1170 Halogen Containing Compounds

13. The compound which contains all the four 1 o ,2 o ,3 o and

4o carbon atoms is [J & K 2005]
(a) 2, 3-dimethyl pentane
(b) 3-chloro-2, 3-dimethylpentane
(c) 2, 3, 4-trimethylpentane
(d) 3, 3-dimethylpentane
Introduction of Halogen containing compounds
Preparation of Halogen containing compounds
1. How many structural isomers are possible for a
compound with molecular formula C 3 H 7 Cl [MH CET 2001] 1. The following reaction is known as
(a) 2 (b) 5 C 2 H 5 OH  SOCl 2   C 2 H 5 Cl  SO 2  HCl
Pyridine

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

(d) 1, 1-phenyl-6, 6-chlorohexane (a) CH 3  Br (b) CH 3 COI

9. Number of   bonds present in B.H.C. (Benzene (c) CH 3 COOH (d) None of these
hexachloride) are [RPMT 1999] Cl
(a) 6 (b) Zero
(c) 3 (d) 12 6. Diazonium salts  Cu 2 Cl 2  HCl  , the reaction
10. The general formula for alkyl halides is
(a) C n H 2n 1 X (b) C n H 2n  2 X is known as [Kerala (Med.) 2002]
(a) Chlorination (b) Sandmeyer’s reaction
(c) C n H n 1 X (d) C n H 2n X
(c) Perkin reaction (d) Substitution reaction
11. Which of the following is a primary halide [DCE 2004] 7. When ethyl alcohol (C 2 H 5 OH ) reacts with thionyl
(a) Isopropyl iodide (b) Secondary butyl iodide
chloride, in the presence of pyridine, the product
(c) Tertiary butyl bromide (d) Neo hexyl chloride obtained is
12. Full name of DDT is [KCET 1993] [AIIMS; CBSE PMT 2001]
(a) 1, 1, 1-trichloro-2, 2-bis(p-chlorophenyl) ethane (a) CH 3 CH 2 Cl  HCl
(b) 1, 1-dichloro-2, 2-diphenyl trimethylethane
(b) C 2 H 5 Cl  HCl  SO 2
(c) 1, 1-dichloro-2, 2-diphenyl trichloroethane
(d) None of these (c) CH 3 CH 2 Cl  H 2 O  SO 2
(d) CH 3 CH 2 Cl  HCl  SO 2
 Halogen Containing Compounds 1171

8. Preparation of alkyl halides in laboratory is least In the above reaction, the reactivity of different alcohols is
preferred by [DPMT 2000] [CPMT 1997]
(a) Treatment of alcohols (a) Tertiary > Secondary > Primary
(b) Tertiary < Secondary < Primary
(b) Addition of hydrogen halides to alkenes
(c) Tertiary < Secondary > Primary
(c) Halide exchange (d) Secondary < Primary < Tertiary
(d) Direct halogenation of alkanes
18. C 6 H 6  Cl 2  
UV Light
Product. In above reaction
9. Which of the following organic compounds will give a
product is [CPMT 1997]
mixture of 1-chlorobutane and 2-chlorobutane on
chlorination [CPMT 2001] (a) CCl 3 CHO (b) C 6 H 6 Cl 6
(a) CH 3  CH  CH  CH 2 (c) C 6 H 12 Cl 6 (d) C 6 H 9 Cl 2
|
19. Benzene reacts with chlorine to form benzene
CH 3
hexachloride in presence of [MP PET 1999]
H (a) Nickel (b) AlCl3
|
(b) HC  C  C  CH 2 (c) Bright sunlight (d) Zinc
20. The final product obtained by distilling ethyl alcohol with
(c) CH 2  CH  CH  CH 2 the excess of chlorine and Ca(OH ) 2 is [MP PET 1996]
(d) CH 2  CH  CH 2  CH 3 (a) CH 3 CHO (b) CCl 3 CHO
10. The chlorobenzene is generally obtained from a (c) CHCl 3 (d) (CH 3 ) 2 O
corresponding diazonium salt by reacting it with 21. When ethyl alcohol and KI reacted in presence of
[MP PMT 2000] Na 2 CO 3 , yellow crystals of...... are formed [AFMC 1989]
(a) Cu 2 Cl 2 (b) CuSO 4 (a) CHI 3 (b) CH 3 I
(c) Cu (d) Cu (NH 3 )42  (c) CH 2 I 2 (d) C 2 H 5 I
11. Decreasing order of reactivity of HX in the reaction 22. In preparation of CHCl 3 from ethanol and bleaching
ROH  HX  RX  H 2 O powder, the latter provides [BHU 1986]
[RPET 2000; AIIMS 1983; MP PET 1996]
(a) Ca(OH ) 2 (b) Cl 2
(a) HI  HBr  HCl  HF (b) HBr  HCl  HI  HF (c) Both (a) and (b) (d) None of these
23. Which one of the following processes does not occur
(c) HCl  HBr  HI  HF (d) HF  HBr  HCl  HI during formation of CHCl 3 from C 2 H 5 OH and
12. The product of the following reaction :
bleaching powder
CH 2  CH  CCl 3  HBr [RPET 2000] [DPMT 1984]
(a) CH 3  CH (Br)  CCl 3 (b) CH 2 (Br)  CH 2  CCl 3 (a) Hydrolysis (b) Oxidation
(c) Reduction (d) Chlorination
(c) BrCH 2  CHCl  CHCl 2 (d) CH 3  CH 2  CCl 3 24. Which of the following is obtained when chloral is boiled
13. Chlorobenzene is prepared commercially by with NaOH [CBSE PMT 1991; RPMT 1999]
[JIPMER 2000; CPMT 1976; Pb. CET 2002] (a) CH 3 Cl (b) CHCl 3
(a) Raschig process (b) Wurtz Fitting reaction (c) CCl 4 (d) None of these
(c) Friedel-Craft’s reaction (d) Grignard reaction 25. Chloroform can be obtained from [MNR 1986]
14. In methyl alcohol solution, bromine reacts with ethylene (a) Methanol (b) Methanal
to yield BrCH 2 CH 2 OCH 3 in addition to 1, 2- (c) Propanol-1 (d) Propanol-2
dibromoethane because [Pb. PMT 1998] 26. Chlorine reacts with ethanol to give
[MP PMT 1989; CPMT 1997; KCET 1998; JIPMER 1999]

(a) The ion formed initially may react with Br or (a) Ethyl chloride (b) Chloroform
CH 3 OH (c) Acetaldehyde (d) Chloral
(b) The methyl alcohol solvates the bromine 27. On heating diethyl ether with conc. HI, 2 moles of which
of the following is formed
(c) The reaction follows Markownikoff's rule
[IIT-JEE 1983; MP PET 1990; EAMCET 1990;
(d) This is a free-radical mechanism AFMC 1993; JIPMER 2001]
15. C3 H 8  Cl 2   C3 H7 Cl  HCl is an example of
Light (a) Ethanol (b) Iodoform
(c) Ethyl iodide (d) Methyl iodide
which of the following types of reactions
28. Lucas reagent is [MP PMT 1996; MP PET 1992, 95;
[AFMC 1997; CPMT 1999]
CPMT 1986, 89; AIIMS 1980; Kurukshetra CEE 2002]
(a) Substitution (b) Elimination (a) Concentrated HCl  anhydrous ZnCl 2
(c) Addition (d) Rearrangement
(b) Dilute HCl  hydrated ZnCl 2
16. Which of the following would be produced when acetylene
reacts with HCl [MH CET 1999] (c) Concentrated HNO 3  anhydrous ZnCl 2
(a) CH 3 CH 2 Cl (b) CH 3 CHCl 2 (d) Concentrated HCl  anhydrous MgCl2
(c) CHCl  CHCl (d) CH 2  CHCl 29. Which compound does not form iodoform with alkali and
iodine [IIT-JEE 1985]
17. R  OH  HX  R  X  H 2 O
 1172 Halogen Containing Compounds
(a) Acetone (b) Ethanol (c) Gammexane (d) DDT
(c) Diethyl ketone (d) Isopropyl alcohol 42. Which of the following acids adds to propene in the
30. Which compound gives yellow ppt. with iodine and alkali presence of peroxide to give anti-Markownikoff’s product
[IIT-JEE 1984] [MP PET 2003]
(a) 2-hydroxy propane (b) Acetophenone (a) HF (b) HCl
(c) Methyl acetone (d) Acetamide (c) HBr (d) HI
31. Acetone reacts with I 2 in presence of NaOH to form 43. Propene on treatment with HBr gives [CPMT 1986]
(a) Isopropyl bromide (b) Propyl bromide
[MP PMT 1992]
(c) 1, 2-dibromoethane (d) None of the above
(a) C 2 H 5 I (b) C 2 H 4 I 2
44. The catalyst used in Raschig's process is
(c) CHI 3 (d) CH 3 I (a) LiAlH4 (b) Copper chloride
32. Ethanol is converted into ethyl chloride by reacting with
(c) Sunlight (d) Ethanol Na
[MP PET 1991; MP PMT 1990; BHU 1997]
(a) Cl 2 (b) SOCl 2 45. The compound formed on heating chlorobenzene with
chloral in the presence of concentrated sulphuric acid, is
(c) HCl (d) NaCl [AIEEE 2004]
33. C 6 H 5 Cl prepared by aniline with [IIT-JEE 1984] (a) Freon (b) DDT
(a) HCl (c) Gammexene (d) Hexachloroethane
(b) Cu 2 Cl 2 46. Acetone is mixed with bleaching powder to give
(c) Cl 2 in presence of anhydrous AlCl3 [AFMC 2004]
(a) Chloroform (b) Acetaldehyde
(d) HNO 2 and then heated with Cu 2 Cl 2
(c) Ethanol (d) Phosgene
34. The starting substance for the preparation of CH 3 I is 47. Which of the following compounds gives
[CPMT 1975] trichloromethane on distilling with bleaching powder
(a) CH 3 OH (b) C 2 H 5 OH [KCET 2004; EAMCET 1986]
(a) Methanal (b) Phenol
(c) CH 3 CHO (d) (CH 3 )2 CO
(c) Ethanol (d) Methanol
35. A Grignard's reagent may be made by reacting 48. The product formed on reaction of ethyl alcohol with
magnesium with [CPMT 1973, 83, 84] bleaching powder is[Orissa JEE 2004; DPMT 1978; AIIMS 1991]
(a) Methyl amine (b) Diethyl ether (a) CHCl 3 (b) CCl 3 CHO
(c) Ethyl iodide (d) Ethyl alcohol
(c) CH 3 COCH 3 (d) CH 3 CHO
36. Which of the following is responsible for iodoform
reaction 49. Ethylene reacts with bromine to form [Pb. CET 2000]
[CPMT 1980; RPMT 1997] (a) Chloroethane (b) Ethylene dibromide
(a) Formalin (b) Methanol (c) Cyclohexane (d) 1-bromo propane
(c) Acetic acid (d) Ethanol 50. Best method of preparing alkyl chloride is [MH CET 2004]
37. When a solution of sodium chloride containing ethyl (a) ROH  SOCl 2 
alcohol is electrolysed, it forms (b) ROH  PCl5 

(a) Ethyl alcohol (b) Chloral
(c) Chloroform (d) Acetaldehyde (c) ROH  PCl3 

38. Which reagent cannot be used to prepare an alkyl halide (d) ROH  HCl  
anhy. ZnCl
2

from an alcohol [CPMT 1989, 94] 51. DDT is prepared by reacting chlorobenzene with
(a) HCl  ZnCl2 (b) NaCl [BHU 1998, 2005]

(c) PCl5 (d) SOCl 3 (a) CCl 4 (b) CCl 3  CHO

(c) CHCl 3 (d) Ethane
39. Ethyl benzoate reacts with PCl5 to give [KCET 2003]
52. Which compound needs chloral in its synthesis
(a) C 2 H 5 Cl  C6 H 5 COCl  POCl3  HCl [Pb. PET 2003]
(b) C 2 H 5 Cl  C6 H 5 COCl  POCl3 (a) D. D. T. (b) Gammexane
(c) Chloroform (d) Michler’s Ketone
(c) CH 3 COCl  C6 H 5 COCl  POCl3
53. To get DDT, chlorobenzene has to react with which of the
(d) C 2 H 5 Cl  C6 H 5 COOH  POCl3 following compounds in the presence of concentrated
sulphuric acid [KCET (Engg/Med.) 2001]
40. On treatment with chlorine in presence of sunlight,
(a) Trichloroethane (b) Dichloroacetone
toluene giv.es the product
(c) Dichloroacetaldehyde (d) Trichloroacetaldehyde
[Orissa JEE 2003; MH CET 1999, 2002]
54. What will be the product in the following reaction
(a) o-chloro toluene (b) 2, 5-dichloro toluene
CH2
(c) p-chloro toluene (d) Benzyl chloride NBS [BHU 2005]
41. When chlorine is passed through warm benzene in
presence of the sunlight, the product obtained is[KCET 2003] B
r CH3 CH3
(a) Benzotrichloride (b) Chlorobenzene

B
r
 Halogen Containing Compounds 1173

(a) (b) 8. A mixture of two organic chlorine compounds was treated

with sodium metal in ether solution. Isobutane was
CH3 obtained as a product. The two chlorine compounds are[KCET 198
CH2Br
(a) Methyl chloride and propyl chloride
(c) (d)
(b) Methyl chloride and ethyl chloride
B (c) Isopropyl chloride and methyl chloride
r (d) Isopropyl chloride and ethyl chloride
Properties of Halogen containing compounds 9. Alkyl halides can be converted into Grignard reagents by
CCl3 [KCET 1989]
(a) Boiling them with Mg ribbon in alcoholic solution
1.   A. Compounds A is
1 eqv. of Br2 / Fe
(b) Warming them with magnesium powder in dry ether
[Orissa JEE 2005]
(c) Refluxing them with MgCl2 solution
CCl3 CCl3
(d) Warming them with MgCl2
Br
(a) (b) 10. Which is not present in Grignard reagent
Br [CBSE PMT 1991]
(a) Methyl group (b) Magnesium
CCl3 CCl3
(c) Halogen (d) COOH group
(c) (d) 11. The reactivity of ethyl chloride is [KCET 1986]

Br Br (a) More or less equal to that of benzyl chloride

Br (b) More than that of benzyl chloride
2. Ethyl bromide can be converted into ethyl alcohol by (c) More or less equal to that of chlorobenzene
[KCET 1989] (d) Less than that of chlorobenzene
(a) Heating with dilute hydrochloric acid and zinc 12. The reactivity of halogen atom is minimum in[KCET 1985]
(b) Boiling with an alcoholic solution of KOH (a) Propyl chloride (b) Propyl iodide
(c) The action of moist silver oxide (c) Isopropyl chloride (d) Isopropyl bromide
(d) Refluxing methanol 13. Chlorobenzene is
3. Reaction of ethyl chloride with sodium leads to (a) Less reactive than benzyl chloride
[NCERT 1984] (b) More reactive than ethyl bromide
(a) Ethane (b) Propane (c) Nearly as reactive as methyl chloride
(c) n-butane (d) n-pentane (d) More reactive than isopropyl chloride
4. Treatment of ammonia with excess of ethyl chloride will 14. The reactivities of methyl chloride, propyl chloride and
yield [AIIMS 1992] chlorobenzene are in the order [KCET 1988]
(a) Diethyl amine (a) Methyl chloride > propyl chloride > chlorobenzene
(b) Ethane (b) Propyl chloride > methyl chloride > chlorobenzene
(c) Tetraethyl ammonium chloride (c) Methyl chloride > chlorobenzene > propyl chloride
(d) Methyl amine (d) Chlorobenzene > propyl chloride > methyl chloride
5. 2CHCl 3  O 2 
X
2COCl 2  2 HCl 15. Which of the following compound will make precipitate
most readily with AgNO 3 [CPMT 1992]
In the above reaction, X stands for [CPMT 1985]
(a) CCl 3 CHO (b) CHCl 3
(a) An oxidant (b) A reductant
(c) Light and air (d) None of these (c) C 6 H 5 CH 2 Cl (d) CHI 3
6. Phosgene is the common name for 16. Carbylamine is liberated when..... is heated with
[DPMT 1983; CPMT 1993; MP PMT 1994; chloroform and alcoholic potash [KCET 1992]
Kurukshetra CEE 1998; RPMT 2000, 02] (a) An aldehyde (b) A primary amine
(a) CO 2 and PH 3 (b) Phosphoryl chloride (c) A secondary amine (d) A phenol
17. Salicylic acid can be prepared using Reimer-Tiemann's
(c) Carbonyl chloride (d) Carbon tetrachloride
reaction by treating phenol with [KCET 1989]
7. When chloroform is treated with amine and KOH, we get (a) Methyl chloride in the presence of anhydrous
[CPMT 1979] aluminium chloride
(a) Rose odour smell (b) Carbon dioxide under pressure in sodium hydroxide
(b) Sour almond like smell solution
(c) Carbon tetrachloride and concentrated sodium
(c) Offensive odour
hydroxide
(d) Sour oil of winter green like smell (d) Sodium nitrite and a few drops of concentrated
sulphuric acid
 1174 Halogen Containing Compounds
18. Grignard reagent is prepared by the reaction between (c) Hoffmann-Saytzeff product
[CBSE PMT 1994; DPMT 1996; Pb. PMT 1999; (d) Markownikoff product
MH CET 1999] 29. Ethylene difluoride on hydrolysis gives
(a) Zinc and alkyl halide (a) Glycol (b) Fluoroethanol
(b) Magnesium and alkyl halide (c) Difluoroethanol (d) Freon
(c) Magnesium and alkane
30. Benzyl chloride when oxidised by pb(NO 3 ) 2 gives
(d) Magnesium and aromatic hydrocarbon
19. Reaction of t-butyl bromide with sodium methoxide [MP PMT 1989]
produces [CBSE PMT 1994] (a) Benzoic acid (b) Benzaldehyde
(a) Isobutane (b) Isobutylene (c) Benzene (d) None
(c) Sodium t-butoxide (d) t-butyl methyl ether 31. Which of the following statements about chloroform is
20. War gas is formed from [BHU 1995] false
(a) PH 3 (b) C 2 H 2 [Manipal MEE 1995]
(a) It is a colourless, sweet-smelling liquid
(c) Zinc phosphate (d) Chloropicrin
(b) It is almost insoluble in water
21. What happens when CCl 4 is treated with AgNO 3
(c) It is highly inflammable
[EAMCET 1987; CBSE PMT 1988; MP PET 2000]
(d) It can be used as an inhalational anaesthetic agent
(a) NO 2 will be evolved
32. CCl 4 cannot give precipitate with AgNO 3 due to
(b) A white ppt. of AgCl will be formed [CPMT 1979]
(c) CCl 4 will dissolve in AgNO 3 (a) Formation of complex with AgNO 3
(d) Nothing will happen (b) Evolution of Cl 2 gas
22. If we use pyrene (CCl 4 ) in the Riemer-Tiemann reaction
(c) Chloride ion is not formed
in place of chloroform, the product formed is
(d) AgNO 3 does not give silver ion
[CBSE PMT 1989; MP PMT 1990; MH CET 1999]
(a) Salicylaldehyde (b) Phenolphthalein 33. On heating CHCl 3 with aq. NaOH, the product is
(c) Salicylic acid (d) Cyclohexanol [CPMT 1971, 78; BHU 1997; EAMCET 1998;
23. C 6 H 5 CH 2 Cl  KCN (aq.)  X  Y JIPMER (Med.) 2002]
Compounds X and Y are [BHU 1979] (a) CH 3 COONa (b) HCOONa
(a) C 6 H 6  KCl (b) C 6 H 5 CH 2 CN  KCl (c) Sodium oxalate (d) CH 3 OH
(c) C 6 H 5 CH 3  KCl (d) None of these 34. Ethyl bromide reacts with lead-sodium alloy to form
24. The bad smelling substance formed by the action of [MP PMT/PET 1988; MP PET 1997]
alcoholic caustic potash on chloroform and aniline is (a) Tetraethyl lead (b) Tetraethyl bromide
[MP PMT 1971, 92, 2001; CPMT 1971, 86; AFMC 2002; (c) Both (a) and (b) (d) None of the above
RPMT 1999] 35. Iodoform heated with Ag powder to form [DPMT 1985]
(a) Phenyl isocyanide (b) Nitrobenzene (a) Acetylene (b) Ethylene
(c) Phenyl cyanide (d) Phenyl isocyanate (c) Methane (d) Ethane
25. Ethylidene chloride on treatment with aqueous KOH
36. Ethyl bromide reacts with silver nitrite to form
gives
[DPMT 1985; IIT-JEE 1991]
[MP PMT 1986]
(a) Nitroethane
(a) Ethylene glycol (b) Acetaldehyde
(c) Formaldehyde (d) None (b) Nitroethane and ethyl nitrite
26. Reaction (c) Ethyl nitrite
C 2 H 5 I  C 5 H 11 I  2 Na  C 2 H 5  C 5 H 11  2 NaI is (d) Ethane
called 37. Which of the following reactions leads to the formation of
chloritone [RPMT 2003]
[MP PMT 1992]
(a) Hoffmann's reaction (a) CHCl 3  CH 3 COCH 3 (b) CCl 4  Acetone
(b) Dow's reaction (c) CHCl 3  KOH (d) CHCl 3  HNO 3
(c) Wurtz's reaction
38. CH 3  CH 2  CH 2 Br  KOH (alc.)  Product Product in
(d) Riemer-Tiemann's reaction
above reaction is [RPMT 2003]
27. In presence of AlCl3 , benzene and n-propyl bromide
(a) CH 3  CH  CH 2 (b) CH 3  CH 2  CH 3
react in Friedal-Craft's reaction to form [MP PMT 1991]
(a) n-propyl benzene (c) (a) and (b) both (d) None of these
(b) 1, 2-dinormal propyl benzene 39. A  CCl 4  KOH  Salicylic acid
(c) 1, 4-dinormal propyl benzene ‘A’ in above reaction is [RPMT 2003]
(d) Isopropyl benzene
OH NO 2
28. The dehydrobromination of 2-bromobutane gives
CH 3 CH  CHCH 3 . The product is
(a) (b)
(a) Hofmann product
(b) Saytzeff product
 Halogen Containing Compounds 1175

CHO (d) C 2 H 5 Br with AgCN forms ethyl isocyanide

49. When chloroform is exposed to air and sunlight, it gives
(c) (d) [NCERT 1984; CPMT 1978, 87; CBSE PMT 1990;
EAMCET 1993; MNR 1994; MP PET 1997, 2000;
BHU 2001; AFMC 2002]
40. Identify X and Y in the following sequence
(a) Carbon tetrachloride (b) Carbonyl chloride
C2 H 5 Br 
X
product 
Y
C3 H 7 NH 2 (c) Mustard gas (d) Lewsite
[Orissa JEE 2005] 50. An organic halide is shaken with aqueous NaOH
(a) X  KCN , Y  LiAlH4 followed by the addition of dil. HNO 3 and silver nitrate
solution gave white ppt. The substance can be[JIPMER 1997]
(b) X  KCN , Y  H 3 O 
(a) C 6 H 4 (CH 3 )Br (b) C 6 H 5 CH 2 Cl
(c) X  CH 3 Cl, Y  AlCl3 / HCl
(c) C 6 H 5 Cl (d) None of these
(d) X  CH 3 NH 2 , Y  HNO 2
51. A compound A has a molecular formula C2Cl3 OH . It
41. 1-chlorobutane reacts with alcoholic KOH to form reduces Fehling solution and on oxidation gives a
[IIT-JEE 1991; AFMC 1998] monocarboxylic acid (B). A is obtained by action of
(a) 1-butene (b) 2-butane chlorine on ethyl alcohol. A is
(c) 1-butanol (d) 2-butanol [CBSE PMT 1994; MP PET 1997; KCET 2005]
42. Which of the following reactions gives (a) Chloral (b) CHCl 3
H 2 C  C  C  CH 2 [Roorkee Qualifying 1998] (c) CH 3 Cl (d) Chloroacetic acid
(a) CH 2 Br  CBr  CH 2 
Zn / Ch 3 OH
52. Following equation illustrates

(b) HC  C  CH 2  COOH  Aq. K 2 CO 3

200 250 C
C6 H 5 Cl  2 NaOH   C6 H 5 OH  NaCl  H 2 O
o
40 o C
200atm
(c) CH 2 Br  C  C  CH 2 Br 

Zn
Heat
[Bihar CEE 1995]
(d) 2CH 2  CH  CH 2 I 
(a) Dow's process (b) Kolbe's process
43. When ethyl amine is heated with chloroform and (c) Carbylamine test (d) Haloform reaction
alcoholic KOH, a compound with offensive smell is 53. One of the following that cannot undergo dehydro-
obtained. This compound is [CPMT 1983, 84; RPMT 2002] halogenation is [J & K 2005]
(a) A secondary amine (b) An isocyanide (a) Iso-propyl bromide (b) Ethanol
(c) A cyanide (d) An acid (c) Ethyl bromide (d) None of these
44. Chlorobenzene on fusing with solid NaOH gives 54. A compound X on reaction with chloroform and NaOH
[DPMT 1981; CPMT 1990] gives a compound with a very unpleasant odour. X is
[MP PMT 1999]
(a) Benzene (b) Benzoic acid
(c) Phenol (d) Benzene chloride (a) C 6 H 5 CONH 2 (b) C 6 H 5 NH 2
45. DDT can be prepared by reacting chlorobenzene (in the (c) C 6 H 5 CH 2 NHCH 3 (d) C 6 H 5 NHCH 3
presence of conc. H 2 SO 4 ) with
OH
(a) Cl 2 in ultraviolet light (b) Chloroform O C2 H 5

(c) Trichloroacetone (d) Chloral hydrate 55.  C 2 H 5 I   P roduct

Anhydrous (C H OH )
2 5

46. When phenol reacts with CHCl 3 and KOH, the product
obtained would be [RPMT 1997] In the above reaction product is
(a) Salicylaldehyde (b) p-hydroxy benzaldehyde
(a) C6 H 5 OC2 H 5 (b) C 2 H 5 OC2 H 5
(c) Both (a) and (b) (d) Chloretone
47. Ethyl chloride on heating with silver cyanide forms a (c) C6 H 5 OC6 H 5 (d) C6 H 5 I
compound X. The functional isomer of X is
56. C 2 H 5 Cl  KCN  X 
 Y . 'X' and 'Y' are
Hydrolysis
[EAMCET 1997; KCET 2005]
[MP PET 1995]
(a) C 2 H 5 NC (b) C 2 H 5 CN
(a) C 2 H 6 and C 2 H 5 CN
(c) H 3 C  NH  CH 3 (d) C 2 H 5 NH 2
(b) C 2 H 5 CN and C2 H 6
48. Which of the following statements is incorrect [CPMT 1977]
(c) C 2 H 5 CN and C 2 H 5 CH 2 NH 2
(a) C 2 H 5 Br reacts with alco. KOH to form C 2 H 5 OH
(d) C 2 H 5 CN and C 2 H 5 COOH
(b) C 2 H 5 Br when treated with metallic sodium gives
ethane 57. Iodoform is formed on warming I 2 and NaOH with
(c) C 2 H 5 Br when treated with sodium ethoxide forms [MP PET 1995; DCE 1999; RPET 1999; RPMT 2002]
(a) C 2 H 5 OH (b) CH 3 OH
diethyl ether
 1176 Halogen Containing Compounds
(c) HCOOH (d) C 6 H 6 (d) Chlorobenzene, vinyl chloride chloroethane
58. Which of the following reacts with phenol to give 70. Alkyl halides react with Mg in dry ether to form
salicylaldehyde after hydrolysis [MP PMT 1995] [DPMT 2000; MP PET 2001]
(a) Dichloromethane (b) Trichloromethane (a) Magnesium halide (b) Grignard’s reagent
(c) Methyl chloride (d) None of these (c) Alkene (d) Alkyne
59. Dehydrohalogenation in monohaloalkanes produces 71. In the following sequence of reactions
(a) A single bond (b) A double bond
CH 3 CH 2CH 2 Br  ( A) 
KOH(alc)
(B) 
HBr
 (C),
KOH (aq.)
(c) A triple bond (d) Fragmentation
The product (C) is [JIPMER 2001]
60. When chloroform is treated with conc. HNO 3 it gives
(a) Propan – 2 - ol (b) Propan – l – ol
[CPMT 1986; MP PMT 1989; AFMC 1998, 99;
EAMCET 1991; BHU 1999]
(c) Propyne (d) Propene
(a) CHCl 2 NO 2 (b) CCl 3 NO 2 72. Alkyl halide on heating with alc. NH 3 in a sealed tube
results… [Orissa JEE 2002]
(c) CHCl 2 HNO 3 (d) None of these
(a) 1° amine (b) 2° amine
61. A sample of chloroform being used as anaesthetic is tested
(c) 3° amine (d) All of these
by [AIIMS 1980; CPMT 1983]
(a) Fehling solution 73. When CH 3 CH 2 CHCl 2 is treated with NaNH 2, the
(b) Ammoniacal Cu 2 Cl 2 product formed is [CBSE PMT 2002]
(c) AgNO 3 solution (a) CH 3  CH  CH 2 (b) CH 3  C  CH

(d) AgNO 3 solution after boiling with alcoholic KOH (c) CH 3 CH 2 CH (NH 2 )(Cl) (d) CH 3 CH 2C(NH 2 )2
solution 74. By heating a mixture of CHCl 3 with silver powder, the
62. Dehydrohalogenation of an alkyl halide is [MP PMT 1996] compound formed is [Kurukshetra CET 2002]
(a) An addition reaction (b) A substitution reaction (a) Acetylene (b) Silver acetate
(c) An elimination reaction (d) An oxidation reaction (c) Methanol (d) None of these
63. Reaction of aqueous sodium hydroxide on (i) ethyl 75. Chloropicrin is [Kurukshetra CET 2002]
bromide and (ii) chlorobenzene gives (a) Trichloro acetaldehyde (b) Nitrochloroform
(a) (i) Ethene and (ii) o-chlorophenol
(c) 2,4,6-trinitro phenol (d) None of these
(b) (i) Ethyl alcohol and (ii) o-chlorophenol
76. Which of the following are correct statements about
(c) (i) Ethyl alcohol and (ii) phenol
C 2 H 5 Br [Roorkee 1999]
(d) (i) Ethyl alcohol and (ii) no reaction
64. 2-bromopentane is heated with potassium ethoxide in (a) It reacts with metallic Na to give ethane
ethanol. The major product obtained is [CBSE PMT 1998] (b) It gives nitroethane on heating with aqueous
(a) Pentene-1 (b) cis pentene-2 ethanolic solution of AgNO2
(c) trans pentene-2 (d) 2-ethoxypentane (c) It gives C 2 H 5 OH on boiling with alcoholic potash
65. What is the product formed in the following reaction
(d) It forms ethylacetate on heating with silver acetate
C 6 H 5 OH  CCl 4   
(1) NaOH
[KCET 1998]
(2) H  77. Aryl halide is less reactive than alkyl halide towards
nucleophilic substitution because [RPMT 2002]
(a) p-hydroxybenzoic acid (b) o-hydroxybenzoic acid
(c) Benzaldehyde (d) Salicylaldehyde (a) Less stable carbonium ion
66. When chloroform is treated with excess oxygen it forms (b) Due to large C  Cl bond energy
[MH CET 1999] (c) Inductive effect
(a) COCl 2  HCl (d) Resonance stabilization and sp 2 - hybridisation of C
(b) COCl 2  Cl 2  H 2 attached to halide
78. Methyl chloride reacts with silver acetate to yield
(c) COCl 2  Cl 2  H 2 O
[BVP 2003]
(d) No product will be formed (a) Acetaldehyde (b) Acetyl chloride
67. Which isomer of cyclohexane hexachloride is a very (c) Methyl acetate (d) Acetic acid
strong insecticide [MP PET 2003] 79. Chloroform for anesthetic purposes is tested for its purity
(a)  (b)  with the reagent [DPMT 2001]
(a) Silver nitrate (b) Lead nitrate
(c)  (d) 
(c) Ammoniacal Cu 2 Cl 2 (d) Lead nitrate
68. Haloalkane in the presence of alcoholic KOH undergoes
80. 2, 6 - Dimethylheptane on monochlorination
[KCET (Engg/Med.) 2002]
produces……. derivatives [DPMT 2001]
(a) Elimination (b) Polymerisation (a) 5 (b) 6
(c) Dimerisation (d) Substitution (c) 3 (d) 4
69. The set of compounds in which the reactivity of halogen 81. The less reactivity of chlorine atom in CH 2  CH  Cl is
atom in the ascending order is [KCET (Engg.) 2002]
due to [DCE 2001]
(a) Vinyl chloride, chlorethane, chlorobenzene (a) Inductive effect (b) Resonance stabilization
(b) Vinyl chloride, chlorobenzene, chloroethane (c) Electromeric effect (d) Electronegativity
(c) Chloroethane, chlorobenzene, vinyl chloride
 Halogen Containing Compounds 1177

82. CH 3  CH 2  Br   CH 3 CH 2CN  X

alc.KCN HOH 93. Phenol reacts with CHCl 3 and NaOH (at 340 K ) to give
In this reaction, product X is [MH CET 2002] [MP PMT 1997; CBSE PMT 2002]
(a) Acetic acid (b) Propionic acid (a) o-chlorophenol (b) Salicylaldehyde
(c) Butyric acid (d) Formic acid (c) Benzaldehyde (d) Chlorobenzene
83. In alkaline hydrolysis of a tertiary alkyl halide by aqueous 94. Iodoform on heating with KOH gives [MP PMT 2000]
alkali if concentration of alkali is doubled, then the (a) CH 3 CHO (b) CH 3 COOK
reaction
[MH CET 2002] (c) HCOOK (d) HCHO
(a) Will be doubled (b) Will be halved 95. Which reaction is correct in the conversion of chloroform
(c) Will remain constant (d) Can’t say to acetylene [Pb. PMT 2000]
84. AgNO 3 does not give precipitate with CHCl 3 because (a) CHCl 3  AgNO3 (b) CHCl 3  O 2
[MP PET 1999; CPMT 2002] (c) CHCl 3  HNO 3 (d) CHCl 3  Ag
(a) CHCl 3 does not ionise in water
96. Which of the following gases are poisonous
(b) AgNO3 does not reacts with CHCl 3 [Pb. PMT 2000]
(c) CHCl 3 is chemically inert (a) CHCl 3 (b) CO 2
(d) None of these (c) None of these (d) CO
85. The reaction between chlorobenzene and chloral in the
97. Which of the following alkyl halide is used as a
presence of concentrated sulphuric acid produces
methylating agent [KCET (Med.) 2000; MP PET 1999]
[Pb. PMT 2001]
(a) Gammexane (a) CH 3 I (b) C 2 H 5 Br
(b) p,p-dichloro diphenyl trichloro ethane (c) C 2 H 5 Cl (d) C6 H 5 Cl
(c) Chloropicrin
98. C6 H 6 Cl 6 , on treatment with alcoholic KOH , yields
(d) Benzene hexachloride
86. False statement is [RPET 1999] [AFMC 2000]
(a) Chloroform is heavier than water (a) C 6 H 6 (b) C 6 H 3 Cl 3
(b) CCl 4 is non-inflammable (c) (C 6 H 6 ) OH (d) C 6 H 6 Cl 4
(c) Vinyl chloride is more reactive than allyl chloride 99. When ethyl iodide is heated with silver nitrate, the
(d) Br  is a good nucleophile as compared to I  product obtained is [CPMT 2000]
87. Chloroform is slowly oxidise by air in presence of light to (a) C 2 H 5 Ag (b) Ag  O  NO 2
form [MH CET 1999; UPSEAT 2001, 02; RPMT 2003]
(a) Formyl chloride (b) Phosgene (c) C 2 H 5 O  NO 2 (d) C 2 H 5 I  NO 2
(c) Trichloroacetic acid (d) Formic acid 100. CHCl 3 and HF lead to the formation of a compound of
88. Alcoholic potash is used to bring about fluorine of molecular weight 70. The compound is
[KCET (Engg.) 2001]
[RPET 2000]
(a) Dehydrogenation (b) Dehydration
(a) Fluoroform (b) Fluorine monoxide
(c) Dehydrohalogenation (d) Dehalogenation
(c) Fluorine dioxide (d) Fluromethanol
89. Vinyl chloride reacts with HCl to form [JIPMER 2000]
101. Chloroform with zinc dust in water gives [UPSEAT 2000]
(a) 1, 1- dichloro ethane
(a) CH 4 (b) Chloropicrin
(b) 1, 2- dichloro ethane
(c) Tetrachloro ethylene (c) CCl 4 (d) CH 2 Cl 2
(d) Mixture of 1, 2 and 1, 1 – dichloro ethane 102. Which of the following is used as a catalyst for preparing
90. R  X  NaOH  ROH  NaX Grignard reagent [KCET 1998]
The above reaction is classified as (a) Iron powder (b) Iodine powder
[BHU 1982; CBSE PMT 1991; RPET 2000] (c) Activated charcoal (d) Manganese dioxide
(a) Nucleophilic substitution 103. For a given alkyl group the densities of the halides follow
(b) Electrophilic substitution the order [MP PMT 1997]
(c) Reduction (a) RI  RBr  RCl (b) RI  RCl  RBr
(d) Oxidation (c) RBr  RI  RCl (d) RCl  RBr  RI
91. Reduction of acetyl chloride with H 2 in presence of Pd 104. Which halide will be least reactive in respect to hydrolysis
gives [MP PMT 2001] [MP PET 2003]
(a) CH 3 COCH 3 (b) C 2 H 5 OH (a) Vinyl chloride (b) Allyl chloride
(c) Ethyl chloride (d) t-Butyl chloride
(c) CH 3 COOH (d) CH 3 CHO
105. In nucleophilic aliphatic substitution, the nucleophiles are
92. When methyl bromide is heated with Zn it gives generally
[MP PMT 2001] (a) Acids (b) Bases
(a) CH 4 (b) C 2 H 6 (c) Salts (d) Neutral molecules
(c) C 2 H 4 (d) CH 3 OH 106. Which one of the following compounds does not react
with bromine [DPMT 1983]
 1178 Halogen Containing Compounds
(a) Ethylamine (b) Propene (d) Nitric acid on chlorobenzene
(c) Phenol (d) Chloroform 116. In Wurtz reaction alkyl halide react with [MH CET 2004]
107. Allyl chloride on dehydro chlorination gives (a) Sodium in ether (b) Sodium in dry ether
[Kerala (Med.) 2003] (c) Sodium only (d) Alkyl halide in ether
117. Chloroform, when kept open, is oxidised to [CPMT 2004]
(a) Propadiene (b) Propylene
(a) CO 2 (b) COCl 2
(c) Acetylchloride (d) Acetone
108. Toluene reacts with excess of Cl 2 in presence of sunlight (c) CO 2 , Cl 2 (d) None of these

to give a product which on hydrolysis followed by reaction 118. Chloroform reacts with concentrated HNO 3 to give
with NaOH gives [Orissa JEE 2004] [Pb. CET 2000]
(a) Water gas (b) Tear gas
COOH COONa (c) Laughing gas (d) Producer gas
(a) (b) 119. When ethyl chloride and alcoholic KOH are heated, the
compound obtained is [MH CET 2003]
COONa (a) C 2 H 4 (b) C 2 H 2
(c) (d) None of these
Na (c) C6 H 6 (d) C 2 H 6
109. An alkyl bromide produces a single alkene when it reacts 120. Chloroform, on warming with Ag powder, gives
with sodium ethoxide and ethanol. This alkene undergoes [MH CET 2003]
hydrogenation and produces 2-methyl butane. What is (a) C 2 H 6 (b) C 3 H 8
the identity of the alkyl bromide [Kerala PMT 2004]
(c) C 2 H 4 (d) C 2 H 2
(a) 1-bromo-2, 2-dimethylpropane
121. When alkyl halide is heated with dry Ag2 O , it produces
(b) 1-bromobutane
[CPMT 1997; BHU 2004]
(c) 1-bromo-2-methylbutane (a) Ester (b) Ether
(d) 2-bromo-2-methylbutane (c) Ketone (d) Alcohol
(e) 2-bromopentane 122. Reaction of alkyl halides with aromatic compounds in
110. On treating a mixture of two alkyl halides with sodium presence of anhydrous AlCl3 is known as [UPSEAT 2004]
metal in dry ether, 2-methyl propane was obtained. The (a) Friedal-Craft reaction
alkyl halides are [KCET 2004] (b) Hofmann degradation
(a) 2-chloropropane and chloromethane (c) Kolbe’s synthesis
(b) 2-chloropropane and chloroethane (d) Beckmann rearrangement
(c) Chloromethane and chloroethane 123. Two percent of ethanol is added during the oxidation of
chloroform to stop the formation of carbonyl chloride. In
(d) Chloromethane and 1-chloropropane this reaction ethanol acts as [Pb. CET 2001]
111. In which case formation of butane nitrile is possible (a) Auto catalyst (b) Negative catalyst
[Orissa JEE 2004] (c) Positive catalyst (d) None of these
(a) C3 H7 Br  KCN (b) C4 H 9 Br  KCN 124. When benzene is heated with chlorine in the presence of
sunlight, it forms [Pb. CET 2000]
(c) C3 H7 OH  KCN (d) C4 H 9 OH  KCN (a) B.H.C. (b) Cyclopropane
112. The reaction of an aromatic halogen compound with an (c) p-dichlorobenzene (d) None of these
alkyl halides in presence of sodium and ether is called 125. Ethylene di bromide on heating with metallic sodium in
[MP PMT 2004] ether solution yields [Pb. CET 2004]
(a) Wurtz reaction (a) Ethene (b) Ethyne
(b) Sandmeyer’s reaction (c) 2-butene (d) 1-butene
(c) Wurtz-fittig reaction 126. The reaction, CH 3 Br  Na  Product , is called
(d) Kolbe reaction
[Pb. CET 2003]
113. The compound added to prevent chloroform to form
phosgene gas is [MP PET 2004] (a) Perkin reaction (b) Levit reaction
(a) C2 H 5 OH (b) CH 3 COOH (c) Wurtz reaction (d) Aldol condensation
127. At normal temperature iodoform is [MP PET 2004]
(c) CH 3 COCH 3 (d) CH 3 OH
(a) Thick viscous liquid (b) Gas
114. Among the following, the one which reacts most readily (c) Volatile liquid (d) Solid
with ethanol is [AIIMS 2004]
128. Which of the following statements about benzyl chloride
(a) p-nitrobenzyl bromide
is incorrect [KCET 2004]
(b) p-chlorobenzyl bromide
(a) It is less reactive than alkyl halides
(c) p-methoxybenzyl bromide
(d) p-methylbenzyl bromide (b) It can be oxidised to benzaldehyde by boiling with
115. Chloropicrin is obtained by the reaction of copper nitrate solution
[CBSE PMT 2004] (c) It is a lachrymatory liquid and answers Beilstein’s
(a) Chlorine on picric acid test
(b) Nitric acid on chloroform (d) It gives a white precipitate with alcoholic silver
(c) Steam on carbon tetrachloride nitrate
 Halogen Containing Compounds 1179

129. Ethylene dichloride and ethylidine chloride are isomeric [BCECE 2005]
compounds. The false statement about these isomers is (a) Nucleophilic substitution reaction
that they [DCE 2003] (b) Elimination reaction
(a) React with alcoholic potash and give the same (c) Both nucleophilic substitution and elimination
product reaction
(b) Are position isomers (d) Rearrangement
(c) Contain the same percentage of chlorine 139. The major product formed in the following reaction is
(d) Are both hydrolysed to the same product CH 3
|
130. An alkyl bromide (X) reacts with Na to form 4, 5- CH 3  C  CH 2 Br 
3

CH O
[AIIMS 2005]
diethyloctane. Compound X is [Roorkee 1999] | CH 3 OH

(a) CH 3 (CH 2 )3 Br H
CH 3
(b) CH 3 (CH 2 )5 Br |
(a) CH 3  C  CH 2 OCH 3 (b) CH 3  C H  CH 2 CH 3
(c) CH 3 (CH 2 )3 CH .Br.CH 3 | |
H OCH 3
(d) CH 3 (CH 2 )2 CH .Br.CH 2 CH 3
CH 3 CH 3
131. In the following reaction X is | |
CH 3 NH 2  X  KOH  CH 3 NC (highlyoffensive odour) (c) CH 3  C  CH 2 (d) CH 3  C  CH 3
|
[MP PET 1994] OCH 3
(a) CH 2 Cl 2 (b) CHCl 3 140. The major product obtained on treatment of
(c) CH 3 Cl (d) CCl 4 CH 3 CH 2 CH (F)CH 3 with CH 3 O  / CH 3 OH is
[AIIMS 2005]
132. Which metal is used in Wurtz synthesis
[CPMT 1986; DPMT 1979; MP PET 2002]
(a) CH 3 CH 2 CH (OCH 3 )CH 3
(a) Ba (b) Al (b) CH 3 CH  CHCH 3
(c) Na (d) Fe (c) CH 3 CH 2 CH  CH 2
133. Which of the following is boiled with ethyl chloride to (d) CH 3 CH 2 CH 2 CH 2 OCH 3
form ethyl alcohol [MNR 1982]
(a) Alcoholic KOH (b) Aqueous KOH 141. When phenyl magnesium bromide reacts with tbutanol,
the product would be [IIT 2005]
(c) H 2 O (d) H 2 O 2
(a) Benzene (b) Phenol
134. Why is chloroform put into dark coloured bottles (c) tbutyl benzene (d) tbutyl phenyl ether
[MP PET 2002] 142. Alkyl halides react with dialkyl copper reagents to give
(a) To prevent evaporation [AIEEE 2005]
(b) To prevent from moisture (a) Alkenes (b) Alkyl copper halides
(c) To prevent it from oxidation to form phosgene (c) Alkanes (d) Alkenyl halides
(d) To prevent its reaction with glass 143. Which of the following is liquid at room temperature
135. DDT is [AFMC 2005]
(a) A solid (b) A liquid (a) CH 3 I (b) CH 3 Br
(c) A gas (d) A solution
(c) C2 H 5 Cl (d) CH 3 F
136. Bottles containing C6 H 5 I and C6 H 5 CH 2 I lost their
original labels. They were labelled A and B for testing. A 144. Which of the following haloalkanes is most reactive
and B were separately taken in test tubes and boiled with [KCET 2005]
NaOH solution. The end solution in each tube was made (a) 1-chloropropane (b) 1-bromopropane
acidic with dilute HNO 3 and then some AgNO 3 solution (c) 2-chloropropane (d) 2-bromopropane
was added. Substance B give a yellow precipitate. Which 145. Grignard reagent adds to [KCET 2005]
one of the following statements is true for this experiment (a) C O (b) C  N
[AIEEE 2003]
(c) CS (d) All of the above
(a) A was C6 H 5 I
146. Analyse the following reaction and identify the nature of
(b) A was C6 H 5 CH 2 I A and B [Kerala CET 2005]
(c) B was C6 H 5 I
(d) Addition of HNO 3 was unnecessary B 
HBr
 A
HBr
hv
137. Which of the following statements is incorrect regarding
benzyl chloride [KCET 2003] Br
(a) It gives white precipitate with alcoholic AgNO3
(a) Both A and B are
(b) It is an aromatic compound with substitution in the
side chain
(c) It undergoes nucleophilic substitution reaction
(d) It is less reactive than vinyl chloride (b) Both A and B are
Br
138. Alkyl halide can be converted into alkene by Br
 1180 Halogen Containing Compounds
(d) Only in absence of CO 2
(c) A is & B is 7. CFx Cl y [where x + y = 4]. These compounds are not used
Br
Br because [RPET 2000]
(a) These are fluoro carbons
(d) A is Br& B is (b) These are difficult to synthesise
(c) They deplete ozone layer
(d) None of the these
8. The molecular formula of DDT has [MP PMT 1997]
(e) A is & B is
Br Br (a) 5 chlorine atoms (b) 4 chlorine atoms
(c) 3 chlorine atoms (d) 2 chlorine atoms
9. What is the reagent used for testing fluoride ion in water
[EAMCET 2003]
Uses of Halogen Containing Compounds (a) Alizarin - S (b) Quinalizarin
(c) Phenolphthalein (d) Benzene
1. Which of these can be used as moth repellant 10. Chloropicrin is used as [UPSEAT 2000]
[CPMT 1987] (a) Solvent (b) Anaesthetic
(a) Benzene hexachloride (b) Benzal chloride (c) Perfume (d) Tear gas
11. Which is used in the manufacture of plastic
(c) Hexachloroethane (d) Tetrachloroethane
(a) CH 2  CHCl (b) CH  CH
2. Which one of the following is the correct formula of
dichlorodiphenyl trichloroethane [AIIMS 1982] (c) CH 2  CH  CH 2 I (d) CCl 4
H Cl 12. Freon (dichlorodifluoro methane) is used
| | [CPMT 1986; DPMT 1983; CBSE PMT 2001]
(a) Cl C ––– C ––– (a) As local anaesthetic
Cl (b) For dissolving impurities in metallurgical process
|
Cl (c) In refrigerator
(d) In printing industry
13. Which of the following is known as freon which is used as
Cl a refrigerant[DPMT 1982; CPMT 1979, 81, 89; AFMC 1995;
H Cl Manipal MEE 1995; MP PET 1995, 2004]
| |
(a) CCl 2 F2 (b) CHCl 3
(b) C ––– C –––
Cl (c) CH 2 F2 (d) CF4
|
14. Benzene hexachloride (BHC) is used as
Cl
[MP PMT 1994; KCET 1999]

H Cl (a) Dye (b) Antimalerial drug

| | (c) Antibiotic (d) Insecticide
(c) Cl C ––– C ––– 15. Which plastic is obtained from CHCl 3 as follows
Cl
| HF 800o C Polymerisation
Cl CHCl 3 
 X  Y 
 Plastic
SbF3

Cl Cl (a) Bakelite (b) Teflon

| | (c) Polythene (d) Perspex
(d) Cl C ––– C –––
Cl Cl
|
Cl 16. C  CCl 3 . The above structural
|

OH Cl H
Cl |
3. The compound (CH 3 )2 .CCCl 3 is formula refers to [MP PET 1997]
(a) Chloretone (b) Chloroquin (a) BHC (b) DNA
(c) Chloropicrin (d) Chloropropyl chloride (c) DDT (d) RNA
4. Depletion of ozone layer is caused by [RPMT 2002] 17. The commercial uses of DDT and benzene hexachloride
(a) Freon (b) Alkane are
(c) Gringard reagent (d) All of these (a) DDT is a herbicide, benzene hexachloride is a
5. Which of the following is Teflon [RPMT 2002] fungicide
(a) [CF2  CF2 ]n (b) CF2  CF2 (b) Both are insecticides
(c) CF  CF (d) None of these (c) Both are herbicides
6. Statement “Ozone in atmosphere is decreased by chloro- (d) DDT is a fungicide and benzene hexachloride is a
fluoro-carbon (Cl 2 F2 C) ” [RPET 1999] herbicide
(a) Is true 18. Which of the following is used in fire extinguishers
(b) Is false [AFMC 1993]
(c) Only in presence of CO 2 (a) CH 4 (b) CHCl 3
 Halogen Containing Compounds 1181

(c) CH 2 Cl 2 (d) CCl 4 (b) NO 2 withdraws e  from meta position

19. Iodoform can be used as [NCERT 1981]
(c) denotes e  at meta position
(a) Anaesthetic (b) Antiseptic
(d) NO 2 withdraws e  from ortho/para positions
(c) Analgesic (d) Antifebrin
20. Which of the following is an anaesthetic [AFMC 1989] 6. Among the following one with the highest percentage of
chlorine is [MNR 1989; BHU 1998; MH CET 1999]
(a) C 2 H 4 (b) CHCl 3
(a) Chloral (b) Pyrene
(c) CH 3 Cl (d) C 2 H 5 OH (c) PVC (d) Gammexene
21. An important insecticide is obtained by the action of 7. In which alkyl halide, SN 2 mechanism is favoured
chloral on chlorobenzene. It is [KCET 1989] maximum [RPMT 1997]
(a) BHC (b) Gammexene (a) CH 3 Cl (b) CH 3 CH 2 Cl
(c) DDT (d) Lindane
(c) (CH 3 )2 CHCl (d) (CH 3 )3 C  Cl
22. In fire extinguisher, pyrene is [DPMT 1985]
(a) CO 2 (b) CCl 4 8. Which conformation of C 6 H 6 Cl 6 is most powerful
insecticide
(c) CS 2 (d) CHCl 3
(a) aaeeee (b) aaaeee
23. B.H.C. is used as [Pb. CET 2002] (c) aaaaee (d) aaaaaa
(a) Insecticide (b) Pesticide 9. The odd decomposition of carbon chlorine bond form
(c) Herbicide (d) Weedicide [UPSEAT 1999]
24. The use of the product obtained as a result of reaction (a) Two free ions (b) Two-carbanium ion
between acetone and chloroform is [RPMT 1999] (c) Two carbanion (d) A cation and an anion
(a) Hypnotic (b) Antiseptic 10. A new carbon-carbon bond formation is possible in
(c) Germicidal (d) Anaesthetic [IIT-JEE 1998]
25. Use of chlorofluoro carbons is not encouraged because (a) Cannizzaro reaction (b) Friedel-Craft's
[KCET 2005] alkylation
(a) They are harmful to the eyes of people that use it (c) Clemmensen reduction (d) Reimer-Tiemann
reaction
(b) They damage the refrigerators and air conditioners
11. An isomer of C 3 H 6 Cl 2 on boiling with aqueous KOH
(c) They eat away the ozone in the atmosphere
(d) They destroy the oxygen layer gives acetone. Hence, the isomer is [UPSEAT 2000]
(a) 2, 2-dichloropropane (b) 1, 2-dichloropropane
(c) 1, 1-dichloropropane (d) 1, 3-dichloropropane
12. Which of the following is the example of SN 2 reaction
[CPMT 1999]
(a) CH 3 Br  OH  CH 3 OH  Br 

(b) CH 3 CHCH 3  OH   CH 3 CHCH 3  Br 

| |
1. Among the following, the molecule with the highest dipole Br OH
moment is [IIT-JEE (Screening) 2003] H O
(c) CH 3 CH 2 OH 
2
 CH 2  CH 2
(a) CH 3 Cl (b) CH 2 Cl 2
CH 3 CH 3
(c) CHCl 3 (d) CCl 4 | |

2. When CHCl3 is boiled with NaOH, It gives (d) CH 3  C  CH 3  OH   CH 3  C  O  CH 3  Br 

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[Orissa JEE 2003]
Br H
(a) Formic acid (b) Trihydroxy methane
13. Wurtz reaction of methyl iodide yields an organic
(c) Acetylene (d) Sodium formate
compound X. Which one of the following reactions also
3. The hybridization state of carbon atoms in the product yields X
formed by the reaction of ethyl chloride with aqueous [EAMCET 2003]
potassium hydroxide is [EAMCET 1997]
dryether
(a) sp (b) sp 2 (a) C 2 H 5 Cl  Mg 

(c) sp 3 (d) sp 3 d (b) C 2 H 5 Cl  LiAlH4 

4. Which of the following compounds does not undergo (c) C 2 H 5 Cl  C 2 H 5 ONa 
nucleophilic substitution reactions [KCET 1998]
(a) Vinyl chloride (b) Ethyl bromide (d) CHCl 3  
Ag powder

(c) Benzyl chloride (d) Isopropyl chloride 14. Ethyl orthoformate is formed by heating with sodium
5. Replacement of Cl of chlorobenzene to give phenol ethoxide [EAMCET 2003]
requires drastic conditions but chlorine of 2, 4- (a) CHCl 3 (b) C 2 H 5 OH
dinitrochlorobenzene is readily replaced because[CBSE PMT 1997]
(a) NO 2 make ring electron rich at ortho and para (c) HCOOH (d) CH 3 CHO
15. 1 , 2 di-bromo cyclohexane on dehydro halogenation gives
 1182 Halogen Containing Compounds
[UPSEAT 2003]

(a) (b)
Read the assertion and reason carefully to mark the correct
option out of the options given below:
(c) (d) None of these (a) If both assertion and reason are true and the reason is
the correct explanation of the assertion.
16. In which one of the following conversions phosphorus (b) If both assertion and reason are true but reason is not
pentachloride is used as a reagent [EAMCET 1997] the correct explanation of the assertion.
(a) H 2 C  CH 2  CH 3 CH 2 Cl (c) If assertion is true but reason is false.
(d) If the assertion and reason both are false.
(b) H 3 C  O  CH 3  CH 3 Cl (e) If assertion is false but reason is true.
(c) CH 3 CH 2 OH  CH 3 CH 2 Cl
(d) HC  CH  CH 2  CHCl 1. Assertion : CHCl 3 is stored in transparent bottles.
17. When but –3-en -2- ol reacts with aq. HBr, the product Reason : CHCl 3 is oxidised in dark. [AIIMS 1996]
formed is [DCE 2001] 2. Assertion : Addition of bromine to trans-2-butene
(a) 3 - bromobut - 1- ene yields meso-2, 3-dibromobutane
(b) 1 - bromobut - 2- ene Reason : Bromine addition to an alkene is an
(c) A mixture of both a and b electrophilic addition.
(d) 2 - bromobut - 2 - ene [IIT-JEE (Screening) 2001]
18. Which of these do not form Grignard reagent 3. Assertion : Alkyl halides are soluble in organic
solvents.
(a) CH 3 F (b) CH 3 Cl
Reason : p-dichlorobenzene possesses low melting
(c) CH 3 Br (d) CH 3 I point.
19. An organic compound A(C4 H 6 Cl) on reaction with 4. Assertion : CCl 4 is not a fire extinguisher.
Na/diethyl ether gives a hydrocarbon, which on Reason : CCl 4 is insoluble in water.
monochlorination gives only one chloro derivative. A is 5. Assertion : Aqueous hydrohalogen acids are used to
[Kerala PMT 2004] prepare alkyl halides from alkenes.
(a) t-butyl chloride (b) s-butyl chloride Reason : Hydrogen iodide readily reacts with alkenes
(c) Isobutyl chloride (d) n-butyl chloride to form alkyl halides.
(e) None of these 6. Assertion : Alkyl halides form alkenes when heated
20. Among the following the most reactive towards alcoholic above 300°C.
KOH is [AIIMS 2004] Reason : CH 3 CH 2 I react slowly with strong base
(a) CH 2  CHBr (b) CH 3 COCH 2 CH 2 Br when compared to CD 3 CH 2 I .
(c) CH 3 CH 2 Br (d) CH 3 CH 2 CH 2 Br 7. Assertion : Halogen acids react with alcohols to form
21. Which one of the following possess highest m.pt. haloalkanes.
[Pb. CET 2004] Reason : Order of reactivity of halogen acids
(a) Chlorobenzene (b) o-dichlorobenzene HCl > HBr > HI
(c) m-dichlorobenzene (d) p-dichlorobenzene CH3 Cl
22. Which chlorine atom is more electronegative in the 8. Assertion : Clis less reactive than towards
following [UPSEAT 2004]
(a) CH 3  Cl (b) CH 3  CH 2  Cl
reactions.
Reason : Tertiary alkyl halides react predominantly
CH 3 CH 3 by S N 1 mechanism.
| |
(c) H  C  Cl (d) CH 3  CH 2  C  Cl 9. Assertion : Electron withdrawing groups in aryl halides
| |
CH 3 CH 3 decrease the reactivity towards nucleophilic
substitution.
23. What would be the product formed when 1-Bromo-3- Reason : 2, 4-Dinitrochlorobenzene is less reactive
chloro cyclobutane reacts with two equivalents of metallic than chlorobenzene.
sodium in ether [IIT-JEE (Screening) 2005] 10. Assertion : Aryl halides undergo electrophilic
Cl substitutions more readily than benzene.
(a) (b) Reason : Aryl halide gives a mixture of o- and p-
products.
Br
11. Assertion : Addition of Br2 to cis-but-2-ene is
(c) (d) stereoselective.
Reason : SN 2 reactions are stereospecific as well as
stereoselective.
12. Assertion : Optically active 2-iodobutane on treatment
with NaI in acetone undergoes
recemization.
 Halogen Containing Compounds 1183

Reason : Repeated Walden inversions on the 81 b 82 b 83 c 84 a 85 b

reactant and its product eventually gives a
86 cd 87 b 88 c 89 a 90 a
racemic mixture.
13. Assertion : Nucleophilic substitution reaction on an 91 d 92 b 93 b 94 c 95 d
optically active alkyl halide gives a mixture 96 d 97 a 98 b 99 c 100 a
of enantiomers.
101 a 102 b 103 d 104 a 105 b
Reason : The reaction occurs by SN 1 mechanism.
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
Introduction of Halogen containing compounds 136 a 137 d 138 b 139 d 140 b
141 a 142 c 143 a 144 d 145 d
1 a 2 b 3 b 4 c 5 b
146 c
6 a 7 b 8 a 9 b 10 a
11 d 12 a 13 b
Uses of Halogen containing compounds

Preparation of Halogen containing compounds 1 c 2 a 3 a 4 a 5 a

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