HALOALKANES AND HALOARENES

1. Which of the following undergoes nucleophilic substitution exclusively by S N 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 (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?
(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 S N1 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.
[NCERT Exemplar]

(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? [NCERT Exemplar]

17. Which of the following alkyl halides will undergo S N1 reaction most readily?
[NCERT Exemplar]
(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? [NCERT Exemplar]

(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? [NCERT Exemplar]

20. Which of the following compounds will give racemic mixture on nucleophilic
substitution by OH” ion? [NCERT Exemplar]
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-djchlorobenzene 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 bromide
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.
Identifay Z in the series

(a) C2H5I (b) C2H5OH (c) CHI3 (d) CH3CHO

Note: In the following questions two or more options may be correct. (Q.21 to
Q.27)
Consider the following reaction and answer the questions No. 21-23.

31. Which of the statements are correct about above reaction? [NCERT Exemplar]
(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.
32. Which of the following statements are correct about this reaction? [NCERT
Exemplar]
(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.
33. Which of the following statements are correct about the reaction
intermediate? (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).
Answer Q. No. 24 and 25 on the basis of the following reaction.
(i) (ii) (iii) (iv)

34. Which of the following statements are correct about the mechanism of this
reaction? [NCERT Exemplar]
(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 other side.
(c) An unstable intermediate will be formed in which OH – and Cl– will be attached
by weak bonds.
(d) Reaction proceeds through SN1 mechanism.
35. Which of the following statements are correct about the kinetics of this
reaction? [NCERT Exemplar]
(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.
36. Haloalkanes contain halogen atom (s) attached to the sp3 hybridised carbon
atom of an alkyl group. Identify haloalkane from the following compounds.
[NCERT Exemplar]
(a) 2-Bromopentane (b) Vinyl chloride (chloroethene)
(c) 2-chloroacetophenone (d) Trichloromethane
37. Ethylene chlonde and ethylidene chloride are isomers. Identify the correct
statements. [NCERT Exemplar]
(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.
38. Match the the compounds given in Column I with the effects given in Column
II. [NCERT Exemplar]
Column I Column II

(a) Chloramphenicol (i) Malaria

 (b) Thyroxine (ii) Anaesthetic

(c) Chloroquine (iii) Typhoid fever

(d) Chloroform (iv) Goiter

(v) Blood substituent

39. Match the items of Column I and Column II. [NCERT Exemplar]
Column I Column II

(a) SN1 reaction (i) vio-dibromides

(b) Chemicals in fire extinguisher (ii) gem-dihalides

(c) Bromination of alkenes (iii) Racemisation

(d) Alkylidene halides (iv) Saytzeffrule

(e) Elimination of HX from (v)

alkylhalide Chlorobromocarbons

40. Match the reactions given in Column I with the types of reactions given in
Column II. [NCERT Exemplar]

Note: In the following questions a statement of assertion followed by a statement

of reason is given. Choose the correct answer out of the following choices. (Q.31
to Q.35)
(a) Assertion and reason both are correct and reason is correct explanation of
assertion.
(b) Assertion and reason both are wrong statements.
(c) Assertion is correct but reason is wrong statement.
(d) Assertion is wrong but reason is correct statement.
(e) Assertion and reason both are correct statements but reason is not correct
explanation of assertion.
41. Assertion: KCN reacts with methyl chloride to give methyl isocyanide.
Reason: CN– is an ambident nucleophile. [NCERT Exemplar]
42. Assertion: tert-Butyl bromide undergoes Wurtz reaction to give 2, 2, 3, 3-
tetramethylbutane.
Reason: In Wurtz reaction, alkyl halides react with sodium in dry ether to give
hydrocarbon containing double the number of carbon atoms present in the halide.
[NCERT Exemplar]
43. Assertion: Presence of a nitro group at ortho or para position increases the
reactivity of haloarenes towards nucleophilic substitution.
Reason: Nitro group, being an electron withdrawing group decreases the electron
density over the benzene ring. [NCERT Exemplar]
44. Assertion: In monohaloarenes, further electrophilic substitution occurs at
ortho and para positions.
Reason: Halogen atom is a ring deactivator. [NCERT Exemplar]
45. Assertion: Aryl iodides can be prepared by reaction of arenes with iodine in
the presence of an oxidising agent.
Reason: Oxidising agent oxidises I2 into HI. [NCERT Exemplar]
46. Chloromethane on treatment with excess of ammonia gives __________
47. The isomer of C4H9Br, (optical active) is __________ .
48. Out of chlorobenzene, o-chlorotoluene, m-chloro toluene, least reactive
towards nucleophilic substitution is __________ .
49.

is allylic halide. [True or False]

50. When benzene reacts with Cl2 and FeCl3, the attacking electrophile is Cl+.
[True or False]