 ]−
14. Ethylidene chloride is a/an ................ . NCERT Page N-162
(a) vic-dihalide (b) gem-dihalide
(c) allylic halide (d) vinylic halide

15. What is ' A ' in the following reaction? NCERT Page-295/N-165

16. A primary alkyl halide would prefer to undergo NCERT Page-301 / N-171
(a) SN 1 reaction (b) SN 2 reaction
(c) 𝛼-elimination (d) racemization

17. Which of the following alkyl halides will undergo 𝑆𝑁 1 reaction most readily? NCERT Page-304 / N-174
(a) (CH3 )3 C − F (b). (CH3 )3 C − Cl
(c) (CH3 )3 C − Br (d) (CH3 )3 C − I

18. Which is the correct IUPAC name for

(a) 1-bromo-2-ethylpropane NCERT Page-291 / N-161
(b) 1-bromo-2-ethyl-2-mehylethane
(c) 1-bromo-2-methylbutane
(d) 2-methyl-1-bromobutane

19. What should be the correct IUPAC name for diethylbromomethane? NCERT Page-291 / N-161
(a) 1-bromo-1,1-diethylmethane (b) 3-bromopentane
(c) 1-bromo-1-ethylpropane (d) 1-bromopentane

20. The reaction of toluene with chlorine in the presence of iron and in the absence of light yields___

NCERT PAGE N- 166

21. Molecules whose mirror image is non - superimposable over them are known as chiral. Which of the
following molecules is chiral in nature? NCERT Page-306 / N-176
(a) 2 – bromobutane (b) 1 - bromobutane
(c) 2 – bromopropane (d) 2-bromopropan - 2-ol

22. Reaction of C6 H5 CH2 Br with aqueous sodium hydroxide follows______ NCERT Page-312 / N-182
(a) SN 1 mechanism
(b) SN 2 mechanism
(c) Any of the above two depending upon the temperature of reaction
(d) Saytzeff rule

23. Which of the carbon atoms presents in the molecule given below are asymmetric? NCERT Page-306/N-176

(a) 1,2,3,4 (b) 2,3 (c) 1,4 (d) 1,2,3

24. Which of the following compounds will give racemic mixture on nucleophilic substitution by OH − ion?

(a) (i) (b) (i), (ii) and (iii) NCERT 304/ N- 174
(c) (ii) and (iii) (d) (i) and (iii)

DIRECTION (Q. No. 25 to 28) : In the questions 25 to 28 arrange the compounds in increasing order of rate of
reaction towards nucleophilic substitution. NCERT Page-311 & 313 / N-181 & 183

25.
(a) (i) < (ii) < (iii) (b) (iii) < (ii) < (i) (c) (i) < (iii) < (ii) (d) (iii) < (i) < (ii)

26.
(a) (i) < (ii) < (iii) (b) (i) < (iii) < (ii) (c) (iii) < (ii) < (i) (d) (ii) < (iii) < (i)

27.
(a) (iii) < (ii) < (i) (c) (i) < (iii) < (ii) (b) (ii) < (iii) < (i) (d) (i) < (ii) < (iii)

28.
(a) (iii) < (ii) < (i) (b) (ii) < (i) < (iii) (c) (iii) < (ii) < (i) (d) (i) < (iii) < (ii)

29. Which is the correct increasing order of boiling points of the following compounds? NCERT -298 / N-168
1 - iodobutane, 1 - bromobutane, 1 - chlorobutane, Butane
(a) Butane < 1-chlorobutane < 1 - bromobutane < 1 - iodobutabe
(b) 1 - iodobutane < 1 - bromobutane < 1 - chloroubutane < Butane
(c) Butane < 1 - iodobutane < 1 - bromobutane < 1 - chlorobutane
(d) Butane < 1 - chlorobutane < 1 - iodobutane < 1 - bromobutane

30. Which is the correct increasing order of boiling points of the following compounds? NCERT -298 / N-168
1 - bromoethane, 1 - bromopropane, 1 - bromobutane, Bromobenzene
(a) Bromobenzene < 1 - bromobutane < 1 - bromopropane < 1 – bromoethane
 (b) Bromobenzene < 1 - bromobutane < 1 bromopropane < 1 – bromobutane
(c) 1 - bromopropane < 1 - bromorpropane < 1 - bromoethane < Bromobenzene
(d) 1 - bromoethane < 1 - bromopropane < 1 - bromobutane < Bromobenzene

PAST YEARS NEET

31. The given compound is an example of NCERT Page-290 / N-160 | NEET 2023
(a) Benzylic halide (b) Aryl halide
(c) Allylic halide (d) Vinylic halide
32. The incorrect statement regarding chirality is: NCERT Page-302 & 303 / N-175 & 177 | NEET 2022
a) The product obtained by SN 2 reaction of haloalkane having chirality at the reactive site shows
inversion of configuration.
b) Enantiomers are superimposable mirror images of each other.
c) A racemic mixture shows zero optical rotation.
d) SN 1 reaction yields 1:1 mixture of both enantiomers.

33. The major product formed in dehydrohalogenation reaction of 2-Bromo pentane is Pent-2-ene. This
product formation is based on? NCERT Page-310 / N-180 | WEETI 2021, C
(a) Huckel's Rule (b) Saytzeff's Rule (c) Hund's Rule (d) Hofmann Rule

34. Which of the following alkane cannot be made in good yield by Wurtz reaction?
(a) 2,3-Dimethylbutane (b) 𝑛-Heptane NCERT Page-311 / N-181 | NEET 𝟐𝟎𝟐𝟎, 𝐂
(c) 𝑛-Butane (d) 𝑛-Hexane

35. Elimination reaction of 2-Bromo-pentane to form pent-2ene is: NCERT Page-310/N-180 | [NEET 2020, C
(A) 𝛽-Elimination reaction (B) Follows Zaitsev rule
(C) Dehydrohalogenation reaction (D) Dehydration reaction
(a) (A), (C), (D)
(b) (B), (C), (D)
(c) (A), (B), (D)
(d) (A), (B), (C)
36. Which of the following alkane cannot be made in good yield by Wurtz reaction?
(a) 2,3-Dimethylbutane (b) 𝑛 − H eptane NCERT Page-311/N-181 NEET 2020
(c) 𝑛-Butane (d) 𝑛-Hexane

37. The hydrolysis reaction that takes place at the slowest rate, among the following is

NCERT Page-311/N-181, NEETI Odisha 2019

(a)
 3Cl2 /Δ Br2 /Fe Zn/HCl
38. The compound C7 H8 undergoes the following reactions: C7 H8 → A → B → C. The product C is
(a) 𝑚-bromotoluene (b) o-bromotoluene ncert n-165, 166 & neet 2018, s
(c) 𝑝-bromotoluene (d) 3-bromo-2,4,6-trichlorotoluene

39. For the following reactions: NCERT Page-300 & 309 / N-166, 170 & 179 | NEET 2016, A
(1). CH3 CH2 CH2 Br + KOH ⟶ CH3 CH = CH2 + KBr + H2 O

(2)

(3)
Which of the following statements is correct?
(a) (1) and (2) are elimination reaction and (3) is addition reaction
(b) (1) is elimination, (2) is substitution and (3) is addition reaction
(c) (1) is elimination, (2) and (3) are substitution reactions
(d) (1) is substitution, (2) and (3) are addition reaction
 Answer Keys
NCERT BASED TOPIC WISE MCQS
1 (b) 10 (b) 19 (b) 28 (d) 37 (c) 46 (d) 55 (a) 64 (d) 73 (c) 82 (d)

2 (b) 11 (c) 20 (b) 29 (a) 38 (a) 47 (c) 56 (a) 65 (a) 74 (d) 83 (b)

3 (a) 12 (b) 21 (c) 30 (c) 39 (c) 48 (c) 57 (a) 66 (c) 75 (b)

4 (d) 13 (d) 22 (a) 31 (a) 40 (c) 49 (c) 58 (c) 67 (d) 76 (c)

5 (c) 14 (c) 23 (a) 32 (c) 41 (d) 50 (b) 59 (c) 68 (d) 77 (d)

6 (c) 15 (b) 24 (c) 33 (c) 42 (d) 51 (d) 60 (d) 69 (c) 78 (b)

7 (b) 16 (c) 25 (c) 34 (a) 43 (a) 52 (c) 61 (b) 70 (b) 79 (a)

8 (a) 17 (b) 26 (c) 35 (d) 44 (b) 53 (d) 62 (a) 71 (c) 80 (d)

9 (d) 18 (c) 27 (d) 36 (a) 45 (b) 54 (d) 63 (b) 72 (d) 81 (d)

Exercise 2:
𝟏 (b) 𝟓 (a) 𝟗 (b) 𝟏𝟑 (b) 𝟏𝟕 (d) 𝟐𝟏 (a) 𝟐𝟓 (c) 𝟐𝟗 (a) 𝟑𝟑 (b) 𝟑𝟕 (b)

𝟐 (d) 𝟔 (a) 𝟏𝟎 (a) 𝟏𝟒 (b) 𝟏𝟖 (c) 𝟐𝟐 (a) 𝟐𝟔 (d) 𝟑𝟎 (d) 𝟑𝟒 (b) 𝟑𝟖 (a)

𝟑 (a) 𝟕 (a) 𝟏𝟏 (b) 𝟏𝟓 (d) 𝟏𝟗 (b) 𝟐𝟑 (b) 𝟐𝟕 (d) 𝟑𝟏 (c) 𝟑𝟓 (d) 𝟑𝟗 (b)

𝟒 (b) 𝟖 (c) 𝟏𝟐 (a) 𝟏𝟔 (b) 𝟐𝟎 (d) 𝟐𝟒 (a) 𝟐𝟖 (c) 𝟑𝟐 (b) 𝟑𝟔 (b)

 HINTS & SOLUTIONS
EXERCISE -1
1. (b) Haloarenes contain halogen atoms attached to 𝑠𝑝2 hybridised carbon atom at the anyl group.

2. (b)

(vic-dihalide) (gem-dihalide)
2∘
3. (a) In isopropyl chloride CH3 − C HCl − CH3 , chlorine atom is attached to 2∘ carbon atom.

4. (d) 4-Bromobut-l-ene is not an allylic halide BrH2 C − CH2 − CH = CH2

5. (c)

6. (c) The compound is C3 H6 Cl2 and the number of possible isomeric compunds is 5

7. (b) IUPAC name : 2-Chloro-2-methylpropane. Br

8. (a) 2-bromo-1-chloro but-1-ene

9. (d) COCl2

10. (b) In haloalkanes, carbon of C − X is 𝑠𝑝3 hybridised while in haloarenes it is sp2 hybridised.

11. (c) Due to resonance in chlorobenzene.

UV light
12. (b) RH + Cl2 → RCl + HCl

Oxidation No. of Cl is decreasing from 0 (in Cl2 ) to -1 (in RCl ).

13. (d) Ethylene dichloride can be prepared by adding HCl to ethylene glycol (CH2 OH. CH2 OH).
Pyridine
14. (c) R − OH + SOCl2 → RCl + SO2 ↑ +HCl ↑
SO2 and HCl being gases escape leaving behind pure alkyl halide.
𝑎𝑐𝑒𝑡𝑜𝑛𝑒
15. (b) R − X + NaI → R − I + NaX ↓
Soluble in Insoluble in 𝐂𝐇𝟑 𝐎𝐇, 𝐌𝐞𝟐 𝐂𝐎 )
(𝐂𝐇𝟑 𝐎𝐇, 𝐌𝐞𝟐 𝐂𝐎) (where 𝐗 = 𝐂𝐥 or 𝐁𝐫 )
16. (c) Ethyl alcohol forms ethyl chloride with thionyl chloride in presence of pyridine.
Pyridine
CH3 CH2 OH + SOCl2 → CH3 CH2 Cl + SO2 + HCl

17. (b) Chlorine atom is highly reactive so it will react with all types of hydrogen available while the Br atom is
highly selective so it will react with that hydrogen which gives the highly stabilised tertiary alkyl radical so
only one product is formed.

18. (c)

19. (b) This method is not applicable for the preparation of aryl halides because the C − O bond in phenol has
a partial double bond character and is difficult to break being stronger than a single bond.

20. (b)

21. (c) For the same alkyl group, the boiling points of alkyl halides decrease in the order:
RI > RBr > RCl > RF

This is because with the increase in size and mass of halogen atom, the magnitude of van der Waal's forces
increases.

22. (a) Boiling point of CH3 I is 42∘ C which indicates that it is liquid at room temperature. CH3 I is larger
molecule so it has stronger vander Waal's force of attraction than others.

23. (a) CH3 Cl is gas at room temperature.

24. (c) 1,4-dicholorbenzene (para isomers are more symmetric than ortho and meta isomers)
25. (c) SN 1 reactions involve the formation of carbocations, hence higher the stability of carbocation, more
will be reactivity of the parent alkyl halide. Thus tertiary carbocation formed from (c) is stabilized by two
phenyl groups and one methyl group, hence most stable.
dry ether
26. (c) CH3 CH2 I + Mg → CH3 CH2 MgI
Ethyl magnesium iodide

27. (d) SN 1 reaction involves carbocation which are planar ( 𝑠𝑝2 hybridised) and thus can be attacked on
either face of the carbon.

28. (d) Weaker the C − X bond, greater is the reactivity.

29. (a) 1∘ Alkyl halides (having least steric hindrance at 𝛼-carbon atom) are most reactive towards SN 2
reaction.

30. (c) Isopropyl chloride, being 2∘ alkyl halides, can undergo SN 1 as well as SN 2 mechanism.

31. (a) Due to steric hindrance tertiary alkyl halide do not react by SN 2 mechanism they react by SN 1
mechanism. SN 2 mechanisam is followed in case of primary and secondary alkyl halides ofCH3 − X >
CH3 − CH2 X > (CH3 )2 − CH. X > (CH3 )3 − C − X.

32. (c) The compound containing a chiral carbon atom (a carbon atom attached to
four different atoms is optically active.

33. (c)
1. The reaction is favoured by weak nucleophile as strong nucleophile will favour elimination over
substitution reaction.
2. If the substituents are bulky then it will stabilise the intermediate R⊕
3. The nucleophile Y ⊖ can attack the planar R⊕ from both the sides. Hence, the reaction is accompanied
by racemization.
4. Polar solvent helps to separate the ion pair.
34. (a) The process of separation of racemic modification into their 𝑑-and ℓ-enantiomers is called resolution.

35. (d) We have been given a bulky base, hence elimination will take place & not substitution.

36. (a) A mixture of equal amounts of the two enantiomers is called a racemic mixture.

37. (c) Optically inactive compounds have nonsuperimposable mirror image of each other.
38. (a) Although all the three compounds can be used for preparing Grignard reagents, diethyl ether is
considered as the best because it provides electron pairs to Mg of the reagent fully for coordination, in
case of C6 H5 OCH3 and C6 H5 N(CH3)2 electron pair on O and N are partialy delocalised over the benzene
and hence are less available for coordination with Mg.

39. (c) Potassium ethoxide is a strong base, and 2- bromopentane is a 2∘ bromide, so elimination raction
predominates
OC2 H−
5
CH3 CH(Br)CH2 CH2 CH3 → CH3 CH = CHCH2 CH3 +CH2 = CHCH2 CH2 CH3
trans-2-Pentene (major) Pentene-1(minor)

Since trans-alkene is more stable than cis. Thus trans-pentene -2 is the main product.

40. (c) Wurtz reaction : It involves the interaction of two molecules of an alkyl halide (preferably bromide or
iodide) with metallic sodium in presence of dry ether to form symmetrical alkanes containing double the
number of carbon atoms present in the alkyl halide. For example,
Dry ether
R − X + 2Na + X − R → R − R + 2NaX
Alkyl halide Alkane

41. (d) CH2 = CH − CH2 − CH3

In this reaction both hydrogen and halogen atom has been removed, so it is known as dehydrohalogenation
reaction.

42. (d) CH3 CH2 CH2 Br + Mg ⟶ CH3 CH2 CH2 MgBr

(Propyl bromide)

CH3 CH2 CH2 MgBr + H2 O ⟶ CH3 CH2 CH3 + MgBrOH

43. (a)
44. (b)
45. (b)

46. (d) The reaction sequence is as follows

47. (c)

48. (c) No bond to the chiral centre has cleaved. Terefore, the configuration of the reactant is retained.

49. (c) During ammonolysis of alkyl halide, the acid liberated during the reaction combines with the amine
and forms amine salt. For liberating the free amine from amine salt a base is needed.
R − X + NH3 ⟶ RNH3+ + X −
R − NH3+ + OH − ⟶ RNH2 + H2 O
With each substitution reaction, acidic concentration increases in reaction mixture. So to remove
acidic impurities, NaOH is added.
Mg CH3 CH2 OH
50. (b) C6 H5 Cl → C6 H5 MgCl → C6 H6 + CH3 CH2 OMgCl
51. (d) Rearrangement of carbocation occur.
52. (c)

53. (d) More the stability of the carbocation, higher will be the reactivity of the parent chloride. Allyl chloride
> vinyl chloride > chlorobenzene.
h𝑣
54. (d) Chlorination of 𝑛-butane takes place via free radical formation i.e., Cl2 → Cl∘ + Cl∘

Cl∘ may attack on either side and give a racemic mixture of 2-chlorobutane which contain 50%𝑑 form
and 50%𝑙-form.

55. (a) First draw possible different structures obtained on monochlorination of 2-methylbutane,

Thus structures (i) and (iii) are optically active, each has one chiral carbon; so each structure will give one
enantiomeric pair; thus total enantiomeric pairs will be two.

56. (a)

Since 𝑆𝑁 1 reactions involve the formation of carbo-cation as intermediate in the rate determining step,
more is the stability of carbocation higher will be the reactivity of alkyl halides towards SN 1 route. Now
 we know that stability of carbocations follows the order: 3∘ > 2∘ > 1∘ , so SN 1 reactivity should also
follow the same order.
3∘ > 2∘ > 1∘ > Methyl (S𝐍 1 reactivity)

57. (a) A strong nucleophile favours the SN 2 reaction and a weak nucleophile favours the SN 1 reaction. First
reaction is SN 1 reaction because C2 H5 OH is used as solvent which is a weak nucleophile. Second reaction
is SN 2 reaction because C2 H5 O− is strong nucleophile.
58. (c) For SN 2 reaction polar aprotic solvent is needed.

59. (c) In SN 1 reaction carbocation acts as an intermediate.

Carbocation produced by (C) is more stable than carbocation produced by (D) due to +I effect of −OCH3
group. Further in (A) there is formation of tertiary carbocation after rearrangement while (B) is primary
carbocation.

So, the correct order is (C) > (D) > (A) > (B).
60. (d)

Inversion of configuration takes place at the carbon in which nuclephile attacks but at the stereogenic
carbon, retention of configuration takes place.

61. (b) A good nucleophile possesses two properties

(i) It is a good leaving group
(ii) It is a good attacking reagent
' 𝐹 ' is not a good leaving group, hence to convert 𝑅 − 𝐹 into R − OH, first it is treated with NaI to
convert it into R − I ( I is good base) and then R − I is treated with NaOH to produce R − OH ( I is good
leaving group)
62. (a) E1 reaction proceeds via carbocation formation, therefore greater the stability of carbocation, faster
will be the E1 reaction.

Thus, correct decreasing order of the given halides towards dehydrohalogenation by E1 is: D > B > C > A

63. (b) Nitro group act as an electron withdrawing group and strongly deactivates the ring and nitration occur
to that compound which contains electron donating group.

D<B<E<A<C
64. (d) Reactivity of SN 1 ∝ stability of carbocation

65. (a) Dehydrohalogenation ( 𝛽-elimination) occurs as:

66. (c)

67. (d) For nucleophilic substitution, the correct order is:

−NO2 group is a strong electron withdrawing group and it activates the aromatic ring towards nucleophillic
substituion.

68. (d)

69. (c) Rate of SN 2 = k[R − X] [Base]

only (c) is occuring via SN 2 pathway.
70. (b)
71. (c) Chlorofluorocarbons causes ozone layer depletion.

72. (d) CCl4 vapours are non-inflammable (i.e. do not catch fire). Hence used as fire extinguishers under the
name pyrene.

73. (c) Tetrachloromethane (carbon tetrachloride) is also used as feedstock in the synthesis of
chlorofluorocarbons and other pharmaceutical manufacturing and general solvents etc.

74. (d) Dichloromethane is widely used as solvent as a paint remover, as a propellant in aerosols and as a
process solvent in the manufacture of drugs. It is also used as a metal cleansing and finishing solvent.

75. (b) Haloforms (CHX3 ) are trihalogen derivatives of methane. Example: Chloroform CHCl3 .

76. (c) Pyrene is the technical name of CCl4 which has highest chlorine content.

77. (d) Dizziness, nausea and tingling, Skin burning, Impaired hearing and vision are some harmful effects of
CH2 Cl2 .
light
78. (b) 2CHCl3 + O2 → 2COCl2 + 2HCl
Phosgene

79. (a)

1,1,1-trichloro-2, 2-bis( 𝑝-chlorophenyl) ethane

80. (d) All the given points about freons are correct.

81. (d) Ethyl alcohol retards the oxidation of CHCl3 to phosgene as well as it converts any phosgene formed to
harmless ethyl carbonate.
COCl2 + 2C2 H5 OH ⟶ (C2 H5 )2 CO3 + 2HCl
Ethyl carbonate
82. (d)
83. (b)

EXERCISE - 2
1. (b) Alchols and halogen acid react through SN 1 mechanism.
+
CH3 − CH2 − CH2 − OH ⟶ CH3 − CH2 − CH + OH −

In this case, 1∘ carbocation is formed. It is least stable. So, here 𝑆𝑁 2 mechanism is followed. In this 𝑆𝑁 2
mechanism a transition state is observed in which 𝛼 - carbon is linked with two nucleophilies.

2∘ Carbocation (more stable than 1∘ carbocation)

3∘ carbocation (most stable)

Greater the stability of carbocation, greater will be the possibilities of attack of X − ion on the carbocation.
Order of stability of carbocation is : 3∘ > 2∘ > 1.
So order of reactivity will be C > B > A.

2. (d) Reaction of alcohols with conc. HCl at room temperature follows SN 1 mechanism.
The attack of nucleophile to the carbocation is possible only on stable carbocation as at room
temperature only 3∘ carbocation is stable.

Step I

Step II
3. (a) It is an example of Sandmeyer’s reaction

4. (b)

As electrophile Cl+ attacks on electron rich benzene ring and substitutes hydrogen on ortho and para position
w.r.to. −CH3 group. So, the reaction is electrophilic substitution reaction.

5. (a) Halogen exchange reactions are those reactions in which one hailde replaces another (Finkelstein
reaction).

6. (a) It is a substitution reaction which involves the replacement of 1∘ and 2∘ hydrogen of alkanes by
chlorine. It occurs in presence of ultraviolet light.
UV
Step 1: Cl − Cl → 2Ċl
light
∙ ∙
C + CH3 − CH2 − CH2 − CH3 ⟶ CH3 CH2 CH2 − CH2 + HCl
∙ ∙
Step 2: CH3 − CH2 − CH2 − CH2 + Cl2 ⟶ CH3 − CH2 − CH2 − CH2 Cl + Cl
∙ ∙ ∙
CH3 − CH2 − CH − CH3 + Cl2 → CH3 − CH2 − CHCl − CH3 − Cl
∙
˙ 2 + C1 → CH3 CH2 CH2 CH2 Cl
Step 3 : CH3 − CH2 − CH2 − CH
∙ ∙ ∙
CH3 − CH2 − CH − CH3 + Cl → CH3 − CH2 − CHCl − CH3
7. (a) Density is directly related to molecular mass. Higher the molecular mass, higher will be the density of
the compound. The order of molecular mass is benzene < chlorobenzene < dichlorobenzene. <
bromochlorbenzene

8. (c) Greater the surface area, greater will be the boiling point of a compound. Surface area decreases with
increases in branching.

Increasing order of boiling point (H3 C)3 − C − Br3 < (H3 C)2 CHCH2 Br2 < CH3 CH2 CH2 CH2 Br

9. (b) Carbon atom in which all four valencies are different is known as Asymmetrical/chiral.

10. (a) Enantiomers are the steroismers which are related to each other as non - superimposable mirror
images. The enantiomer of molecule (A) is

11. (b) Halides in which two halogen atoms are present on the two adjacent carbon atoms are known as vic -
dihalides.

12. (a) Compounds in which the halogen atom is bonded to 𝑠𝑝3 hybridised carbon atom next to carbon
carbon-double bond are known as allyl halides.

CH3 CH = CHC(Br)(CH3 )2
13. (b) AlCl3 + Cl2 ⟶ [AlCl4 ]− + Cl+

14. (b) If halogen atoms present on the same carbon atom then they are known as gem - dihalides or
alkylidene halides.

15. (d) Addition of HCl takes place in accordance with Markovnikov's rule.

16. (b) It would prefer to undergo SN 2 reaction. SN 2 reactions occur if there is less steric crowding on 𝛼 -
carbon of alkyl halide. In case of primary aklyl halides, steric crowding is very less. So, it would prefer to
undergo SN 2 reaction.
17. (d) All compounds are tertiary alkyl but bond formed between carbon and iodine (C − I) is weakest bond
due to higher difference in size of carbon and iodine.

18. (c) IUPAC name

1-Bromo-2-methylbutane

19. (b)

IUPAC name is 3-bromopentane.

20. (d) Toluene react with chlorine in presence of iron and in absence of light, by substitution on benzene ring.

21. (a) Carbon in which four bonds are different is known as Chiral carbon.
⊕
22. (a) In C6 H5 CH2 Br carbocation is C6 H5 C H2 which is stable due to resonance.

23. (b) If carbon atom has all four valencies with four different groups then it is called as asymmetric/chiral
carbon.

24. (a) All those compounds which follow 𝑆𝑁 1 mechanism during nucleophilic subsitution reaction will give
racemic mixture. Order of reactivity of alkyl halides for SN 1.
3∘ > 2∘ > 1∘ CH3 X

Thus, contains a 2∘ carbon so gives a racemic product.

25. (c) The substitution is faster, if the electron withdrawing group is at ortho and para position, because
electron density is high at these positions as chlorine is electron donating group which increase electron
density at ortho and para position. Therefore, it has partial double bond character, and is not easy to
break.
In compound (ii) and (iii) both has one electron withdrawing group but in compound (ii) electron
withdrawing (−NO2 ) group is present at ortho position, so rate of reaction in compound (ii) is more than
that of (iii) while (i) has no electron withdrawing group.
26. (d) If electron releasing group is present at ortho or para position, it decreases the rate of nucleophilic
substitution reaction. In compound (iii) electron releasing group is present at meta position w.r.t. chlorine,
so the impact is nothing but in compound (ii) it is present at ortho position.

27. (d) If electron withdrawing group is present at ortho and para position, then the nucleophilic substitution
reaction rate increases.

28. (c) If electron releasing group is present at ortho and para position w.r.t. to chlorine it decreases the rate
of nucleophilic substitution reaction.

29. (a) Greater the surface area, greater will be the intermolecular forces of attraction and intermolecular
forces of attraction is directly proportional to boiling point. Surface area is larger for larger size of halogen.

30. (d) Boiling point is directly proportional to size of the molecule. All contains same halogen atom but
different hydrocarbon part. Larger the different hydrocarbon part larger the boiling point.

31. (c) Allylic halides are the compound where halogen atom attached to sp3 hybridised carbon atom next to
double bond.

32. (b) Enantiomers are non-superimposable mirror images of each other.

33. (b) According to Saytzeff's rule, in dehydrohalogenation reactions, highly subsituted alkene is the major
product.

34. (b) Wurtz reaction is used to prepare symmetrical alkanes like R1 − R1 , as

Dry ether
R1 − X + 2Na + X − R1 → R1 − R1 + 2NaX
If 𝑅1 and 𝑅2 are different, then mixture of alkanes may be obtained as
Dry ether
R1 − X + 2Na + R 2 − X → R1 − R1 + R1 − R 2 + R 2 − R 2 + 2NaX
Hence, 𝑛-heptane cannot be made in good yield using Wurtz reaction, since it is unsymmetrical alkene.

35. (d)

Mechanism :
 It is an 𝛽 elimination reaction as 𝛽 hydrogen is abstracted and results more substituted alkene, which
fallows Zaitsev's rule. Since ' H ' and ' Br ' are removed, it is dehydro-halogenation.

36. (b) Wurtz reaction is used to prepare symmetrical alkanes like 𝑅1 − 𝑅1 , as

Dry ether
R1 − X + 2Na + X − R1 → R1 − R1 + 2NaX

If 𝑅1 and 𝑅2 are different, then mixture of alkanes may be obtained as

Dry ether
R1 − X + 2Na + R 2 − X → R1 − R1 + R1 − R 2 + R 2 − R 2 + 2NaX

Hence, 𝑛-heptane cannot be made in good yield using Wurtz reaction, since it is unsymmetrical alkene. (a)

37. (b) Aryl halides do not give substitution reactions due to partial double bond character between carbon
and halogen.
38. (a)

𝑚-Bromotoluene

39. (b) (1) CH3 CH2 CH2 − Br + KOH ⟶ CH3 CH = CH2 + KBr + H2 O
This is dehydrohalogenation reaction which is an example of elimination reaction.

Replacement of Br − by OH − is substitution reaction thus it is a nucleophilic substitution reaction.

Above reaction involves addition of Br2 across double bond. Thus it is called addition reaction.