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EXERCISE

Halogen Derivatives
ENGLISH MEDIUM
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Chemistry : Halogen Derivatives
Pre-Medical

EXERCISE-I (Conceptual Questions) Build Up Your Understanding

GENERAL METHOD OF PREPARATION
6. A compound containing two –OH groups
1. Alkyl halides can be obtained by all methods attached with one carbon atoms is unstable but
excepts which one of the following is stable
ZnCl OH
(1) CH3—CH2—OH + HCl 
2
→ (1) CH3CH
(2) CH2 = CH—CH3 + HBr → OH
OH
(3) C2H5OH + NaCl →
hν
(4) CH3COOAg + Br2 / CCl4  → CH3–C–OH
(2)

HD0001 OH
OH
2. Which of the following will not give iodoform test (3) Cl3C–CH
OH

®
(1) CH3 – C – CH3
(4) All
O
CC0006
(2) C2H5 – C –C2H5
CHEMICAL PROPERTIES
O
(3) H–CH2 – CH –C2H5 7. Arrange the following compounds in decreasing
order of reactivity in SN1 reaction :-
OH
Cl
(4) I–CH2 – C –CH2–H
O (a) Ph–CH2–Cl (b)

Cl CH3
HD0002
CH3–C–CH2–Cl
3. Which of the following product is obtained when (c) (d)
bleaching powder is distilled with acetone CH3
(1) CCl4 (2) CHCl3 (1) a > c > b > a (2) c > d > b > a
(3) CH3—CH3 (4) All (3) a > b > c > d (4) b > a > c > d
HD0007
HD0003
8. The purity of CHCl3 can be checked by
4. Which will give yellow ppt. with iodine and (1) treating CHCl3 by NaOH
alkali (2) treating CHCl3 by HCl
(1) Propan–2–ol
(3) treating CHCl3 with aq. AgNO3
(2) Benzophenone
(4) treating CHCl3 by C2H5–OH
(3) Methyl acetate
(4) Acetamide HD0009
HD0004 9. Pure CHCl3 and pure CHI3 can be distinguished
by
PHYSICAL PROPERTIES
(1) treating with litmus paper
5. Which of the following has the highest boiling (2) treating with aq. KOH
point (3) treating with HCl
(1) CH3CH2I (2) CH3Cl
(3) CH3I (4) CH3Br (4) treating with aq. AgNO3

HD0005 HD0010

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10. Which of the following undergoes hydrolysis 15. Chloroform on reaction with acetone gives:–
most easily (1) Acetylene
Cl (2) Chloretone
Cl
(1) (2) (3) Nitrochloroform
NO2 (4) Chloroacetone
HD0019
NO2
Cl 16. Chloroform reacts with aniline and aqueous
Cl
KOH gives :-
(3) NO2 (4) 
O2N NO2 (1) Ph–N = C (Phenyl isocyanide)
O2N
(2) Benzene
(3) Phenyl cyanide
HD0012
(4) None of these
11. Which of the following is used as insecticide AM0020
17. Which reaction product is wrong (major) product
(1) D.D.T. (2) Chloretone
Br

®
Zn(dust)
(3) CHCl3 (4) All of them (1) ∆
Br
AH0013 NaI
(2) CH3CH2CH2Br CH3CH2CH2I
dry Acetone
12. Which of the following when heated with KOH
and primary amine gives carbylamine test Zn (dust)
CH3CHCHCH3 CH3CH=CHCH3
(3) ∆
(1) CHCl3 (2) CH2Cl2 Br Br
(3) CH3OH (4) CCl4 (i) NaNH2(excess)
(4) CH3CH2CHCl2 CH3C≡CH
(ii) H+
AM0014
HD0021
13. Which reaction gives elimination as a major 18. Which of the following undergoes nucleophilic
product substitution by SN1 mechanism at fastest rate :
CH3 CH3CH–Cl
 ⊕
(1) CH3–CH2–Cl (2)
(1) CH3–C–ONa + CH3 – Br → CH3

CH3 (3) CH2–Cl (4) Cl

DMSO HD0022
(2) CH3–CH2–Br + NaCN →
19. Which of the following pair is differentiated by
Dry acetone
(3) CH3–CH2–Br + NaI → iodoform test?
CH3 O O
(1)
 ⊕ ,
(4) CH3–C–Br + CH3ONa →
O O
CH3 (2)
H,H H
O
HD0015 O
(3) C
14. When alkyl magnesium halide reacts with R'-NH2, Ph H, H – C – H
the product is O O
(1) R—R (2) R— H (4) I
CH2 , CH
(3) R2NH (4) R—X I
I
HC0018
HD0023

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20. Identify z in the following series 25. In RMgX, C–Mg bond is-

HBr  Hydrolysis 2 I /NaOH

CH2=CH2 → x→ y
→ z (1) Non polar covalent
∆

(1) C2H5I (2) C2H5OH (2) Polar covalent

(3) Ionic
(3) CHI3 (4) CH3CHO
(4) Coordinate
HD0024
HD0057
Cl
21. C6H5CCl3 
2 →X
Fe
26. The incorrect reaction is-
In the above reaction X is
CCl3 Cl OH
CCl3 (1)
(i) NaOH, 280 K
(1) (2) (ii) H+

®
Cl
Cl
Cl OH
CCl3
(i) NaOH , 443 K
Cl (2)
(3) (4) None of these (ii) H+
NO2 NO2
AH0026
Cl Cl OH
NaOH NO2 (i) NaOH , 358 K NO2
22. :- (3)
∆ & pressure (ii) H+

G NO2 NO2
Rate of reaction is maximum if G is :-
Cl OH
(1) –OCH3 (2) –CH3
O2 N NO2 Warm H O O2N NO2
2

(3) –NO2 (4) –H (4)

NO2 NO2
HD0027
23. Hydrolysis of optically active 2-bromobutane HD0058
gives-
Cl
(1) (d)-butan-2-ol (2) ()-butan-2-ol
Conc. H2SO4
27. Q
(3) (d)-butan-2-ol (4) either of these (major)

HD0055 Cl Cl
SO3H
24. When a haloalkane with β-hydrogen is heated (1) (2)
SO3H
with alcoholic solution of KOH the product and
the type of mechanism is- Cl
Cl Cl
(1) Alcohol, SN1
(3) (4) +
(2) Alkene, α-elimination
SO3H
(3) Alcohol, SN2 SO3H SO3H
(4) Alkene, β-elimination
AH0059
HD0056
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28. The correct reaction is - 29. Which of the following is correct

Cl Cl wurtz reaction
(1) 2RX + 2Na → R–R + 2NaX
conc. HNO3
X R
(1) conc. H2SO4
(2) wurtz-fittig
NO2 + Na + R–X reaction + NaX
(major)
Cl Cl X
Fittig
Anhyd. AlCl3 reaction
+ CH3Cl (3) 2 +2Na + 2NaX
(2)

CH3 (4) All of these

(major) HC0061
Cl Cl
30. Incorrect match is-
Anhyd. AlCl3
(3) + CH3COCl
(1) Iodoform - Antiseptic

®
COCH3 (2) Pyrene - Fire extinguisher
(major)
(4) All of these (3) Freon 12 - aerosol propellants
AH0060
(4) DDT - Fat insoluble
HD0062

EXERCISE-I (Conceptual Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 3 2 2 1 1 3 4 3 4 4 1 1 4 2 2
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 1 1 3 2 3 1 3 3 4 2 1 3 4 4 4

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EXERCISE-II (Previous Year Questions) AIPMT/NEET

AIPMT 2009 AIPMT Mains 2012
4. Which of the following compounds will give a
1. Trichloroacetaldehyde, CCl3CHO reacts with
chlorobenzene in presence of sulphuric acid and yellow precipitate with iodine and alkali ?
produces :- (1) Acetamide (2) Propan-1-ol
(1) Cl CH Cl (3) Acetophenone (4) Methyl acetate
CCl3 HD0033
Cl
NEET(UG) 2019 (ODISHA)
(2) Cl C Cl
5. The hydrolysis reaction that takes place at the
CH2Cl
slowest rate, among the following is :-
Cl
aq. NaOH  ⊕

(1) Cl ONa

®
CH3 CH3
(3) Cl C Cl
aq. NaOH
(2) H3C–CH2–Cl 
→ H3C–CH2–OH
H
aq. NaOH
OH (3) H2C=CH–CH2Cl
 → H2C=CH–CH2OH

(4) Cl C Cl aq. NaOH

(4) CH2Cl CH2OH
Cl
HD0063
AH0029
AIPMT 2010 NEET(UG) 2021
6. The correct sequence of bond enthalpy of 'C-X'
2. In the following reaction
1. Mg,Ether bond is
C6H5CH2Br →
+
X,
2.H3 O (1) CH3–F < CH3–Cl < CH3–Br < CH3–I
The product 'X' is :- (2) CH3–F > CH3–Cl > CH3–Br > CH3–I
(1) C6H5CH2OH (3) CH3–F < CH3–Cl > CH3–Br > CH3–I
(2) C6H5CH3
(4) CH3–Cl > CH3–F > CH3–Br > CH3–I
(3) C6H5CH2CH2C6H5
HD0077
(4) C6H5CH2OCH2C6H5
NEET (UG) 2021(Paper-2)
HC0030 7. Which of the following alkyl halides is not
3. Following compounds are given : suitable for Corey house synthesis of alkanes?
(a) CH3CH2OH (b) CH3COCH3 (1) CH3I (2) Br

CH3–CHOH I
(c) (d) CH3OH (3) (4) Br
CH3
HD0078
Which of the above compound(s), on being NEET(UG) 2022
dry H O+
warmed with iodine solution and NaOH, will give 8. RMgX + CO2 → Y 
3
→ RCOOH
ether
iodoform?
What is Y in the above reaction :
(1) Only (a) (2) (a), (b) and (c) – +
(1) R3CO Mg X (2) RCOO–X+
(3) (a) and (b) (4) (a), (c) and (d) (3) (RCOO)2Mg (4) RCOO–Mg+X
HD0031 CC0079

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9. Which of the following is suitable to synthesize Re-NEET(UG) 2022
chlorobenzene ? 10. Predict the order of reactivity of the following
(1) Phenol, NaNO2, HCl, CuCl four isomers towards SN2 reaction.
(I) CH3CH2CH2CH2Cl
(2) , HCl (II) CH3CH2CH(Cl)CH3
(III) (CH3)2CHCH2Cl
NH2
(IV) (CH3)3CCl
(3) , HCl, Heating (1) (IV) > (III) > (II) > (I)
(2) (I) > (II) > (III) > (IV)
(4) Benzene, Cl2, anhydrous FeCl3
(3) (I) > (III) > (II) > (IV)
HD0080
(4) (IV) > (II) > (III) > (I)
HD0081

EXERCISE-II (Previous Year Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10
Ans. 1 2 2 3 1 2 4 4 4 3

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EXERCISE-III (Analytical Questions) Master Your Understanding

1. Which of the following has highest dipole 6. Identify 'Z' in the following reaction series,
moment: aq. NaOH Al O
(1) CH3Cl (2) CH3F CH3.CH2CH2Br
→ (X) 
2 3
→ (Y)
Heat
(3) CH3Br (4) CH3I Cl /H O
HD0040 
2 2
→ (Z)
2. The final product in the reaction is (1) Mixture of CH3–CH–CH2 and CH3–CH–CH2
(1) KOH, ∆
Ph—OH + CCl4 
(2) H⊕
→ product Cl Cl OH OH
(1) Salicylaldehyde
(2) CH3–CH–CH2
(2) Salicylic acid
(3) Methyl salicylate OH Cl
(4) Benzyl chloride
AH0041 (3) CH3–CH–CH2
3. Arrange the following in order of ease of

®
Cl OH
dehydrohalogenation:
Br Br (4) CH3–CH–CH2
(i) (ii)
Cl Cl
Br Br
(iii) (iv) HD0045
7. Arrange the following compound in increasing
(1) (iii) > (iv) > (ii) > (i)
(2) (iii) > (ii) > (i) > (iv) order of reactivity towards aromatic nucleophilic
(3) (ii) > (iii) > (i) > (iv) substitution reaction.
(4) (i) > (ii) > (iii) > (iv)
Cl
HD0042 Cl
4. The product in the following reaction is
(a) (b)
Ph—Cl + Fe / Br2 → Product NO2
(1) o–bromo-chloro benzene
Cl
(2) p–bromo-chloro benzene Cl
(3) both the above (c) (d)
(4) 2,4,6–tribromo chloro benzene
AH0043 NO2 NO2 NO2
5. Isobutyl magnesium bromide with dry ether and
(1) c > d > b > a (2) c > b > a > d
absolute alcohol gives
(3) d > c > b > a (4) a > d > b > c
(1) CH3–CH–CH2OH and CH3CH2MgBr

CH3 HD0046

(2) CH3–CH–CH2––CH2–CH3 and Mg (OH) Br 8. Chloroform when treated with benzene in

presence of anhydrous AlCl3, the product formed
CH3
is

(3) CH3–CH–CH3 , CH2=CH2 and Mg(OH)Br (1) Chlorobenzene

(2) Toulene
CH3
(3) Mixture of ortho and para chlorotoluene
(4) CH3–CH–CH3 and CH3CH2OMgBr
(4) Triphenyl methane
CH3
HC0044 AH0047

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9. Consider the following statements- 14. Which halide ion is the best nucleophile in DMF -
(A) In allylic halides halogen atom is bonded to (1) F (2) Cl
3
an sp carbon adjacent to C=C (3) Br (4) I
HD0069
(B) In benzylic halides halogen atom is bonded to
3
15. Which of the following SN2 reaction is the
sp carbon attached to an aromatic ring
slowest-
(C) In vinylic halides halogen atom is bonded to a
OH
2
sp carbon of a C=C (1) CH3–CH2–CH2–Br
(D) In aryl halides halogen atom is directly CH3–CH2–CH2–OH + Br
2
bonded to a sp carbon of an aromatic ring OH
(2) CH3–CH2–CH2–Cl
Which statement(s) is/are correct CH3–CH2–CH2–OH + Cl
(1) Only A, B, C (2) Only A, C
OH
(3) Only A, C, D (4) All (3) CH3–CH2–CH2–F

®
HD0064 CH3–CH2–CH2–OH + F
10. Which alkane gives 1-chloro-2,2-dimethyl
propane on monochlorination- OH
(4) CH3–CH–CH3 CH3–CH–CH3 + F
(1) Isopentane (2) Isobutane
(3) Neopentane (4) 2,3-dimethyl butane F OH
HD0065
HD0070
11. CH3–CH2–OH NaBr (A) Alc.KOH (B) HBr (C)
 → →  → 16. Rate of SN2 reaction will be maximum in which
H2 SO4 ∆
of the following solvent -
A, B and C are respectively -
(1) CH3CH2HSO4 , CH2=CH2 , BrCH2–CH2–Br (1) H2O (2) CH3OH
(2) CH3–CH2–Br, CH2=CH2, CH3–CH2–Br OH
(3)CH3–CH2–OCH2–CH3, CH2=CH2, CH3–CH2
(3) (4) DMSO
Br
(4) CH2=CH2, CH3–CH2–OH, CH3–CH2–Br HD0071
HD0066
17. Best method to convert alcohol into alkyl
12. Correct order of rate of photo bromination for
chloride is -
following compounds-
(1) ROH + SOCl2 → R–Cl + SO2 + HCl
(I) CH3–CH3 (II) CD3–CD3
CH3 (2) R–OH + PCl3 → R–Cl

(III) CH –C–H (3) R–OH + PCl5 → R–Cl

3
(4) R–OH + HCl → R–Cl + H2O
CH3 HD0072
(1) II < I < III (2) I < II < III
HBr
(3) III < I < II (4) II < III < I 18. Major product ?
HD0067 OH

Br
Cl2 (1) (2)
13. Monochlorination product
hν Br
Number of possible monochloro derivatives
CH2Br
excluding stereo isomers is/are - (3) (4)
(1) 4 (2) 5
Br
(3) 3 (4) 6
HD0073
HD0068
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19. Identify incorrect match in the following -
20. The correct reactivity order for SN1 reactions is-
⊕ 
N2X Cu2X2 (1) > CH2–Br > >
(1) ESR Br
Br Br

(2) < < < CH2–Br

CH3 Br
(2) X2/Fe ESR Br Br
dark
(3) < < CH2–Br <
CH2CH3 Br
Br2/hν Br Br
(3) FRSR
or heat
O2N
(4) > > CH2–Br >
Br
CH2OH Br Br

HCl HD0075
(4) NSR
heat
21. Which of the following is most reactive for SN2

®
OH
reactions.
HD0074
(1) (C6H5)2C(CH3)Br (2) C6H5CH(CH3)Br

(3) (C6H5)3CBr (4) C6H5CH2Br

HD0076

EXERCISE-III (Analytical Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 1 2 2 3 4 2 3 4 4 3 2 1 2 1 4
Que. 16 17 18 19 20 21
Ans. 4 1 2 1 2 4

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