TOPIC : ORGANIC COMPOUNDS CONTAINING HALOGENS
1. When primary amine reacts with chloroform in 6. The IUPAC name of the compound shown below is
ethanolic KOH, then the product is
(a) an isocyanide (b) an aldehyde
(c) a cyanide (d) an alcohol
2. The compound formed on heating chlorobenzene
(a) 2-bromo-6-chlorocyclohexene-1-ene
with chloral in the presence of concentrated
(b) 6-bromo-2-chlorocyclohexene
sulphuric acid, is
(c) 3-bromo-1-chlorocyclohexene
(a) gammexane (d) 1-bromo-3-chlorocyclohexene
(b) hexachloroethane 7. Fluorobenzene (C6H5F) can be synthesized in the
(c) freon laboratory
(d) DDT (a) by heating phenol with HF and KF
3. Tertiary alkyl halides are practically inert to (b) from aniline by diazotization followed by heating
substitution by S N2 mechanism because of the diazonium salt with HBF4
(c) by direct fluorination of benzene with F2 gas
(a) steric hindrance (b) inductive effect
(d) by reacting bromobenzene with NaF solution
(c) instability (d) insolubility
8. Phenyl magnesium bromide reacts with methanol
4. Elimination of bromine from 2-bromobutane results
to give
in the formation of (a) a mixture of anisole and Mg(OH) Br
(a) predominantly 2-butyne (b) a mixture of phenol and Mg(OMe)Br
(b) predominantly 1-butene (c) a mixture of toluene and Mg(OH) Br
(c) predominantly 2-butene (d) a mixture of benzene and Mg(Me) Br
(d) equimolar mixture of 1 and 2-butene 9. CH3Br + Nu CH3 Nu + Br
5. The structure of the major product formed in the The decreasing order of the rate of the above
following reaction reaction with nucleophiles (Nu) (A) to (D) is
[Nu = (A) PhO, (B) AcO (C) HO, (D) CH3O]
(a) D > C > C > A (b) D > C > B > A
(c) A > B > C > D (d) B > D > C > A
10. An alkyl halide may be converted into an alkene by
is (a) Addition (b) Substitution
(c) Elimination (d) Hydrogenation
11. Which of the following alkyl halides has the
maximum density ?
(a) C2H6Cl (b) C2H5Br
(c) C2H5I (d) C2H6F
12. Chlorobenzene on reaction with CH3Cl in the
presence of AlCl3 will give
(a) Toluene
(b) m-Chloro toluene
(c) p-Chloro toluene
(d) A mixture of o- and p-chlorotoluene
13. 2, 2-Dichloropropane on alkaline hydrolysis gives 22. The reaction
(a) 2, 2-Propanediol (b) Propanol Br
|
(c) Propanone (d) Ethanal
CH 2 CH CH 3 HBr CH 3 C H CH 3
14. If chloroform is left open in the air in the presence
is
of sunlight
(a) Nucleophilic addition
(a) Explosion takes place
(b) Electrophilic addition
(b) Polymerization takes place
(c) Electrophilic substitution
(c) Poisonous gas phosgene is formed
(d) Free radical addition
(d) No reaction takes place
23. Which of the following has highest chlorine
15. Geminal dihalides on hydrolysis give
content?
(a) Ketones
(a) Pyrene (b) D.D.T.
(b) Aldehydes
(c) Chloral (d) Gammexane
(c) Ketones and aldehydes
24. The best reagent for converting alcohols to alkyl
(d) Alcohols
chlorides is
16. When ethyl iodide is treated with moist silver oxide,
(a) PCI5 (b) PCI3
the product formed is
(c) HCI/ZnCl2 (d) SOCl2
(a) C2H6OH (b) C2H5OC2H5
25. Which of the following halides is not a primary
(c) (d) CH3CHO
halide ?
(a) iso-Pentyl chloride (b) neo-Pentyl chloride
17. When chloroform is exposed to air and sunlight, it
(c) iso-Butyl chloride (d) iso-Propyl chloride
gives
26. Iodobenzene can be converted into diphenyl by
(a) Mustard gas (b) Lewisite
(a) Wurtz reaction (b) Wurtz-Fittig reaction
(c) Carbonyl chloride (d) Carbon tetrachloride
(c) UIlmann reaction (d) Frankland reaction
18. NBS is a specific reagent for
27. During chlorination of benzene using Cl2 in the
(a) Nucleophilic substitution
presence of FeCl3, the attacking species is
(b) Electrophilic substitution
(a) Cl
+
(b) Cl
(c) Allylic substitution
(c) Cl2 (d) FeCl4
(d) Electrophilic addition
28. Chloroalkanes can be converted into iodoalkanes
by
X. The product X is
CH Cl
19. 2
AlCl3 (a) Frankland reaction
(a) Benzyl chloride (b) Benxal chloride (b) Finkelstein reaction
(c) Benzo chloride (d) Diphenyl methane (c) Balz-Shiemann reaction
20. ‘Pyrene’ is the trade name of ….. when used as fire (d) Hunsdiecker reaction
extingulisher 29. Benzene diazonium chloride can be converted into
(a) CO2 (b) CHCl3 chlorobenzene by
(c) CCl4 (d) CH2Cl2 (a) Gattermann reaction
21. CX bond is strongest in (b) Sandmeyer reaction
(a) CH3Cl (b) CH3Br (c) Both of the above
(c) CH3F (d) CH3L (d) None of these
30. When silver propionate is treated with Br2 is CCl4 38. The reaction,
as solvent, the product is C H 2 CH 2 C H 2 CH 2 CH 2
Na
| | ether
(a) Propionyl bromide (b) n-Propyl bromide Cl Cl
CH2
(c) iso-Propyl bromide (d) Ethyl bromide
31. Acetylene is treated with excess HBr and the is known as
resultant compound is then heated with zinc dust. (a) Wurtz reaction
The final product will be (b) Fitting reaction
(a) Ethylene (b) Acetylene (c) Wurtz-Fitting reaction
(c) 1-Butene (d) 2-Butene (d) Freund reaction
32. For the reaction 39. Which of the following nucleophiles would react
C2H5OH + HX C2H5X + H2O, through S N2 mechanism most readily ?
the order of reactivity is ..
(a) HCI > HBr > HI (b) HI > HBr > HCI (a) : O H (b) H 2 O
(c) HBr > HCI > HI (d) HI > HCI > HBr ..
(c) N H 3 (d) : O R
33. Identify Z in the following sequence
40. Reactivity of alkyl halides towards
CH3CH2I X Y Z
KCN Conc. HCI dil. HCI
dehydrohalogenation reaction is
o o o o o o
(a) CH3COCl (b) CH3CONH2 (a) 1 > 2 > 3 (b) 3 > 1 > 2
o o o o o o
(c) CH3COOH (d) CH3CH2COOH (c) 3 > 2 > 1 (d) 2 > 1 > 3
34. 2-Chloro-2-methylbutane, on reaction with alc. KOH
PBr3 NH3
gives X as the major product, X is 41. X Y
(a) 2-Methyl-1-butanol (b) 2-Methyl-1-butene
The compound Y in the above sequence is
(c) 2-Methyl-2-butene (d) 2-Methyl-2-butanol
(a) Cyclohexane
35. Aryl halides are less reactive towards nucleophiles
(b) Cyclohexylamine
than alkyl halides due to
(c) 2-Bromocyclohexylamine
(a) Resonance (b) Stability of carbocations
(d) 4-Bromocyclohexylamine
(c) High boiling point (d) None of the above
42. Which of the following halides can be made in good
36. The reaction described below is yield by free radical halogenation of parent
hydrocarbon ?
CH3
|
(a) CH3CH2CH2Cl (b) CH C CH Cl
3 2
|
2 CH3
(a) E (b) S N1
(c) CH 3 CH 2 C HCH 3 (d) CH3CH2CH2CH2Cl
(c) S N0 (d) S N2 |
Cl
37. Carbylamine test is performed in alcoholic KOH by 43. Benzyl chloride (C6H5CH2Cl) can be prepared from
heating a mixture of toluene by chlorination with
(a) Chloroform and silver powder SO2Cl2 SOCl2 Cl2 NaOCI
(b) Trihalogenated methane and a primary amine I II III IV
(c) An alkyl halide and a primary amine (a) I, II and III (b) I and III
(d) An alkyl cyanide and a primary amine (c) II and III (d) All of the above
44. The order of reactivity of various alkyl halides 48. Arrange the following compounds in order of
towards S N1 reaction is increasing dipole moment
o o o o o o Toluene (I) m-Dichlorobenzene (II)
(1) 3 > 2 > 1 (b) 1 > 2 > 3
o o o o o o o-Dichlorobenzene (III) p-Dichlorobenzene (IV)
(3) 3 = 2 = 1 (4) 1 > 3 > 2
(a) I < IV < II < III (b) IV < I < II < III
45. Dipole moment is shown by
(c) IV < I < III < II (d) IV < II < I < III
(a) 1, 4-Dichlorobenzene
49. Which of the following statements is not correct ?
(b) cis-1, 2-dichlorethylene
(a) C-Cl bond in vinyl chloride is less polar than in
(c) trans-1, 2-dichloroethylene
CH3Cl
(d) Tetrachloromethane
(b) C-Cl bond in vinyl chloride is stronger than in
46. Which of the following statements are not correct ?
CH3Cl
(a) Chlorobenzene is more reactive than benzene
(c) C-Cl bond in vinyl chloride is shorter than in
towards electrophilic substitution reactions
CH3Cl
(b) C-Cl bond in chlorobenzene is less polar than in
(d) Vinyl chloride undergoes nucleophilic
CH3Cl
substitution more readily than CH3Cl
(c) Chlorobenzene is less reactive than CH3Cl
50. Replacement of Cl of chlorobenzene to give phenol
towards nucleophilic substitution reactions
requires drastic conditions but chlorine of 2, 4-
(d) In chlorobenzene further substitution take place
dinitrochlorobenzene is readily replaced because
at ortho and para position
47. neo-Pentyl chloride on dehydrohalogenation (using (a) NO2 makes the ring electron rich at ortho and
low conc. of base) yields mainly para positions
(a) 2-Methylbut-2-ene (b) NO2 withdraws electrons at meta position
(b) 2-Methylbut-1-ene (c) NO2 donate electrons at meta-position
(c) 3-Methylbut-1-ene (d) NO2 withdraws electrons at ortho and para
(d) 2-Pentene positions
ANSWERS KEY
1 A 11 D 21 C 31 D 41 A
2 D 12 D 22 B 32 B 42 B
3 A 13 C 23 A 33 D 43 B
4 C 14 C 24 D 34 C 44 A
5 D 15 C 25 D 35 A 45 B
6 C 16 A 26 C 36 D 46 A
7 B 17 C 27 B 37 B 47 A
8 B 18 C 28 B 38 D 48 B
9 A 19 D 29 C 39 D 49 D
10 C 20 C 30 D 40 C 50 D
