Class-XII (Chemistry)

Chapter: Haloalkanes and haloarenes

1. Which of the following undergoes nucleophilic substitution exclusively by SN 1

mechanism?
(a) Benzyl chloride (b) Ethyl chloride
(c) Chlorobenzene (d) Isopropyl chloride

2. The increasing order of nucleophilicity would be

(a) Cl– < Br– < I– (b) I– < Cl– < Br–
(c) Br– < Cl– < F– (d) I– < Br– < Cl–

3.

4. Which of the following is most reactive towards SN1 reaction?

(a) C6H5C(CH3)C6H5Br (b) C6H5CH2Br
(c) C6H5CH(C6H5)Br (d) C6H5CH(CH3)Br

5. The correct order of increasing the reactivity of C—X bond towards nucleophile in
following compounds

(a) IV < III < I < II (c) I < II < IV < III
(b) III < II < I < IV (d) II < III < I < IV

6. m-Xylene reacts with Br2 in presence of FeBr3, what are products formed
7. Which of the following compound will undergo racemisation when reacts with aq. KOH?

(a) (i) and (ii) (b) (ii) and (iv)

(c) (iii) and (iv) (d) (iv)

8.

9. CH3CH2CH2Br + NaCN → CH3CH2CH2CN + NaBr, will be fastest in

(a) ethanol (b) methanol
(c) N, N dimethyl formamide (d) Water
10.

11. A dihalogen derivative ‘X’ of a hydrocarbon with three carbon atoms react with ale. KOH
and produces hydrocarbon which forms red ppt. with ammonical Cu2Cl2. ‘X’ gives an
aldehyde on reaction with aq. KOH. The compound ‘X’ is
(a) 1, 3-Dichloropropane (b) 1, 2-Dichloropropane
(c) 2, 2-Dichloropropane (d) 1, 1-Dichloropropane

12. The synthesis of alkyl fluoride is best accomplished by

(a) Finkelstein reaction (b) Swartz reaction
(c) Free radical fluorination (d) Sandmeyers reaction

13. How many chiral compounds are possible on monochlorination of 2-methyl butane?
(a) 2 (b) 4
(c) 6 (d) 8

14. The increasing order of reactivity towards SN1 mechanism is

(a) III < II < I (b) II < I < III

(c) I < III < II (d) II < III < I

15. 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)
16. What is ‘A’ in the following reaction?

17. Which of the following alkyl halides will undergo SN1 reaction most readily?
(a) (CH3)3 C—F (b) (CH3)3 C—Cl
(c) (CH3)3 C—Br (d) (CH3)3 C—I

18. Which of the carbon atoms present in the molecule given below are asymmetric?

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

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

20. Which of the following compounds will give racemic mixture on nucleophilic
substitution by OH” ion?
1- Bromoethane, 1-Bromopropane, 1-Bromobutane, Bromobenzene
(a) Bromobenzene < 1-Bromobutane < 1-Bromopropane < 1-Bromoethane
(b) Bromobenzene < 1-Bromoethane < 1-Bromopropane < 1-Bromobutane
(c) 1-Bromopropane < 1-Bromobutane < 1-Bromoethane < Bromobenzene
(d) 1-Bromoethane < 1-Bromopropane < 1-Bromobutane < Bromobenzene

21. SN1 reaction of alkyl halides lead to

(a) Retention of configuration (b) Racemisation
(c) Inversion of configuration (d) None of these

22. p-dichlorobenzene has higher melting point than its o- and m- isomers because
(a) p-dichlorobenzene is more polar than o- and m- isomer.
(b) p-isomer has a symmetrical crystalline structure.
(c) boiling point of p-isomer is more than o- and m-isomer.
(d) All of these are correct reasons.
23. Chloropicrin is formed by the reaction of
(a) steam on carbon tetrachloride. (b) nitric acid on chlorobenzene.
(c) chlorine on picric acid. (d) nitric acid on chloroform.

24. Fitting reaction can be used to prepare

(a) Toluene (b) Acetophenone
(c) Diphenyl (d) Chlorobenzene

25. Identify the end product (C) in the following sequence:

26.

In the above reaction, the product D is

(a) Propane (b) 2, 3-Dimethylbutane
(c) Hexane (d) Allyl bromid

27. Identify X and Y in the following sequence

(a) X = KCN, Y = LiAlH4

(b) X = KCN, Y = H3O+
(c) X = CH3Cl, Y = AlCl3 HCl
(d) X = CH3NH2, Y = HNO2

28. In the following sequence of reactions:

(a) n-propylamine (b) isopropylamine

(c) ethylamine (d) ethylmethylamine

29.

30.
Identify Z in the series
(a) C2H5I (b) C2H5OH
(c) CHI3 (d) CH3CHO

31. Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para
halo compounds. The reaction is
(a) Electrophilic elimination reaction (b) Electrophilic substitution reaction
(c) Free radical addition reaction (d) Nucleophilic substitution reaction

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

(a) Cl2/UV light (b) NaCl + H2SO4

(c) Cl2 gas in dark (d) Cl2 gas in the presence of iron in dark

33. 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]–

34. Ethylidene chloride is a/an .

(a) vic-dihalide (b) gem-dihalide
(c) allylic halide (d) vinylic halide

35. What is ‘A’ in the following reaction?

36. A primary alkyl halide would prefer to undergo .

(a) SN1 reaction (b) SN2 reaction
(c) α–Elimination (d) Racemisation

37. Which of the following alkyl halides will undergo SN1 reaction most readily?
(a) (CH3)3C—F (b) (CH3)3C—Cl
(c) (CH3)3C—Br (d) (CH3)3C—I
38.

(a) 1-Bromo-2-ethylpropane (b) 1-Bromo-2-ethyl-2-methyl ethane

(c) 1-Bromo-2-methylbutane (d) 2-Methyl-1-bromobutane

39. What should be the correct IUPAC name for diethyl bromomethane?
(a) 1-Bromo-1,1-diethoxyethane (b) 3-Bromopentane
(c) 1-Bromo-1-ethyl propane (d) 1-Bromopentane

40. The reaction of toluene with chlorine in the presence of iron and in the absence of light
yields .

41. Chloromethane on treatment with excess of ammonia yields mainly

42. Molecules whose mirror image is non superimposable over them are known as chiral.
Which of the following molecules is chiral in nature?
(a) 2-Bromobutane (b) 1-Bromobutane
(c) 2-Bromopropane (d) 2-Bromopropan-2-ol

43. Reaction of C6H5CH2Br 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

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

(i) (a) (ii) (a), (b), (c)

(iii) (b), (c) (iv) (a), (c)
45. Out of the following compounds which has the lowest boiling point ?
(a) Methyl chloride (b) Methyl bromide
(c) Methyl iodide (d) Methyl fluoride

46. Which of the following has the highest boiling point ?

(a) 1-Chloro-pentane (b) 2-Chloro pentane
(c) 3-Chloro pentane (d) All have equal boiling point.

47. An alkyl halide may be converted into an alkene by

(a) Addition (b) Substitution
(c) Elimination (d) Hydrogenation

48. Acetylene is treated with HBr and the resultant compounds is then heated with zinc dust.
The final product will be
(a) Ethylene (b) Acetylene
(c) 1-Butene (d) 2-Butene

49. Which of the following compounds would be hydrolysed most easily ?

(a) C2H5Cl (b) C2H5Br
(c) C2H5F (d) C2H5I

50. When aqueous KOH reacts with n-propyl chloride the product is
(a) Propylene (b) 2-Propanol
(c) 1-Propanol (d) 2-Propenol

51. Which of the following compounds would be hydrolysed most easily ?

(a) C2H5Br (b) CH3Br
(c) CH2 = CH – Br (d) CH2 = CH – CH2Br

52. A mixture of ethyl iodide and n-propyl iodide is subjected to Wurtz reaction. Which of
the following compounds is not formed during the reaction ?
(a) Butane (b) Propane
(c) Pentane (d) Hexane

53. Which of the following will be most dense ?

(a) C2H5Cl (b) C2H5Br
(c) C2H5I (d) C2H5F

54. 3, 3-Dimethyl-2-butanol, on reaction with conc. H2SO4 at 443 K will give ............ as the
major product.
(a) 3, 3-Dimethyl-1-butene (b) 2, 3-Dimethyl-2-butene
(c) 2, 2-Dimethyl-2-butene (d) 2, 2-Dimethyl-1-butene

55. An alkyl halide on reaction with sodium in the presence of ether gives 2, 2, 5, 5-
tetramethyl hexane. The alkyl halide possibly is
(a) 1-Chloropentane (b) 1-Chloro-2, 2-dimethyl propane
(c) 3-Chloro-2, 2-dimethyl butane (d) 2-Chloro-2-methyl butane

56. Iodoform is a ................ at room temperature.

(a) Gas (b) Thick viscous liquid
(c) Volatile liquid (d) Crystalline solid.

57. Which of the following does not form Grignard reagent on reaction with Mg in the
presence of ether ?
(a) Chloroethane (b) 1-Chloropropane
(c) Bromobenzene (d) Chlorobenzene

58. Chlorobenzene on reaction with CH3Cl in the presence of AlCl3 will give
(a) Toluene (b) m-Chloro toluene
(c) p-Chloro toluene (d) A mixture of o – and p-chlorotoluene
 59. Photochemical chlorination of an alkane is initiated by a process of
(a) Pyrolysis (b) Peroxidation
(c) Homolysis (d) Rearrangement

60. Allylic bromination of olefins is generally carried out with

(a) Phenyl magnesium bromide (b) Dibromo succinic acid
(c) N-Bromo succinimide (d) Pyridine perbromide

Answer the following:

1. A solution of KOH hydrolyses CH3CHClCH2CH3 and CH3CH2CH2CH2Cl. Which one of

these is more easily hydrolysed?
2. Write the IUPAC name of the following compound

3. Draw the structure of major monohalogen product formed in the following reaction

4. In the following pair of compounds, which will react faster by SN1 mechanism and why?

5. Predict the order of reactivity of the following compounds in SN1 reaction :

C6H5CH2Br, C6H5C(CH3) (C6H5)Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br
6. Arrange the following in increasing order of boiling point:
CH3CH2CH2CH2Br, (CH3)3.Br and (CH3)2C.Br
7. Write the IUPAC name of the following compound

8. Identify the chiral molecule in the following pair

9. Write the structure of an isomer of compound C4H9Br which is most reactive towards SN1
reaction
10. Complete the following reaction equations

Assertion Reason type:

(a) Both assertion and reason are correct statements, and reason is the correct explanation of
the assertion.
(b) Both assertion and reason are correct statements, but reason is not the correct
explanation of the assertion.
(c) Assertion is correct, but reason is wrong statement.
(d) Assertion is wrong, but reason is correct statement.
(e) Assertion and reason both are incorrect.

Haloalkanes and Haloarenes

1. Assertion: Iodoalkanes undergo nucleophilic substitution more readily than bromoalkanes.

Reason: Iodine is a better leaving group due to its larger size which makes the covalent
bond weaker.

2. Assertion: SN2 mechanism leads to racemisation.

Reason: The incoming nucleophile attacks the compounds from the side opposite to the
outgoing nucleophle in SN2 mechanism.

3. Assertion: Haloalkanes react with KCN to form cyanoalkanes.

Reason: KCN completely ionises in solution.

4. Assertion: Chlorobenzene is less polar than chloro methane.

Reason: Chlorobenzene has a longer C-Cl bond due to resonance.

5. Assertion: Presence of nitro group at ortho or para position makes nucleophilic

substitution in chlorobenzene easier.
Reason: Nitro group donates electrons to stabilize the intermediate ion formed by the
addition of the incoming nucleophile.

6. Assertion: Chloroform must be stored in dark coloured bottles.

Reason: Chloroform reacts with air to form phosgene.

7. Assertion: Chlorobutane has lower boiling point than 2-Chloro-2-methylpropane.

Reason: The intermolecular forces in straight chain compounds are stronger than in
branched compounds.

8. Assertion: Benzyl chloride undergoes nucleophilic substitution through SN1 mechanism.

Reason: Benzyl carbocation is resonance stabilized.

9. Assertion: Haloalkanes are only sparingly soluble in water.

Reason: Haloalkanes cannot form hydrogen bonds with water molecules.

10. Assertion: Propene reacts with HBr to form 2-bromopropane.

Reason: The intermediate carbocation formed will be secondary since it is more stable
than primary.