Alkyl Halide

Alkyl Halide
1) Which of the following is an example of aralkyl halide?
(a) p-Chlorotoluene (b) Chlorobenzene (c) Allyl chloride (d) Benzyl chloride
2) In which of the following alkyl halides all the hydrogen atoms are equivalent?
(a) iso-Butyl chloride (b) neo-Pentyl chloride (c) n-Butyl chloride (d) tert-Butyl
chloride
3) Which of the following an aralkyl halide?
(a) 4-Chlorotoluene (2) Bromobenzene (c) 1, 4-Dichlorobenzene (d) 1-Chloro-1-
phenyl ethane
4) Whcih of the following compounds can exhibit optical isomerism?
(a) Chlorocyclopropane (b) cis-1, 2-Dichlorocyclopropane (c) trans-1, 2-
Dichlorocyclopropane (d) trans-1, 3-Dichlorocyclobutane
10) Which of the following is not a primary halide?
(a) Isobutyl bromide (b) Neo-Pentyl chloride (c) Isopentyl bromide (d) Isopropyl
chloride
6) IUPAC name of crotyl chloride is
(a) 1-Chloro-2-butene (b) 2-Chloro-2-butene (c) 3-Chloro-1-butene(d)-Chloro-1-
butene
7) C-CI bond length is smallest in
(a) Allyl chloride (b) Vinyl chloride (c) Ethyl chloride (d) Benzyl chloride
8) When silver propionate is treated with Br2 in CCI4 as solvent, the product is
(a) Propionyl bromide (b) n-Propyl bromide (c) iso-Propyl bromide (d) Ethyl bromide
9) Iso-Butylene can be converted into tert-butyl bromide by its reaction with
(a) HBr (b) Br2 (c) HBr in the presence of peroxides (d) HOBr
10) Methane reacts with limited amount of chlorine in the presence of diffused sunlight to
form chloromethane. The reaction takes place through....as intermediates
(a) Carbocations (b) Free radicals (c) Carbanions (d) Carbenes
11) The best reagent for converting an alcohol into the corresponding chloride is
(a) PCI5 (b) PCI3 (c) HCI/ZnCI2 (d) SOCI2
Hint: ROH + SOCI2 to RCI + SO2 + HCI
Side products in this reaction are volatile and can be easily expelled during
distillation
12) Which reagent cannot be used to prepare an alkyl chloride from an alcohol?
(a) HCI + anhyd. ZnCI2 (b) NaCI (c) PCI5 (d) SOCI2
13) Benzyl chloride can be prepared by reacting
(a) Toluene with CI2 in the presence of FeCI3 (b) Benzene with CH3CI in the presence
of AICI3
(c) Toluene with CI2 in the presence of sunlight (d) Benzene with CI2 in the presence of
FeCI3
14) Which of the following has the highest boiling point?
(a) 1-Chloropentane (b) 2-Chloropentane (c) 3-Chloropentane (d) All have equal
boiling point
15) Which of the following alkyl halides has the maximum density?
(a) C2H5CI (b) C2H2Br (c) C2H5I (d) C2H5F
Hint: Density of alkyle halide is in the order of RI>RBr>RCl>RF
16) Dipole moment is shown by

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(a) 1, 4-Dichlorobenzene (b) cis-1, 2-Dichloroethylene (c) trans-1, 2-

Dichloroethylene (d) Tetrachloromethane
17) Out of the following compounds which one will have zero dipole moment?
(a) Chloromethane (b) Dichloromethane (c) Trichloromethane (d) None of these
compounds
18) Which of the following is lighter than water?
(a) 1-Chlorobutane (b) 1-Bromopropane (c) 2-Bromopropane (d) 1-Bromobutane
19) Which of the following compounds will reacts with ethanolic KCN?
(a) Chlorobenzene (b) Vinyl chloride (c) Allyl chloride (d) 4-Chlorotoluene
20) Treatment of ammonia with excess ethyl chloride will yield
(a) Triethyl amine (b) Diethyl amine (c) Ethyl amine (d) Tetraethylammonium
chloride
21) Ethyl bromide reacts with Zn-Cu couple in the presence of ethyl alcohol to form
(a) Butane (b) Diethyl ether (c) Methane (d) Ethane
22) Which of the following compounds on oxidation gives benzoic acid
(1) Chlorophenol (b) Chlorotoluence (c) Chlorobenzene (d) Benzyl chloride
23) When tert-butyl chloride is made to react with sodium methoxide, the major product
is
(a) Dimethyl ether (b) Di-tert butyl ether (c) Tert-Butyl methyl ether (d) Isobutylene
24) Among the following, the molecule with the highest dipole moment is :
(a) CH3Cl (b) CH2Cl2 (c) CHCl3 (d) CCl4
25) NBS is a specific reagent for
(a) Nucleophilic substitution (b) Electrophilic substitution (c) Allyic substitution (d)
Electrophilic addition
26) 2-Chloro-2-methyl butane, on reaction with alc. KOH gives X as the major product X
is
(a) 2-Butene (b) 2-Methyl propene (c) 1-Butene (d) 2-Methyl-2-propanol
27) 2-Chloro-2-methyl propane, on reaction with aq. KOH gives X as the major product
X is
(a) 2-Butene (b) 2-Methyl propene (c) 1-Butene (d) 2-Methyl-2-propanol
28) An alkyl halide may be converted into an alken by
(a) Addition (b) Substitution (c) Elimination (d) Hydrogenation
29) Which of the following compounds would be hydrolysed most easily?
(a) C2H5CI (b) C2H5Br (c) C2H5F (d) C2H5I
30) Which of the following compounds would be hydrolysed most easily?
(a) C2H5Br (b) CH3Br (c) CH2 = CH - Br (d) CH2 = CH- CH2Br
31) Ethylene chloride and ethylidene chloride are isomeric compounds. Identify the
statement that is not applicable to both of them
(a) Both of them are dihalogen derivatives (b) Both of them give Beilstein test (c)
Both of them react with alc. KOH and give same product (d) Both of them react with
aqueous KOH and gives same product
32) A mixture of ethyl iodine nad n-propyl iodide is subjected to Wurtz reaction. Which
of the following compounds is not formed during the reaction?
(a) Butane (b) Propane (c) Pentane (d) Hexane
33) When aqueous KOH reacts with n-propyl chloride, the product is
(a) Propylene (2) 2-Propanol (c) 1-Propanol (d) 1-Propenol
34) An alkyl halide on reaction with sodium in the presence of ether gives 2, 2, 5, 5-
tetramethyl hexane. The alkyl halide possibly is
(a) 1-Chloropentane (b) 1-Chloro-2, 2-dimethyl propane (c) 3-Chloro-2, 2-dimethyl
butane (d) 2-Chloro-2-methyl butane

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35) Which of the following does not form Grignard reagent on reaction with Mg in the
presence of ether?
(a) Chloroethane (b) 1-Chloropropane (c) Bromobenzene (d) Chlorobenzene
36) Chlorobenzene on reaction with CH3CI in the presence of AICI3 will give
(a) Toluene (b) m-Chloro toluene (c) p-Chloro toluene (d) A mixture of o-and p-
chlorotoluence
37) Most reactive halide towards SN1 reaction is
(a) n-Butyl chloride (b) sec-Butyl chloride (c) tert-Butyl chloride (d) Allyl chloride
38) Mg reacts with RBr best in
(a) C2H5OC2H5 (b) C6H5OCH3 (c) C6H5N(CH3)2 (d) Equally in all the three.
39) Photochemical chlorination of an alkane is initited by a process of
(a) Pyrolysis (b) Peroxidation (c) Homolysis (d) Rearrangement
40) Allylic bromination of olenfins is generally carried out with
(a) Phenyl magnesium bromide (b) Dibromo succinic acid (c) N-Bromo succinimide
(d) Pyridiine perbromide
41) 2, 2-Dichloropropane on alkaline hydrolysis gives
(a) 2, 2-Propanediol (b) Propanol (c) Propanone (d)Ethanal
42) Grigand reagent is prepared by the reaction between alkyl halide and
(a) zinc in the presence of alcohol (b) magnesium in the presence of dry ether (c)
magnesium in the presence of alcohol (d) magnesium in the presence of moist ether
43) Which one of the following is likely to give a precipitate with AgNO3 solution?
(a) CCI4 (b) CH3-CH2-CI (c) (CH3)3CCI (d) CHC
Hint: 30 halides undergo Nucleophilic substitution most readily. (CH3)3CCI is a 30
halide.
44) An alkyl chloride produces a single alkene on reaction with sodium ethoxide and
ethanol. The alkene further undergoes hydrogenation to yield-2-methylbutane. Identify
the alkyl chloride from amongst the following.
(a) CICH2 C(CH3)2CH3 (b) CICH2CH2CH2CH2CH3
(c) CICH2CH(CH3)CH2CH3 (d) CH3C(CI)(CH3)CH2CH3
45) Geminal dihalides on hydrolysis give
(a) Ketones (b) Aldehydes (c) Ketones and aldehydes (d) Alcohols
46) When ethyl iodide is treated with moist silver oxide, the product formed is
(a) C2H5OH (b) C2H5OC2H5 (c) CH3CHO (d) none of above
47) The reaction of an alkyl halide with RCOOAg produces
(a) ester (b) ether (c) aldehyde (d) ketone
48) The reaction of 4-bromobenzyl chloride with NaCN in ethanol leads to
(a) 4-Bromobenzyl cyanide (b) 4-Cyanobenzyl chloride (c) 4-Cyanobenzyl cyanide
(d) 4-Bromo-2-cyanobenzyl chloride
49)Grignard reagent is not prepared in aqueous medium but prepared in ether medium,
because
(a) the reagent is highly reactive in ether (b) the reagent is insoluble in water (c) the
reagent becomes inactive in water (d) the reagent reacts with water
50) Ethylbromide reacts with sodium-lead alloy to form
(a) Tetraethyl lead (b) Ethyl sodium (c) Ethane (d) Ethene
51) The order of reactivities of the following alkyl halides of a SN2 reaction is
(a) RF > RCl > RBr > RI (b) RF > RBr > RCl > RI (c) RCl > RBr > RF > RI (d) RI >
RBr > RCl > RF
Hint: The alkyl halide having weaker C-X bond has greater reactivity.
52) An alkyl halide may be converted into an alcohol by
(a) Addition (b) Elimination (c) Substitution (d) Hydrogenation

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53) For the reaction

C2H5OH + HX to C2H5X + H2O the order of reactivity is
(a) HCI > HBr > HI (b) HI >HBr >HCI
(c) HBr >HCI >HI (d) HI >HCI >HBr.
54) 1-Phenyl-2-chloropropane when treated with alcoholic KOH gives.....as the major
product
(a) 1-Phenylopropene (b) 3-Phenylpropene (c) 1-Phenyl-2-propanol (d) 3-Phenyl-1-
propanol
Hint: 1-Phenylopropene is more stable because double bond is in conjugation with
benzene ring and is more substituted
55) Which of the following is most reactive towards Nucleophilic substitution reaction?
(a) KCN (b) AgCN (c) CH3CN (d) CH3NC
56) Which one of the following is most reactive towards Nucleophilic substitution
reaction?
(a) CH2 = CH - CI (b) C6H5CI (c) CH3CH = CH - CI (d) CICH2-CH=CH2
57) Which of the following is not true for SN1 reaction?
(a) They occur through a single step concerted reaction (b) They are favoured by polar
solvents (c) 30 alkyl halides generally react through this mechanism (d) Concentration of
nucleophile does not affect the rate of such reactions
Hint: SN1 reactions occur through a two step mechanism involving intermediate
carbocation and not through single step reaction.
58) Chlorination of toluene in the presence in the presence of light and heat followed by
treatment with aqueous NaOH gives
(a) o-Cresol (b) p-Cresol (c) 2, 4-Dihydroxytoluene (d) Benzoic acid
59) Only two isomeric monochloro derivatives are possible for
(a) n-Butane (b) 2, 4-Dimethulpentane (c) Benzene (d) 2, 2-Dimethylopropane
60) The major product of reaction of alcoholic silver nitriate with ethyl bromide is
(a) Ethane (b) Nitroethane (c) Ethyl nitrite (d) Ethyl alcohol
61) Isopropyliden on reaction with aqueous KOH yields
(a) 1, 2-Propanediol (b) Propanone (c) Propanal (d) iso-Propyl alcohol
62) IUPAC name of Gannexane is
(a) Hexachlorobenzene (b) Benzene hexachloride (c) 1, 2, 3, 4, 5, 6-
Hexachlorocyclohexane (d) None of these
63) Chloral on treatment with aqueous NaOH produces?
(a) Ethanal (b) Propanol (c) Chloroform (d) Chloroethanal
64) n-Propyl bromide on treatment with ethanolic potassium hydroxide produces
(a) Propane (b) Propene (c) Propyne (d) Propanol
65) 'Westron' is
(a) 1, 1, 2, 2-Tetrachloroethane (b) 1, 1-Dichloropropanone (c) 1, 3-
Dichloropropanone (d) 1, 2-Dichloroethene
66) 'Mustard gas' is
(a) 2, 2-Dichlorodiethyl sulphide (b) Dichlorodimethyl sulphide (c) Dichlorodiethyl
ether (d) None of these
67) 'Westrosol' is
(a) Trichloroethene (b) 1, 1, 1-Trichloroethane (c) 1, 1, 2-Trichloroethane (d)
Trichloromethanoel
68) Which of the following would not yield iodoform on reaction with NaOH and I2?
(a) Ethanol (b) Propanal (c) Propanone (d) 2-Propanol
69) On Warming with silver powder, chloroform is converted into
(a) acetylene (b) hexachloroethane (c) 1, 1, 2, 2-tetrachloroethane (d) ethylene

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Hint: 2CHCI3 + 6Ag to HC equal CH + 6AgCI.

70) The starting substance for the preparation of CHI3 is any of the following except
(a) C2H5OH (b) CH3OH (c) CH3CHO (d) CH3-CO-CH3
71) In the preparation of CHCI3 from ethanol and bleaching powder, the latter provides
(a) CI2 (b) Ca(OH)2 (c) Both (d) None
72) Which of the following with aqueous KOH will give acetaldhyde
(a) 1, 2-Dichloroethane (b) 1, 1-Dichloroethane (c) Chloroacetic acid (d) Ethyl
chloride
73) Benzene on reaction with CCI4 in the presence of AICI3 gives
(a) Benzotrichloride (b) DDT (c) Triphenyl chlorobenzene (d) Triphenyl chloromethane
74) Carbylamine test is performed in alcoholic KOH by heating a mixture of
(a) Chloroform and silver powder (b) Chloroform and a primary amine
(c) An alkyl halide and a primary amine (d) An alkyl cyanide and a primary amine
75) Which of the following compounds is used as a refrigerant?
(a) CCI4 (b) CH2CI2 (c) CF4 (d) CF2CI2
76) When ethanol and I2 are heated in the presence of Na2CO3, the yellow crystals
obtained are of
(a) C2H5I (b) CH3I (c) CHI3 (d) CH2I2
77) Idoform in medicines is used as
(a) Antibiotic (b) Antiseptic (c) Analgesic (d) Antipyretic
78) DDT is formed form
(a) Benzene and chlorobenzene (b) Chloral and chlorobenzene (c) Chloral and
benzene (d) Chlorobenzene and chlorine
79) 1-Chlorobutane on reaction with alcoholic potash gives
(a) 1-Butene (b) 1-Butanol (c) 2-Butene (d) 2-Butanol
80) Reaction of ethylamine with chloroform in alcoholic KOH produces
(a) CH3OH (b) CH3NC (c) C2H5NC (d) C2H5CN
81) Chloroform on reaction with conc. HNO3 yields
(a) Nitromethane (b) Chloropicrin (c) Chloroprene (d) CO2NO2 and H2O
82) Industrial preparation of chloroform employs acetone and
(a) CI2 (b) COCI2 (c) NaCI (d) Calcium hypochlorite
83) Chlorination of CS2 gives
(a) CHCI3 (b) CCI4 (c) CS2CI2 (d) COCI2
84) What happens when CCI4 is treated with AgNO3 solution?
(a) NO2 will be evolved (b) A white ppt. of AgCI will from (c) CCI4 will dissolve in
AgNO3 solution (d) Nothing will happen
85) Which of the following rectants will not liberate ethyne?
(a) Ethylene bromide and alc. KOH (b) Ethylidene bromide and alc. KOH (c)
Chloroform and silver (d) Aluminium carbide and water
86) Which one of the following has nil dipole moment ?
a) Toluene b) m-dichlorobenzene c) o-dichlorobenzene d) p-dichlorobenzene
Hint:p-Dichlorobenzene has zero dipole moment because the two C-Cl bonds are
oppositely directed.
87) Acetylene is treated with excess HBr and the resultant compound is then heated with
zinc dust. The final product will be
(a) Ethylene (b) Acetylene (c) 1-Butene (d) 2-Butene
88) Iodoform is a.......at room temperature
(a) Gas (b) Thick viscous liquid (c) Volatile liquid (d) Crystalline solid
89) If chloroform is left open in the air in the presence of sunlight

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(a) Explosion takes place (b) Polymerization takes place (c) Poisonous gas phosgene
is formed (d) No reaction takes place
90) When chloroform is exposed to air and sunlight, it gives
(a) Mustard gas (b) Lewisite (c) Carbonyl chloride (d) Carbon tetrachloride
91) When chloroform reacts with acetone, the product is
(a) Chloral (b) Dichloroacetone (c) Chloropicrin (d) Chloretone
92) Which of the following is an anaesthetic?
(a) CCI4 (b) CH3CI (c) C2H5OH (d) CHCI3
93) Which of the following represents a gem-dihalide?
(a) Ethylene chloride (b) 2, 2-dichloropropane (c) 1, 3-dichloropropane (d) 1, 2-
dichloropropane
94) Which of the following will react with water?
(a) CHCl3 (b) CCl3.CHO (c) CCl4 (d) ClCH2.CH2Cl
95) Chlorobenzene can be prepared by reacting benzenediazonium chloride with
(a) Hydrochloric acid (b) Cuprous chloride (c) Chloride in presence of anhydrous
aluminium chloride (d) Nitrous acid
96)Chlorination of toluene in the presence of light and heat followed by treatment with
aqueous NaOH gives
(a) o-Cresol (b) p-Cresol (c) 2, 4-Dihydroxytoluene (d) Benzyl alcohol
97) Chlorobenzene can be prepared by reacting aniline with
(a) Hydrochloric acid (b) Cuprous chloride (c) Chlorine in the presence of aluminium
chloride (d) Nitrous acid followed by heating with cuprous
98) Toluene when refluxed with Br2 in the presence light mainly gives
(a) o-Bromotoluene (b) p-Bromotoluene (c) Mixture of o-and p-bromotoluene (d) Benzyl
bromide
99) Benzene diazonium chloride can be converted into flurorobenzene by
(a) Sandmeyer's reaction (b) Gattermann's reaction (c) Balz shiemann reaction (d)
Fitting reaction
100) Bromination of toluene gives
(a) Only m-substituted product (b) Only p-substituted product (c) Mixture of ortho-
and para-substituted products (d) Mixture of ortho and m-substituted products
101) Benzene reacts with CI2 in the presence of FeCI3 (or halogen carrier) and in
absence of sunlight to form(1) Benzyl chloride (b) Benzal chloride (c) Chlorobenzene (d)
Benzenehexachloride
102) Friedel-Crafts reaction of bromobenzene with methyl iodide gives
(a) o-Bromotoluene (b) p-Bromotoluene (c) o-and-p-Bromotoluenes (d) m-
Bromotoluene
103) The decreasing order of reactivity of m-nitro-bromobenzene (I); 2,4,6-
trinitrobromobenzene (II); p-nitrobromobenzene (III) ; 2,4-dinitrobromobenzene (IV);
Towards OH- ions is
(a) I >II >III >IV (b) II >IV >III >I
(c) IV >II >III >I (d) II >IV >I >III
104) When chloroform reacts with benzene in the presence of aluminium chloride, the
product formed is
(a) 1, 1, 1-Trichloroethane (b) Trichlorophenyl methane (c) Triphenyl methane (d)
Triphenyl chloromethane
105) Which of the following groups is an ortho-para directing as well as deactivating a
group?
(a) OH (b) NH2 (c) CH3 (d) CI
106) The order of reactivity of various alkyl halides towards SN1 reaction is

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(a) 30 > 20 >1 (b) 10 >20 >3

(c) 30 = 20 = 10 (d) 10 >30 >20
107) Alkyl halides can be converted to ethers through
(a) Frankland reaction (b) Williamson synthesis (c) Fittig reaction (d) Grignard
reaction
108) Which of the following groups is ortho-para directing as well as deactivating, when
attached to benzene ring?
(a) NO2 (b) OH (c) OCH3 (d) Cl
109) The order of reactivity of various alkyl halides towards nucleophilic substitution
follows the order:
(a) RI > RBr >RCl >RF (b) RF >RCl >RBr >RI (c) RCl >RBr >RI >RF (d) RBr >RI
>RCl >RF
110) The products of reaction of alcoholic silver nitrite with ethyl bromide are
(a) Ethane (b) Ethene (c) Nitroethane (d) Ethyne
111) A compound that will form an offensive smell when heated with chloroform and
alcoholic potash is
(a) C2H5NH2 (b) (C2H5)2NH (c) (CH3)3N (d) CH3CN
112) The correct order of boiling points is
(a) CH3I > CH3Br >CH3Cl >CH3F (b) CH3F >CH3Cl >CH3Br >CH3I
(c) CH3I >CH3I >CH3F >CH3Cl >CH3Br (d) CH3Br >CH3Cl >CH3F >CH3I
113) Dehalogenation of meso-2, 3-dibromobutane results in
(a) cis-2-Butene (b) trans-2-Butene (c) n-Butane (d) A mixture of cis-and trans-2-
Butene
114) Which of the following statements is/are not correct?
(a) Alkyl iodides are heavier than water (b) Alkyl bromides are lighter than water (c)
Ethyne reacts with excess HCl to form ethylidene dichloride (d) Vinyl chloride does
not undergo nucleophilic substitution easily
115) Which of the following reactions do not result in the formation of a new C-C bond?
(a) Ullmann reaction (b) Fitting reaction (c) Williamson synthesis (d) Wurtz reaction
116) Which of the following represents a geminal dihalide?
(a) Ethylene dichloride (b) 2, 2-Dichloropropane, (c) 1, 3-Dichloropropane (d) 1, 2-
Dichloropropane
117) The order of reactivity of alkyle halides through SN1 is
a) 30>20>10 b) 20>10 >30 c) 10>20 >30 d) 20>30 >10
118) Carbon tetrachloride does not have net dipole moment because of
(1) Its planar structure (b) Its regular tetrahedral structure (c) Similar sizes of
carbon and chlorine atoms (d) Similar electron affinities of carbon and chlorine
119) Carbylamine test is performed in alcoholic KOH by heating a mixture of
(a) Chloroform and silver powder (b) Trihalogenated methane and a primary amine
(c) An alkyl halide and a primary amine (d) An alkyl cyanide and a primary amine
120) Chlorobenzene can be prepared by reacting aniline with
(1) Hydrochloric acid (b) Cuprous chloride (c) Chlorine in hte presence of anhydrous
aluminium chloride (d) Nitrous acid followed by heating with cuprous chloride
Hint:Sandmeyer's reaction
121) Out of the following compounds, which one will have zero dipole moment?
(a) 1, 1-Dichloroethylene (b) cis-1, 2-Dichloroethylene (c) trans-1, 2-
Dichloroethylene (d) None of these compounds
Hint:trans-1, 2-Dichloroethylene has zero dipolemoment because dipoles of the two
C-Cl bonds are oppositely directed and hence cancel each other

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