ALKYL HALIDE

EXERCISE - V
(JEE ADVANCED PREVIOUS YEAR)

H x Br2
4.  (mixture)  
1. The ether O — CH2 — H2 O

5 compounds of molecular formula C4H8Br2

Number of compounds in X will be:
when treated with HI produces
[IIT ‘2003]
[IIT 1999]
(A) 2 (B) 3 (C) 4 (D) 5

(A) CH2I OH

–
OC2H5
5. + C2H5I
anhyd. C2H5OH
(B) CH2OH
[IIT 2003]
(A) C6H5OC2H5 (B) C2H5OC2H5
(C) C6H5OC6H5 (D) C6H5I

(C) I
6. Benzamide on treatment with POCl3 gives
[IIT 2004]
(A) aniline (B) benzonitrile
(C) chlorobenzene (D) benzyl amine
(D) OH

7. The following compound on hydrolysis in

aqueous acetone will give : [IIT 2005]
2. The order of reactivity of the following alkyl halides CH 3 CH3 CH3
for a SN2 reaction is : [IIT 2000]
NO2
(A) RF > RCl > R—Br > R—l (K)
(B) R—F > R—Br > R—Cl > R—l H Cl CH3

(C) R—Cl > R—Br > RF > Rl CH 3 CH3 CH3

(D) R—l > RBr > R — Cl > R—F NO2 (L)

H OH CH3
3. Identify the set of reagents/reaction conditions
'X' and 'Y' in the following set of transformation
CH 3 CH3 CH3
X Y
CH3 – CH2 – CH2Br  Product 
NO2 (M)
CH3 — CH — CH3 [IIT ‘2002]
OH H CH3

Br
CH 3 CH3 CH3
(A) X = dilute aqueous NaOH, 20ºC; Y = HBr/
acetic acid, 20ºC NO2
(B) X = concentrated alcoholic NaOH, 80ºC; Y
H CH3 OH
= HBr/acetic acid, 20ºC
(A) mixture of (K) and (L)
(C) X = dilute aqueous NaOH, 20ºC; Y = Br2/
(B) mixture of (K) and (M)
CHCl3, 0ºC
(C) only (M)
(D) X = concentrated alcoholic NaOH, 80ºC; Y
(D) Only (K)
= Br2/CHCl3, 0ºC

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 ALKYL HALIDE
8. Cyclohexene is best prepared from cyclohexanol 13. The number of stereoisomers obtained by
by which of the following bromination of trans-2-butene is
[IIT ‘2005] [IIT 2007]
(A) conc. H3PO4 (B) conc. HCl/ZnCl2 (A) 1 (B) 2 (C) 3 (D) 4
(C) conc. HCl (D) Conc. HBr
14. The major product of the following reaction is
9. 1–bromo–3–chlorocyclobutane when treated [IIT 2008]
with two equivalents of Na, in the presence of
ether which of the following will be formed? Me Br
[IIT ‘2005]
F
 
Ph S N a
   
dim ethyl formamide
(A) (B)

(C) (D) NO2

Me SPh Me SPh

H ,  (i) O F F
10.   X   3  Y.
(ii) Zn / CH3 COOH
(A) (B)
Identify X and Y. [IIT 2005]

NO2 NO2
11. Match the following : [IIT 2006]
Column I
(A) CH3—CHBr—CD3 on treatment with alc.
KOH gives CH2 = CH — CD3 as a major product
Me Br Me SPh
(B) Ph—CHBr—CH3 reacts faster than Ph—
CHBr—CD3. SPh SPh
(C) Ph—CH2—CH2Br on treatment with C2H5OD/
(C) (D)
C2H5O— gives Ph—CD = CH2 as the product.
(D) PhCH2CH2Br and PhCD2CH2Br react with
same rate NO2
NO2
Column II
(P) E1 reaction
KOH gives CH2 = CH — CD3 as a major product
(Q) E2 reaction 15. The correct stability order for the following
(R) E1 cb reaction gives Ph—CD = CH2 as the species is [IIT ‘2008]
product.
(S) First order reaction
O
(I) (II)
12. The reagent(s) for the following conversion.
[IIT 2007]
Br ?
H H O
Br (III) (IV)
is/are
(A) alcoholic KOH (A) II > IV > I > III
(B) alcoholic KOH followed by NaNH2 (B) I > II > III > IV
(C) aqueous KOH followed by NaNH2 (C) II > I > IV > III
(D) Zn/CH3OH (D) I > III > II > IV
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 ALKYL HALIDE
16. In the following carbocation, H/CH3 that is most O
likely to migrate positively charged carbon is
C
H H (D) N
1 2 4 5
+
H3C – C – C – C – CH3 C
[IIT 2009]
O CH2Cl
HO H CH3

(A) CH3 at C-4 (B) H at C-4

(C) CH3 at C-2 (D) H at C-2 20. The total number of alkenes possible by
dehydrobromination of 3-bromo-3-
17. The synthesis of 3-octyne is achieved by adding cyclopentylhexane using alcoholic KOH is :
a bromoalkane into a mixture of sodium amide [IIT 2011]
and an alkyne. The bromoalkane and alkyne
respectively are – [IIT 2010] 21. The major product of the following reaction is
(A) BrCH2CH2CH2CH2CH3 and CH3CH2CCH [IIT 2011]
(B) BrCH2CH2CH3 and CH3CH2CH2CCH
(C) BrCH2CH2CH2CH2CH3 and CH3CCH RCH2OH
(D) BrCH2CH2CH2CH3 and CH3CH2CCH +
H (anhydrous)
O
18. The bond energy (in kcal mol–1) of a C – C single (A) a hemiacetal (B) an acetal
bond is approximately [IIT 2010] (C) an ether(D) an ester
(A) 1 (B) 10 (C) 100 (D) 1000 22. KI in acetone, undergoes SN2 reaction with each
of P, Q, R and S. The rates of the reaction vary
19. The major product of the following reaction is : as - [IIT 2013]
[IIT 2011] O
Cl
O
H3C–Cl Cl Cl
C
(i) KOH
NH
C P Q R S
(ii) Br CH 2Cl
O (A) P > Q > R > S (B) S > P > R > Q
(C) P > R > Q > S (D) R > P > S > Q
O
23. Match the chemical conversions in List-I with the
C appropritate reagents in List-II and select the
(A) N—CH2 Br correct answer using the code given below this
lists - [IIT 2013]
C
List-I
O
O (P) Cl 

C
(B) N CH2Cl
C (Q) ONa 
 OEt
O
O OH
(R) 

C
(C) N
C
(S) 

O — CH2 Br
OH
List-II
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 ALKYL HALIDE
(1) (i) Hg(OAc)2 (ii) NaBH4
Br Br
(2) NaOEt
(3) Et-Br (A) (B)
(4) (i) BH3 (ii) H2O2 /NaOH Br
Codes :
Br
P Q R S Br
Br
(A) 2 3 1 4 Br Br Br Br
(C) (D)
(B) 3 2 1 4
(C) 2 3 4 1 Br
(D) 3 2 4 1
25. In the following monobromination reaction, the
24. The product (s) of the following reaction se-
number of possible chiral products is :
quence is (are) : [JEE (Advanced) 2016)
[JEE (Advanced) 2016]

NH2 (i) Acetic anhydride/pyridine

(ii) KBrO3/HBr

(iii) H3O+, heat

(iv) NaNO2/HCl, 273-278 K
(v) Cu/HBr

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 ALKYL HALIDE

EXERCISE - VI
1. Which of the following chloro derivatives, on 6. In the given reaction
further chlorination can yield only three dichloro HOH
C 6H5  CH  CH  CH2  Br   [X]  [Y]
derivatives?
(A) 1-Chloropropane
[X] and [Y] are
(B) 2-Chloropropane
(C) Chlorobenzene OH
(A) H C CH2
(D) Chlorocyclohexane 5 6 OH (B) H C
5 6

2. Which of the following statements are correct?

(A) Alkyl chlorides are lighter than water CH2
(B) Tetrachloromethane is heavier than water (C) (D) H 5 C 6
OH
(C) Alkyl chlorides undergo nucleophilic
substitution more easi ly than al kyl
7. Which of the following statements are not
bromides
correct?
(D) Fluorobenzene can be prepapred by
(A) Chlorobenzene is more reactive than
Sandmeyer’s reaction
benzene towards electrophilic subsititution
3. Which of the following compounds would yield reactions
chloroform on warming with bleaching powder (B) C—Cl bond in chlorobenzene is less polar
paste? than in CH3Cl
(A) 1-Propanol (B) Propanone (C) Chlorobenzene is less reactive than CH3Cl
(C) Ethanol (D) Propanal towards nucleophilic substitution reactions
(D) In chlorobenzene further substitution take
4. Which of the following reagents, on reaction with
place at meta position
ethyl bromide, would yield diethyl ether as the
major product?
8. Which of the following reactions result in a
(A) Aqueous KOH
product with more number of carbon atoms
(B) Alcoholic KOH
than the starting compound?
(C) Silver oxide / 
(A) Fitting reaction
(D) Sodium ethoxide
(B) Gattermann reaction

5. Which of the following substrate(s) upon treating (C) Wurtz reaction

with a base at higher temperature will yield (D) Balz-Shiemenn reaction
predominantly Hoffmann’s product

(A) CH3 CH2CH2 CHCH3 9. Benzene yields diphenyl methane on reaction

| with . . . in the presence of anhydrous AlCl3.
F
The missing items can be
(B) CH 3 CH 2 CH 2 CH CH 3 (A) CH2Cl2
I
(B) CH 2Cl
(C)
(C) CHCl3

(D) CH3  C H  C H  CH3 (D) CHCl2

| |
Ph Br

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 ALKYL HALIDE
10. Which of the following (s) aryl halide will react
12. If compound ‘Y’ is treated with NaHCO3 the
with sodamide / liquid ammonia leading to
sustitution via bezyne mechanism gas liberated is
*
(A) CO2 (B) C O
2

*
(C) CO (D) C O
2 3
(A) (B)
13. The number of substitution products formed
when metabromo anisole is treated with KNH2 /

NH3

14. During the preparation of chloroform from

ethanal by treating with Cl2 / base , the number
(C) (D) of base molecules consumed is.

Cl Cl Cl

Comprehension 15. is on
Identify X,Y and Z in the following synthetic
Cl
scheme.
* treating with excess AgNO3 . The number of
Na2 C O3  HCl   X  gas
moles of AgCl formed is

Br

Mg / ether H
 X   LiAlH
4
    Y  Z

11. The compound Z is

(A) C6 H 5CH 2OH

*
(B) C H C OOH
6 5

*
(C) C H C H OH
6 5 2

*
(D) C H CH C OOH
6 5 2

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Rajeev Gandhi Nagar, Kota (Raj.) Pin Code : 324005
 ALKYL HALIDE
ANSWER KEY

EXERCISE - V
1. AD 2. D 3. B 4. B 5. A 6. B 7. A 8. A 9. D

O
10. (x) (y)
CH3–C–(CH2)4–CHO
CH3

11. AQ; BQ; CR,S, ; DP,S, 12. B 13. A 14. A 15. D 16. D 17. D
18. C 19. A 20. 0005 21. B 22. B 23. A 24. B 25. 5

EXERCISE - VI
1. AC 2. AB 3. BC 4. CD 5. AC 6. AB 7. AD 8. AC 9. AB 10. BD
11. C 12. A 13. 3 14. 4 15. 2

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Rajeev Gandhi Nagar, Kota (Raj.) Pin Code : 324005