Sure Shot Questions

Chapter – 06
Haloalkanes and Haloarenes
MCQ (1 mark) (d) Nucleophilic substitution reaction.
1. The order of reactivity of following alcohols with
halogen acids is ________. 5. Which of the following is halogen exchange
reaction?

(a) (I) > (II) > (III) (b) (III) > (II) > (I)
(c) (II) > (I) > (III) (d) (I) > (III) > (II)

2. Which of the following alcohols will yield the

corresponding alkyl chloride on reaction with 6. Which reagent will you use for the following
concentrated HCl at room temperature? reaction?
CH 3CH 2CH 2CH 3  CH 3CH 2CH 2CH 2Cl 
CH 3CH 2CHClCH 3
(a) Cl2 / UV light
(b) NaCl + H2SO4
(c) Cl2 gas in dark
(d) Cl2 gas in the presence of iron in dark.

3. Identify the compound ‘Y’ in the following 7. Arrange the following compounds in the increasing
reaction. order of their densities.

(a) (I) < (II) < (III) < (IV)

(b) (I) < (III) < (IV) < (II)
(c) (IV) < (III) < (II) < (I)
(d) (II) < (IV) < (III) < (I)
4. Toluene reacts with a halogen in the presence of 8. Arrange the following compounds in increasing
iron (III) chloride giving ortho and para halo order of their boiling points.
compounds. The reaction is
(a) Electrophilic elimination reaction
(b) Electrophilic substitution reaction
(c) Free radical addition reaction

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 14. A primary alkyl halide would prefer to undergo
______.
(a) S N I reaction (b) SN2 reaction
(c)  -elimination (d racemization)
(a) (II) < (I) < (III) (b) (I) < (II) < (III)
(c) (III) < (I) < (II) (d) (III) < (II) < (I) 15. Which of the following alkyl halides will undergo
9. In which of the following molecules carbon atom SN1 reaction most readily?
marked with asterisk (*) is asymmetric?
(a) (CH3 )3 C  F (b) (CH3 )3 C  Cl
(c) (CH3 )3 C  Br (d) (CH3 )3 C  I
16. Which is the correct IUPAC name for

(a) (I), (II), (III), (IV) (b) (I), (II), (III)
(c) (II), (III), (IV) (d) (I), (III), (IV)
10. Which of the following structures is enantiomeric
with the molecule (I) given below?
(a) 1-Bromo-2-ethylpropane
(b) 1-Bromo-2-ethyl-2-methylethane
(c) 1-Bromo-2-methylbutane
(d) 2-Methyl-1-bromobutane
17. What should be the correct IUPAC name for
diethylbromomethane?
(a) 1-Bromo-1, 1-diethylmethane
(b) 3-Bromopentane
(c) 1-Bromo-1-ethylpropane
(d) 1-Bromopentane
18. The reaction of toluene with chlorine in the
presence of iron and in the absence of light
yields____.

11. Which of the following is an example of vic- 19. Chloromethane or treatment with excess of
dihalide? ammonia yields mainly
(a) Dichloromethane (a) N, N-dimethylmethanamine
(b) 1, 2-Dichloroethane
(c) Ethylidene chloride
(d) Allyl chloride (b) N-methylmethanamine (CH3 – NH – CH3)
12. The position of -Br in the compound (c) Methanamine (CH3NH2)
CH3CH  CHC (Br)(CH3 )2 can be classified as (d) Mixture containing all these in equal
________. proportion.
(a) allyl (b) aryl 20. Molecules whose mirror image is non-
(c) vinyl (d) secondary superimposable over them are known as chiral.
13. Chlorobenzene is formed by reaction of chlorine Which of the following molecules is chiral in
with benzene in the presence of AlCl3. Which of nature?
the following species attacks the benzene ring in (a) 2-Bromobutane
this reaction? (b) 1-Bromobutane
(c) 2-Bromopropane
(a) Cl  (b) Cl 
(d) 2-Bromopropan-2-ol
(c) AlCl3 (d) [AlCl4 ]
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21. Reaction of C6 H 5CH 2 Br with aqueous sodium
hydroxide follows ________.
(a) SN1 mechanism
(b) SN2 mechanism
(c) Any of the above two depending upon the
temperature of reaction
(d) Saytzeff rule
Assertion-Reasoning (1 mark)
22. Assertion (A): Bonding points of alkyl halides
decrease in the order
R  I  R  Br  R  Cl  R  F .
Reason (R): van der Waals’ forces decrease with
increase in the size of halogen atom.
(a) Both A and R are true and R is the correct
explanation of A.
(b) Both A and R are true and R is not the correct
explanation of A.
(c) A is true but R is false.
(d) A is false but R is true. [2020]
23. Assertion (A): Chlorobenzene is less reactive
towards nucleophilic substitution reaction.
Reason (R): Nitro group in chlorobenzene
increases its reactivity towards nucleophilic
substitution reaction.
(a) Both A and R are true and R is the correct
explanation of A.
(b) Both A and R are true and R is not the correct
explanation of A.
(c) A is true but R is false.
(d) A is false but R is true.
24. Assertion (A): Carbon - halogen bond in aryl halide
has a partial double bond character.
Reason (R): Aryl halides undergo nucleophilic
substitution easily.
a) Both A and R are true and R is the correct
explanation
of A.
b) Both A and R are true but R is not the correct
explanation
of A.
c) A is true but R is false.
d) A is false but R is true.
25. Assertion (A): Bromobenzene upon reaction with Br2/Fe
gives 1, 4 - dibromobenzene as the major product.
Reason (R): In bromobenzene. the inductive effect of the
bromo group is more dominant than the mesomeric
effect in directing the incoming electrophile.
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a) Both A and R are true and R is the correct explanation of
A.
b) Both A and R are true but R is not the correct
explanation of A.
c) A is true but R is false.
d) A is false but R is true.
26. Assertion (A): In monohaloarenes, further electrophilic
substitution occurs at ortho and para positions.
Reason (R): Halogen atom is a ring deactivator.
a) Both A and R are true and R is the correct explanation
of A.
b) Both A and R are true but R is not the correct
explanation
of A.
c) A is true but R is false.
d) A is false but R is true.
27. Assertion (A): SN1 reactions are unimolecular.
Reason (R): SN1 reaction proceed through the formation
of the carbocation, which is slow step of the reaction.
a) Both A and R are true and R is the correct explanation
of A.
b) Both A and R are true but R is not the correct
explanation of A.
c) A is true but R is false.
28. Assertion (A): Benzyl bromide when kept in acetone -
water, it produces benzyl alcohol.
Reason (R): The reaction follows SN2 mechanism.
a) Both A and R are true and R is the correct explanation
of A.
b) Both A and R are true but R is not the correct
explanation of A.
c) A is true but R is false.
d) A is false but R is true.
Case Study
The following questions are case – based questions.
Read the case carefully and answer the questions that
follow:
29. Nucleophilic Substitution
Nucleophilic substitution reaction of haloalkane
can be conducted according to both SN1 and SN2
mechanisms. SN1 is a two step reaction while SN2
is a single step reaction. For any haloalkane which
mechanism is followed depends on factors such
as structure of haloalkane, properties of leaving
group, nucleophilic reagent and solvent.
Influences of solvent polrity: In SN1 reaction, the
polarity of the system increases from the reactant
to the transition state, because a polar solvent
has a greater effect on the transition state than
the reactant, thereby reducing activation energy
and accelerating the reaction. In SN2 reaction, the
polarity of the system generally does not change
from the reactant to the transition state and only
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 charge dispersion occurs. At this time, polar
solvent ha a great stabilizing effect on Nu- than
the transition state, thereby increasing the
activation energy and slow down the reaction (a). When X reacts with CH3COCl in presence of anhy.
AICl3, the reaction is known as:
rate. For example, the decomposition rate (SN1) of
a) Ullmann reaction
tertiary chlorobutane at 250C in water (dielectric b) Fittig reaction
constant 79) is 300000 times faster than in c) Friedel - Crafts acylation reaction
ethanol containing 40% water is twice slower d) Wurtz - Fittig reaction
than in absolute ethanol. Hence, the level of (b) Compound Z is:
solvent polarity has influence on both SN1 and SN2 a) P - chlorophenol b) Phenol
reaction, but with different results. Generally c) P - nitrophenol d) Nitrobenzene
speaking weak polar solvent is favourable for SN2 (c) Identify W:
reaction, while strong polar solvent is favouable
for SN2 reaction, while strong polar solvent is
favourable for SN1. Generally speaking the (a).
substitution reaction of tertiary haloalkane is
based on SN1 mechanism in solvents with a strong
polarity (for example ethanol containing water) (b).
Answer the following questions.
(a) Why racemization occurs in SN1?
(b) Why is ethanol less polar than water? (c).
(c) Which one of the following in each pair is
more reactive towards SN2 reaction?
(d).
(d) Compound Y is:

OR (a).
(c) Arrange the following in the increasing order (b).
of their reactivity towards SN1 reactions:
(i) 2-Bromo – 2 – methylbutane, 1-Bromopentane, (c).
2-Bromopentane
(d).
(ii) 1-Bromo-3-methylbutane, 2-Bromo-2
(e) When X is treated Ni - Al / NaOH the product obtained
methylbutane, 2-Bromo-3-meethylbutane. is:
[2023] a) Benzene b) P - chlorophenol
30. Read the text carefully and answer the questions: c) Phenol d) Triphenyl
Consider the given sequence of reactions:

Questions
31. Why is t-butyl bromide more reactive towards SN1 reaction as compared to n-butyl bromide?
[2019]
32. Write equation for preparation of 1-iodobutane from 1-chlorobutane. [1/3, Al 2019]
33. Write the structure of the major product in each of the following reactions: [2/3, Al 2015]

34. The following haloalkanes are hydrolysed in presence of aq. KOH: [2020 – 21]
(i) 2-Chlorobutane
(ii) 2-Chloro-2-methylpropane
Which of the above is most likely to give a racemic mixture? Justify your answer.

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35. (a) Identify the major product formed when 2-cyclohexylchloroethane undergoes a dehydrohalogenation
reaction. Name the reagent which is used to carry out the reaction.
(b) Why are haloalkanes more reactive towards nucleophilic substitution reactions than haloarenes and vinylic
halides?
OR
(a) Name the possible alkenes which will yield 1-chloro-1-methylcyclohexane on their reaction with HCl. Write
the reactions involved.
(b) Allyl chloride is hydrolysed more readily than n-propyl chloride. Why? [2022 – 23]

36. (i) Write the structure of major alkene formed by  -elimination of 2, 2, 3-trimethyl-3-bromopentane with
sodium ethoxide in ethanol.
(ii) Which one of the compounds in the following pairs is chiral?
(iii) Identify (A) and (B) in the following:
[2020]

37. Give the IUPAC names of the following compounds:

38.What happens when 𝐶𝐻3 __ Br is treated with KCN?

39.Give reasons:

40.

41.How the following conversions can be carried out?

(i) Chlorobenzene to p-nitrophenol
(ii) 2-Bromopropane to 1-bromopropane

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 (iii) Aniline to phenylisocyanide

42.Give reasons for the following :

(i) p-nitrochlorobenzene undergoes nucleophilic substitution faster than
chlorobenzene. Explain giving the resonating structures as well.
(ii) Iodoform is obtained by reaction of acetone with hypoiodite ion but not iodide
ion.

43.Write the IUPAC name of the following compound :

44.Explain the following:

(i) Haloalkanes react with KCN to form alkyl cyanides as main product while 𝐴𝑔𝐶𝑁
forms isocyanides as the major product.
(ii) Neopentyl bromide undergoes nucleophilic substitution reaction very slowly.
(iii) the treatment of alkyl chlorides with aqueous KOH leads to the formation of
alcohols but in presence of alcoholic KOH, alkenes are the major products.

45.Primary alkyl halide (A) 𝐶4 𝐻9 𝐵𝑟 reacted with alcoholic KOH to give compound (B).
Compound (B) is reacted with HBr to give (C) which is an isomer of (A) . when (A) was
reacted with Na metal, it gave a compound 𝐶8 𝐻18 that was different than the compound
when n-butyl bromide was reacted with sodium. Give the structural formula of (A) and
write the equation for all the reactions.

46.Write IUPAC name of the following :

47.Give reasons for the following:

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 (i) Haloalkanes easily dissolve dissolve in organic solvents.
(ii) Halogen compounds used in industry as solvents are alkyl chlorides rather than
bromides and iodides.

48.How the following conversions can be carried out?

(i) Benzyl alcohol to 2-phenylethanoic acid
(ii) Ethanol to propaneitrile
(iii) Aniline to chlorobenzene

49.Which one of the following compounds is more easily hydrolysed by KOH and why?
𝐶𝐻3 𝐶𝐻𝐶𝐼𝐶𝐻2 𝐶𝐻3 𝑜𝑟 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐶𝐼

50.Which compound in each of the following pairs will react faster in 𝑆𝑁 2 reaction with
𝑂𝐻− ?
(i) 𝐶𝐻3 𝐵𝑟 𝑜𝑟 𝐶𝐻3 𝐼
(ii) (𝐶𝐻3 )3 𝐶𝐶𝐼 𝑜𝑟 𝐶𝐻3 𝐶𝐼

51.Write the structure of the major organic product in each of the following reactions:

52.Write the structure of the major organic product in each of the following reactions:

53.How will you bring about the following conversions?

(i) n-Propyl chloride to iso-propyl chloride
(ii) Iso-propyl chloride to n-propyl chloride
(iii) Methyl bromide to acetone

54.Predict the order of reactivity of the following compounds in 𝑆𝑁 1 𝑎𝑛𝑑 𝑆𝑁 2 reactions:

(i) The four isomeric bromobutanes
(ii) 𝐶6 𝐻5 𝐶𝐻2 𝐵𝑟, 𝐶6 𝐻5 𝐶𝐻 (𝐶6 𝐻5 )𝐵𝑟, 𝐶6 𝐻5 𝐶𝐻(𝐶𝐻3 )𝐵𝑟, 𝐶6 𝐻5 𝐶(𝐶𝐻3 )(𝐶6 𝐻5 )𝐵𝑟

55.In the following pairs of halogen compounds, which compound undergoes faster 𝑆𝑁 1
reaction?

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56.Give reasons for the following observations :
(i) Haloarenes are less reactive than haloalkanes towards nucleophillic substitution
reaction.
(ii) The treatment of alkyl chloride with aqueous KOH leads to the formation of
alcohol but in the presence of alcoholic KOH, alkene is the major product.

57.Which alkyl halide from the following pairs would you expect to react more rapidly by an
𝑆𝑁 2 mechanism? Explain your answer.

58.Compound ‘A’ with molecular formula 𝐶4 𝐻9 𝐵𝑟 is treated with aq. KOH solution. The
rate of this reaction depends upon the concentration of the compound ‘A’ only. When
another optically active isomer ‘B’ of this compound was treated with aq. KOH solution,
the rate of reaction was found to be dependent on concentration of compound and
KOH both.
(i) Write down the structural formula of both compounds ‘A’ and ‘B’ .
(ii) Out of these two compounds, which one will be converted to the product with
inverted configuration.

59.Draw the structures of major mono-halo product in each of the following reactions:

60.How will you bring the following conversions?

(i) but -1-ene to but-2-ene
(ii) 1-Chlorobutane to n-octane
(iii) Benzene to biphenyl

61.Give reasons:

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(i) Racemic mixture is optically inactive.
(ii) The presence of nitre group (−𝑁𝑂2 ) at 𝑜/𝑝 positions increases the reactivity of
haloarenes towards nucleophilic substitution reactions.

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