1170 Halogen Containing Compounds

(c) 2, 3, 4-trimethylpentane
(d) 3, 3-dimethylpentane

Preparation of Halogen containing compounds

1. The following reaction is known as

Introduction of Halogen containing compounds C 2 H 5 OH  SOCl 2   C 2 H 5 Cl  SO 2  HCl
Pyridine

[AIIMS 2002]
1. How many structural isomers are possible for a compound with (a) Kharasch effect
molecular formula C 3 H 7 Cl [MH CET 2001] (b) Darzen’s procedure
(a) 2 (b) 5 (c) Williamson’s synthesis
(c) 7 (d) 9 (d) Hunsdiecker synthesis reaction
2. In CH 3 CH 2 Br, % of Br is [DPMT 1996] 2. What is the main product of the reaction between 2-methyl propene
with HBr [RPMT 2002]
(a) 80 (b) 75 (a) 1-bromo butane
(c) 70 (d) 7 (b) 1-bromo-2 methyl propane
3. Gem- dibromide is [RPMT 2000]
(c) 2-bromo butane
(a) CH 3 CH (Br)OH(Br)CH 3 (b) CH 3 CBr2 CH 3 (d) 2-bromo-2 methyl propane
(c) CH 2 (Br)CH 2 CH 2 (d) CH 2 BrCH 2 Br 3. Halogenation of alkanes is [KCET 2002]
(a) A reductive process (b) An oxidative process
4. Ethylidene dibromide is
(c) An isothermal process (d) An indothermal process
(a) CH 3  CH 2  Br (b) Br  CH 2  CH 2  Br

(c) CH 3  CHBr2 (d) CH 2  CBr2 4. N  NBF4

5. Benzylidene chloride is  A
(a) C 6 H 5 CH 2 Cl (b) C 6 H 5 CHCl 2
(c) C 6 H 4 ClCH 2 Cl (d) C 6 H 5 CCl 3
In the above process product A is [Kerala (Engg.) 2002]
6. Which of the following halide is 2 o
(a) Fluorobenzene (b) Benzene
(a) Isopropyl chloride (b) Isobutyl chloride
(c) 1, 4-difluorobenzene (d) 1, 3-difluorobenzene
(c) n-propyl chloride (d) n-butyl chloride
7. Haloforms are trihalogen derivatives of [CPMT 1985] 5. Silver acetate  Br2  . The main product of this reaction is
CS 2

(a) Ethane (b) Methane [Kurukshetra CET 2002]

(c) Propane (d) Benzene (a) CH 3  Br (b) CH 3 COI
8. Benzene hexachloride is (c) CH 3 COOH (d) None of these
(a) 1, 2, 3, 4, 5, 6-hexachlorocyclohexane
Cl
(b) 1, 1, 1, 6, 6, 6-hexachlorocyclohexane
(c) 1, 6-phenyl-1, 6-chlorohexane
(d) 1, 1-phenyl-6, 6-chlorohexane 6. Diazonium salts  Cu 2 Cl 2  HCl  , the reaction is
9. Number of   bonds present in B.H.C. (Benzene hexachloride) known as [Kerala (Med.) 2002]
are [RPMT 1999] (a) Chlorination (b) Sandmeyer’s reaction
(a) 6 (b) Zero (c) Perkin reaction (d) Substitution reaction
(c) 3 (d) 12 7. When ethyl alcohol (C 2 H 5 OH ) reacts with thionyl chloride, in the
10. The general formula for alkyl halides is
presence of pyridine, the product obtained is
(a) C n H 2n 1 X (b) C n H 2n  2 X [AIIMS; CBSE PMT 2001]
(c) C n H n 1 X (d) C n H 2n X (a) CH 3 CH 2 Cl  HCl
11. Which of the following is a primary halide [DCE 2004] (b) C 2 H 5 Cl  HCl  SO 2
(a) Isopropyl iodide (b) Secondary butyl iodide
(c) CH 3 CH 2 Cl  H 2 O  SO 2
(c) Tertiary butyl bromide (d) Neo hexyl chloride
12. Full name of DDT is [KCET 1993] (d) CH 3 CH 2 Cl  HCl  SO 2
(a) 1, 1, 1-trichloro-2, 2-bis(p-chlorophenyl) ethane 8. Preparation of alkyl halides in laboratory is least preferred by[DPMT 2000]
(b) 1, 1-dichloro-2, 2-diphenyl trimethylethane (a) Treatment of alcohols
(c) 1, 1-dichloro-2, 2-diphenyl trichloroethane (b) Addition of hydrogen halides to alkenes
(d) None of these (c) Halide exchange
13. The compound which contains all the four 1 o ,2 o ,3 o and 4 o (d) Direct halogenation of alkanes
carbon atoms is [J & K 2005] 9. Which of the following organic compounds will give a mixture of
(a) 2, 3-dimethyl pentane 1-chlorobutane and 2-chlorobutane on chlorination [CPMT 2001]
(b) 3-chloro-2, 3-dimethylpentane
 Halogen Containing Compounds 1171

(a) CH 3  CH  CH  CH 2 (c) Bright sunlight (d) Zinc

| 20. The final product obtained by distilling ethyl alcohol with the excess
CH 3 of chlorine and Ca(OH ) 2 is [MP PET 1996]
H (a) CH 3 CHO (b) CCl 3 CHO
|
(b) HC  C  C  CH 2 (c) CHCl 3 (d) (CH 3 ) 2 O
(c) CH 2  CH  CH  CH 2 21. When ethyl alcohol and KI reacted in presence of Na 2 CO 3 , yellow
crystals of...... are formed [AFMC 1989]
(d) CH 2  CH  CH 2  CH 3 (a) CHI 3 (b) CH 3 I
10. The chlorobenzene is generally obtained from a corresponding (c) CH 2 I 2 (d) C 2 H 5 I
diazonium salt by reacting it with
[MP PMT 2000] 22. In preparation of CHCl 3 from ethanol and bleaching powder, the
(a) Cu 2 Cl 2 (b) CuSO 4 latter provides [BHU 1986]
(a) Ca(OH ) 2 (b) Cl 2
(c) Cu (d) Cu (NH 3 )42  (c) Both (a) and (b) (d) None of these
11. Decreasing order of reactivity of HX in the reaction 23. Which one of the following processes does not occur during
ROH  HX  RX  H 2 O formation of CHCl 3 from C 2 H 5 OH and bleaching powder
[DPMT 1984]
[RPET 2000; AIIMS 1983; MP PET 1996] (a) Hydrolysis (b) Oxidation
(a) HI  HBr  HCl  HF (b) HBr  HCl  HI  HF (c) Reduction (d) Chlorination
(c) HCl  HBr  HI  HF (d) HF  HBr  HCl  HI 24. Which of the following is obtained when chloral is boiled with
NaOH [CBSE PMT 1991; RPMT 1999]
12. The product of the following reaction :
(a) CH 3 Cl (b) CHCl 3
CH 2  CH  CCl 3  HBr [RPET 2000]
(c) CCl 4 (d) None of these
(a) CH 3  CH (Br)  CCl 3 (b) CH 2 (Br)  CH 2  CCl 3 25. Chloroform can be obtained from [MNR 1986]
(c) BrCH 2  CHCl  CHCl 2 (d) CH 3  CH 2  CCl 3 (a) Methanol (b) Methanal
(c) Propanol-1 (d) Propanol-2
13. Chlorobenzene is prepared commercially by 26. Chlorine reacts with ethanol to give
[JIPMER 2000; CPMT 1976; Pb. CET 2002] [MP PMT 1989; CPMT 1997; KCET 1998; JIPMER 1999]
(a) Raschig process (b) Wurtz Fitting reaction (a) Ethyl chloride (b) Chloroform
(c) Friedel-Craft’s reaction (d) Grignard reaction (c) Acetaldehyde (d) Chloral
14. In methyl alcohol solution, bromine reacts with ethylene to yield 27. On heating diethyl ether with conc. HI, 2 moles of which of the
following is formed
BrCH 2 CH 2 OCH 3 in addition to 1, 2-dibromoethane because[Pb. PMT 1998] [IIT-JEE 1983; MP PET 1990; EAMCET 1990;
AFMC 1993; JIPMER 2001]
(a) The ion formed initially may react with Br  or CH 3 OH
(a) Ethanol (b) Iodoform
(b) The methyl alcohol solvates the bromine (c) Ethyl iodide (d) Methyl iodide
(c) The reaction follows Markownikoff's rule 28. Lucas reagent is [MP PMT 1996; MP PET 1992, 95;
(d) This is a free-radical mechanism CPMT 1986, 89; AIIMS 1980; Kurukshetra CEE 2002]
(a) Concentrated HCl  anhydrous ZnCl 2
15. C3 H 8  Cl 2   C3 H7 Cl  HCl is an example of which of
Light

the following types of reactions (b) Dilute HCl  hydrated ZnCl 2

[AFMC 1997; CPMT 1999] (c) Concentrated HNO 3  anhydrous ZnCl 2
(a) Substitution (b) Elimination (d) Concentrated HCl  anhydrous MgCl2
(c) Addition (d) Rearrangement
29. Which compound does not form iodoform with alkali and iodine[IIT-JEE 1985]
16. Which of the following would be produced when acetylene reacts
with HCl [MH CET 1999] (a) Acetone (b) Ethanol
(c) Diethyl ketone (d) Isopropyl alcohol
(a) CH 3 CH 2 Cl (b) CH 3 CHCl 2
30. Which compound gives yellow ppt. with iodine and alkali
(c) CHCl  CHCl (d) CH 2  CHCl [IIT-JEE 1984]
17. R  OH  HX  R  X  H 2 O (a) 2-hydroxy propane (b) Acetophenone
(c) Methyl acetone (d) Acetamide
In the above reaction, the reactivity of different alcohols is
[CPMT 1997] 31. Acetone reacts with I 2 in presence of NaOH to form
(a) Tertiary > Secondary > Primary [MP PMT 1992]
(b) Tertiary < Secondary < Primary
(a) C2 H 5 I (b) C 2 H 4 I 2
(c) Tertiary < Secondary > Primary
(d) Secondary < Primary < Tertiary (c) CHI 3 (d) CH 3 I
18. C 6 H 6  Cl 2   Product. In above reaction product is [CPMT 1997]
UV Light
32. Ethanol is converted into ethyl chloride by reacting with
[MP PET 1991; MP PMT 1990; BHU 1997]
(a) CCl 3 CHO (b) C 6 H 6 Cl 6
(a) Cl 2 (b) SOCl 2
(c) C 6 H 12 Cl 6 (d) C 6 H 9 Cl 2
(c) HCl (d) NaCl
19. Benzene reacts with chlorine to form benzene hexachloride in
33. C 6 H 5 Cl prepared by aniline with [IIT-JEE 1984]
presence of [MP PET 1999]
(a) Nickel (b) AlCl3 (a) HCl
 1172 Halogen Containing Compounds
(b) Cu 2 Cl 2 47. Which of the following compounds gives trichloromethane on
distilling with bleaching powder
(c) Cl 2 in presence of anhydrous AlCl3 [KCET 2004; EAMCET 1986]
(d) HNO 2 and then heated with Cu 2 Cl 2 (a) Methanal (b) Phenol
(c) Ethanol (d) Methanol
34. The starting substance for the preparation of CH 3 I is
48. The product formed on reaction of ethyl alcohol with bleaching powder
[CPMT 1975] is [Orissa JEE 2004; DPMT 1978; AIIMS 1991]
(a) CH 3 OH (b) C 2 H 5 OH (a) CHCl 3 (b) CCl 3 CHO
(c) CH 3 CHO (d) (CH 3 )2 CO (c) CH 3 COCH 3 (d) CH 3 CHO
35. A Grignard's reagent may be made by reacting magnesium with [CPMT 1973,
49.83, 84]Ethylene reacts with bromine to form [Pb. CET 2000]
(a) Methyl amine (b) Diethyl ether (a) Chloroethane (b) Ethylene dibromide
(c) Ethyl iodide (d) Ethyl alcohol (c) Cyclohexane (d) 1-bromo propane
36. Which of the following is responsible for iodoform reaction 50. Best method of preparing alkyl chloride is [MH CET 2004]
[CPMT 1980; RPMT 1997] (a) ROH  SOCl 2 
(a) Formalin (b) Methanol
(c) Acetic acid (d) Ethanol (b) ROH  PCl5  
37. When a solution of sodium chloride containing ethyl alcohol is (c) ROH  PCl3  
electrolysed, it forms
(d) ROH  HCl 
anhy. ZnCl 2
(a) Ethyl alcohol (b) Chloral
(c) Chloroform (d) Acetaldehyde 51. DDT is prepared by reacting chlorobenzene with
38. Which reagent cannot be used to prepare an alkyl halide from an [BHU 1998, 2005]
alcohol [CPMT 1989, 94] (a) CCl 4 (b) CCl 3  CHO
(a) HCl  ZnCl2 (b) NaCl (c) CHCl 3 (d) Ethane
(c) PCl5 (d) SOCl 3 52. Which compound needs chloral in its synthesis
[Pb. PET 2003]
39. Ethyl benzoate reacts with PCl5 to give [KCET 2003] (a) D. D. T. (b) Gammexane
(a) C 2 H 5 Cl  C6 H 5 COCl  POCl3  HCl (c) Chloroform (d) Michler’s Ketone
53. To get DDT, chlorobenzene has to react with which of the following
(b) C 2 H 5 Cl  C6 H 5 COCl  POCl3 compounds in the presence of concentrated sulphuric acid [KCET (Engg/Med.) 20
(a) Trichloroethane (b) Dichloroacetone
(c) CH 3 COCl  C6 H 5 COCl  POCl3 (c) Dichloroacetaldehyde (d) Trichloroacetaldehyde
(d) C 2 H 5 Cl  C6 H 5 COOH  POCl3 54. What will be the product in the following reaction
40. On treatment with chlorine in presence of sunlight, toluene giv.es CH 2

NBS [BHU 2005]

the product
[Orissa JEE 2003; MH CET 1999, 2002] Br
(a) o-chloro toluene (b) 2, 5-dichloro toluene CH 3
CH 3

(c) p-chloro toluene (d) Benzyl chloride (a) (b)

41. When chlorine is passed through warm benzene in presence of the
sunlight, the product obtained is [KCET 2003] Br
CH Br CH 3

(a) Benzotrichloride (b) Chlorobenzene 2

(c) (d)
(c) Gammexane (d) DDT
42. Which of the following acids adds to propene in the presence of
peroxide to give anti-Markownikoff’s product Br
[MP PET 2003]
Properties of Halogen containing compounds
(a) HF (b) HCl
(c) HBr (d) HI CCl
3

43. Propene on treatment with HBr gives [CPMT 1986]

(a) Isopropyl bromide (b) Propyl bromide 1.   A. Compounds A is
1 eqv. of Br2 / Fe

(c) 1, 2-dibromoethane (d) None of the above [Orissa JEE 2005]

44. The catalyst used in Raschig's process is CCl CCl 3
3

(a) LiAlH4 (b) Copper chloride Br

(a) (b)
(c) Sunlight (d) Ethanol Na
45. The compound formed on heating chlorobenzene with chloral in the Br
presence of concentrated sulphuric acid, is CCl CCl 3
3

[AIEEE 2004]
(a) Freon (b) DDT (c) (d)
(c) Gammexene (d) Hexachloroethane
Br Br
46. Acetone is mixed with bleaching powder to give Br
[AFMC 2004] 2. Ethyl bromide can be converted into ethyl alcohol by
(a) Chloroform (b) Acetaldehyde [KCET 1989]
(c) Ethanol (d) Phosgene (a) Heating with dilute hydrochloric acid and zinc
 Halogen Containing Compounds 1173

(b) Boiling with an alcoholic solution of KOH (c) Nearly as reactive as methyl chloride
(c) The action of moist silver oxide (d) More reactive than isopropyl chloride
(d) Refluxing methanol 14. The reactivities of methyl chloride, propyl chloride and
3. Reaction of ethyl chloride with sodium leads to chlorobenzene are in the order [KCET 1988]
[NCERT 1984] (a) Methyl chloride > propyl chloride > chlorobenzene
(a) Ethane (b) Propane (b) Propyl chloride > methyl chloride > chlorobenzene
(c) n-butane (d) n-pentane (c) Methyl chloride > chlorobenzene > propyl chloride
(d) Chlorobenzene > propyl chloride > methyl chloride
4. Treatment of ammonia with excess of ethyl chloride will yield[AIIMS 1992]
15. Which of the following compound will make precipitate most readily
(a) Diethyl amine
with AgNO 3 [CPMT 1992]
(b) Ethane
(c) Tetraethyl ammonium chloride (a) CCl 3 CHO (b) CHCl 3
(d) Methyl amine (c) C 6 H 5 CH 2 Cl (d) CHI 3
5. 2CHCl 3  O 2  2COCl 2  2 HCl
X
16. Carbylamine is liberated when..... is heated with chloroform and
alcoholic potash [KCET 1992]
In the above reaction, X stands for [CPMT 1985]
(a) An aldehyde (b) A primary amine
(a) An oxidant (b) A reductant
(c) A secondary amine (d) A phenol
(c) Light and air (d) None of these
17. Salicylic acid can be prepared using Reimer-Tiemann's reaction by
6. Phosgene is the common name for treating phenol with [KCET 1989]
[DPMT 1983; CPMT 1993; MP PMT 1994; (a) Methyl chloride in the presence of anhydrous aluminium chloride
Kurukshetra CEE 1998; RPMT 2000, 02] (b) Carbon dioxide under pressure in sodium hydroxide solution
(a) CO 2 and PH 3 (b) Phosphoryl chloride (c) Carbon tetrachloride and concentrated sodium hydroxide
(d) Sodium nitrite and a few drops of concentrated sulphuric acid
(c) Carbonyl chloride (d) Carbon tetrachloride 18. Grignard reagent is prepared by the reaction between
7. When chloroform is treated with amine and KOH, we get [CBSE PMT 1994; DPMT 1996; Pb. PMT 1999;
[CPMT 1979] MH CET 1999]
(a) Rose odour smell (a) Zinc and alkyl halide
(b) Magnesium and alkyl halide
(b) Sour almond like smell
(c) Magnesium and alkane
(c) Offensive odour (d) Magnesium and aromatic hydrocarbon
(d) Sour oil of winter green like smell 19. Reaction of t-butyl bromide with sodium methoxide produces[CBSE PMT 1994]
8. A mixture of two organic chlorine compounds was treated with (a) Isobutane (b) Isobutylene
sodium metal in ether solution. Isobutane was obtained as a product. (c) Sodium t-butoxide (d) t-butyl methyl ether
The two chlorine compounds are [KCET 1988] 20. War gas is formed from [BHU 1995]
(a) Methyl chloride and propyl chloride (a) PH 3 (b) C 2 H 2
(b) Methyl chloride and ethyl chloride (c) Zinc phosphate (d) Chloropicrin
(c) Isopropyl chloride and methyl chloride 21. What happens when CCl 4 is treated with AgNO 3
(d) Isopropyl chloride and ethyl chloride [EAMCET 1987; CBSE PMT 1988; MP PET 2000]
9. Alkyl halides can be converted into Grignard reagents by (a) NO 2 will be evolved
[KCET 1989]
(b) A white ppt. of AgCl will be formed
(a) Boiling them with Mg ribbon in alcoholic solution
(c) CCl 4 will dissolve in AgNO 3
(b) Warming them with magnesium powder in dry ether
(d) Nothing will happen
(c) Refluxing them with MgCl2 solution
22. If we use pyrene (CCl 4 ) in the Riemer-Tiemann reaction in place
(d) Warming them with MgCl2 of chloroform, the product formed is
[CBSE PMT 1989; MP PMT 1990; MH CET 1999]
10. Which is not present in Grignard reagent
(a) Salicylaldehyde (b) Phenolphthalein
[CBSE PMT 1991] (c) Salicylic acid (d) Cyclohexanol
(a) Methyl group (b) Magnesium
23. C 6 H 5 CH 2 Cl  KCN (aq.)  X  Y
(c) Halogen (d) COOH group Compounds X and Y are [BHU 1979]
11. The reactivity of ethyl chloride is [KCET 1986]
(a) C 6 H 6  KCl (b) C 6 H 5 CH 2 CN  KCl
(a) More or less equal to that of benzyl chloride
(b) More than that of benzyl chloride (c) C 6 H 5 CH 3  KCl (d) None of these
(c) More or less equal to that of chlorobenzene 24. The bad smelling substance formed by the action of alcoholic caustic
potash on chloroform and aniline is
(d) Less than that of chlorobenzene [MP PMT 1971, 92, 2001; CPMT 1971, 86; AFMC 2002;
12. The reactivity of halogen atom is minimum in [KCET 1985] RPMT 1999]
(a) Propyl chloride (b) Propyl iodide (a) Phenyl isocyanide (b) Nitrobenzene
(c) Isopropyl chloride (d) Isopropyl bromide (c) Phenyl cyanide (d) Phenyl isocyanate
13. Chlorobenzene is 25. Ethylidene chloride on treatment with aqueous KOH gives
[MP PMT 1986]
(a) Less reactive than benzyl chloride
(a) Ethylene glycol (b) Acetaldehyde
(b) More reactive than ethyl bromide (c) Formaldehyde (d) None
 1174 Halogen Containing Compounds
26. Reaction C 2 H 5 I  C 5 H 11 I  2 Na  C 2 H 5  C 5 H 11  2 NaI (c) CHCl 3  KOH (d) CHCl 3  HNO 3
is called 38. CH 3  CH 2  CH 2 Br  KOH (alc.)  Product Product in
[MP PMT 1992]
(a) Hoffmann's reaction above reaction is [RPMT 2003]
(b) Dow's reaction (a) CH 3  CH  CH 2 (b) CH 3  CH 2  CH 3
(c) Wurtz's reaction (c) (a) and (b) both (d) None of these
(d) Riemer-Tiemann's reaction
39. A  CCl 4  KOH  Salicylic acid
27. In presence of AlCl3 , benzene and n-propyl bromide react in
‘A’ in above reaction is [RPMT 2003]
Friedal-Craft's reaction to form [MP PMT 1991]
(a) n-propyl benzene OH NO 2
(b) 1, 2-dinormal propyl benzene
(c) 1, 4-dinormal propyl benzene (a) (b)
(d) Isopropyl benzene
28. The dehydrobromination of 2-bromobutane gives CHO
CH 3 CH  CHCH 3 . The product is
(a) Hofmann product (c) (d)
(b) Saytzeff product
(c) Hoffmann-Saytzeff product 40. Identify X and Y in the following sequence
(d) Markownikoff product
C2 H 5 Br 
X
product 
Y
C3 H 7 NH 2
29. Ethylene difluoride on hydrolysis gives
(a) Glycol (b) Fluoroethanol [Orissa JEE 2005]
(c) Difluoroethanol (d) Freon (a) X  KCN , Y  LiAlH4
30. Benzyl chloride when oxidised by pb(NO 3 ) 2 gives (b) X  KCN , Y  H 3 O 
[MP PMT 1989]
(a) Benzoic acid (b) Benzaldehyde (c) X  CH 3 Cl, Y  AlCl3 / HCl
(c) Benzene (d) None (d) X  CH 3 NH 2 , Y  HNO 2
31. Which of the following statements about chloroform is false
41. 1-chlorobutane reacts with alcoholic KOH to form
[Manipal MEE 1995]
[IIT-JEE 1991; AFMC 1998]
(a) It is a colourless, sweet-smelling liquid
(a) 1-butene (b) 2-butane
(b) It is almost insoluble in water
(c) It is highly inflammable (c) 1-butanol (d) 2-butanol
(d) It can be used as an inhalational anaesthetic agent 42. Which of the following reactions gives H 2 C  C  C  CH 2 [Roorkee Qualify
32. CCl 4 cannot give precipitate with AgNO 3 due to (a) CH 2 Br  CBr  CH 2  
Zn / Ch 3 OH

[CPMT 1979]
(a) Formation of complex with AgNO 3 (b) HC  C  CH 2  COOH  
Aq. K 2 CO 3
40 o C
(b) Evolution of Cl 2 gas (c) CH 2 Br  C  C  CH 2 Br 

Zn
Heat
(c) Chloride ion is not formed
(d) AgNO 3 does not give silver ion (d) 2CH 2  CH  CH 2 I 
33. On heating CHCl 3 with aq. NaOH, the product is 43. When ethyl amine is heated with chloroform and alcoholic KOH, a
[CPMT 1971, 78; BHU 1997; EAMCET 1998; compound with offensive smell is obtained. This compound is [CPMT 1983, 84; R
JIPMER (Med.) 2002] (a) A secondary amine (b) An isocyanide
(a) CH 3 COONa (b) HCOONa (c) A cyanide (d) An acid
(c) Sodium oxalate (d) CH 3 OH 44. Chlorobenzene on fusing with solid NaOH gives
[DPMT 1981; CPMT 1990]
34. Ethyl bromide reacts with lead-sodium alloy to form
(a) Benzene (b) Benzoic acid
[MP PMT/PET 1988; MP PET 1997]
(c) Phenol (d) Benzene chloride
(a) Tetraethyl lead (b) Tetraethyl bromide
(c) Both (a) and (b) (d) None of the above 45. DDT can be prepared by reacting chlorobenzene (in the presence of
35. Iodoform heated with Ag powder to form [DPMT 1985] conc. H 2 SO 4 ) with
(a) Acetylene (b) Ethylene (a) Cl 2 in ultraviolet light (b) Chloroform
(c) Methane (d) Ethane
(c) Trichloroacetone (d) Chloral hydrate
36. Ethyl bromide reacts with silver nitrite to form
[DPMT 1985; IIT-JEE 1991] 46. When phenol reacts with CHCl 3 and KOH, the product obtained
(a) Nitroethane would be [RPMT 1997]
(b) Nitroethane and ethyl nitrite (a) Salicylaldehyde (b) p-hydroxy benzaldehyde
(c) Ethyl nitrite (c) Both (a) and (b) (d) Chloretone
(d) Ethane 47. Ethyl chloride on heating with silver cyanide forms a compound X.
37. Which of the following reactions leads to the formation of chloritone[RPMT 2003] The functional isomer of X is
(a) CHCl 3  CH 3 COCH 3 (b) CCl 4  Acetone [EAMCET 1997; KCET 2005]
(a) C 2 H 5 NC (b) C 2 H 5 CN
 Halogen Containing Compounds 1175

(c) H 3 C  NH  CH 3 (d) C 2 H 5 NH 2 (a) C 2 H 5 OH (b) CH 3 OH

48. Which of the following statements is incorrect [CPMT 1977] (c) HCOOH (d) C 6 H 6
(a) C 2 H 5 Br reacts with alco. KOH to form C 2 H 5 OH 58. Which of the following reacts with phenol to give salicylaldehyde
(b) C 2 H 5 Br when treated with metallic sodium gives ethane after hydrolysis [MP PMT 1995]
(a) Dichloromethane (b) Trichloromethane
(c) C 2 H 5 Br when treated with sodium ethoxide forms diethyl (c) Methyl chloride (d) None of these
ether 59. Dehydrohalogenation in monohaloalkanes produces
(d) C 2 H 5 Br with AgCN forms ethyl isocyanide (a) A single bond (b) A double bond
(c) A triple bond (d) Fragmentation
49. When chloroform is exposed to air and sunlight, it gives
[NCERT 1984; CPMT 1978, 87; CBSE PMT 1990;
60. When chloroform is treated with conc. HNO 3 it gives
EAMCET 1993; MNR 1994; MP PET 1997, 2000; [CPMT 1986; MP PMT 1989; AFMC 1998, 99;
BHU 2001; AFMC 2002] EAMCET 1991; BHU 1999]
(a) Carbon tetrachloride (b) Carbonyl chloride (a) CHCl 2 NO 2 (b) CCl 3 NO 2
(c) Mustard gas (d) Lewsite (c) CHCl 2 HNO 3 (d) None of these
50. An organic halide is shaken with aqueous NaOH followed by the 61. A sample of chloroform being used as anaesthetic is tested by[AIIMS 1980; CPMT
addition of dil. HNO 3 and silver nitrate solution gave white ppt. (a) Fehling solution
The substance can be [JIPMER 1997] (b) Ammoniacal Cu 2 Cl 2
(a) C 6 H 4 (CH 3 )Br (b) C 6 H 5 CH 2 Cl
(c) AgNO 3 solution
(c) C 6 H 5 Cl (d) None of these
(d) AgNO 3 solution after boiling with alcoholic KOH solution
51. A compound A has a molecular formula C2Cl3 OH . It reduces 62. Dehydrohalogenation of an alkyl halide is [MP PMT 1996]
Fehling solution and on oxidation gives a monocarboxylic acid (B). A (a) An addition reaction (b) A substitution reaction
is obtained by action of chlorine on ethyl alcohol. A is (c) An elimination reaction (d) An oxidation reaction
[CBSE PMT 1994; MP PET 1997; KCET 2005] 63. Reaction of aqueous sodium hydroxide on (i) ethyl bromide and (ii)
(a) Chloral (b) CHCl 3 chlorobenzene gives
(a) (i) Ethene and (ii) o-chlorophenol
(c) CH 3 Cl (d) Chloroacetic acid (b) (i) Ethyl alcohol and (ii) o-chlorophenol
52. Following equation illustrates (c) (i) Ethyl alcohol and (ii) phenol
200  250 C o (d) (i) Ethyl alcohol and (ii) no reaction
C 6 H 5 Cl  2 NaOH   C 6 H 5 ONa  NaCl  H 2 O
200 atm 64. 2-bromopentane is heated with potassium ethoxide in ethanol. The
[Bihar CEE 1995] major product obtained is [CBSE PMT 1998]
(a) Dow's process (b) Kolbe's process (a) Pentene-1 (b) cis pentene-2
(c) Carbylamine test (d) Haloform reaction (c) trans pentene-2 (d) 2-ethoxypentane
65. What is the product formed in the following reaction
53. One of the following that cannot undergo dehydro-halogenation is [J & K 2005]
(a) Iso-propyl bromide (b) Ethanol C 6 H 5 OH  CCl 4   
(1) NaOH
[KCET 1998]
(2) H 
(c) Ethyl bromide (d) None of these
(a) p-hydroxybenzoic acid (b) o-hydroxybenzoic acid
54. A compound X on reaction with chloroform and NaOH gives a
compound with a very unpleasant odour. X is (c) Benzaldehyde (d) Salicylaldehyde
[MP PMT 1999] 66. When chloroform is treated with excess oxygen it forms
[MH CET 1999]
(a) C 6 H 5 CONH 2 (b) C 6 H 5 NH 2
(a) COCl 2  HCl
(c) C 6 H 5 CH 2 NHCH 3 (d) C 6 H 5 NHCH 3
(b) COCl 2  Cl 2  H 2
OH (c) COCl 2  Cl 2  H 2 O
O C2 H 5
55.  C 2 H 5 I   P roduct (d) No product will be formed
Anhydrous (C H OH )
2 5 67. Which isomer of cyclohexane hexachloride is a very strong
insecticide [MP PET 2003]
In the above reaction product is (a)  (b) 
(a) C6 H 5 OC2 H 5 (b) C 2 H 5 OC2 H 5 (c)  (d) 
(c) C6 H 5 OC6 H 5 (d) C6 H 5 I 68. Haloalkane in the presence of alcoholic KOH undergoes
[KCET (Engg/Med.) 2002]
56. C 2 H 5 Cl  KCN  X    Y . 'X' and 'Y' are
Hydrolysis
(a) Elimination (b) Polymerisation
[MP PET 1995] (c) Dimerisation (d) Substitution
(a) C 2 H 6 and C 2 H 5 CN 69. The set of compounds in which the reactivity of halogen atom in the
ascending order is [KCET (Engg.) 2002]
(b) C 2 H 5 CN and C2 H 6
(a) Vinyl chloride, chlorethane, chlorobenzene
(c) C 2 H 5 CN and C 2 H 5 CH 2 NH 2 (b) Vinyl chloride, chlorobenzene, chloroethane
(d) C 2 H 5 CN and C 2 H 5 COOH (c) Chloroethane, chlorobenzene, vinyl chloride
57. Iodoform is formed on warming I 2 and NaOH with (d) Chlorobenzene, vinyl chloride chloroethane
70. Alkyl halides react with Mg in dry ether to form
[MP PET 1995; DCE 1999; RPET 1999; RPMT 2002]
[DPMT 2000; MP PET 2001]
 1176 Halogen Containing Compounds
(a) Magnesium halide (b) Grignard’s reagent 84. AgNO 3 does not give precipitate with CHCl 3 because
(c) Alkene (d) Alkyne [MP PET 1999; CPMT 2002]
71. In the following sequence of reactions (a) CHCl 3 does not ionise in water
CH 3 CH 2CH 2 Br  ( A) 
KOH(alc)
(B) 
HBr
 (C),
KOH (aq.)
(b) AgNO3 does not reacts with CHCl 3
The product (C) is [JIPMER 2001]
(c) CHCl 3 is chemically inert
(a) Propan – 2 - ol (b) Propan – l – ol
(d) None of these
(c) Propyne (d) Propene 85. The reaction between chlorobenzene and chloral in the presence of
72. Alkyl halide on heating with alc. NH 3 in a sealed tube results…[Orissa JEE 2002] concentrated sulphuric acid produces
[Pb. PMT 2001]
(a) 1° amine (b) 2° amine
(a) Gammexane
(c) 3° amine (d) All of these
(b) p,p-dichloro diphenyl trichloro ethane
73. When CH 3 CH 2 CHCl 2 is treated with NaNH 2, the product (c) Chloropicrin
formed is [CBSE PMT 2002] (d) Benzene hexachloride
(a) CH 3  CH  CH 2 (b) CH 3  C  CH 86. False statement is [RPET 1999]
(a) Chloroform is heavier than water
(c) CH 3 CH 2 CH (NH 2 )(Cl) (d) CH 3 CH 2C(NH 2 )2 (b) CCl 4 is non-inflammable
74. By heating a mixture of CHCl 3 with silver powder, the compound (c) Vinyl chloride is more reactive than allyl chloride
formed is [Kurukshetra CET 2002]
(d) Br  is a good nucleophile as compared to I 
(a) Acetylene (b) Silver acetate 87. Chloroform is slowly oxidise by air in presence of light to form[MH CET 1999; U
(c) Methanol (d) None of these (a) Formyl chloride (b) Phosgene
75. Chloropicrin is [Kurukshetra CET 2002] (c) Trichloroacetic acid (d) Formic acid
(a) Trichloro acetaldehyde (b) Nitrochloroform 88. Alcoholic potash is used to bring about
(c) 2,4,6-trinitro phenol (d) None of these [KCET (Engg.) 2001]
76. Which of the following are correct statements about C 2 H 5 Br [Roorkee 1999] (a) Dehydrogenation (b) Dehydration
(c) Dehydrohalogenation (d) Dehalogenation
(a) It reacts with metallic Na to give ethane
(b) It gives nitroethane on heating with aqueous ethanolic solution 89. Vinyl chloride reacts with HCl to form [JIPMER 2000]
of AgNO2 (a) 1, 1- dichloro ethane
(b) 1, 2- dichloro ethane
(c) It gives C 2 H 5 OH on boiling with alcoholic potash (c) Tetrachloro ethylene
(d) It forms ethylacetate on heating with silver acetate (d) Mixture of 1, 2 and 1, 1 – dichloro ethane
77. Aryl halide is less reactive than alkyl halide towards nucleophilic
substitution because [RPMT 2002] 90. R  X  NaOH  ROH  NaX
(a) Less stable carbonium ion The above reaction is classified as
[BHU 1982; CBSE PMT 1991; RPET 2000]
(b) Due to large C  Cl bond energy
(a) Nucleophilic substitution
(c) Inductive effect
(b) Electrophilic substitution
(d) Resonance stabilization and sp 2 - hybridisation of C attached (c) Reduction
to halide (d) Oxidation
78. Methyl chloride reacts with silver acetate to yield 91. Reduction of acetyl chloride with H 2 in presence of Pd gives[MP PMT 2001]
[BVP 2003]
(a) Acetaldehyde (b) Acetyl chloride (a) CH 3 COCH 3 (b) C 2 H 5 OH
(c) Methyl acetate (d) Acetic acid (c) CH 3 COOH (d) CH 3 CHO
79. Chloroform for anesthetic purposes is tested for its purity with the
reagent [DPMT 2001] 92. When methyl bromide is heated with Zn it gives
(a) Silver nitrate (b) Lead nitrate [MP PMT 2001]
(c) Ammoniacal Cu 2 Cl 2 (d) Lead nitrate (a) CH 4 (b) C 2 H 6
80. 2, 6 - Dimethylheptane on monochlorination produces……. derivatives (c) C2 H 4 (d) CH 3 OH
[DPMT 2001]
(a) 5 (b) 6 93. Phenol reacts with CHCl 3 and NaOH (at 340 K ) to give
(c) 3 (d) 4 [MP PMT 1997; CBSE PMT 2002]
81. The less reactivity of chlorine atom in CH 2  CH  Cl is due to[DCE 2001] (a) o-chlorophenol (b) Salicylaldehyde
(a) Inductive effect (b) Resonance stabilization (c) Benzaldehyde (d) Chlorobenzene
(c) Electromeric effect (d) Electronegativity 94. Iodoform on heating with KOH gives [MP PMT 2000]
CH 3  CH 2  Br   CH 3 CH 2CN  X
alc.KCN HOH
82. (a) CH 3 CHO (b) CH 3 COOK
In this reaction, product X is [MH CET 2002] (c) HCOOK (d) HCHO
(a) Acetic acid (b) Propionic acid 95. Which reaction is correct in the conversion of chloroform to
(c) Butyric acid (d) Formic acid acetylene [Pb. PMT 2000]
83. In alkaline hydrolysis of a tertiary alkyl halide by aqueous alkali if
concentration of alkali is doubled, then the reaction (a) CHCl 3  AgNO3 (b) CHCl 3  O 2
[MH CET 2002] (c) CHCl 3  HNO 3 (d) CHCl 3  Ag
(a) Will be doubled (b) Will be halved
(c) Will remain constant (d) Can’t say 96. Which of the following gases are poisonous
[Pb. PMT 2000]
 Halogen Containing Compounds 1177

(a) CHCl 3 (b) CO 2 (c) 1-bromo-2-methylbutane

(d) 2-bromo-2-methylbutane
(c) None of these (d) CO
97. (e)MP 2-bromopentane
Which of the following alkyl halide is used as a methylating agent[KCET (Med.) 2000; PET 1999]
110. On treating a mixture of two alkyl halides with sodium metal in dry
(a) CH 3 I (b) C 2 H 5 Br ether, 2-methyl propane was obtained. The alkyl halides are[KCET 2004]
(c) C 2 H 5 Cl (d) C6 H 5 Cl (a) 2-chloropropane and chloromethane
98. C6 H 6 Cl 6 , on treatment with alcoholic KOH , yields (b) 2-chloropropane and chloroethane
[AFMC 2000] (c) Chloromethane and chloroethane
(a) C 6 H 6 (b) C 6 H 3 Cl 3 (d) Chloromethane and 1-chloropropane
111. In which case formation of butane nitrile is possible
(c) (C 6 H 6 ) OH (d) C 6 H 6 Cl 4 [Orissa JEE 2004]
99. When ethyl iodide is heated with silver nitrate, the product obtained (a) C3 H7 Br  KCN (b) C4 H 9 Br  KCN
is [CPMT 2000]
(a) C 2 H 5 Ag (b) Ag  O  NO 2 (c) C3 H7 OH  KCN (d) C4 H 9 OH  KCN

(c) C 2 H 5 O  NO 2 (d) C 2 H 5 I  NO 2 112. The reaction of an aeromatic halogen compound with an alkyl
halides in presence of sodium and ether is called
100. CHCl 3 and HF lead to the formation of a compound of fluorine of [MP PMT 2004]
molecular weight 70. The compound is (a) Wurtz reaction
[RPET 2000] (b) Sandmeyer’s reaction
(a) Fluoroform (b) Fluorine monoxide (c) Wurtz-fittig reaction
(d) Kolbe reaction
(c) Fluorine dioxide (d) Fluromethanol
113. The compound added to prevent chloroform to form phosgene gas
101. Chloroform with zinc dust in water gives [UPSEAT 2000] is [MP PET 2004]
(a) CH 4 (b) Chloropicrin (a) C2 H 5 OH (b) CH 3 COOH
(c) CCl 4 (d) CH 2 Cl 2 (c) CH 3 COCH 3 (d) CH 3 OH
102. Which of the following is used as a catalyst for preparing Grignard 114. Among the following, the one which reacts most readily with ethanol
reagent [KCET 1998] is [AIIMS 2004]
(a) Iron powder (b) Iodine powder (a) p -nitrobenzyl bromide
(c) Activated charcoal (d) Manganese dioxide (b) p-chlorobenzyl bromide
(c) p-methoxybenzyl bromide
103. For a given alkyl group the densities of the halides follow the order [MP PMT 1997]
(d) p-methylbenzyl bromide
(a) RI  RBr  RCl (b) RI  RCl  RBr 115. Chloropicrin is obtained by the reaction of
(c) RBr  RI  RCl (d) RCl  RBr  RI [CBSE PMT 2004]
104. Which halide will be least reactive in respect to hydrolysis (a) Chlorine on picric acid
(b) Nitric acid on chloroform
[MP PET 2003]
(c) Steam on carbon tetrachloride
(a) Vinyl chloride (b) Allyl chloride (d) Nitric acid on chlorobenzene
(c) Ethyl chloride (d) t-Butyl chloride 116. In Wurtz reaction alkyl halide react with [MH CET 2004]
105. In nucleophilic aliphatic substitution, the nucleophiles are generally (a) Sodium in ether (b) Sodium in dry ether
(a) Acids (b) Bases (c) Sodium only (d) Alkyl halide in ether
(c) Salts (d) Neutral molecules 117. Chloroform, when kept open, is oxidised to [CPMT 2004]
106. Which one of the following compounds does not react with bromine[DPMT 1983] (a) CO 2 (b) COCl 2
(a) Ethylamine (b) Propene (c) CO 2 , Cl 2 (d) None of these
(c) Phenol (d) Chloroform 118. Chloroform reacts with concentrated HNO 3 to give
107. Allyl chloride on dehydro chlorination gives [Pb. CET 2000]
[Kerala (Med.) 2003] (a) Water gas (b) Tear gas
(a) Propadiene (b) Propylene (c) Laughing gas (d) Producer gas
(c) Acetylchloride (d) Acetone 119. When ethyl chloride and alcoholic KOH are heated, the compound
108. Toluene reacts with excess of Cl 2 in presence of sunlight to give a obtained is [MH CET 2003]
(a)
product which on hydrolysis followed by reaction with NaOH gives[Orissa JEE 2004] C 2 H 4 (b) C 2 H 2

(c) C6 H 6 (d) C 2 H 6
COOH COONa
(a) (b) 120. Chloroform, on warming with Ag powder, gives
[MH CET 2003]
COONa (a) C2 H 6 (b) C 3 H 8
(c) (d) None of these
(c) C2 H 4 (d) C 2 H 2
Na
109. An alkyl bromide produces a single alkene when it reacts with 121. When alkyl halide is heated with dry Ag2 O , it produces
sodium ethoxide and ethanol. This alkene undergoes hydrogenation [CPMT 1997; BHU 2004]
and produces 2-methyl butane. What is the identity of the alkyl (a) Ester (b) Ether
bromide [Kerala PMT 2004] (c) Ketone (d) Alcohol
(a) 1-bromo-2, 2-dimethylpropane 122. Reaction of alkyl halides with aromatic compounds in presence of
(b) 1-bromobutane anhydrous AlCl3 is known as [UPSEAT 2004]
 1178 Halogen Containing Compounds
(a) Friedal-Craft reaction (d) To prevent its reaction with glass
(b) Hofmann degradation 135. DDT is
(c) Kolbe’s synthesis (a) A solid (b) A liquid
(d) Beckmann rearrangement (c) A gas (d) A solution
123. Two percent of ethanol is added during the oxidation of chloroform 136. Bottles containing C6 H 5 I and C6 H 5 CH 2 I lost their original
to stop the formation of carbonyl chloride. In this reaction ethanol
acts as [Pb. CET 2001]
labels. They were labelled A and B for testing. A and B were
(a) Auto catalyst (b) Negative catalyst separately taken in test tubes and boiled with NaOH solution. The
(c) Positive catalyst (d) None of these end solution in each tube was made acidic with dilute HNO 3 and
124. When benzene is heated with chlorine in the presence of sunlight, it then some AgNO 3 solution was added. Substance B give a yellow
forms [Pb. CET 2000] precipitate. Which one of the following statements is true for this
(a) B.H.C. (b) Cyclopropane experiment
(c) p-dichlorobenzene (d) None of these [AIEEE 2003]
125. Ethylene di bromide on heating with metallic sodium in ether (a) A was C6 H 5 I
solution yields [Pb. CET 2004]
(b) A was C6 H 5 CH 2 I
(a) Ethene (b) Ethyne
(c) 2-butene (d) 1-butene (c) B was C6 H 5 I
126. The reaction, CH 3 Br  Na  Product , is called (d) Addition of HNO 3 was unnecessary
[Pb. CET 2003] 137. Which of the following statements is incorrect regarding benzyl
(a) Perkin reaction (b) Levit reaction chloride [KCET 2003]
(c) Wurtz reaction (d) Aldol condensation (a) It gives white precipitate with alcoholic AgNO3
127. At normal temperature iodoform is [MP PET 2004] (b) It is an aromatic compound with substitution in the side chain
(a) Thick viscous liquid (b) Gas (c) It undergoes nucleophilic substitution reaction
(c) Volatile liquid (d) Solid (d) It is less reactive than vinyl chloride
128. Which of the following statements about benzyl chloride is incorrect[KCET 138.
2004] Alkyl halide can be converted into alkene by
(a) It is less reactive than alkyl halides [BCECE 2005]
(b) It can be oxidised to benzaldehyde by boiling with copper (a) Nucleophilic substitution reaction
nitrate solution (b) Elimination reaction
(c) It is a lachrymatory liquid and answers Beilstein’s test (c) Both nucleophilic substitution and elimination reaction
(d) It gives a white precipitate with alcoholic silver nitrate (d) Rearrangement
129. Ethylene dichloride and ethylidine chloride are isomeric compounds. 139. The major product formed in the following reaction is
The false statement about these isomers is that they [DCE 2003] CH 3
(a) React with alcoholic potash and give the same product |
CH 3  C  CH 2 Br  
CH 3 O
[AIIMS 2005]
(b) Are position isomers | CH 3 OH
(c) Contain the same percentage of chlorine H
(d) Are both hydrolysed to the same product CH 3
130. An alkyl bromide ( X) reacts with Na to form 4, 5-diethyloctane. |

Compound X is [Roorkee 1999] (a) CH 3  C  CH 2 OCH 3 (b) CH 3  C H  CH 2 CH 3

| |
(a) CH 3 (CH 2 )3 Br H OCH 3
(b) CH (CH ) Br CH 3 CH 3
3 2 5
| |
(c) CH 3 (CH 2 )3 CH .Br.CH 3 (c) CH 3  C  CH 2 (d) CH 3  C  CH 3
|
(d) CH 3 (CH 2 )2 CH .Br.CH 2 CH 3 OCH 3
131. In the following reaction X is 140. The major product obtained on treatment of
CH 3 NH 2  X  KOH  CH 3 NC (highlyoffensive odour) CH 3 CH 2 CH (F)CH 3 with CH 3 O  / CH 3 OH is
[MP PET 1994] [AIIMS 2005]
(a) CH 2 Cl 2 (b) CHCl 3 (a) CH 3 CH 2 CH (OCH 3 )CH 3
(b) CH 3 CH  CHCH 3
(c) CH 3 Cl (d) CCl 4
132. Which metal is used in Wurtz synthesis (c) CH 3 CH 2 CH  CH 2
[CPMT 1986; DPMT 1979; MP PET 2002] (d) CH 3 CH 2 CH 2 CH 2 OCH 3
(a) Ba (b) Al 141. When phenyl magnesium bromide reacts with tbutanol, the
(c) Na (d) Fe product would be [IIT 2005]
133. Which of the following is boiled with ethyl chloride to form ethyl (a) Benzene (b) Phenol
alcohol [MNR 1982]
(c) tbutyl benzene (d) tbutyl phenyl ether
(a) Alcoholic KOH (b) Aqueous KOH 142. Alkyl halides react with dialkyl copper reagents to give
(c) H 2 O (d) H 2 O 2 [AIEEE 2005]
134. Why is chloroform put into dark coloured bottles (a) Alkenes (b) Alkyl copper halides
[MP PET 2002] (c) Alkanes (d) Alkenyl halides
(a) To prevent evaporation 143. Which of the following is liquid at room temperature
(b) To prevent from moisture [AFMC 2005]
(c) To prevent it from oxidation to form phosgene (a) CH 3 I (b) CH 3 Br
 Halogen Containing Compounds 1179

(c) C2 H 5 Cl (d) CH 3 F
144. Which of the following haloalkanes is most reactive
OH
[KCET 2005] |
(a) 1-chloropropane (b) 1-bromopropane 3. The compound (CH 3 )2 .CCCl 3 is
(c) 2-chloropropane (d) 2-bromopropane (a) Chloretone (b) Chloroquin
145. Grignard reagent adds to [KCET 2005] (c) Chloropicrin (d) Chloropropyl chloride
4. Depletion of ozone layer is caused by [RPMT 2002]
(a) C O (b) C  N
(a) Freon (b) Alkane
(c) CS (d) All of the above (c) Gringard reagent (d) All of these
146. Analyse the following reaction and identify the nature of A and B 5. Which of the following is Teflon [RPMT 2002]
[Kerala CET 2005] (a) [CF2  CF2 ]n (b) CF2  CF2
(c) CF  CF (d) None of these
B 
HBr
 A
HBr 6. Statement “Ozone in atmosphere is decreased by chloro-fluoro-
hv carbon (Cl 2 F2 C) ” [RPET 1999]
Br (a) Is true
(b) Is false
(a) Both A and B are (c) Only in presence of CO 2
(d) Only in absence of CO 2
7. CFx Cl y [where x + y = 4]. These compounds are not used because
(b) Both A and B are
Br [RPET 2000]
Br (a) These are fluoro carbons
(b) These are difficult to synthesise
(c) A is & B is (c) They deplete ozone layer
Br (d) None of the these
Br
8. The molecular formula of DDT has [MP PMT 1997]
(a) 5 chlorine atoms (b) 4 chlorine atoms
(d) A is & B is (c) 3 chlorine atoms (d) 2 chlorine atoms
Br
9. What is the reagent used for testing fluoride ion in water
[EAMCET 2003]
(e) A is & B is (a) Alizarin - S (b) Quinalizarin
Br Br (c) Phenolphthalein (d) Benzene
10. Chloropicrin is used as [UPSEAT 2000]
(a) Solvent (b) Anaesthetic
Uses of Halogen Containing Compounds (c) Perfume (d) Tear gas
11. Which is used in the manufacture of plastic
(a) CH 2  CHCl (b) CH  CH
1. Which of these can be used as moth repellant
(c) CH 2  CH  CH 2 I (d) CCl 4
[CPMT 1987]
(a) Benzene hexachloride (b) Benzal chloride 12. Freon (dichlorodifluoro methane) is used
[CPMT 1986; DPMT 1983; CBSE PMT 2001]
(c) Hexachloroethane (d) Tetrachloroethane (a) As local anaesthetic
2. Which one of the following is the correct formula of (b) For dissolving impurities in metallurgical process
dichlorodiphenyl trichloroethane [AIIMS 1982] (c) In refrigerator
H Cl (d) In printing industry
| |
(a) C ––– C ––– Cl 13. Which of the following is known as freon which is used as a
Cl | refrigerant [DPMT 1982; CPMT 1979, 81, 89; AFMC 1995;
Cl Manipal MEE 1995; MP PET 1995, 2004]
(a) CCl 2 F2 (b) CHCl 3
(c) CH 2 F2 (d) CF4
Cl 14. Benzene hexachloride (BHC) is used as
H Cl [MP PMT 1994; KCET 1999]
| |
(b) C ––– C ––– Cl (a) Dye (b) Antimalerial drug
| (c) Antibiotic (d) Insecticide
Cl
15. Which plastic is obtained from CHCl 3 as follows
HF 800o C Polymerisation
H Cl CHCl 3 
 X  Y 
 Plastic
| | SbF3

(c) Cl C ––– C ––– Cl (a) Bakelite (b) Teflon

|
Cl (c) Polythene (d) Perspex

Cl
Cl Cl 16. C  CCl 3 . The above structural
| | |
(d) Cl C ––– C ––– Cl Cl H
|
Cl formula refers to [MP PET 1997]

Cl
 1180 Halogen Containing Compounds
(a) BHC (b) DNA (c) Benzyl chloride (d) Isopropyl chloride
(c) DDT (d) RNA 5. Replacement of Cl of chlorobenzene to give phenol requires drastic
17. The commercial uses of DDT and benzene hexachloride are conditions but chlorine of 2, 4-dinitrochlorobenzene is readily
(a) DDT is a herbicide, benzene hexachloride is a fungicide replaced because [CBSE PMT 1997]
(b) Both are insecticides (a) NO 2 make ring electron rich at ortho and para
(c) Both are herbicides (b) NO 2 withdraws e  from meta position
(d) DDT is a fungicide and benzene hexachloride is a herbicide
18. Which of the following is used in fire extinguishers (c) denotes e  at meta position
[AFMC 1993] (d) NO 2 withdraws e  from ortho/para positions
(a) CH 4 (b) CHCl 3 6. Among the following one with the highest percentage of chlorine is[MNR 1989; B
(c) CH 2 Cl 2 (d) CCl 4 (a) Chloral (b) Pyrene
19. Iodoform can be used as [NCERT 1981]
(c) PVC (d) Gammexene
(a) Anaesthetic (b) Antiseptic 7. In which alkyl halide, SN 2 mechanism is favoured maximum[RPMT 1997]
(c) Analgesic (d) Antifebrin (a) CH 3 Cl (b) CH 3 CH 2 Cl
20. Which of the following is an anaesthetic [AFMC 1989]
(c) (CH 3 )2 CHCl (d) (CH 3 )3 C  Cl
(a) C 2 H 4 (b) CHCl 3
8. Which conformation of C 6 H 6 Cl 6 is most powerful insecticide
(c) CH 3 Cl (d) C 2 H 5 OH (a) aaeeee (b) aaaeee
21. An important insecticide is obtained by the action of chloral on (c) aaaaee (d) aaaaaa
chlorobenzene. It is [KCET 1989] 9. The odd decomposition of carbon chlorine bond form
(a) BHC (b) Gammexene [UPSEAT 1999]
(c) DDT (d) Lindane (a) Two free ions (b) Two-carbanium ion
22. In fire extinguisher, pyrene is [DPMT 1985] (c) Two carbanion (d) A cation and an anion
(a) CO 2 (b) CCl 4 10. A new carbon-carbon bond formation is possible in
[IIT-JEE 1998]
(c) CS 2 (d) CHCl 3 (a) Cannizzaro reaction (b) Friedel-Craft's alkylation
23. B.H.C. is used as [Pb. CET 2002] (c) Clemmensen reduction (d) Reimer-Tiemann reaction
(a) Insecticide (b) Pesticide 11. An isomer of C 3 H 6 Cl 2 on boiling with aqueous KOH gives
(c) Herbicide (d) Weedicide acetone. Hence, the isomer is [UPSEAT 2000]
24. The use of the product obtained as a result of reaction between (a) 2, 2-dichloropropane (b) 1, 2-dichloropropane
acetone and chloroform is [RPMT 1999] (c) 1, 1-dichloropropane (d) 1, 3-dichloropropane
(a) Hypnotic (b) Antiseptic 12. Which of the following is the example of SN 2 reaction
(c) Germicidal (d) Anaesthetic [CPMT 1999]
25. Use of chlorofluoro carbons is not encouraged because  
[KCET 2005]
(a) CH 3 Br  OH CH 3 OH  Br

(a) They are harmful to the eyes of people that use it (b) CH 3 CHCH 3  OH  CH 3 CHCH 3  Br 
(b) They damage the refrigerators and air conditioners | |
(c) They eat away the ozone in the atmosphere Br OH
(d) They destroy the oxygen layer H O
(c) CH 3 CH 2 OH 
2
 CH 2  CH 2
CH 3 CH 3
| |
(d) CH 3  C  CH 3  OH   CH 3  C  O  CH 3  Br 
| |
Br H
13. Wurtz reaction of methyl iodide yields an organic compound X.
Which one of the following reactions also yields X
1. Among the following, the molecule with the highest dipole moment [EAMCET 2003]
is [IIT-JEE (Screening) 2003]
dryether
(a) CH 3 Cl (b) CH 2 Cl 2 (a) C 2 H 5 Cl  Mg 

(c) CHCl 3 (d) CCl 4 (b) C 2 H 5 Cl  LiAlH4 

2. When CHCl is boiled with NaOH, It gives
3 (c) C 2 H 5 Cl  C 2 H 5 ONa 
[Orissa JEE 2003]
(a) Formic acid (b) Trihydroxy methane (d) CHCl 3  
Ag powder

(c) Acetylene (d) Sodium formate 14. Ethyl orthoformate is formed by heating with sodium ethoxide[EAMCET 2003]
3. The hybridization state of carbon atoms in the product formed by
the reaction of ethyl chloride with aqueous potassium hydroxide is [EAMCET 1997] (a) CHCl 3 (b) C 2 H 5 OH

(a) sp (b) sp 2 (c) HCOOH (d) CH 3 CHO

15. 1 , 2 di-bromo cyclohexane on dehydro halogenation gives
(c) sp 3 (d) sp 3 d [UPSEAT 2003]
4. Which of the following compounds does not undergo nucleophilic
substitution reactions [KCET 1998] (a) (b)
(a) Vinyl chloride (b) Ethyl bromide
 Halogen Containing Compounds 1181

(c) (d) None of these

1. Assertion : CHCl 3 is stored in transparent bottles.
16. In which one of the following conversions phosphorus pentachloride
is used as a reagent [EAMCET 1997] Reason : CHCl 3 is oxidised in dark. [AIIMS 1996]
(a) H 2 C  CH 2  CH 3 CH 2 Cl 2. Assertion : Addition of bromine to trans-2-butene yields meso-
2, 3-dibromobutane
(b) H 3 C  O  CH 3  CH 3 Cl Reason : Bromine addition to an alkene is an electrophilic
addition.
(c) CH 3 CH 2 OH  CH 3 CH 2 Cl
[IIT-JEE (Screening) 2001]
(d) HC  CH  CH 2  CHCl 3. Assertion : Alkyl halides are soluble in organic solvents.
17. When but –3-en -2- ol reacts with aq. HBr, the product formed is[DCE 2001] Reason : p-dichlorobenzene possesses low melting point.
(a) 3 - bromobut - 1- ene 4. Assertion : CCl 4 is not a fire extinguisher.
(b) 1 - bromobut - 2- ene Reason : CCl 4 is insoluble in water.
(c) A mixture of both a and b 5. Assertion : Aqueous hydrohalogen acids are used to prepare
(d) 2 - bromobut - 2 - ene alkyl halides from alkenes.
18. Which of these do not form Grignard reagent Reason : Hydrogen iodide readily reacts with alkenes to form
(a) CH 3 F (b) CH 3 Cl alkyl halides.
6. Assertion : Alkyl halides form alkenes when heated above
(c) CH 3 Br (d) CH 3 I 300°C.
19. An organic compound A(C4 H 6 Cl) on reaction with Na/diethyl Reason : CH 3 CH 2 I react slowly with strong base when
ether gives a hydrocarbon, which on monochlorination gives only compared to CD 3 CH 2 I .
one chloro derivative. A is
[Kerala PMT 2004] 7. Assertion : Halogen acids react with alcohols to form
(a) t-butyl chloride (b) s-butyl chloride haloalkanes.
(c) Isobutyl chloride (d) n-butyl chloride Reason : Order of reactivity of halogen acids
(e) None of these HCl > HBr > HI
20. Among the following the most reactive towards alcoholic KOH is[AIIMS 2004] CH3 Cl
(a) CH 2  CHBr (b) CH 3 COCH 2 CH 2 Br 8. Assertion : Cl is less reactive than towards
(c) CH 3 CH 2 Br (d) CH 3 CH 2 CH 2 Br reactions.
21. Which one of the following possess highest m.pt. Reason : Tertiary alkyl halides react predominantly by S N 1
[Pb. CET 2004] mechanism.
(a) Chlorobenzene (b) o-dichlorobenzene 9. Assertion : Electron withdrawing groups in aryl halides
(c) m-dichlorobenzene (d) p-dichlorobenzene decrease the reactivity towards nucleophilic
22. Which chlorine atom is more electronegative in the following substitution.
[UPSEAT 2004] Reason : 2, 4-Dinitrochlorobenzene is less reactive than
chlorobenzene.
(a) CH 3  Cl (b) CH 3  CH 2  Cl
10. Assertion : Aryl halides undergo electrophilic substitutions
CH 3 CH 3 more readily than benzene.
| | Reason : Aryl halide gives a mixture of o- and p- products.
(c) H  C  Cl (d) CH 3  CH 2  C  Cl 11. Assertion : Addition of Br2 to cis-but-2-ene is stereoselective.
| |
CH 3 CH 3
Reason : SN 2 reactions are stereospecific as well as
23. What would be the product formed when 1-Bromo-3-chloro stereoselective.
cyclobutane reacts with two equivalents of metallic sodium in ether[IIT-JEE 12.
(Screening) 2005]
Assertion : Optically active 2-iodobutane on treatment with NaI
Cl in acetone undergoes recemization.
(a) (b) Reason : Repeated Walden inversions on the reactant and its
product eventually gives a racemic mixture.
Br 13. Assertion : Nucleophilic substitution reaction on an optically
(c) (d) active alkyl halide gives a mixture of enantiomers.
Reason : The reaction occurs by SN 1 mechanism.

Read the assertion and reason carefully to mark the correct option out of
the options given below:
(a) If both assertion and reason are true and the reason is the correct Introduction of Halogen containing compounds
explanation of the assertion.
(b) If both assertion and reason are true but reason is not the correct 1 a 2 b 3 b 4 c 5 b
explanation of the assertion.
(c) If assertion is true but reason is false. 6 a 7 b 8 a 9 b 10 a
(d) If the assertion and reason both are false. 11 d 12 a 13 b
(e) If assertion is false but reason is true.
 1182 Halogen Containing Compounds

1 c 2 a 3 a 4 a 5 a
Preparation of Halogen containing compounds
6 a 7 c 8 a 9 a 10 d
1 b 2 d 3 b 4 a 5 a 11 a 12 c 13 a 14 d 15 b
6 b 7 d 8 d 9 b 10 a 16 c 17 b 18 d 19 b 20 b
11 a 12 b 13 a 14 a 15 a 21 c 22 b 23 a 24 a 25 c
16 b 17 a 18 b 19 c 20 c
21 a 22 c 23 c 24 b 25 d
26 d 27 c 28 a 29 c 30 b
31 c 32 b 33 d 34 a 35 c
36 d 37 c 38 b 39 b 40 d
41 c 42 c 43 a 44 b 45 b
46 a 47 c 48 a 49 b 50 a
51 b 52 a 53 d 54 a

Properties of Halogen containing compounds

1 a 2 c 3 c 4 c 5 c
6 c 7 c 8 c 9 b 10 d
11 b 12 c 13 a 14 a 15 d
16 b 17 c 18 b 19 b 20 d
21 d 22 c 23 b 24 a 25 b
26 c 27 d 28 b 29 a 30 b
31 c 32 c 33 b 34 a 35 a
36 a 37 a 38 a 39 a 40 a
41 a 42 c 43 b 44 c 45 d
46 c 47 b 48 ab 49 b 50 b
51 a 52 a 53 b 54 b 55 a
56 d 57 a 58 b 59 b 60 b
61 c,d 62 c 63 c 64 c 65 b
66 c 67 c 68 a 69 d 70 b
71 a 72 d 73 d 74 a 75 b
76 b,d 77 d 78 c 79 a 80 d
81 b 82 b 83 c 84 a 85 b
86 cd 87 b 88 c 89 a 90 a
91 d 92 b 93 b 94 c 95 d
96 d 97 a 98 b 99 c 100 a
101 a 102 b 103 d 104 a 105 b
106 d 107 a 108 b 109 c 110 a
111 a 112 c 113 a 114 c 115 b
116 a 117 b 118 b 119 a 120 d
121 b 122 a 123 b 124 a 125 c
126 c 127 d 128 a 129 d 130 d
131 b 132 c 133 b 134 c 135 a
136 a 137 d 138 b 139 d 140 b
141 a 142 c 143 a 144 d 145 d
146 c

Uses of Halogen containing compounds