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CET ORG CHEM HALOGEN DERIVS

MHT - CET - Chemistry

1. Introduction of alkyl or aryl group in chlorobenzene by reacting it with methyl chloride in the presence of [1]
anhydrous aluminum chloride is known as ________.

a) Sandmeyer reaction b) Williamson synthesis

c) Friedel-Craft reaction d) Wurtz-Fittig reaction

2. Alkaline hydrolysis of CH3Br with aqueous KOH is which order reaction? [1]

a) zero b) 2nd

c) 3rd d) 1st

3. In the alkaline hydrolysis of tert-butyl bromide, ________. [1]

a) Rate = k [(CH3)3C - Br][OH-] b) Rate = k[(CH3)3C - Br]

c) Rate = k[(CH3)3C - Br] + [OH-] d) Rate = k[OH-]

4. Treatment of sec-butyl bromide with alcoholic KOH form ________ as the major product. [1]

a) but-2-ene b) but-1-ene

c) butan-1-ol d) butan-2-ol
5. Chlorobenzene when heated with a mixture of concentrated H2SO4 and concentrated HNO3 yeilds ________ as [1]
a major product.

a) b)

c) d)

6. Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to [1]
________.

a) the inductive effect b) longer carbon halogen bond

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 c) weaker carbon halogen bond d) resonance stabilisation
7. Which of the following is a primary alkyl halide? [1]

a) (CH3)3CCl b) (CH3)2CHCH2Cl

c) C6H5CHClCH3 d) CH3CHClCH2CH3

8. Which of the following acid adds to propene in the presence of peroxide to give anti-Markovnikov’s product? [1]

a) HF b) HCl

c) HBr d) HI
9. Identify the INCORRECT statement. [1]
A. The major product of dehydrohalogenation reaction of 2 -bromobutane is but-2 -ene.
B. The mixture of concentrated HCl and anhydrous ZnCl2 is called the Lucas reagent.

C. SN1 reaction involves formation of carbocation intermediate.

D. Sulphuric acid is preferred to H3PO4 to prepare HI in situ.

a) Option (B) b) Option (C)

c) Option (A) d) Option (D)

10. 1,2-Dichloroethane is which type of halide? [1]

a) Allylic halide b) Vicinal halide

c) Alkylidene halide d) Geminal halide

11. Example(s) of nucleophile(s) is/are ________. [1]

I. OH-
∙∙

II. NH 3

III. R - NH2

a) (I) b) (I), (II) and (III)

c) (I) and (II) d) (III)

12. Which of the following haloalkane is most reactive? [1]

a) 2-Bromopropane b) 1-Chloropropane

c) 1-Bromopropane d) 2-Chloropropane
13. Arenes on treatment with chlorine in presence of ferric chloride as a catalyst undergo what type of reaction? [1]

a) Electrophilic addition b) Electrophilic substitution

c) Nucleophilic addition d) Nucleophilic substitution

14. Which of the following is the CORRECT order for the strength of C-X bond? [1]

a) CH3F > CH3Cl > CH3Br > CH3I b) CH3Cl > CH3Br > CH3F > CH3I

c) CH3F < CH3Cl < CH3Br < CH3I d) CH3I > CH3F > CH3Cl > CH3Br

15. Which of the following statements is TRUE in case of alkyl halides? [1]

a) They can form hydrogen bonds. b) They are polar in nature.

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 c) They are highly soluble in water. d) They undergo addition reactions.
16. The reaction of C6H5CH = CHCH3 with HBr produces ________. [1]

a) C6 H5 CH2 C HCH3 b)
|

Br

c) C6 H5 C HCH2 CH3 d) C6H5CH2CH2CH2Br

|

Br

17. Identify the product (X). [1]

a) CHCl = CH-CH3 b) CH ≡ C-CH2Cl

c) CH2 = CCl-CH3 d) CH2 = CH - CH2Cl

18. Which of the following forms a poisonous compound phosgene when exposed to air and light? [1]

a) CCl4 b) CHCl3

c) CHl3 d) CH2Cl2

19. The compound which contains all the four 1o, 2o, 3o, and 4o carbon atoms is ________. [1]

a) 2,3-dimethylpentane b) 3-chloro-2,3-dimethylpentane

c) 1-chloro-2,3,3-trimethylpentane d) 3,3-dimethylpentane
20. Which of the following is a halogen derivative of aromatic hydrocarbon? [1]

a) Hexachlorobenzene b) Hexachlorocyclohexane

c) Carbon tetrachloride d) Chloroform

21. When ethyl alcohol (C2H5OH) reacts with thionyl chloride, the products obtained are ________. [1]

a) CH3COCl + HCl + SO2 b) CH3CH2Cl + HCl

c) CH3CH2Cl + H2O + SO2 d) C2H5Cl + HCl + SO2

22. A + HBr ⟶ C5H11Br. [1]

A is most likely to be an ________.

a) arene b) alkane

c) alkene d) alkyne
23. The SN1 mechanism for the hydrolysis of an alkyl halide to alcohol involves the formation of ________. [1]

a) planar carbocation b) pentavalent carbon in the transition state

c) carbanion d) free radical

light

24. C3H8 + Cl2 −−→ C3H7Cl + HCl is an example of which of the following types of reactions? [1]

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 a) Rearrangement b) Elimination

c) Addition d) Substitution
25. Identify the CORRECT statements from the following. [1]
I. Aryl halides are insoluble in water but soluble in organic solvents.
II. The isomeric dihalobenzenes have nearly the same boiling points.
III. Para isomer of dihalobenzenes has symmetrical structure which closely packs in the crystal lattice.
IV. The isomeric dihalobenzenes have nearly the same melting points.

a) (I), (III) and (IV) b) (I), (II) and (III)

c) (I) and (II) d) (I) and (IV)

26. To get alkyl isocyanide from an alkyl halide, the latter is heated with ________. [1]

a) alc. AgCN b) alc. NH3

c) alc. KCN d) aq. KCN

27. The order of reactivity of following alcohols with a given haloacid is ________. [1]
i. RCH2 - CH2 - OH

ii. RCH 2
− CH − OH
|

C H3

iii. CH 3 CH2 − C − OH
|

a) (i) > (ii) > (iii) b) (i) > (iii) > (ii)

c) (ii) > (i) > (iii) d) (iii) > (ii) > (i)
28. Which of the following has the lowest boiling point? [1]

a) CH3F b) CH3l

c) CH3Cl d) CH3Br

29. The product (X) formed in the following reaction is ________. [1]
H2 O2

Ph − CH = CH2 + HBr ⟶ (X)

|

Major

a) Ph(CH2)2-Br: b) Ph-CH(Br)CH3:

Anti-Markovnikov’s product Anti-Markovnikov’s product

c) Ph(CH2)2-Br: Markovnikov’s product d) Ph-CH(Br)CH3:

Markovnikov’s product
30. CH3CH = CHC(Cl)(CH3)2 is which type of halide is based on the position of -Cl? [1]

a) Allylic b) Secondary

c) Vinylic d) Aryl
31. About a racemic mixture, some statements are given below: [1]
i. It is a mixture of (d) and (/) isomers in equimolar proportion.

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 ii. It is optically inactive.
iii. It may be laevo-rotatory or dextrorotatory.
iv. It rotates the plane of polarized light towards the left.
The FALSE statements are ________.

a) (ii), (iii) and (iv) b) (i) and (iii)

c) (iii) and (iv) d) (ii) and (iii)

NaI /H3 P O4

32. R - OH −−−−−−−→? [1]

Δ

The general formula of the organic compound obtained in the above reaction is ________.

a) R - ONa b) R - R

c) R - I d) R - H
33. The reactivity of various types of alkyl halides towards SN1 reaction is ________. [1]

a) secondary > primary > tertiary b) secondary > tertiary > primary

c) primary > secondary > tertiary d) tertiary > secondary > primary
34. Which of the following is formed when alkyl halide is treated with sodium alkoxide? [1]

a) R-CN b) R-O-R'

c) R-O-Na d) R-NC
35. If starting compound is laevo rotatory, after the SN1 reaction, the product is ________ [1]

a) racemic mixture b) partially optically active

c) dextro rotatory d) laevo rotatory

36. Consider the following wedge formula. [1]

According to the representation, which bond lies below the plane of the paper?

a) C - Br b) C - H

c) C - Cl d) C - F
37. Chlorination of ethane is carried out in presence of ________. [1]

a) zinc chloride b) mercuric chloride

c) anhydrous AlBr3 d) ultraviolet light

38. The optically active product obtained from SN2 reaction of a Dextro rotatory compound will be: [1]

a) racemic mixture b) laevo rotatory

c) partially optically active d) dextro rotatory

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 O

||
[1]
Δ

39. C2H5 - Br + CH3 - C - OAg −

→

Identify the functional group in X.

a) Ketone b) Ester

c) Ether d) Alcohol
40. The order of reactivity of HX in the following reaction is ________. [1]
Alkene + HX ⟶ RX

a) HBr > HCl > HI > HF b) HF > HBr > HCl > HI

c) HCl > HBr > HI > HF d) HI > HBr > HCl > HF
41. Which of the following CANNOT be prepared by direct halogenation of benzene? [1]

a) Iodobenzene b) Chlorobenzene

c) Bromobenzene d) Fluorobenzene
42. The CORRECT order of increasing reactivity of C - X bond towards nucleophile in the following compounds is [1]
________.

I.

II.

III. (CH3)3C - X);

IV. (CH3)2CH - X

a) III < II < I < IV b) I < II < IV < III

c) IV < III < I < II d) II < III < I < IV

43. Which one is most reactive towards SN1 reaction? [1]

a) PhCH2Cl b) PhCH(Ph)Cl

c) PhCH(CH3)Cl d) PhC(CH3)(Ph)Cl

44. Ethanol is converted to ethyl chloride by reacting with ________. [1]

a) HCl b) SOCl2

c) Cl2 d) NaCl

45. The compound X in the reaction [1]

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 is ________.

a) b)

c) d)

46. The isomer of C4H9I which is capable of producing but-2-ene with ale. KOH solution is ________. [1]

a) 1-iodo-2-methylpropane b) 2-iodo-2-methylpropane

c) 1-iodobutane d) 2-iodobutane
47. Acetonitrile is prepared by treating methyl iodide with an alcoholic solution of ________. [1]

a) hydrogen cyanide b) ammonia

c) silver cyanide d) potassium cyanide

48. Which of the following alkyl halide is more reactive toward nucleophilic substitution reaction? [1]

a) H3C -CH2- I b) H3C - CH2 - F

c) H3C - CH2 - Cl d) H3C - CH2 - Br

49. The functional group present in westrosol is ________ group. [1]

a) iodo b) fluoro

c) chloro d) bromo
50. In SN2 reactions, the CORRECT order of reactivity for the following compounds; CH3Cl, CH3CH2Cl, [1]
(CH3)2CHCl and (CH3)3CCl is ________.

a) (CH3)2CHCl > CH3CH2Cl > CH3Cl > b) CH3CH2Cl > CH3Cl > (CH3)2CHCl >
(CH3)3CCl (CH3)3CCl

c) CH3Cl > CH3CH2Cl > (CH3)2CHCl > d) CH3Cl > (CH3)2CHCl > CH3CH2Cl >
(CH3)3CCl (CH3)3CCl

51. The product of the reaction [1]

But-2-ene + HBr ⟶?

a) CH3CH2CH(Br)CH3 b) CH3CH(Br)CH2CH3

c) both CH3CH(Br)CH2CH3 and d) CH2(Br)CH2CH2CH3

CH3CH2CH(Br)CH3

52. In the dehydrohalogenation reaction, the conversion that takes place is ________. [1]

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 a) alkene to haloalkane b) alkene to alcohol

c) alcohol to alkene d) haloalkane to alkene

53. When 2-bromo-2-methylbutane is heated with alcoholic KOH, the possible products are ________. [1]
i. (CH3)2C = CHCH3

ii. CH2 = C - CH2CH3

|

CH3

iii. (CH3)2CH - CH = CH2

a) (ii), (iii) b) (i), (ii), (iii)

c) (i), (iii) d) (i), (ii)

54. Which of the following is CORRECT? [1]
Δ

I. RX + ale. KCN −
→ RNC

II. RX + ale. AgCN −

→ RCN

III. RX + KNO2 ⟶ R - 0 - N = 0

IV. RX + AgNO2 ⟶ RNO2

a) III, IV b) II, III

c) I, IV d) I, II
55. Which compound among the following on reaction with ethyl magnesium bromide gives ethane? [1]

a) C2H5CN b) Solid CO2

c) H2O d) CH3CHO

56. Iodination of CH4 to CH3I is carried out in the presence of HIO3 which ________. [1]

a) acts as a reducing agent b) acts as an oxidising agent

c) acts as a source of iodine d) acts as a dehydrating agent

57. Which compound shows SN1 mechanism as well as optical isomerism? [1]

a) Benzyl chloride b) Allyl chloride

c) 1-Chlorobutane d) 1-Bromo-1-phenylethane
58. Which of the following statements is INCORRECT? [1]
A. Optical activity of a substance is expressed numerically in terms of optical rotation.
B. A compound which rotates the plane of plane polarized light towards right is laevorotatory in nature.
C. The optical isomers which are nonsuperimposable mirror image of each other are called enantiomorphs.
D. Enantiomers have identical chemical properties except towards optically active reagents.

a) Option (B) b) Option (A)

c) Option (C) d) Option (D)

59. C4H9Br can represent ________. [1]

a) a 3o bromoalkane b) all of these

c) d)

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 a 1o bromoalkane a 2o bromoalkane
60. Best method of preparing alkyl chloride is ________. [1]
anhydrousZnC l2
a) ROH + HCl −−−−−−−−−→ b) ROH + PCl3 ⟶

c) ROH + SOCl2 ⟶ d) ROH + PCl5 ⟶

61. Which of the following statements is FALSE about SN1 mechanism? [1]

a) It results into racemisation. b) It is favoured by higher concentration of the

nucleophilic reagent.

c) It involves the formation of an intermediate. d) It is a first order reaction.

62. In alkaline hydrolysis of tert-butyl bromide, the order of reaction with respect to nucleophile is ________. [1]

a) zero b) second

c) pseudo d) first
63. C2H5Br gives C2H5CN on reaction with alcoholic KCN, while with alcoholic AgCN the major product is [1]
C2H5NC. The reason is ________.

a) Ag is more electropositive as compared to K b) Ag is noble metal

c) AgCN is electrovalent d) AgCN is covalent

64. In the reaction, [1]

X is ________.

a) anhydrous FeCl3 b) dry ether

c) cone. HCl d) cone. H2SO4

65. Alkyl halides can be converted into Grignard reagent by ________. [1]

a) warming with magnesium in dry ether b) warming with MgCl2

c) refluxing with MgCl2 solution d) boiling with magnesium ribbon in alcoholic

solution
66. IUPAC name of C2H5 - CH2 - CBr - CH3 is ________. [1]
|

C2 H5

a) 2-ethyl-3-bromopentane b) 3-bromo-3-methylhexane

c) 2-bromo-3-ethylpentane d) 3-bromo-2-ethylpentane
67. Identify optically inactive compound from the following. [1]

a) 3-Bromohexane b) 2-Bromopentane

c) 2-Bromo-3-methylbutane d) 2-Bromo-2-methylbutane
68. ________ is obtained when benzenediazonium salt reacts with Cucl/HCl. [1]

a) 1,2-Dichlorobenzene b) Benzene

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 c) Aniline d) Chlorobenzene
69. Which of the following halide undergoes hydrolysis on warming with water/aqueous NaOH? [1]

a) b)

c) d)

70. In haloalkanes, a halogen atom is bonded to ________ hybridized carbon atom. [1]

a) sp3d b) sp3

c) sp2 d) sp
boil

71. Substrate + ale. KCN −→

− Butanenitrile [1]

Identify the substrate in the above reaction.

a) C3H7OH b) C4H9OH

c) C3H7Br d) C4H9Cl

72. Alkaline hydrolysis of a tertiary alkyl halide involves ________. [1]

a) four steps b) three steps

c) two steps d) only one step

73. When n-butyl magnesium bromide is treated with water, the product is ________. [1]

a) n-butyl alcohol b) isobutyl alcohol

c) n-butane d) isobutene
74. An alkyl iodide (X) reacts with sodium in ether to form 4,5-diethyloctane, the compound (X) is ________. [1]

a) CH3(CH2)5I b) CH3(CH2)2CH(I)CH2CH3

c) CH3(CH2)3CH(I)CH3 d) CH3(CH2)3I

75. Amongst the following, which is/are TRUE for SN2 reaction? [1]

A. The rate of reaction is independent of the concentration of the nucleophile.

B. The nucleophile attacks the carbon atom on the side of the molecule opposite to the group being displaced.
C. The reaction proceeds with simultaneous bond formation and bond rupture.
D. Both The nucleophile attacks the carbon atom on the side of the molecule opposite to the group being
displaced and The reaction proceeds with simultaneous bond formation and bond rupture.

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a) Option (A) b) Option (D)

c) Option (B) d) Option (C)

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