Haloalkanes and Haloarenes

Organic chemistry
Class : 12th

Roll No. : T
Date : 07 Nov 2023

1. Which of the following undergoes nucleophilic substitution exclusively by SN1 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 followin
compounds
 (a) IV < III < I < II (b) III < II < I < IV
(c) I < II < IV < III (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?

8. The reaction of C6H5—CH==CH—CH3 with HBr produces

(a) C6H5CH2CH2CH2Br
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 alc. KOH a
produces hydrocarbon which forms red ppt. with ammonical Cu2Cl2. ‘X’ gives an aldehyde
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

II CH3CH2CH2Cl
III p—CH3O—C6H4—CH2Cl
(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)3C—F (b) (CH3)3C—Cl

(c) (CH3)3C—Br (d) (CH3)3C—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 b
ion?
20. Which is the correct increasing order of boiling points of the following compounds?
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. Consider the following reaction and answer the questions No. 21–23.

Which of the statements are correct about above reaction? [NCERT Exemplar Problem]
(a) (i) and (v) both are nucleophiles.
(b) In (iii) carbon atom is sp3 hybridised.
(c) In (iii) carbon atom is sp2 hybridised.
(d) (i) and (v) both are electrophiles.

22. Consider the following reaction and answer the questions No. 21–23.

Which of the following statements are correct about this reaction? [NCERT Exemplar Pro
(a) The given reaction follows SN2 mechanism.
(b) (ii) and (iv) have opposite configuration.
(c) (ii) and (iv) have same configuration.
(d) The given reaction follows SN1 mechanism.

23. Consider the following reaction and answer the questions No. 21–23.

Which of the following statements are correct about the reaction intermediate? [NCERT E
Problem]
(a) Intermediate (iii) is unstable because in this carbon is attached to 5 atoms.
(b) Intermediate (iii) is unstable because carbon atom is sp2 hybridised.
(c) Intermediate (iii) is stable because carbon atom is sp2 hybridised.
(d) Intermediate (iii) is less stable than the reactant (ii).
24.

Which of the following statements are correct about the mechanism of this reaction? [NCE
Exemplar Problem]
(a) A carbocation will be formed as an intermediate in the reaction.
(b) OH– will attach the substrate (ii) from one side and Cl– will leave it simultaneously from
side.
(c) An unstable intermediate will be formed in which OH– and Cl– will be attached by wea
(d) Reaction proceeds through SN1 mechanism.

25.

Which of the following statements are correct about the kinetics of this reaction? [NCERT
Problem]
(a) The rate of reaction depends on the concentration of only (ii).
(b) The rate of reaction depends on concentration of both (i) and (ii).
(c) Molecularity of reaction is one.
(d) Molecularity of reaction is two.

26. Haloalkanes contain halogen atom (s) attached to the sp3 hybridised carbon atom of an a
group. Identify haloalkane from the following compounds. [NCERT Exemplar Problem]
(a) 2-Bromopentane
(b) Vinyl chloride (chloroethene)
(c) 2-chloroacetophenone
(d) Trichloromethane

27. Ethylene chloride and ethylidene chloride are isomers. Identify the correct statements. [N
Exemplar Problem]
(a) Both the compounds form same product on treatment with alcoholic KOH.
(b) Both the compounds form same product on treatment with aq.NaOH.
(c) Both the compounds form same product on reduction.
(d) Both the compounds are optically active.

28. Match the the compounds given in Column I with the effects given in Column II.

Column I Column II
(a)
(i) Malaria
Chloramphenicol
(b) Thyroxine (ii) Anaesthetic
(iii) Typhoid
(c) Chloroquine
fever
 (d) Chloroform (iv) Goiter
(v) Blood
substituent

29. Match the items of Column I and Column II.

Column I Column II
(a) SN1 reaction (i) vic-dibromides
(b) Chemicals in fire extinguisher (ii) gem-dihalides
(c) Bromination of alkenes (iii) Racemisation
(d) Alkylidene halides (iv) Saytzeff rule
(e) Elimination of HX from (v)
alkylhalide Chlorobromocarbons

30. Match the reactions given in Column I with the types of reactions given in Column II.

31. Chloromethane on treatment with excess of ammonia gives _________.

32. The isomer of C4H9Br, (optical active) is _________.

33. Out of chlorobenzene, o-chlorotoluene, m-chloro toluene, least reactive towards nucleoph
substitution is _________.

34.

35. When benzene reacts with Cl and FeCl , the attacking electrophile is Cl+. [True or False
2 3

36. IUPAC name of Diethyl bromomethane is 3-Bromopentane. [True or False]

37. Among isobutyl bromide, n-Butyl bromide, secondary butyl bromide and tertiary butyl brom
Butyl bromide has lowest boiling point. [True or False]

38. Reactivity order of HI > HBr > HCl > HBr towards nucleophilic substitution reaction. [True
False]

39. Tert. halides undergo elimination reaction faster than nucleophilic substitution reaction. [T
False]

40. 3-methyl pent-2-ene on reaction with HBr in presence of peroxide forms an addition produ
number of possible stereoisomers for the product are
(a) 6 (b) 0
(c) 2 (d) 4

41.
42. Toluene reacts with Br2 in presence of sunlight to give
(a) o–Bromo toluene (b) p–bromo toluene
(c) Benzyl bromide (d) All of these

43.

44.

45. The order of reactivity of alcohols with halogen acids follows.

(a) 1° > 2° > 3° (b) 2° > 1° > 3°
(c) 3° > 1° > 2° (d) 3° > 2° > 1°

46. A primary alkyl halide would prefer to undergo _____________. [NCERT Exemplar Proble
(a) SN1 reaction (b) SN2 reaction
(c) α–Elimination (d) Racemisation

47. Which of the following structures is enantiomeric with the molecule (A) given below:
48. Identify the compound Y in the following reaction.

49. Alkyl halides are prepared from alcohols by treating with [NCERT Exemplar Problem]
(a) HCl + ZnCl2 (b) Red P + Br2
(c) H2SO4 + KI (d) All the above

50. Alkyl fluorides are synthesised by heating an alkyl chloride/bromide in presence of

____________ or ____________.

(a) CaF2 (b) CoF2

(c) Hg2F2 (d) NaF

51. Which of the following compounds can be classified as aryl halides? [NCERT Exemplar P
(a) p-ClC6H4CH2CH(CH3)2
(b) p-CH3CHCl(C6H4)CH2CH3
(c) o-BrH2C-C6H4CH(CH3)CH2CH3
(d) C6H5-Cl

52. Match the reactions given in Column I with the names given in Column II.
53. Out of chlorobenzene, p-chloronitrobenzene, 2,4,6-Trinitrobenzene, most reactive toward
nucleophilic substitution reaction is _________.

54.

55. Chlorobenzene, although–Cl group is electron with drawing but o and p-directly. [True/Fal

56. C6H5NH2 reacts with CHCl3 and KOH to form (offensive smelling) is called
carbylamine reaction. [True/False]

57. CH3CH2OH reacts with I2 and NaOH forms CHI3 which acts as antiseptic. [True/False]

58. Complete the following chemical equation :

H3CCH2CH==CH2 + HBr ___________.