CHEMISTRY Halogen Compounds

EXERCISE-I [Fundamental Questions]

1. When propylene reacts with HBr in 8. A gem dichloride is formed in the
presence of peroxide, the product formed reaction -
is - (1) CH3CHO and PCl5
(1) n-Propyl alcohol
(2) CH3COCH3 and PCl5
(2) Propylene peroxide
(3) n-Propyl bromide (3) CH2=CHCl and HCl
(4) 1,3-Dibromo propene (4) All the above

2. In reaction 9. 2,2-dichloropropane on hydrolysis yields -

C2H5OH + HX ZnX 2  C2H5X + H2O (1) Acetone

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the order of reactivity of HX is - (2) 2,2-Propane diol
(1) HBr > HI > HCl (2) HI > HCl > HBr
(3) Isopropyl alcohol
(3) HCl > HBr > HI (4) HI > HBr > HCl
(4) Acetaldehyde

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3. Which of the following leads to the
formation of an alkyl halide - 10. The oxidation of CHCl3 by air & light is
Re d P  Br2
(1) C H OH  
2 5
prevented by adding -
(1) CH3COOH (2) C2H5OH
(2) C2H5OH  
SOCl2

KBr  Conc , H2 SO4

(3) C2H5OH    IT (3) CH3CHO (4) CH3COOCH3
CH
(4) All the above 11. CHCl3 is kept in brown bottles well
4. Which reaction is termed as Darzen’s stoppered and also with 1% alcohol so
Reaction - that it may not form -
(1) ROH + HCl (2) ROH + PCl5 (1) CH2Cl2 (2) COCl2
P

(3) ROH + SOCl2 (4) ROH + PCl3 (3) CCl4 (4) None of these
EE

5. In Finkelstein Reaction, which reactants 12. Chloroform can be obtained from -

are used -
(1) Methanol (2) Methanal
(1) NaI + C2H5OH
D

(3) 1-Propanol (4) 2-Propanol

(2) NaCl + acetone
(3) NaBr + CH3COCH3
A

13. Which of the following statement is

(4) NaI + CH3COCH3
wrong -
PR

6. C2H5Cl + AgF C2H5F + AgCl (1) All carbonyl compounds like CH3–C–R gives
The above reaction is called - O
(1) Hunsdiecker (2) Swart a positive iodoform test
(3) Strecker (4) Wurtz (2) All secondary alcohols give iodoform
reaction
7. A vicinal dihalide is not formed in the
(3) Alkanols of the structure CH3CH(OH)–R
reaction-
(where R=H, alkyl or aryl) give iodoform
(1) HOCH2–CH2OH PBr 
3 
reaction
(2) CH3–CH = CH2 
Br2
 (4) The only aldehyde giving iodoform
(3) CHCH    
HBr HBr
reaction is acetaldehyde.
(4) CH3–CH=CHBr HBr
 Peroxide

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 Halogen Compounds CHEMISTRY

14. Which of the following hydrocarbon with 20. 2-Bromobutane on heating with alcoholic
formula C8H18 gives one monochloro alkali forms -
derivatives ? (1)  - Butylene only
(1) n-Octane (2)  - Butylene only
(2) 3-Methyl heptane
(3) 20% of -Butylene+ 80% of -Butylene
(3) 2,2,4-Trimethyl butane
(4) 2,2,3,3-Tetramethyl butane (4) 80% -Butylene + 20% -Butylene

Cl2 aq.KOH (O)

15. The SN2 reactivity order for halides :- 21. (A) 
 (B)   (C)  CH3CHO,
(1) R - F > R - Cl > R - Br > R - I Identify A, B & C -
(2) R - I > R - Br > R - Cl > R - F

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(1) Ethylalcohol, Ethyl chloride & Ethane
(3) R - Br > R - l > R - Cl > R - F
(2) Ethane, Ethylchloride & CH3CH2OH
(4) R - Cl > R - Br > R - F > R - I
(3) Propane, Propylchloride &
16. In SN1 reaction, the first step involves the CH3CH2CH2OH

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formation of : - (4) All the above
(1) Free radical (2) Carbanion
(3) Carbocation (4) Final product 22. Ethylthioalcohol can be obtained when

17. The rate law for the reaction,

RCl + NaOH (aq)  ROH + NaCl IT C2H5Br reacts with -
(1) KSH (2)NaOH (3) K2S (4) Na2S
CH
is given by, rate = K1 [RCl]. The rate of
the reaction will be : - 23. The given reaction is called as -
(1) Doubled on doubling the C2H5ONa + BrC2H5  C2H5OC2H5 + NaBr
concentration of sodium hydroxide (1) Frankland reaction
(2) Halved on reducing the concentration
P

(2) Wurtz reaction

of alkyl halide to half (3) Williamson’s synthesis
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(3) Decreased on increasing the (4) Cannizzaro reaction

temperature of the reaction
(4) All the above
24. An alkyl halide reacts with metallic
D

18. Which of the following statements is sodium in dry ether, the reaction is
invalid- known as -
A

(1) The more stable the carbocation the faster it (1) Frankland’s reaction
is formed (2) Sandmeyer’s reaction
PR

(2) Propyl cation changes to more stable (3) Wurtz’s reaction

isopropyl carbocation by 1,2 shift of a (4) Kolbe’s reaction
hydride
(3) Isopropyl chloride reacts with sodium 25. Silver benzoate reacts with bromine in
ethoxide to form 1-ethoxypropane
CCl4 to form -
(4) All the above
Br COBr

19. Which of the following reaction is the (1) (2)

most common among alkyl halides -
(1) Nucleophilic addition COOAg
(2) Nucleophilic substitution
(3) Electrophilic addition (3) (4)
Br
(4) Electrophilic substitution

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 CHEMISTRY Halogen Compounds

26. What happens when CCl4 is treated with 32. Treatment of ethylidene chloride with aq.
AgNO3 - KOH gives -
(1) A white ppt. of AgCl will be formed (1) Ethylene (2) Acetaldehyde
(2) Nothing will happen (3) Formaldehyde (4) None of these
(3) NO2 will be evolved
33. The reaction of chloroform with acetone
(4) CCl4 will dissolved in AgNO3
gives-
(1) Mesitylene
    ?
H2 O,
27. CH3CHI2 KCN  (2) Ethylidene chloride
Here the end product would be - (3) Chloretone

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(1) 2-Cyano propionic acid (4) Chloral
(2) Ethane-1,1-dicarboxylic acid
(3) 2-Methyl ethanoic acid 34. CCl4 is used as a fire extinguisher
(4) Propionic acid because-

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(1) Of its covalent bond
28. Among following which is an SN1 reaction- (2) Of its low b.p.
(1) (CH3)3CBr + H2O ––  (3) Of its high m.p.
(4) It gives incombustible vapours


(2) CH3CH2CH2Cl + I– ––
(3) (CH3)3CBr + CN– ––  IT 35. (CH3)3CBr + H2O – (CH3)3COH + HBr
CH
 (4) CH3CHBrCH3 + KOH(alc.) –– Which of the following statements is true
for the above reaction –
29. Treatment of ammonia with excess ethyl (1) If we double [RBr] the rate become
chloride will give - four times
(2) If we reduce [OH]– to half, there is
P

(1) Diethylamine
(2) Ethane no change in the rate.
EE

(3) Methylamine (3) If we double [RBr] the rate does not

(4) Tetraethyl ammonium chloride change.
(4) If we double [OH]– the rate become
D

30. In the reaction the main product is - double

CH3CH2CHBrCH3 + (CH3)3COK – ?
A

36. For CH3Br + OH– –––– CH3OH + Br–

(1) CH3CH2CHCH3
the rate of reaction is given by the
PR

OC(CH3)3
expression-
(2) CH3CH2CHCH3
(1) rate = k [CH3Br]
OH
(2) rate = k [OH–]
(3) CH3CH2CH=CH2
(3) rate = k [CH3Br] [OH–]
(4) CH3CH=CHCH3
(4) rate = k [CH3Br]0 [OH–]0
31. The iodoform test is used to show one
37. Arrange the following in decreasing
particular structural unit in -
order of C-halogen bond length -
(1) Aliphatic alcohols
(1) CH3I > CH3Br > CH3Cl > CH3F
(2) Aromatic acids
(3) Aliphatic acid (2) CH3F > CH3Br > CH3I > CH3Cl
(4) Hydrocarbons (3) CH3CI > CH3Br > CH3I > CH3F
(4) CH3I > CH3Cl > CH3Br > CH3F
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 Halogen Compounds CHEMISTRY

38. Freon - 112 is - 43. Which of the following reactions will not
(1) C2Cl4F2 (2) CCl2 F2 give an isocyanide -
(3) CCl3F (4) C2Br4F2 (1) CH3CH2Br + AgCN 
(2) CH3CH2NH2 + CHCl3 + KOH heat 
heat
39. CH3CCl3 alkaline
  A AgOH
Br2
 C
 B  (3) CH3CH2CONH2 + P2O5  
hydrolysis CCl4
(4) All of the above
A and C in the above sequence are
respectively - 44. Which of the following processes does
(1) Acetic acid, ethyl bromide not occur during the formation of CHCl3
(2) Acetic acid, ethyl chloride
from C2H5OH and bleaching powder -
(3) Acetic acid, methyl bromide

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(1) Oxidation (2) Chlorination
(4) Acetic acid, methyl chloride
(3) Hydrolysis (4) Reduction
40. In the reaction 45. Which of the following reactions is not

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RCOOAg + Br2 CCl 4  RBr+CO2+AgBr expected to give a satisfactory yield of
the intermediate formed is - alkyl iodide -
(1) R–COOBr (2) RCOO• (1) CH3CH2OH + KI + H3PO4 
(3) R• (4) all of these (2) CH3CH2OH + PI3 heat

41. Consider the following reaction IT 

acetone
(3) CH3CH2Br + NaI  
(4) CH3CH2COOAg + I2 CCl


4 
CH
Heat
sequence.
CH3CCH aq .H 2SO 4
  A PCl 5  B
HgSO4 heat 46. Consider the following sequence of
The product (A) and (B) are, respectively - reactions.
(1) CH3COCH3 and CH3CCl2CH3 C2H5Cl  KCN 
 X H3O Y
P

(2) CH3CH2CHO and CH3CH2CHCl2 The products (X) and (Y) are,
EE

(3) CH3CHOHCH3 and CH3CHClCH3 respectively -

(4) CH3CH2CH2OH and CH3CH2CH2Cl (1) C2H5CN and C2H5CH2NH2
(2) C2H5CN and C2H5CONH2
D

42. Neopentyl bromide is allowed to react (3) C2H5NC and C2H5NHCH3

with sodium ethoxide in ethanol. The (4) C2H5CN and C2H5COOH
A

major substitution product formed in the

reaction is - 47. 2-Bromopentane is heated with
PR

CH3 potassium ethoxide in ethanol. The major

(1) CH3–C–CH2–OC2H5 product is -
CH3 (1) trans-2-pentene (2) 2-ethoxypentane
CH3 (3) 1-pentene (4) cis-2-pentene
(2) CH3CH2–C–OC2H5
CH3
48. The order of decreasing SN1 reactivities
CH3 of the halides is -
CH3CH2CH2Cl CH2=CHCHClCH3
(3) CH3–CH–CHCH 3
I II
OC2H5
CH3CH2CHClCH3
(4) CH3–CH–CH2–CH2–OC2H5
III
CH3 (1) I > II > III (2) II > I > III
(3) II > III > I (4) III > II > I
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CHEMISTRY Halogen Compounds

49. In the preparation of ethyl chloride by the 53. Which of the following reactions is
reaction expected to take place by SN2 mechanism?
anhydrous
C2H5OH + HCl 
ZnCl
 C2H5Cl + H2O CH3
2
H2O
the major reason for using anhydrous (1) CH3–CH2–C–Br+AgOH
ZnCl2 as a catalyst is that CH3
(1) It absorbs water formed in the reaction CH3CO2 Na
(2) CH3CH2CHBrCH3  
CH COOH
and drives the equilibrium to the right. 3

(2) It coordinates with the product DMSO

(3) (CH3)2CHBr + AgCN 
CH3CH2Cl and drives the reaction to the (4) All the above

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right.
(3) It assists in forming the nucleophile
54. An alkyl bromide (A) forms Grignard’s
Cl– from HCl
(4) It coordinates with oxygen of ethyl reagent which on treatment with water

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alcohol and increases the leaving group yields n-Hexane.
ability of the –OH group (A) with sodium/ether forms 4, 5-diethyl
octane. (A) is –

IT
50. Consider the following reaction sequence. (1) CH3(CH2)5Br
HCl
CH3C  CH 2  (A) aq.

KOH
 (B)
mole heat (2) CH3(CH2)3CH(Br)CH3
CH
The products (A) and (B) are, (3) CH3–(CH2)2–CH(Br)CH2CH3
respectively,
(1) CH3CH2CHCl2 and CH3CH2CHO (4) CH3(CH2)2CH(Br)CH=CH2
(2) CH3CCl2CH3 and CH3COCH3
P

(3) CH3CCl2CH3 and CH3CCH 55. Major product for the reaction is -
EE

(4) CH3CHClCH2Cl and Br


2
CH3CHOHCH2OH hv

Br
D

51. In the following reaction (1) Br (2)

Br + HCCNa  
 ? Br
A

Product will be
(3) (4)
(1) CCH (2) =CH2 Br
PR

(3) (4) CC–CH3

56. Grignard reagent can be prepared by –
52. In which of the following product of the
(1) CH3–CH2–Cl + Mg dry

reaction respond positively to the ether

iodoform test ? (2) CH3–CH–CH2 + Mg  dry

 ether
(1) (CH3)2C=CH2 H3O Cl Cl
heat

(2) CH3–CH=CH2 1

.B 2 H 6
  CH3
2.H 2O 2 / OH
(3) CH3–C–Cl + Mg dry

1. B 2 H 6 ether
(3) CH3–CCH  

CH3
2.H 2O 2 / OH

H 2O
(4) CH3–CC–CH3 Hg
 2
 (4) All of these

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 Halogen Compounds CHEMISTRY

57. What are (A) & (B) in the following 60. A compound containing two-OH groups
reaction ? attached with one carbon atoms is
Cl unstable but which one of the following
is stable –
(i) Mg/Et 2O (ii)CH3CHO
  [A]   [B] OH
Br (iii)H 2 O OH
(1) CH3CH (2) CH3–C–CH3
MgCl CHOHCH3 OH
OH
OH
(1) & (3) Cl3C–CH (4) All of above
Br Br OH
Cl Cl
61. An organic compound on treatment with

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(2) & alcoholic KOH gives a hydrocarbon of a
MgBr CHOHCH3
molecular fromula C4H8. Oxidation of the
MgCl MgCl
hydrocarbon gives propionic acid and

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CO2. The organic compound should be -
(3) &
Br CHOHCH3 (1) C2H5–CH2–CH2Cl
(4) None of these CH3
(2) CH3–C–Cl
58. Identify (Z) in the following reaction
series,
IT CH3
(3) CH3–CH–CH–CH3
CH
Al O Cl
CH3CH2CH2Braq. NaOH
 (X)23  (Y)
Heat (4) CH3–CH–CH–CH 2Cl
Cl / H O
2 
2
 (Z) Cl
(1) CH3–CH–CH2 (2) CH3–CH–CH2
P

OH OH OH Cl 62. An aromatic primary amine (A) is heated

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with another compound (B) in the presence

(3) CH3–CH–CH2 (4) CH3–CH–CH2 of alcoholic KOH to give a bad-smelling
Cl OH
compound having the formula C6H5NC.
Cl Cl
The compound (B) can be prepared by
D

heating another compound (C) with

59. A compound (A) formula of C3H6Cl2 on
chlorine and slaked lime. The compound
A

reaction with alkali can give (B) of (C) is -

formula C3H6O or (C) of formula C3H4. (1) C6H5NH2 (2) C2H5OH
PR

(B) on oxidation gave a compound of the (3) CHCl3 (4) CH3OCH3

formula C3H6O2. (C) with dilute H2SO4
containing Hg2+ ion gave (D) of formula 63. CH3–C–CH3 2 I Ag
 (A)  (B) 
2

H O
 (C)
NaOH Hg
C3H6O, which with bromine and alkali O
gave the sodium salt of C2H4O2. Then Product A, B & C are -
(A) is – (1) Iodoform, Acetylene & Acetaldehyde
(1) CH3CH2CHCl2 (2) Triiodomethane, Ethyne & Acetone
(3) Iodoform, Ethene & Ethylene glycol
(2) CH3CCl2CH3
(4) Ethene, iodoform & Ethylhydrogen
(3) CH2ClCH2CH2Cl sulphate
(4) CH3CHClCH2Cl

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CHEMISTRY Halogen Compounds

64. Consider the following sequence of C–CH2–C–OH  NaOH

reactions. 68. || || 
 A 
I
 B+C
2
O O
1. B H 6
(A ) alc.KOH
 (B) 2  (C) Products B and C are –
( C3 H 6Cl 2 ) heat 2. H 2O 2 / OH
C–CH3
aq.KOH
(A)   (C) (1) || + CH3–COOH
O
The compound (A) is - C–CH2–COONa
(2) || + CHI3
(1) CH3CH2CHCl2 (2) CH3CCl2CH3 O
(3) CH3CHClCH2Cl (4) ClCH2CH2CH2Cl
(3) + CH3–C–CH3
65. Consider the following reaction sequence. ||
O

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CH3
1.HBr
  COONa
CH3–C–CH=CH2 2.KOH  EtOH/heat
(4) + CHI3
CH3
The major end product formed is

TO
CH3 69. CH3–C–CH2–CH2–CH2Cl CH MgBr
3  A,
H3C CH3 ||
O
(1) CH3–C–––CH–CH3 (2) CH3–C–CH–CH3
product A is -
CH3 OH OC2H5 CH3

IT
|
CH3 (1) CH3CCH2CH2CH2Cl
|
(3) CH3–C–CH=CH 3 (4) CH3–C===C–CH3 OH
CH
(2) CH3CCH2CH2CH2CH3
CH3 ||
CH 3 CH3 O
CH3
Cl (3)
THF CO2 H 3O  O CH3
66. + Mg  A  B   C.
P

H3C CH3
(1mole )
(4)
EE

Br O
End product C is - H3C
COOH Cl
CH3 H CH3
D

(1) (2)
70. MeO NO2
A

COOH COOH
COOH H Cl CH3
Cl
on hydrolysis mainly produces -
PR

(3) (4) CH3H CH3

(1) MeO NO2
Br H OH CH3
67. A compound (X), C4H8Cl2, on hydrolysis CH3 H CH3
with aqueous KOH gives a product (Y) (2) MeO NO2
which on heating with I2 and dilute OH H CH3
NaOH gives a yellow precipitate of CH3H CH3
iodoform. The compound (X) is - (3) MeO NO2
(1) CH3CH2CH2CHCl2 H CH3OH
(2) CH3CH2CHClCH2Cl (4) All the above
(3) CH3CH2CCl2CH3
(4) ClCH2CH2CH2CH2Cl

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PR
A
D
EE
P
CH
IT
TO
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