VELAMMAL VIDYALAYA-VIRAGANOOR

SUB-XII CHEMISTRY
MCQ - HALO ALKANES& HALOARENES
1.General formula of Alkene is
(a) CnH2n
(b) CnH2n+2
(c) CnH2n-2
(d) none of these
2.Hybridisation of carbon in ethane is
(a) sp3
(b) sp2
(c) sp
(d) sp3d2
3.Number of π bonds in ethyne is
(a) 1
(b) 2
(c) 3
(d) 4
4.Which of the following is not correctly matched with its IUPAC name?
(a) CHF2CBrClF : 1-Bromo-1-chIoro-1, 2, 2-trifluoroethane
(b) (CCl3)3CCl : 2-(Trichloromethyl)-1, 1, 2, 3, 3-heptachloropropane
(c) CH3C (p-ClC6H4)2CH(Br)CH3 : 2-Bromo-3, 3-bis (4- chlorophenyl) butane
(d) o-BrC6H4CH (CH3) CH2CH3 : 2-Bromo-l- methylpropylbenzene
5.SN1 reaction of alkyl halides lead to
(a) Retention of configuration
(b) Racemisation
(c) Inversion of configuration
(d) None of these
6.Fitting reaction can be used to prepare
(a) Toluene
(b) Acetophenone
(c) Diphenyl
(d) Chlorobenzene
7.
In the above reaction, the product D is
(a) Propane
(b) 2, 3-Dimethylbutane
(c) Hexane(d) Allyl bromide

8. Ans:(a)
9.. Which of the following is most reactive towards SN1 reaction?
(a)C6H5C(CH3)C6H5Br
(b)C8H5CH2Br
(c)C6H5CH(C6H5)Br
(d)C6H5CH(CH3)Br
10.CH3CH2CH2Br + NaCN → CH3CH2CH2CN + NaBr, will be fastest in
(a)ethanol
(b)methanol
(c)N, N-dimethylformamide
(d)Water
11. A Grignard reagent may be made by reacting magnesium with
a)Methyl amine
b)Diethyl ether
c)Ethyl iodide
d)Ethyl alcohol
12.The decreasing order of boiling points of alkyl halides is
(a)RF > RCl > RBr > RI
(b)RBr > RCl > RCl > RF
(c)RI > RBr > RCl > RF
(d)RCl > RF > RI > RBr
13.Phosgene is commonly known as
(a)thionyl chloride
(b)carbonyl chloride
(c)carbon dioxide and phosphine
(d)phosphoryl chloride
14.The reaction of tert butyl bromide with sodium methoxide produces mainly
(a)isobutane
(b)isobutylene
(c)tert-butyl methyl ether
(d)sodium tert butoxide
15)ethyl chloride is converted into diethyl ether by
a)wurtz reaction
b)Grignard reaction
c)perkin's reaction
d) williamson's synthesis
16.The alkyl halide is converted into an alcohol by
a) Addition reaction
b)Substitution
c)Dehydrohalogenation
d)Elimination
17.
Answer:2
18.A yellow precipitate is obtained when aqueous AgNO3 is added to a solution of the
compound:
(a)CCl3CHO
(b)CHI3
(c)CHCl3
(d)C6H5CH2Cl
19.Friedel Crafts reaction of bromobenzene with methyl iodide gives:
(a) o- bromo toluene
(b) p- bromo toluene
© o-& p- bromo toluenes
(d) m- bromo toluene
20.Benzyl chloride can be prepared from toluene by chlorination with:
a)SO2Cl2
b)SOCl
c)S2Cl2
d)NaOCl2

21.
(a)wurtz reaction
(b)fittig reaction
(c)Frankland's reaction
(d)Finkelstein's reaction
22.Elimination of HBr from 2- bromobutane results in the formation of,
(a)equimolar mixture of 1- butene and 2- butene
(b)predominantly 2 - butene
(c)predominantly 1- butene
(d)predominantly 2- butyne
23.
(a)propene
(b)propyne
© propan-1-ol
(d) propan -2-ol

24.
a)The product is,

Answer:3
25.Arrange the following three chlorides in decreasing order towards SN1 reactivity.

1.

Answer:2
26.Chloroform and conc. HNO3 react to produce
(a) CHCl2NO2 (b) CHCl2HNO3
(c) CCl3NO2 (d) CCl3NO3

27.Benzene diazonium chloride reacts with hypophosphorous acid to produce:

(a) phenol
(b) benzene
(c) p-hydroxyazobenzene
(d) benzonitrile
28. B.H.C. is used as an
(a) Insecticide (b)Disinfectant
(c) Mosquito repellent
(d) Antiseptic

29.Which one of the following produces acyl halide by treatment with PCl5?
(a) Alcohols
(b) Esters
(c) Acids
(d) Carbonyl compounds

30 .Among the following, the most reactive towards alcoholic KOH is :

(a) CH2=CHBr
(b) CH3COCH2CH2Br
(c) CH3CH2Br (d) CH3CH2CH2Br

31.Which of the following compounds has the highest boiling point?

(a) CH3CH2CH2Cl
(b) CH3CH2CH2CH2Cl
(c) CH3CH(CH3 )CH2Cl
(d) (CH3)3CCl

32.The synthesis of alkyl fluorides is best accomplished by

(a) Finkelstein reaction
(b) Swarts reaction
(c) Free radical fluorination
(d) Sandmeyer's reaction

33.IUPAC name of CH3CH2C(Br) = CH—Cl is

(a) 2-bromo-1-chloro butene
(b) 1-chloro-2-bromo butene
(c) 3-chloro-2-bromo butene
(d) None of the above

34.. C – X bond is strongest in

(a) CH3Cl
(b) CH3Br
(c) CH3F
(d) CH3I

35.The catalyst used in the preparation of an alkyl chloride by the action of dry HCl on an
alcohol is
(a) anhydrous AlCl3
(b) FeCl3
(c) anhydrous ZnCl2
(d) Cu

36.Which of the following possesses highest melting point?

(a) Chlorobenzene
(b) m-dichlorobenzene
(c) o-dichlorobenzene
(d) p-dichlorobenzene

37.Which one is most reactive towards SN1 reaction ?

(a) C6H5CH(C6H5 )Br
(b) C6H5CH(CH3 )Br
(c) C6H5C(CH3)(C6H5 )Br
(d) C6H5CH2Br
38.2-Bromopentane is heated with potassium ethoxide in ethanol. The major product obtained is
(a) 2-ethoxypentane
(b) pentene-1
(c) trans-2-pentene
(d) cis-pentene-2

39.Which of the following compounds is optically active ?

(a) CH3CHClCOOH
(b) CH3CH2CH2CH3
(c) (CH3)2CHOH
(d) (CH3)3CCl

40.Which of the following undergoes nucleophilic substitution exclusively by SN1 mechanism?

(a)Benzyl Chloride
(b)Ethyl chloride
(c)Chlorobenzene
(d)Isopropyl chloride
41.The markownikoff’s rule reverses in the presence of peroxide, but this is possible only in
case of
(a) HI.
(b) HBr.
(c) HCl.
(d) HF.
42.Dehydrohalogenation or elimination reactions of alkyl halides having strongly acidic ?-
hydrogen takes place through
(a) E1 mechanism.
(b) E2 mechanism.
(c) E1cB mechanism.
(d) Benzyne mechanism.
43.The nucleophilicity order of different halide ions is as
(a) I->Br->Cl->F-.
(b) Br->Cl->F->I-.
(c) Cl->F->I->Br-.
(d) F->I->Br->Cl-.
45.The iodoalkanes can be prepared from corresponding chloro or bromoalkanes by heating
with NaI in acetone or methanol, this reaction is called as
(a) Etard’s reaction.
(b) Swarts reaction.
(c) Finkelstein reaction.
(d) Birnbaum-Simonini reaction.
46.Assertion: Phosphorus chlorides (tri and penta) are preferred over thionyl chloride for the
preparation of alkyl chlorides from alcohols.
Reason: Phosphorus chlorides give pure alkyl halides.
a)Both assertion and reason are correct.
b)assertion is correct but reason is incorrect.
c)both assertion and reason are incorrect.
d)assertion is incorrect but reason is correct.
47.Assertion: The boiling points of alkyl halides decrease in the order :
RI > RBr > RCl > RF
Reason: The boiling points of alkyl chlorides, bromides and iodides are considerably higher
than that of the hydrocarbon of comparable molecular mass.
a)assertion is correct and reason is wrong.
b)assertion and reason are incorrect.
c)assertion is correct but reason is wrong.
d)both assertion and reason are correct.
48.Assertion: KCN reacts with methyl chloride to give methyl isocyanide
Reason: CN–is an ambident nucleophile.
a)assertion and reason both are correct and reason is correct explanation of assertion.
b)assertion and reason both are incorrect.
c)assertion is wrong but reason is correct.
d)assertion is wrong but reason is correct.
49.Assertion: tert-Butyl bromide undergoes Wurtz reaction to give 2, 2, 3, 3-tetramethylbutane.
Reason: In the Wurtz reaction, alkyl halides react with sodium in dry ether to give hydrocarbons
containing double the number of carbon atoms present in the halide.
a)assertion and reason both are correct and reason is correct explanation of assertion.
assertion and reason are correct
(b)assertion and reason both are incorrect.
c)assertion is correct but reason is incorrect.
d)assertion is wrong but reason is correct.
50.Assertion: Presence of a nitro group at ortho or para position increases the reactivity of
haloarenes towards nucleophilic substitution.
Reason: Nitro group, being an electron-withdrawing group, decreases the electron density over
the benzene ring.
a)assertion and reason both are correct and reason is correct explanation of assertion.
assertion and reason are correct.
(b)assertion and reason both are incorrect.
c)assertion is wrong but reason is correct.
d)assertion is correct but reason is
incorrect.
51. Assertion: In mono haloarenes, further electrophilic substitution occurs at ortho and para
positions.
Reason: Halogen atom is a ring deactivator.
a)both assertion and reason are correct and reason is the correct explanation for assertion.
b)assertion and reason both are correct but reason is not correct explanation of
assertion.
c)assertion is wrong but reason is correct.
d)assertion is correct but reason is
incorrect.
52.Assertion:Aryl iodides can be prepared by reaction of arenes with iodine in the presence of
an oxidising agent.
Reason:Oxidising agent oxidises
a)both assertion and reason are correct and reason is the correct explanation for assertion.
b)assertion and reason both are correct but reason is not correct explanation of assertion.
c)assertion and reason both are incorrect.
d)assertion is correct but reason is wrong.
53.Assertion: It is difficult to replace chlorine by –OH in chlorobenzene in comparison to that in
chloroethane.
Reason: Chlorine-carbon (C—Cl) bond in chlorobenzene has a partial double bond character
due to resonance.
a)both assertion and reason are correct and reason is the correct explanation for
assertion.
b)assertion and reason both are incorrect.
c)assertion is correct but reason is wrong.
d)assertion is wrong but reason is correct.
54. Assertion: Hydrolysis of (–)-2-bromooctane proceeds with inversion of configuration.
Reason: This reaction proceeds through the formation of a carbocation.
a)both assertion and reason are correct and reason is the correct explanation for assertion.
b)assertion and reason both are incorrect.
c)assertion is correct but reason is wrong.
d)assertion is wrong but reason is correct.
55.Assertion: Nitration of chlorobenzene leads to the formation of m-nitrochlorobenzene
Reason: —NO2 group is a m-directing group.
a)a)both assertion and reason are correct and reason is the correct explanation for assertion.
b)assertion and reason both are correct but reason is not correct explanation of assertion.
c)assertion is correct but reason is incorrect.
d)assertion is incorrect but reason is correct.
56.The freshly prepared diazonium salt is mixed with copper (I)chloride to prepare
chlorobenzene.Name the reaction.--------(Sandmeyer's reaction)
57.In allylic halide ,the halogen atoms are bonded to a ----- hybrid carbon atom.(SP3)
58.A mixture of 50% d-form and 50% l- form of 2-bromobutane is called------ (racemic
modification).
59.Give the IUPAC Name of the CHF2CBrClF is ---(1-bromo-1-chloro-1,2,2-trifluoroethane)
60.CH3-CH=C(CH3)2+HBr--->??
(CH3-CH2-(CH3)2Br)
61..Match the following:
Match the items of Column I and Column II.

Column I Column II
(i) SNl reaction(a) vic- dibromides
(ii) Chemicals in fire extinguisher
(b) gem- dihalides
(iii) Bromination of alkenes
(c) Racemisation
(iv) Alkylidene halides
(d) Saytzeff rule
(v) Elimination of HX from alkyl halide (e) Chloro Bromo Carbons
Ans. (i)-(c) Racemisation
(ii)-(e) Chloro Bromo Carbons
(iii)-(a) vic-dibromides
(iv)- (b) gem-dihalides
(v)- (d) Saytzeff rule
62. Match the structures of compounds given in Column I with the classes of compounds
given in Column I &II

Ans. (i)- (b) Alkyl halide

(ii)- (d) Allyl halide
(iii)-(a) Aryl halide
(iv)-(c) Vinyl halide

63. Match the reactions given in Column I with the types of reactions given in Column II.
Ans. (i)-(b) Electrophilic aromatic substitution
(ii)-(d) Electrophilic addition
(iii)-(e) Nucleophilic substitution (SNI )
(iv)-(a) Nucleophilic aromatic substitution
(v)- (c) Saytzeff elimination

64.Match the reactions given in Column I with the names given in Column II.

Ans. (i)-(b) Wurtz- Fittig reaction

(ii)-(a) Fittig reaction
(iii)-(d) Sandmeyer reaction
(iv)-(c) Finkelstein reaction
60.case study question 1:
Read the passage given below and answer the following questions:

Nucleophilic substitution reactions are of two types; substitution nucleophilic bimolecular (SN2)
and substitution nucleophilic unimolecular (SN1) depending on molecules taking part in
determining the rate of reaction. Reactivity of alkyl halide towards SN1 and SN2 reactions
depends on various factors such as steric hindrance, stability of intermediate or transition state
and polarity of solvent. SN2 reaction mechanism is favoured mostly by primary alkyl halide or
transition state and polarity of solvent, SN2 reaction mechanism is favoured mostly by primary
alkyl halide then secondary and then tertiary. This order is reversed in case of SN1 reactions.

The following questions are multiple choice question. Choose the most appropriate answer:

(i) Which of the following is most reactive towards nucleophilic substitution reaction?
(a) C6H5Cl
(b) CH2=CHCl
(c) ClCH2CH=CH2
(d) CH3CH=CHCl

(ii) Isopropyl chloride undergoes hydrolysis by

(a) SN1 mechanism
(b) SN2 mechanism
(c) SN1 and SN2 mechanism
(d) neither SN1 nor SN2 mechanism

(iii) The most reactive nucleophile among the following is

(a) CH3O-
(b) C6H5O-
(c) (CH3)2CHO-
(d) (CH3)3CO-
(iv) Tertiary alkyl halides are practically inert to substitution by SN2 mechanism because of
(a) insolubility
(b) instability
(c) inductive effect
(d) steric hindrance
65.Read the passage given below and answer the following questions:
Nucleophilic substitution reactions are of two types; substitution nucleophilic bimolecular (SN2)
and substitution nucleophilic unimolecular (SN1) depending on molecules taking part in
determining the rate of reaction. Reactivity of alkyl halide towards SN1 and SN2 reactions
depends on various factors such as steric hindrance, stability of intermediate or transition state
and polarity of solvent. SN2 reaction mechanism is favoured mostly by primary alkyl halide then
secondary and then tertiary. This order is reversed in case of SN1 reactions.
The following questions are multiple choice questions. Choose the most appropriate answer:
(i) Which of the following is most reactive towards nucleophilic substitution reaction?
(a) C6H5Cl
(b) CH2=CHCl
(c) ClCH2CH=CH2
(d) CH3CH=CHCl
(ii) Isopropyl chloride undergoes hydrolysis by
(a) SN1 mechanism
(b) SN2 mechanism
(c) SN1 and SN2 mechanism
(d) neither SN1 and SN2mechanism
(iii) The most reactive nucleophile among the following is
(a) CH3O- (b) C6H5O- (c) (CH3)2CHO- (d) (CH3)3CO-
(iv) Tertiary alkyl halides are practically inert to substitution by SN2 mechanism because of
(a) insolubility (b) instability (c) inductive effect (d) stearic hindrance.