4.

18 Onganic Compounds Containi ng Halogens (Haloalkanes and Haloarenes)

MULTIPLE-CHOICE QUESTIONS

Straight Objective Type Questions

(Single Choice only) H-CH,CH,
(b)
n-Propyl bromide on treatment with ethanolic potas
sium hydroxide produces -CH,- CH CH,
(a) Propane (b) Propene (c) B
(c) Fropyne (d) Propanol
CH, - CH, -CH,Br
2. Which is the best solvent to use for the solvolysis (d)
reaction of t- butyl chloride?
(a) Water 10. The compound most reactive towards SN' reaction
(b) Carbon tetrachloride is
(c) Formic acid
(a) Me,C - CH,CI (b) MeOCH,CI
(d) Heptane
3. 1-Chlorobutane on reaction with alcoholic potash (c) PhCH,CH,CI (0) -CI
gives
(a) 1-Butene (b) 1-Butanol 11. The starting substance for the preparation of iodo
(d) 2-Butanol.
form is any one of the following, cxcept
(c) 2-Butene
(a) CHCH(OH)CH, (b) CH,CH,OH
4. Corect order of B. P. for the alkyl halide is (c) HCH,0H (d) CH,COOH,
(a) CH,CI > cHBr> C.HÊ 12. The reaction of -bromobenzyl chloride with NaCN
(b) CHÊ > C,HBr> CH,CI in ethanol leads to:
(c) CHÊ > C,H,C|> CHBr (a) 4-bromo-2-cyanobenzyl chloride
(d) CHBr> CHI>CHCI (b) 4-cyanobenzyl cyanide
S. Chlorination of toluene in presence of light and heat (c) 4-cyanobenzyl chloride
followed by treatment with aqueous NaOH gives (d) 4-bromobenzyl cyanide
(a) o-Cresol 13. Which of the following reagents could be used to
(b) p-Cresol convert cyclohexanol to chlorocyclohexane?
(c) 2, 4-Dihydroxytoluene (a) Ci, light (b) SOCI,
(d) Benzoic acid. (c) PBr, (d) none of these
6. Which of the following represents the correct order 14. Which of the following bases would give the best
of densities? yield for the substitution product when reacted with
(a) CCi,> CHCI,> CH,Ci,> CH,CI >H,0 2- chloropropane?
(b) CCI,> CHCI, S CHCi, >H0>CHCI (a) CH,C00 (b) OH
(e) HO>CH,CI >CH,CI, >CHCI, >CCI, (c) NH, (d) CH,CH;o
(d) CCI,> CHCI,> H,0 >CH,CI, >CH,CI 15. Arrange the following compounds in order
7. Which of the following has the highest normal boil of increasing dipole moment: Toluene (1), m
ing point? dichlorobenzene (I), o-dichlorobenzene (Ill), and
(a) iodobenzene (b) bromobenzene p-dichlorobenzene (IV).
(c) chlorobenzene (d) fluorobenzene (a) I<IV <II <II (b) IV <I<Il <II
8. Among the following alkyl halides, choose the onc (c) IV <I<II<I (d) IV <II <|<II.
with the lowest boiling point. 16. The following transformation proceeds through
(a) t-butyl chloride (b) n-butyl chloride CI
(c) -butylbromide (d) n-butyl iodide ,NO, ,NO,
Dil. NaOH
9. Propyl benzene reacts with bromine in presence of
light or hecat to gjve
Br NO, NO,
CH, - H - CH, (a) benzyne intermediate
(a) (b) oxirane
 Haloarenes)
Organic Compounds Containing Halogens (Haloalkanes and 4.19

(c) clectrophillie -addition 23. The pesticide DDT slowly charges to:
(d) activated nucleophillic substitution (a) p, p'-dichlorodiphenyldichloroethene
(b) p, p'-dichlorodiphenyldichloroethane
17. Which of the following is the best nucleophile is an (c) p, p'-dichlorodiphenylethene
S2 rerction where competition from E2 is unim (d) CCl,-CHO and chlorobenzene
portant?
(a) HOO0 (b) H,0 24. When chlorine is passed through propene at 400°C,
(c) CI (d) OH which of the following is formed?
(a) allyl chloride (b) PVC
18. Which of the following compounds will undergo an
SN2reaction most readily? (c) vinylchloride (d) 1,2-dichloroethane
25. The conversion of 2,3-dibromobutane to 2-butene
(a) (CH,),cCHI
(6) (CH),CCI with Zn and alcohol is
(c) (CH),CHI (a) B-Elimination
(b) Redox reaction
(G) (CH),CHCH,CH;CH! (c) Both B-elimination and redox reaction
19. CH,CD,CHBrCHcD, on reaction with al. KOH (d) a-Elimination
gives:
Perox1de
(a) CH,CD,CH - CHCD, 26. CH, FCH, + HBr (A)
(b) CHCD =C - CHCD
(c) CD,CD,CH = CHCH, (A)is:
(d) CHCD-CHCH,CD,
20. What is the product of the reaction of the following
(@) CH
Br
) -CH,Br
compound with alcoholic potassium hydroxide?
Br
(b) CHH,
Br Br
Br Br
CH,
(a) 1- methylcyclohexane only
(c)
CHCH,
(b) 1- Methyleyclohexane only
(c) 3- methylocyclohexene (major product), ) BrCH CHBr
1- methyleyclohexene (minor product)
(d) 3- methylhexene only 27. Nucleophilicity order is correctly represented by
21. Which of the following is example of SN' reaction? (a) NH, >F> HO> CH,
(b) CH, > NH, > HO > F
(a) CHBr + OH ’ CH,OH + Br (c) CH, <NH, < HO <F
(b) CH, -CH - CH, + OH ’ (d) CH, NH, > OH F
Br 28. In SN' reaction, the racemization takes place. It is
due to:
CH, - CH-CH, +Br (a) conversion of configuration
OH (b) retention of configuration
(c) inverSion of configuration
- H,0 (d) both (a) and (b)
(c) CH, - CH, -OH H,C - CH,
CH, 29. Arrange the following halides in the decrcasing
CH, order of SN' reactivity:

(d) CH,-C-CH, + OHCH, C-CH, +Br () CH,CH,CH,CI,

(1) CH, - CHCH(CIl)CH,
OH (III) CH,CH,CH(CI)CH,
Br (b) II >II >I
(a) I> I > II
22. Toluene when refluxed with Br, in the presence of (c) II >I> II (d) III > I|>|
light mainly gives treated with sodamide
(a) p- bromotoluene
30. o-Methoxybromobenzene is product formed is
and then with ammonia. The
(b) benzyl bromide (a) methoxyaniline (b) m-methoxyaniline
(c) o-bromotoluene .1:..
4.20
Organic Compounds Containing Halogens
(Haloalkanes and Haloarenes)
31. Which of the following undergoes E, climination in
the presence of a strong base to yicld one product? (a) CH,CH, -CCI, -CH,CH,
(a) 3- bromo -2- methylpentanc (b) CH, -CCI,CH,CH,CH,
(b) 1- bromo -]- methyleyclohexane (c) CH, -CCI, -CCi, -CH,CH,
(c) 1- bromo -3,3- dimethylbutane CI
(d)
(d) 3- bromo -3- methyl pentane
32. Isopropyl chlornde undergoes hydrolysis by
CHC
(a) SN' and SN² mechanisms 41. Allyl chloride on dehydrochlorination gives
(b) neither SN' nor SN? mechanisms (a) propylene (b) acetone
(c) SN' mechanism only (c) propadiene (d) allyl alcohol
(d) SN mechanism only 42. Which of the following most readily undergoes
S,1
33. Which one of the following is most reactive
towards displacements?
nucleophillic substitution reaction? (a) 1- Bromopentane
(a) CHcI (b) CH, = CH - CI (b) 2- Bromopentane
(c) CICH, - CH = CH, () CHCH - CH-CI (c) 2- Bromo-2- methylbutane
34. Which of the following will have the (d) 1- Bromo-2- methylbutane
maximum 43. The most reactive nucleophiles among the following
dipole moment?
(a) CHCI (b) CH,Br
(c) CHÊ (d) CHF (a) CH,0 (b) (CH),co
35. Most reactive alkyl halide towards E2 mechanism (c) (CHJ),CHO (d) CH0
44. Which of the following are arranged in the decreas
ing order of dipole moment?
(a) CHC- CHBr
(b) CHCHCHBCH, (a) CH,CI,CH,Br, CHF (b) CH,CI, CHF, CHBr
(c) CHCH,-CHCH,Br (c) CH,Br, CH,CI, CHF (d) CH,Br, CHF, CHCI
(d) CHC- CHCHBr 45. Consider the following reactions:
X+ HCI
anhyd. AlCI,
CHCH, (addition)
36. Most reactive halide towards SN' reaction is
(a) sec-butyl chlonide anyhd. ZnCl,/HCI
(b) tert-butyl chioride (substitution)
(c) n-butyl chloride Y can be converted to X on heating with at
(d) allyl chioride temperature.
37. The order of reactivity of alkyl halides towards (a) Cu, 300°C
elimination reaction is (b) Al,0,, 350°C
(a) 1°> 2° > 3 (b) 2° > 1>3° (c) NaOHI,, 60°C
(c) 3> 2° > 1° (d) 3°> 1°>2° (d) Ca(OH), + CaOCi,, 60°C
38. The reactivity order of halides for dehydrohalogena 46. Which one of the following is a frce radical substitu
tson is tion reaction?
(a) R-FR-CI >R- Br> R-I
(b) R-IR- Br >R-C >R -F (a) CH,CHO +HCN ’ CH,CH(OH)CN
(c) R-l>R-CI>R-Br > R-F
(d) R-F>R-I>R- Br >R-CI (b) + CH,CI Anhy. AlCI,
39. A set of compounds in which the eactivity of halo CH,
gen atomn in the ascending order is
(a) chloroethane, chlorobenzene, Vinyl chloride
(b) chlorobenzene, vinyl chlornde, chloroethane
(c) vinyl chloride, chloroethane, chlorobenzene CH,CI
(d) vinyl chloride, chlorobenzene, chlorocthane (c) + AgNO,
40. What is the major product of the following reac
tion? CH,NO,
CH _C= C-CH CH CI, (I mole)
 Haloarenes) 4.21
Organic Compounds Containing Halogens (Haloalkanes and
H,0, 3.NaBH,, OH
CH, +Cl,
Boiling
(d) NaNH,/NH, 2. Br, light, 3. HH,0
(d) 55. The major product formed in the following reaction is
CH,CI CH,
CH, -C- CH,Br CHO
47. Which of the following substrate is most reactive CH,OH
towards methoxide ion (Me 0°)? H
CH,
(a) CH, -0- s0,O-CH,
(b) CH, -I (a) CH, - C-CH,0CH,
(c) CH -CI
(d) CH, -0- SO, - CF, H
48. ldentify A and B in the following reaction: (b) CH, - CH- CH,CH,
B
C,H,CI AcHOH
(a) A -AgNO,; B - KNO, OCH,
(b) A- aq. NaOH; B - AgNO, CH, CH,
(c) A =alc. KOH /A; B= aq. NaOH
(d) A=aq. KOH; B =AgOH (c) CH, - C - CH, (a) CH, -C-CH,
49. Which of the following is least reactive in a nuclco OCH,
phillic substitution reaction?
(a) (CH),C -Ci (b) CH, = CHCI 56. The major product obtained on treatment of
() CH, - CHCH,CI CH,CH,CH(F)CH, with CH,0/CH,OH is
(c) CH,CHCI
(a) CHCHCH(OCH,)CH, (b) CHCH = CHCH,
S0. 12-dibromoethane reacts with alcoholic KOH to (c) CH,CH,CH = CH,
yicld aproduct X. The hybridization state of the
carbons present in X, respectively are () CH,CH,CH,CH,OCH,
(a) sp², sp (b) sp, sp 57. Compound (A) is
(c) sp', sp² (d) sp', sp
2 ÇCl,
51. What is the major products of the reaction of
bromopcntane with sodium ethoxide in ethanol? leq. of Br/Fe (A)
(a) trans-2- pentene
b) 2- ethoxypentane
(c) cis -2 pentene CCl,
(d) both A and C Br
S2. Identify A and B in the following reaction: a (b)
Br
Ag. NaOH, A AgOH B CC1,
CH,OH ÇCl,
çci
(a) A-CJH, B-CHCi (d)
(c)
(b) A-CH,CI, B- CHCi Br Br
(c) A-CH, B-CH Br
(4) A-CJH,CC, B- CH, 58. Fluorobenzene (CHF) can be synthesized in the
53. Among the following the strongest nucleophiles is laboratory
(a) CHSH (b) CH,C00 (a) by heating petrol with HF and KE
(c) CH)NH, (0) NCCH (b) from aniline by diazotization followed by heat
54. Which of the following sets of reagents willconvert ing the diazonium salt with HBF,
1- bromo -2- phenylethane to 1- phenylethanol? (c) bydirect fluorination of benzene with F, gas.
(a) H,SO, and heat (d) by reacting bromobenzene with NaF solution.
(b) 1. NaOCH,CH/CH,CH,OH, 2. BH/diglyme, 59. An alkyl bromide produces a single alkene when it
3.H20,, OH reacts with sodium ethoxide and ethanol. This alkene
(c) 1. NaOC(CH.) J(CH),COH. 2. He(OAc). /THF nderanes hudrngenatinn and nrondees 2. methvlhe
 422 Ogate Componds Containing Halogens (Haloalkanes and Haloarenes)
tane What is the identif of the aikyi bromide 6 Whieh ehloroderivative of nitrobenzenes among the
(a) 1- bromobtene
following would ndergn hydrolysis, most readily
with aqueos NaOH?
(b) 1- bromo 2- methbute
(c) 2- broho-2- methbutene NO,
(e) 1- bromo-2, 2- dimethyipropene (a) -ci
60 The structre of the njor prodct formed in the
given reaction
NO,
CHA NeCN
DMF
NO,
CH,CI
CHCN (c)
b) CN
oN
CN o
(d)
CH,C CH,CN
(d) oN
66. The correct increasing order of the reactivity of
CN halides for SN, reaction is
61. in the rcaction. (a) CH, CH,-X<(CH),CH -X<CH, -CH CH,x
<PhCH, -X
R-X ak KCN B (b) (CH),CH X <CH, -CH, - X<CH, - CH
CH, -X< PhCH, -X
The prouct B is (e) PhCH, -X<(CH),CH -X <CH, CH, X<
(a) alkyi chiondc (b) aldehy de CH, - CH -CH, -X
(c) carboxyluc acad () ketone (4) CH,-CH -CH, - X< PhCH, -X<(CH),CHX
62 Which of thx foliowing rcacts under S,2 conditions
<CH, CH,- X
wth sod1unm cyanade NaCN, to produce the follow 67. The major product formed in the foilowing reaction
aq KOH
ng product?
is CH,CHCHCH,-CHOH
(a) CH,CH - CH-CH,OH
CN (b) CH, - CH -CH -CH,OH
CH H (c) CH, - CH - CH,
(a) ras i-odo-2-uet1yicy clopentanc 0CH,
() csiodo-2neiylcy chopcatane (4) CH, -CH-CH, -CHOH
(e) ar2 mottylcyiopcalaoole
O
¬3. Whch of tx followg coapounds as te higthcal
68 HB cacts with CH, -CH-oCH, under anhydrous
bokog pog conditions al oom temperatuwe lo give
(e) CH,CHCHa (a) BCHCHO and CH,OH
(b) CHCH,CHCH,a (b) CH,CHO snd CH,B
(e) CH,CHHCH HC () CH, CHB-0CH,
(4) (CHJcci (4) BCH,-CH, -0CH,
64. Which of the following scquease of scachoas 69. Replacement of Cl of chiorobenzene to give phenol
chloine of 2, 4
(rcagents) can b used fo the conservaton of requires drastis condi tions but
cH,CH,CH, into CH, CH -CH,? is readily replaced because
dinitrochlorobenzene
rich at ortho and
94 (a) SOCi, ; H,O (b) So,Ci,,ale KOH (a) NO, makes the ring clectron
para positions
(c) CI,hv , H0 (d) sOCi, , ale KOH withdrawselectrons at meta -
meitinn
(hì -NO
94,
 4.23
Halogens (Haloalkanes and Haloarenes)
Compounds Containing elimination.
Organic
(c) 2, 4-dinitrophenol is formed via an mech
electrons at
meta-position
addition nuclcophilic aromatic substitution
(c) -NO, donate para
withdraws electrons at ortho and anism.
(d) -NO, addition
positions (d) 2, 4-dinitrophenol is formed via an
substitution
compound, which shows
complete elimination nucleophilic aromatic
70. The organic chloro is
stercochemical inversion during a SN' reaction, mechanism.
reaction
(b) (CH,),ccl likely mechanism for the
(a) (C,H), CHCI 75. Predict the most
(e) (CH),CHCI (d) CH,CI shown below.
S,1reaction most C
71. Which of the following shows
readily? HO.
CI

(a) S1
C1 (b) S,2
CH, (c) El
(b) CH; (d) E2
reaction:
76. Identify (Z) in the following
(c) CHs
CI
+ Mg THF CO;
(d) CH: CH, lmole
Br
Br
72. Consider the following alkyl halide. (Y) H (2)
C1
Cl COOH

(a) (b)
one
If one mole of this dibromide is mixed with
mole of Nal in acetone, what is the principal product OOH OOH
of the reaction? COOH COOH
(a) 1- chloro -3- iodohexane
(b) 3- chloro-1- iodohexane (d)
(c) 1,3- düodohexane
(d) Both A and B Br
73. In a SN' substitution reaction of the type
R- Br + CI
DMF R - Cl + Br Brainteasers Objective Type Questions
Which one of the following has the highest relative(Single choice only)
rate? 77. How many structural isomers of CHCIBr are pos
CH, sible and how many of them are optically active
respectively?
(a) CH, - C-CHBr (a) 5, 2 (b) 5,3
(c) 4,2 (d) 3, 2
CH, nucleophilicity among the
(b) CH,CHBr 78. The decreasing order of
(c) CH, - CH, - CHBr nucleophiles
(1) CH, -C-0 (2) CH,0
(d) CH, - CH- CH,Br

CH,
74. When 2, 4-dinitrochlorobenzeneis treated with (4) H,C
(3) CN
sodium hydroxide at 100°C followed by protonation:
(a) 2, 4-dinitrophenol is formed via an electrophilic (b) 3>2>1>4
aromatic substitution mechanism. (a) 2>3>1>4
(d) 4 >3>2>1
(b) 3,5-dinitrophenol is formed via an electrophilic (c) 1>2 >3>4