Halogen Containing Compounds

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

Introduction of Halogen containing compounds
4 o carbon atoms is [J & K 2005]
(a) 2, 3-dimethyl pentane
1. How many structural isomers are possible for a compound with (b) 3-chloro-2, 3-dimethylpentane
molecular formula C 3 H 7 Cl [MH CET 2001] (c) 2, 3, 4-trimethylpentane
(a) 2 (b) 5 (d) 3, 3-dimethylpentane
(c) 7 (d) 9
2. In CH 3 CH 2 Br , % of Br is [DPMT 1996] Preparation of Halogen containing compounds
(a) 80 (b) 75
(c) 70 (d) 7 1. The following reaction is known as
Pyridine
3. Gem- dibromide is [RPMT 2000] C 2 H 5 OH  SOCl 2   C 2 H 5 Cl  SO 2  HCl
CH 3 CH (Br )OH (Br )CH 3 (b)
(a) [AIIMS 2002]

CH 3 CBr 2 CH 3 (a) Kharasch effect

(b) Darzen’s procedure
(c) CH 2 (Br )CH 2 CH 2 (d) CH 2 BrCH 2 Br (c) Williamson’s synthesis
4. Ethylidene dibromide is (d) Hunsdiecker synthesis reaction
(a) CH 3  CH 2  Br (b) 2. What is the main product of the reaction between 2-methyl
propene with HBr [RPMT 2002]
Br  CH 2  CH 2  Br (a) 1-bromo butane
(c) CH 3  CHBr 2 (d) CH 2  CBr 2 (b) 1-bromo-2 methyl propane
(c) 2-bromo butane
5. Benzylidene chloride is
(d) 2-bromo-2 methyl propane
(a) C 6 H 5 CH 2 Cl (b) C 6 H 5 CHCl 2 3. Halogenation of alkanes is [KCET 2002]
(c) C 6 H 4 ClCH 2 Cl (d) C 6 H 5 CCl 3 (a) A reductive process (b) An oxidative process
(c) An isothermal process (d) An indothermal process
6. Which of the following halide is 2 o

(a) Isopropyl chloride (b) Isobutyl chloride N  NBF4
(c) n-propyl chloride (d) n-butyl chloride 
4.  A
7. Haloforms are trihalogen derivatives of [CPMT 1985]
(a) Ethane (b) Methane
(c) Propane (d) Benzene
8. Benzene hexachloride is In the above process product A is [Kerala (Engg.) 2002]
(a) 1, 2, 3, 4, 5, 6-hexachlorocyclohexane (a) Fluorobenzene (b) Benzene
(b) 1, 1, 1, 6, 6, 6-hexachlorocyclohexane (c) 1, 4-difluorobenzene (d) 1, 3-difluorobenzene
(c) 1, 6-phenyl-1, 6-chlorohexane CS 2
5. Silver acetate  Br2  . The main product of this reaction is
(d) 1, 1-phenyl-6, 6-chlorohexane
[Kurukshetra CET 2002]
9. Number of   bonds present in B.H.C. (Benzene
(a) CH 3  Br (b) CH 3 COI
hexachloride) are [RPMT 1999]
(a) 6 (b) Zero (c) CH 3 COOH (d) None of these
(c) 3 (d) 12 Cl
10. The general formula for alkyl halides is
6. Diazonium salts  Cu 2 Cl 2  HCl  , the reaction is
(a) C n H 2 n 1 X (b) C n H 2n 2 X
known as [Kerala (Med.) 2002]
(c) C n H n 1 X (d) C n H 2n X
(a) Chlorination (b) Sandmeyer’s reaction
11. Which of the following is a primary halide [DCE 2004]
(c) Perkin reaction (d) Substitution reaction
(a) Isopropyl iodide (b) Secondary butyl iodide
7. When ethyl alcohol (C 2 H 5 OH ) reacts with thionyl
(c) Tertiary butyl bromide (d) Neo hexyl chloride
12. Full name of DDT is [KCET 1993] chloride, in the presence of pyridine, the product obtained is
[AIIMS; CBSE PMT 2001]
(a) 1, 1, 1-trichloro-2, 2-bis(p-chlorophenyl) ethane
(b) 1, 1-dichloro-2, 2-diphenyl trimethylethane (a) CH 3 CH 2 Cl  HCl
(c) 1, 1-dichloro-2, 2-diphenyl trichloroethane (b) C 2 H 5 Cl  HCl  SO 2
(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

8. Preparation of alkyl halides in laboratory is least preferred by [AFMC 1997; CPMT 1999]
[DPMT 2000] (a) Substitution (b) Elimination
(a) Treatment of alcohols (c) Addition (d) Rearrangement
(b) Addition of hydrogen halides to alkenes 16. Which of the following would be produced when acetylene
(c) Halide exchange reacts with HCl [MH CET 1999]
(d) Direct halogenation of alkanes (a) CH 3 CH 2 Cl (b) CH 3 CHCl 2
9. Which of the following organic compounds will give a
(c) CHCl  CHCl (d) CH 2  CHCl
mixture of 1-chlorobutane and 2-chlorobutane on chlorination
[CPMT 2001] 17. R  OH  HX  R  X  H 2 O
CH 3  CH  CH  CH 2 In the above reaction, the reactivity of different alcohols is
(a) |
[CPMT 1997]
CH 3 (a) Tertiary > Secondary > Primary
(b) Tertiary < Secondary < Primary
H
(b) | (c) Tertiary < Secondary > Primary
HC  C  C  CH 2 (d) Secondary < Primary < Tertiary
UV Light
18. C 6 H 6  Cl 2   Product. In above reaction product is
(c) CH 2  CH  CH  CH 2
[CPMT 1997]
(d) CH 2  CH  CH 2  CH 3 (a) CCl 3 CHO (b) C 6 H 6 Cl 6
10. The chlorobenzene is generally obtained from a corresponding (c) C 6 H 12 Cl 6 (d) C 6 H 9 Cl 2
diazonium salt by reacting it with
19. Benzene reacts with chlorine to form benzene hexachloride in
[MP PMT 2000] presence of [MP PET 1999]
(a) Cu 2 Cl 2 (b) CuSO 4 (a) Nickel (b) AlCl 3
Cu (NH 3 )42  (c) Bright sunlight (d) Zinc
(c) Cu (d)
20. The final product obtained by distilling ethyl alcohol with the
11. Decreasing order of reactivity of HX in the reaction excess of chlorine and Ca (OH ) 2 is [MP PET 1996]
ROH  HX  RX  H 2 O (a) CH 3 CHO (b) CCl 3 CHO
[RPET 2000; AIIMS 1983; MP PET 1996]
(c) CHCl 3 (d) (CH 3 ) 2 O
(a) HI  HBr  HCl  HF (b)
21. When ethyl alcohol and KI reacted in presence of
HBr  HCl  HI  HF Na 2 CO 3 , yellow crystals of...... are formed [AFMC 1989]
(c) HCl  HBr  HI  HF (d)
(a) CHI 3 (b) CH 3 I
HF  HBr  HCl  HI
(c) CH 2 I 2 (d) C2 H 5 I
12. The product of the following reaction :
CH 2  CH  CCl 3  HBr 22. In preparation of CHCl 3 from ethanol and bleaching
[RPET 2000] powder, the latter provides [BHU 1986]

(a)CH 3  CH (Br )  CCl 3 (b) (a) Ca (OH ) 2 (b) Cl 2

(c) Both (a) and (b) (d) None of these
CH 2 (Br )  CH 2  CCl 3
23. Which one of the following processes does not occur during
(c) BrCH 2  CHCl  CHCl 2 (d) formation of CHCl 3 from C 2 H 5 OH and bleaching
CH 3  CH 2  CCl 3 powder
[DPMT 1984]
13. Chlorobenzene is prepared commercially by (a) Hydrolysis (b) Oxidation
[JIPMER 2000; CPMT 1976; Pb. CET 2002] (c) Reduction (d) Chlorination
(a) Raschig process (b) Wurtz Fitting reaction 24. Which of the following is obtained when chloral is boiled with
(c) Friedel-Craft’s reaction (d) Grignard reaction NaOH [CBSE PMT 1991; RPMT 1999]
14. In methyl alcohol solution, bromine reacts with ethylene to (a) CH 3 Cl (b) CHCl 3
yield BrCH 2 CH 2 OCH 3 in addition to 1, 2- (c) CCl 4 (d) None of these
dibromoethane because [Pb. PMT 1998] 25. Chloroform can be obtained from [MNR 1986]
(a) The ion formed initially may react with Br  or (a) Methanol (b) Methanal
CH 3 OH (c) Propanol-1 (d) Propanol-2
26. Chlorine reacts with ethanol to give
(b) The methyl alcohol solvates the bromine [MP PMT 1989; CPMT 1997; KCET 1998; JIPMER 1999]
(c) The reaction follows Markownikoff's rule (a) Ethyl chloride (b) Chloroform
(d) This is a free-radical mechanism (c) Acetaldehyde (d) Chloral
Light 27. On heating diethyl ether with conc. HI, 2 moles of which of the
15. C 3 H 8  Cl 2   C 3 H 7 Cl  HCl is an example of following is formed
which of the following types of reactions [IIT-JEE 1983; MP PET 1990; EAMCET 1990;
 Halogen Containing Compounds

AFMC 1993; JIPMER 2001] 38. When a solution of sodium chloride containing ethyl alcohol is
(a) Ethanol (b) Iodoform electrolysed, it forms
(c) Ethyl iodide (d) Methyl iodide (a) Ethyl alcohol (b) Chloral
28. Lucas reagent is [MP PMT 1996; MP PET 1992, 95; (c) Chloroform (d) Acetaldehyde
CPMT 1986, 89; AIIMS 1980; Kurukshetra CEE 2002]
39. Which reagent cannot be used to prepare an alkyl halide from
(a) Concentrated HCl  anhydrous ZnCl 2 an alcohol [CPMT 1989, 94]
(b) Dilute HCl  hydrated ZnCl 2 (a) HCl  ZnCl 2 (b) NaCl
(c) Concentrated HNO 3  anhydrous ZnCl 2 (c) PCl 5 (d) SOCl 3
(d) Concentrated HCl  anhydrous MgCl 2
40. Ethyl benzoate reacts with PCl 5 to give [KCET 2003]
29. Which compound does not form iodoform with alkali and
iodine [IIT-JEE 1985] (a) C 2 H 5 Cl  C 6 H 5 COCl  POCl 3  HCl
(a) Acetone (b) Ethanol (b) C 2 H 5 Cl  C 6 H 5 COCl  POCl 3
(c) Diethyl ketone (d) Isopropyl alcohol
30. Which compound gives yellow ppt. with iodine and alkali (c) CH 3 COCl  C 6 H 5 COCl  POCl 3
[IIT-JEE 1984] (d) C 2 H 5 Cl  C 6 H 5 COOH  POCl 3
(a) 2-hydroxy propane (b) Acetophenone
41. On treatment with chlorine in presence of sunlight, toluene
31. (c) giv.es the product
Methyl acetone
[Orissa JEE 2003; MH CET 1999, 2002]
(d)
(a) o-chloro toluene (b) 2, 5-dichloro toluene
AcetamideAcetone reacts with I 2 in presence of NaOH
(c) p-chloro toluene (d) Benzyl chloride
to form
42. When chlorine is passed through warm benzene in presence of
[MP PMT 1992]
the sunlight, the product obtained is [KCET 2003]
(a) C2 H 5 I (b) C 2 H 4 I2 (a) Benzotrichloride (b) Chlorobenzene
(c) CHI 3 (d) CH 3 I (c) Gammexane (d) DDT
43. Which of the following acids adds to propene in the presence of
Ethanol is converted into ethyl chloride by reacting with
peroxide to give anti-Markownikoff’s product
32. Acetone reacts with I 2 in presence of NaOH to form [MP PET 2003]
[MP PMT 1992] (a) HF (b) HCl
(a) C2 H 5 I (b) C 2 H 4 I2 (c) HBr (d) HI
(c) CHI 3 (d) CH 3 I 44. Propene on treatment with HBr gives [CPMT 1986]
(a) Isopropyl bromide (b) Propyl bromide
33. Ethanol is converted into ethyl chloride by reacting with
[MP PET 1991; MP PMT 1990; BHU 1997] (c) 1, 2-dibromoethane (d) None of the above
45. The catalyst used in Raschig's process is
(a) Cl 2 (b) SOCl 2
(a) LiAlH 4 (b) Copper chloride
(c) HCl (d) NaCl
34. C 6 H 5 Cl prepared by aniline with [IIT-JEE 1984] (c) Sunlight (d) Ethanol Na
(a) HCl 46. The compound formed on heating chlorobenzene with chloral
in the presence of concentrated sulphuric acid, is
(b) Cu 2 Cl 2 [AIEEE 2004]
(c) Cl 2 in presence of anhydrous AlCl 3 (a) Freon (b) DDT
(c) Gammexene (d) Hexachloroethane
(d) HNO 2 and then heated with Cu 2 Cl 2
47. Acetone is mixed with bleaching powder to give
35. The starting substance for the preparation of CH 3 I is [AFMC 2004]
[CPMT 1975] (a) Chloroform (b) Acetaldehyde
(c) Ethanol (d) Phosgene
(a) CH 3 OH (b) C 2 H 5 OH
48. Which of the following compounds gives trichloromethane on
(c) CH 3 CHO (d) (CH 3 ) 2 CO distilling with bleaching powder
[KCET 2004; EAMCET 1986]
36. A Grignard's reagent may be made by reacting magnesium with
[CPMT 1973, 83, 84] (a) Methanal (b) Phenol
(a) Methyl amine (b) Diethyl ether (c) Ethanol (d) Methanol
(c) Ethyl iodide (d) Ethyl alcohol 49. The product formed on reaction of ethyl alcohol with bleaching
powder is [Orissa JEE 2004; DPMT 1978; AIIMS 1991]
37. Which of the following is responsible for iodoform reaction
[CPMT 1980; RPMT 1997] (a) CHCl 3 (b) CCl 3 CHO
(a) Formalin (b) Methanol (c) CH 3 COCH 3 (d) CH 3 CHO
(c) Acetic acid (d) Ethanol 50. Ethylene reacts with bromine to form [Pb. CET 2000]
(a) Chloroethane (b) Ethylene dibromide
 Halogen Containing Compounds

(c) Cyclohexane (d) 1-bromo propane (c) Offensive odour

51. Best method of preparing alkyl chloride is [MH CET 2004] (d) Sour oil of winter green like smell
(a) ROH  SOCl 2  8. A mixture of two organic chlorine compounds was treated with
sodium metal in ether solution. Isobutane was obtained as a
(b) ROH  PCl5 
product. The two chlorine compounds are [KCET 1988]
(c) ROH  PCl3  (a) Methyl chloride and propyl chloride
anhy. ZnCl 2
(d) ROH  HCl    (b) Methyl chloride and ethyl chloride
(c) Isopropyl chloride and methyl chloride
(d) Isopropyl chloride and ethyl chloride
Properties of Halogen containing compounds 9. Alkyl halides can be converted into Grignard reagents by
[KCET 1989]
CCl3
(a) Boiling them with Mg ribbon in alcoholic solution
1. 1 eqv. of Br2 / Fe
   A. Compounds A is (b) Warming them with magnesium powder in dry ether
[Orissa JEE 2005] (c) Refluxing them with MgCl 2 solution

CCl3 CCl3 (d) Warming them with MgCl 2

Br
(a) (b) 10. Which is not present in Grignard reagent
[CBSE PMT 1991]
Br
(a) Methyl group (b) Magnesium
CCl3
CCl3 (c) Halogen (d) COOH group
(c) (d) 11. The reactivity of ethyl chloride is [KCET 1986]
(a) More or less equal to that of benzyl chloride
Br Br
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 yield 14. The reactivities of methyl chloride, propyl chloride and
[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
X 15. Which of the following compound will make precipitate most
5. 2 CHCl 3  O 2  2 COCl 2  2 HCl
readily with AgNO 3 [CPMT 1992]
In the above reaction, X stands for [CPMT 1985]
(a) An oxidant (b) A reductant (a) CCl 3 CHO (b) CHCl 3
(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 chloroform
[DPMT 1983; CPMT 1993; MP PMT 1994; 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
(c) Carbonyl chloride (d) Carbon tetrachloride 17. Salicylic acid can be prepared using Reimer-Tiemann's 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 aluminium
[CPMT 1979]
chloride
(a) Rose odour smell (b) Carbon dioxide under pressure in sodium hydroxide solution
(b) Sour almond like smell (c) Carbon tetrachloride and concentrated sodium hydroxide
 Halogen Containing Compounds

(d) Sodium nitrite and a few drops of concentrated sulphuric (d) Isopropyl benzene
acid 28. The dehydrobromination of 2-bromobutane gives
18. Grignard reagent is prepared by the reaction between CH 3 CH  CHCH 3 . The product is
[CBSE PMT 1994; DPMT 1996; Pb. PMT 1999;
MH CET 1999] (a) Hofmann product
(a) Zinc and alkyl halide (b) Saytzeff product
(b) Magnesium and alkyl halide (c) Hoffmann-Saytzeff product
(c) Magnesium and alkane (d) Markownikoff product
(d) Magnesium and aromatic hydrocarbon 29. Ethylene difluoride on hydrolysis gives
19. Reaction of t-butyl bromide with sodium methoxide produces (a) Glycol (b) Fluoroethanol
[CBSE PMT 1994] (c) Difluoroethanol (d) Freon
(a) Isobutane (b) Isobutylene
30. Benzyl chloride when oxidised by pb (NO 3 ) 2 gives
(c) Sodium t-butoxide (d) t-butyl methyl ether
20. War gas is formed from [BHU 1995] [MP PMT 1989]
PH 3 C2 H 2 (a) Benzoic acid (b) Benzaldehyde
(a) (b)
(c) Benzene (d) None
(c) Zinc phosphate (d) Chloropicrin 31. Which of the following statements about chloroform is false
21. What happens when CCl 4 is treated with AgNO 3 [Manipal MEE 1995]
[EAMCET 1987; CBSE PMT 1988; MP PET 2000] (a) It is a colourless, sweet-smelling liquid
(a) NO 2 will be evolved (b) It is almost insoluble in water
(c) It is highly inflammable
(b) A white ppt. of AgCl will be formed
(d) It can be used as an inhalational anaesthetic agent
(c) CCl 4 will dissolve in AgNO 3 CCl 4 cannot give precipitate with AgNO 3 due to
32.
(d) Nothing will happen [CPMT 1979]
22. If we use pyrene (CCl 4 ) in the Riemer-Tiemann reaction in (a) Formation of complex with AgNO 3
place of chloroform, the product formed is
[CBSE PMT 1989; MP PMT 1990; MH CET 1999] (b) Evolution of Cl 2 gas
(a) Salicylaldehyde (b) Phenolphthalein (c) Chloride ion is not formed
(c) Salicylic acid (d) Cyclohexanol AgNO 3 does not give silver ion
(d)
23. C 6 H 5 CH 2 Cl  KCN (aq.)  X  Y
33. On heating CHCl 3 with aq. NaOH, the product is
Compounds X and Y are [BHU 1979]
[CPMT 1971, 78; BHU 1997; EAMCET 1998;
(a) C 6 H 6  KCl (b) JIPMER (Med.) 2002]
C 6 H 5 CH 2 CN  KCl (a) CH 3 COONa (b) HCOONa
(c) C 6 H 5 CH 3  KCl (d) None of these (c) Sodium oxalate (d) CH 3 OH
24. The bad smelling substance formed by the action of alcoholic 34. Ethyl bromide reacts with lead-sodium alloy to form
caustic potash on chloroform and aniline is [MP PMT/PET 1988; MP PET 1997]
[MP PMT 1971, 92, 2001; CPMT 1971, 86; AFMC 2002;
(a) Tetraethyl lead (b) Tetraethyl bromide
RPMT 1999]
(a) Phenyl isocyanide (b) Nitrobenzene (c) Both (a) and (b) (d) None of the above
(c) Phenyl cyanide (d) Phenyl isocyanate 35. Iodoform heated with Ag powder to form [DPMT 1985]
25. Ethylidene chloride on treatment with aqueous KOH gives (a) Acetylene (b) Ethylene
[MP PMT 1986] (c) Methane (d) Ethane
(a) Ethylene glycol (b) Acetaldehyde 36. Ethyl bromide reacts with silver nitrite to form
(c) Formaldehyde (d) None [DPMT 1985; IIT-JEE 1991]
26. Reaction (a) Nitroethane
C 2 H 5 I  C 5 H 11 I  2 Na  C 2 H 5  C 5 H 11  2 NaI (b) Nitroethane and ethyl nitrite
is called (c) Ethyl nitrite
[MP PMT 1992] (d) Ethane
(a) Hoffmann's reaction 37. Which of the following reactions leads to the formation of
(b) Dow's reaction chloritone [RPMT 2003]
(c) Wurtz's reaction (a) CHCl 3  CH 3 COCH 3 (b) CCl 4  Acetone
(d) Riemer-Tiemann's reaction
(c) CHCl 3  KOH (d) CHCl 3  HNO 3
27. In presence of AlCl 3 , benzene and n-propyl bromide react
in Friedal-Craft's reaction to form [MP PMT 1991] 38. CH 3  CH 2  CH 2 Br  KOH (alc.)  Product
(a) n-propyl benzene Product in above reaction is [RPMT 2003]
(b) 1, 2-dinormal propyl benzene (a) CH 3  CH  CH 2 (b) CH 3  CH 2  CH 3
(c) 1, 4-dinormal propyl benzene
(c) (a) and (b) both (d) None of these
 Halogen Containing Compounds

39. A  CCl 4  KOH  Salicylic acid (c) H 3 C  NH  CH 3 (d) C 2 H 5 NH 2

‘A’ in above reaction is [RPMT 2003] 48. Which of the following statements is incorrect [CPMT 1977]
OH NO 2 (a) C 2 H 5 Br reacts with alco. KOH to form
C 2 H 5 OH
(a) (b)
(b) C 2 H 5 Br when treated with metallic sodium gives
CHO ethane
(c) C 2 H 5 Br when treated with sodium ethoxide forms
(c) (d)
diethyl ether
(d) C 2 H 5 Br with AgCN forms ethyl isocyanide
40. Identify X and Y in the following sequence
X Y
49. When chloroform is exposed to air and sunlight, it gives
C 2 H 5 Br  product  C 3 H 7 NH 2 [NCERT 1984; CPMT 1978, 87; CBSE PMT 1990;
[Orissa JEE 2005] EAMCET 1993; MNR 1994; MP PET 1997, 2000;
X  KCN , Y  LiAlH 4 BHU 2001; AFMC 2002]
(a)
(a) Carbon tetrachloride (b) Carbonyl chloride
(b) X  KCN , Y  H 3 O  (c) Mustard gas (d) Lewsite
50. An organic halide is shaken with aqueous NaOH followed
(c) X  CH 3 Cl , Y  AlCl 3 / HCl
by the addition of dil. HNO 3 and silver nitrate solution gave
(d) X  CH 3 NH 2 , Y  HNO 2 white ppt. The substance can be [JIPMER 1997]
41. 1-chlorobutane reacts with alcoholic KOH to form (a) C 6 H 4 (CH 3 )Br (b) C 6 H 5 CH 2 Cl
[IIT-JEE 1991; AFMC 1998]
(a) 1-butene (b) 2-butane (c) C 6 H 5 Cl (d) None of these
(c) 1-butanol (d) 2-butanol 51. A compound A has a molecular formula C 2 Cl 3 OH . It
42. Which of the following reactions gives reduces Fehling solution and on oxidation gives a
H 2 C  C  C  CH 2 [Roorkee Qualifying 1998] monocarboxylic acid (B). A is obtained by action of chlorine on
Zn / Ch 3 OH ethyl alcohol. A is
(a) CH 2 Br  CBr  CH 2    [CBSE PMT 1994; MP PET 1997; KCET 2005]
Aq . K 2 CO 3 CHCl 3
(b) HC  C  CH 2  COOH    (a) Chloral (b)
40 o C
(c) CH 3 Cl (d) Chloroacetic acid
Zn
(c) CH 2 Br  C  C  CH 2 Br 

Heat 52. Following equation illustrates

(d) 2 CH 2  CH  CH 2 I  200  250 C o

C 6 H 5 Cl  2 NaOH    C 6 H 5 ONa  NaCl  H 2 O
200 atm
43. When ethyl amine is heated with chloroform and alcoholic
[Bihar CEE 1995]
KOH, a compound with offensive smell is obtained. This
compound is [CPMT 1983, 84; RPMT 2002]
(a) Dow's process (b) Kolbe's process
(c) Carbylamine test (d) Haloform reaction
(a) A secondary amine (b) An isocyanide
53. One of the following that cannot undergo dehydro-halogenation
(c) A cyanide (d) An acid
is [J & K 2005]
44. Chlorobenzene on fusing with solid NaOH gives
(a) Iso-propyl bromide (b) Ethanol
[DPMT 1981; CPMT 1990]
(c) Ethyl bromide (d) None of these
(a) Benzene (b) Benzoic acid
54. A compound X on reaction with chloroform and NaOH gives a
(c) Phenol (d) Benzene chloride compound with a very unpleasant odour. X is
45. DDT can be prepared by reacting chlorobenzene (in the [MP PMT 1999]
presence of conc. H 2 SO 4 ) with (a) C 6 H 5 CONH 2 (b) C 6 H 5 NH 2
(a) Cl 2 in ultraviolet light (b) Chloroform (c) C 6 H 5 CH 2 NHCH 3 (d) C 6 H 5 NHCH 3
(c) Trichloroacetone (d) Chloral hydrate OH
46. When phenol reacts with CHCl 3 and KOH, the product O C2 H 5
obtained would be [RPMT 1997] 55.  C 2 H 5 I       Product
Anhydrous (C H OH )
2 5
(a) Salicylaldehyde (b) p-hydroxy benzaldehyde
(c) Both (a) and (b) (d) Chloretone
In the above reaction product is
47. Ethyl chloride on heating with silver cyanide forms a
compound X. The functional isomer of X is (a) C 6 H 5 OC 2 H 5 (b) C 2 H 5 OC 2 H 5
[EAMCET 1997; KCET 2005]
(c) C 6 H 5 OC 6 H 5 (d) C6 H 5 I
(a) C 2 H 5 NC (b) C 2 H 5 CN
 Halogen Containing Compounds

(b) COCl 2  Cl 2  H 2
Hydrolysis
56. C 2 H 5 Cl  KCN  X    Y . 'X' and 'Y' are
[MP PET 1995] COCl 2  Cl 2  H 2 O
(c)
(a) C 2 H 6 and C 2 H 5 CN
(d) No product will be formed
(b) C 2 H 5 CN and 67. Which isomer of cyclohexane hexachloride is a very strong
C2 H 6 insecticide [MP PET 2003]
(a)  (b) 
(c) C H CN and
2 5
(c)  (d) 
C 2 H 5 CH 2 NH 2
68. Haloalkane in the presence of alcoholic KOH undergoes
(d) C 2 H 5 CN and C 2 H 5 COOH [KCET (Engg/Med.) 2002]
(a) Elimination (b) Polymerisation
57. Iodoform is formed on warming I 2 and NaOH with
(c) Dimerisation (d) Substitution
[MP PET 1995; DCE 1999; RPET 1999; RPMT 2002]
69. The set of compounds in which the reactivity of halogen atom
(a) C 2 H 5 OH (b) CH 3 OH in the ascending order is [KCET (Engg.) 2002]
(c) HCOOH (d) C6 H 6 (a) Vinyl chloride, chlorethane, chlorobenzene
58. Which of the following reacts with phenol to give (b) Vinyl chloride, chlorobenzene, chloroethane
salicylaldehyde after hydrolysis [MP PMT 1995] (c) Chloroethane, chlorobenzene, vinyl chloride
(a) Dichloromethane (b) Trichloromethane (d) Chlorobenzene, vinyl chloride chloroethane
(c) Methyl chloride (d) None of these 70. Alkyl halides react with Mg in dry ether to form
59. Dehydrohalogenation in monohaloalkanes produces [DPMT 2000; MP PET 2001]
(a) A single bond (b) A double bond (a) Magnesium halide (b) Grignard’s reagent
(c) A triple bond (d) Fragmentation (c) Alkene (d) Alkyne
60. When chloroform is treated with conc. HNO 3 it gives 71. In the following sequence of reactions
[CPMT 1986; MP PMT 1989; AFMC 1998, 99;
EAMCET 1991; BHU 1999] KOH(alc) HBr KOH (aq .)
CH 3 CH 2 CH 2 Br  ( A)  (B)   (C ),
(a) CHCl 2 NO 2 (b) CCl 3 NO 2 The product (C) is [JIPMER 2001]
(c) CHCl 2 HNO 3 (d) None of these (a) Propan – 2 - ol (b) Propan – l – ol
61. A sample of chloroform being used as anaesthetic is tested by (c) Propyne (d) Propene
[AIIMS 1980; CPMT 1983] 72. Alkyl halide on heating with alc. NH 3 in a sealed tube
(a) Fehling solution results… [Orissa JEE 2002]
(b) Ammoniacal Cu 2 Cl 2 (a) 1° amine (b) 2° amine
(c) AgNO 3 solution (c) 3° amine (d) All of these

AgNO 3 solution after boiling with alcoholic KOH 73. When CH 3 CH 2 CHCl 2 is treated with NaNH 2, the
(d)
product formed is [CBSE PMT 2002]
solution
62. Dehydrohalogenation of an alkyl halide is [MP PMT 1996] (a) CH 3  CH  CH 2 (b) CH 3  C  CH
(a) An addition reaction (b) A substitution reaction CH 3 CH 2 CH ( NH 2 )(Cl )
(c) (d)
(c) An elimination reaction (d) An oxidation reaction
63. Reaction of aqueous sodium hydroxide on (i) ethyl bromide and CH 3 CH 2 C(NH 2 )2
(ii) chlorobenzene gives
74. By heating a mixture of CHCl 3 with silver powder, the
(a) (i) Ethene and (ii) o-chlorophenol
(b) (i) Ethyl alcohol and (ii) o-chlorophenol compound formed is [Kurukshetra CET 2002]
(c) (i) Ethyl alcohol and (ii) phenol (a) Acetylene (b) Silver acetate
(d) (i) Ethyl alcohol and (ii) no reaction (c) Methanol (d) None of these
64. 2-bromopentane is heated with potassium ethoxide in ethanol. 75. Chloropicrin is [Kurukshetra CET 2002]
The major product obtained is [CBSE PMT 1998] (a) Trichloro acetaldehyde (b) Nitrochloroform
(a) Pentene-1 (b) cis pentene-2 (c) 2,4,6-trinitro phenol (d) None of these
(c) trans pentene-2 (d) 2-ethoxypentane 76. Which of the following are correct statements about
65. What is the product formed in the following reaction C 2 H 5 Br [Roorkee 1999]
(1) NaOH
C 6 H 5 OH  CCl 4    [KCET 1998] (a) It reacts with metallic Na to give ethane
(2) H 
(b) It gives nitroethane on heating with aqueous ethanolic
(a) p-hydroxybenzoic acid (b) o-hydroxybenzoic acid
solution of AgNO 2
(c) Benzaldehyde (d) Salicylaldehyde
66. When chloroform is treated with excess oxygen it forms (c) It gives C 2 H 5 OH on boiling with alcoholic potash
[MH CET 1999]
(d) It forms ethylacetate on heating with silver acetate
(a) COCl 2  HCl 77. Aryl halide is less reactive than alkyl halide towards
nucleophilic substitution because [RPMT 2002]
 Halogen Containing Compounds

(a) Less stable carbonium ion 89. Vinyl chloride reacts with HCl to form [JIPMER 2000]
(b) Due to large C  Cl bond energy (a) 1, 1- dichloro ethane
(c) Inductive effect (b) 1, 2- dichloro ethane
(d) Resonance stabilization and sp 2 - hybridisation of C (c) Tetrachloro ethylene
attached to halide (d) Mixture of 1, 2 and 1, 1 – dichloro ethane
78. Methyl chloride reacts with silver acetate to yield 90. R  X  NaOH  ROH  NaX
[BVP 2003] The above reaction is classified as
(a) Acetaldehyde (b) Acetyl chloride [BHU 1982; CBSE PMT 1991; RPET 2000]
(c) Methyl acetate (d) Acetic acid (a) Nucleophilic substitution
79. Chloroform for anesthetic purposes is tested for its purity with (b) Electrophilic substitution
the reagent [DPMT 2001]
(c) Reduction
(a) Silver nitrate (b) Lead nitrate
(d) Oxidation
(c) Ammoniacal Cu 2 Cl 2 (d) Lead nitrate
91. Reduction of acetyl chloride with H 2 in presence of Pd gives
80. 2, 6 - Dimethylheptane on monochlorination produces……. [MP PMT 2001]
derivatives [DPMT 2001]
(a) 5 (b) 6 (a) CH 3 COCH 3 (b) C 2 H 5 OH
(c) 3 (d) 4 (c) CH 3 COOH (d) CH 3 CHO
81. The less reactivity of chlorine atom in CH 2  CH  Cl is
92. When methyl bromide is heated with Zn it gives
due to [DCE 2001]
[MP PMT 2001]
(a) Inductive effect (b) Resonance stabilization
(c) Electromeric effect (d) Electronegativity (a) CH 4 (b) C2 H 6
82. CH 3  CH 2  Br   CH 3 CH 2 CN  X
alc.KCN HOH
(c) C2 H 4 (d) CH 3 OH
In this reaction, product X is [MH CET 2002]
93. Phenol reacts with CHCl 3 and NaOH (at 340 K ) to give
(a) Acetic acid (b) Propionic acid
(c) Butyric acid (d) Formic acid [MP PMT 1997; CBSE PMT 2002]
83. In alkaline hydrolysis of a tertiary alkyl halide by aqueous (a) o-chlorophenol (b) Salicylaldehyde
alkali if concentration of alkali is doubled, then the reaction (c) Benzaldehyde (d) Chlorobenzene
[MH CET 2002] 94. Iodoform on heating with KOH gives [MP PMT 2000]
(a) Will be doubled (b) Will be halved
(c) Will remain constant (d) Can’t say (a) CH 3 CHO (b) CH 3 COOK
84. AgNO 3 does not give precipitate with CHCl 3 because (c) HCOOK (d) HCHO
[MP PET 1999; CPMT 2002] 95. Which reaction is correct in the conversion of chloroform to
(a) CHCl 3 does not ionise in water acetylene [Pb. PMT 2000]

AgNO 3 does not reacts with CHCl 3 (a) CHCl 3  AgNO 3 (b) CHCl 3  O 2
(b)
(c) CHCl 3 is chemically inert (c) CHCl 3  HNO 3 (d) CHCl 3  Ag
(d) None of these 96. Which of the following gases are poisonous
85. The reaction between chlorobenzene and chloral in the presence [Pb. PMT 2000]
of concentrated sulphuric acid produces (a) CHCl 3 (b) CO 2
[Pb. PMT 2001]
(a) Gammexane (c) None of these (d) CO
(b) p,p-dichloro diphenyl trichloro ethane 97. Which of the following alkyl halide is used as a methylating
(c) Chloropicrin agent [KCET (Med.) 2000; MP PET 1999]
(d) Benzene hexachloride (a) CH 3 I (b) C 2 H 5 Br
86. False statement is [RPET 1999]
(a) Chloroform is heavier than water (c) C 2 H 5 Cl (d) C 6 H 5 Cl
(b) CCl 4 is non-inflammable 98. C 6 H 6 Cl 6 , on treatment with alcoholic KOH , yields
(c) Vinyl chloride is more reactive than allyl chloride [AFMC 2000]
(d) Br is a good nucleophile as compared to I 

(a) C6 H 6 (b) C 6 H 3 Cl 3
87. Chloroform is slowly oxidise by air in presence of light to form
[MH CET 1999; UPSEAT 2001, 02; RPMT 2003] (c) (C 6 H 6 ) OH (d) C 6 H 6 Cl 4
(a) Formyl chloride (b) Phosgene 99. When ethyl iodide is heated with silver nitrate, the product
(c) Trichloroacetic acid (d) Formic acid obtained is [CPMT 2000]
88. Alcoholic potash is used to bring about (a) C 2 H 5 Ag (b) Ag  O  NO 2
[KCET (Engg.) 2001]
(a) Dehydrogenation (b) Dehydration (c) C 2 H 5 O  NO 2 (d) C 2 H 5 I  NO 2
(c) Dehydrohalogenation (d) Dehalogenation
 Halogen Containing Compounds

100. CHCl 3 and HF lead to the formation of a compound of 7. CFx Cl y [where x + y = 4]. These compounds are not used
fluorine of molecular weight 70. The compound is because [RPET 2000]
[RPET 2000] (a) These are fluoro carbons
(a) Fluoroform (b) Fluorine monoxide (b) These are difficult to synthesise
(c) They deplete ozone layer
(c) Fluorine dioxide (d) Fluromethanol
(d) None of the these
8. The molecular formula of DDT has [MP PMT 1997]
(a) 5 chlorine atoms (b) 4 chlorine atoms
Uses of Halogen Containing Compounds (c) 3 chlorine atoms (d) 2 chlorine atoms
9. What is the reagent used for testing fluoride ion in water
[EAMCET 2003]
1. Which of these can be used as moth repellant (a) Alizarin - S (b) Quinalizarin
[CPMT 1987] (c) Phenolphthalein (d) Benzene
(a) Benzene hexachloride (b) Benzal chloride 10. Chloropicrin is used as [UPSEAT 2000]
(c) Hexachloroethane (d) Tetrachloroethane (a) Solvent (b) Anaesthetic
(c) Perfume (d) Tear gas
2. Which one of the following is the correct formula of 11. Which is used in the manufacture of plastic
dichlorodiphenyl trichloroethane [AIIMS 1982]
H Cl (a) CH 2  CHCl (b) CH  CH
| |
(a) Cl C ––– C ––– Cl (c) CH 2  CH  CH 2 I (d) CCl 4
| 12. Freon (dichlorodifluoro methane) is used
Cl [CPMT 1986; DPMT 1983; CBSE PMT 2001]
(a) As local anaesthetic
(b) For dissolving impurities in metallurgical process
Cl (c) In refrigerator
H Cl (d) In printing industry
| | 13. Which of the following is known as freon which is used as a
(b) C ––– C ––– Cl refrigerant [DPMT 1982; CPMT 1979, 81, 89; AFMC 1995;
| Manipal MEE 1995; MP PET 1995, 2004]
Cl (a) CCl 2 F2 (b) CHCl 3
(c) CH 2 F2 (d) CF4
H Cl
| | 14. Benzene hexachloride (BHC) is used as
(c) Cl C ––– C ––– Cl [MP PMT 1994; KCET 1999]
|
(a) Dye (b) Antimalerial drug
Cl
(c) Antibiotic (d) Insecticide
15. Which plastic is obtained from CHCl 3 as follows
Cl Cl
(d)
| | HF 800 o C Polymerisa tion
Cl C ––– C ––– Cl CHCl 3 
 X  Y  
 Plastic
SbF3
|
Cl (a) Bakelite (b) Teflon
(c) Polythene (d) Perspex
OH
Cl Cl
3. The compound | is
(CH 3 )2 .CCCl 3 C  CCl 3
16. | . The above structural
(a) Chloretone (b) Chloroquin Cl H
(c) Chloropicrin (d) Chloropropyl chloride
4. Depletion of ozone layer is caused by [RPMT 2002]
formula refers to [MP PET 1997]
(a) Freon (b) Alkane
(c) Gringard reagent (d) All of these (a) BHC (b) DNA
5. Which of the following is Teflon [RPMT 2002] (c) DDT (d) RNA
(a) [CF2  CF2 ]n (b) CF2  CF2 17. The commercial uses of DDT and benzene hexachloride are
(a) DDT is a herbicide, benzene hexachloride is a fungicide
(c) CF  CF (d) None of these
(b) Both are insecticides
6. Statement “Ozone in atmosphere is decreased by chloro-fluoro-
(c) Both are herbicides
carbon (Cl 2 F2 C ) ” [RPET 1999]
(d) DDT is a fungicide and benzene hexachloride is a
(a) Is true herbicide
(b) Is false 18. Which of the following is used in fire extinguishers
(c) Only in presence of CO 2 [AFMC 1993]
(d) Only in absence of CO 2 (a) CH 4 (b) CHCl 3
(c) CH 2 Cl 2 (d) CCl 4
 Halogen Containing Compounds

19. Iodoform can be used as [NCERT 1981] 11 b 12 c 13 a 14 a 15 d

(a) Anaesthetic (b) Antiseptic 16 b 17 c 18 b 19 b 20 d
(c) Analgesic (d) Antifebrin 21 d 22 c 23 b 24 a 25 b
20. Which of the following is an anaesthetic [AFMC 1989] 26 c 27 d 28 b 29 a 30 b
(a) C2 H 4 (b) CHCl 3 31 c 32 c 33 b 34 a 35 a

(c) CH 3 Cl (d) C 2 H 5 OH 36 a 37 a 38 a 39 a 40 a
41 a 42 c 43 b 44 c 45 d
21. An important insecticide is obtained by the action of chloral on
chlorobenzene. It is [KCET 1989] 46 c 47 b 48 ab 49 b 50 b
(a) BHC (b) Gammexene 51 a 52 a 53 b 54 b 55 a
(c) DDT (d) Lindane 56 d 57 a 58 b 59 b 60 b
22. In fire extinguisher, pyrene is [DPMT 1985] 61 c,d 62 c 63 c 64 c 65 b
(a) CO 2 (b) CCl 4 66 c 67 c 68 a 69 d 70 b
71 a 72 d 73 d 74 a 75 b
(c) CS 2 (d) CHCl 3
76 b,d 77 d 78 c 79 a 80 d
23. B.H.C. is used as [Pb. CET 2002] 81 b 82 b 83 c 84 a 85 b
(a) Insecticide (b) Pesticide 86 cd 87 b 88 c 89 a 90 a
(c) Herbicide (d) Weedicide
91 d 92 b 93 b 94 c 95 d
24. The use of the product obtained as a result of reaction between
96 d 97 a 98 b 99 c 100 a
acetone and chloroform is [RPMT 1999]
(a) Hypnotic (b) Antiseptic
(c) Germicidal (d) Anaesthetic Uses of Halogen containing compounds
25. Use of chlorofluoro carbons is not encouraged because
1 c 2 a 3 a 4 a 5 a
[KCET 2005]
6 a 7 c 8 a 9 a 10 d
(a) They are harmful to the eyes of people that use it
(b) They damage the refrigerators and air conditioners 11 a 12 c 13 a 14 d 15 b
(c) They eat away the ozone in the atmosphere 16 c 17 b 18 d 19 b 20 b
(d) They destroy the oxygen layer 21 c 22 b 23 a 24 a 25 c

Introduction of Halogen containing compounds

1 a 2 b 3 b 4 c 5 b
6 a 7 b 8 a 9 b 10 a
11 d 12 a 13 b

Preparation of Halogen containing compounds

1 b 2 d 3 b 4 a 5 a
6 b 7 d 8 d 9 b 10 a
11 a 12 b 13 a 14 a 15 a
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

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