Lakshya JEE Main (2025)

MANTHAN
Chemistry Haloalkanes Haloarenes
Exercise -1 8. Which one of the following statement is wrong about SN2
reaction?
HALOALKANES (a) The rate of reaction is independent of the concentration
PREPARATION OF ALKYL HALIDE of nucleophile.
(b) Nucleophile attacks the carbon from the side opposite
1. In reaction: C 2 H 5 OH + HX  ü 2
→ C 2 H 5 X + H 2 O. to where the leaving group is attached.
The order of reactivity of HX is (c) Reaction occurs only in one step and the bond formation
(a) HBr > HI > HCl (b) HI > HCl > HBr & bond breaking takes place simultaneously.
(c) HCl > HBr > HI (d) HI > HBr > HCl (d) The rate of reaction ∝ [substrate][nucleophile].
2. What is the main product of the reaction between 9. Identify X and Y in the following reaction sequence.
2-methyl propene with HBr? X Y
C2 H 5 Br 
→ product  → C3 H 7 NH 2
(a) 1-bromobutane
(b) 1-bromo-2-methylpropane (a) X = KCN, Y = LiAlH4
(c) 2-bromobutane (b) X = KCN, Y = H3O+
(d) 2-bromo-2-methylpropane (c) X = CH3Cl, Y = AlCl3 / HCl
3. When propylene reacts with HBr in presence of peroxide,
(d) X = CH3NH2, Y = HNO2
the product formed is
(a) n-Propyl alcohol (b) Propylene peroxide 10. The least reactive alkyl chloride towards substitution
(c) n-Propyl bromide (d) 1, 3-Dibromopropene reaction is:
4. Best method for preparing alkyl chloride is (a) Methyl chloride
(a) ROH + SOCl2 →
(b) Allyl chloride
(b) ROH + PCl5 →
(c) ROH + PCl3 → (c) Ethyl chloride

(d) ROH + HCl  anhy.ZnCl2

→ (d) Vinyl chloride
5. The general formula for alkyl halides is 11. In the following reaction, the most probable product will be:
(a) CnH2n+1X (b) CnH2n+2X Br
H CH3
(c) CnHn+1X (d) CnH2nX OH
6. Which of the following does not give white precipitate when H 3C H
SN 2

boiled with alcoholic silver nitrate?

C2H5
(a) Allyl chloride
(b) t-butyl chloride OH CH3
(c) Chlorobenzene
H CH3 H OH
(d) Benzyl chloride
(a) (b)
H 3C H H 3C H
SUBSTITUTION REACTION (SN1/SN2/SNi) C2H5 C2H5

7. Following reaction (CH3)3CBr + C2H5OH →

(CH3)3COC2H5 + HBr is an example of: C2H5 CH3
(a) Elimination reaction H CH3 HO H
(b) Free radical substitution (c) (d)
H 3C H H 3C H
(c) Nucleophilic substitution
(d) Electrophilic substitution OH C2H5

1
12. The order of reactivity of the following halides towards 18. Find the product of the following reaction:
hydrolysis by aqueous KOH is: Cl
(a) CH2 = CHCl < CH3CH2CH2Cl < CH2 = CHCH2Cl H2O
(b) CH2 = CHCl < CH2 = CHCH2Cl < CH3CH2CH2Cl
OH
(c) CH2 = CHCH2Cl < CH2 = CHCl < CH3CH2CH2Cl
(a) (b)
(d) CH3CH2CH2Cl < CH2 = CHCl < CH2 = CHCH2Cl OH
13. The reaction: OH
(c) (d)
C2H5ONa + BrC2H5 → C2H5–O–C2H5 + NaBr is called-
(a) Frankland reaction 19. For which alkyl halide, SN2 mechanism is most favoured?
(b) Wurtz reaction
(a) CH3Cl (b) CH3CH2Cl
(c) Williamson’s synthesis
(c) (CH3)2 CHCl (d) (CH3)3C – Cl
(d) Cannizzaro reaction
14. What is the final product of the given reaction? 20. Which of the following reaction is most favoured by SN2 reaction?
CH3 −CH2 − I
Na →  (a) CH 3 Br + OH − → CH 3 OH + Br −
CH3 – C ≡ CH  → Product
Br OH
(a) CH2 = CH – CH2 – CH3
(b) CH3 – CH2 – C ≡ C – CH2 – CH3
(b) +HBr
(c) CH ≡ C – CH2 – CH2 – CH3 H2O

(d) CH3 – C ≡ C – CH2 – CH3

+
H
15. In the given reaction [X] and [Y] will be: (c) CH 3 CH 2 OH  → CH 2 = CH 2
CH3 CH3
( )
HCl 1 eq

— —

— —
CH3 – CH2 – CH2 – O – CH3 → [X] + [Y] (d) CH3—C—CH3+OH–® CH3—C—CH3+Br –
(a) CH3–CH2 –CH2OH & CH3–Cl
Br OH
(b) CH3–CH2–CH2–Cl & CH3OH
21. Which is the major product of the following reaction?
(c) CH3–CH2–CH2–Cl & CH2Cl2 CN
1. NaOH (excess)
(d) CH3–CH2 –CH2OH & CH3–OH Product
2. H O, H+ 2
16. (R)-2-Bromobutane is allowed to react with aqueous KCN. CH2—Cl heat

Identify the product formed in the given reaction. O

CH3 CN
C
(a) H CN (a) (b) OH
C2H5 CH2—OH
CH2—Cl
CH3 O
(b) NC H
C
C2H5 (c) (d)
OH
(c) Equimolar amounts of (a) and (b)
CH2—OH
(d) Slight excess of (b)
22. Which of the reagents shown below would accomplish the
17. Which of the following reaction is most expected to take following transformations?
place by SN2 mechanism?
Cl OH
—

CH3 1. (A)
— —

H2O 2. (B)
(a) CH3—CH2—C—Br + AgOH
(A) (B)
CH3 (a) NaOH BH3 – THF; H2O2/NaOH
(b) (CH 3 )3 C — Br + KOH 
H2 O
→ (b) H3O+ BH3 – THF; H2O2/NaOH
(c) CH 3 CH 2 CHBrCH 3 + CH 3 CO 2 Na 
CH3 CO2 H
→ (c) HBr in ether Hg(OAc)2/H2O2; NaBH4
dimethyl sulphoxide (d) NaNH2/D Hg(OAc)2/H2O2; NaBH4
(d) (CH 3 ) 2 CHBr + KCN  →

2
 23. MeO Br KCN
(X) (2)
(MOM bromide)
(Methoxy methyl bromide) Cl

Product (X) of the reaction is
(3)
(a) Me–O–CH2–CH2–CN (b) MeO CN Cl
CN (a) 1 > 2 > 3 (b) 2 > 3 > 1
(c) Br CN (d) (c) 2 > 1 > 3 (d) 3 > 2 > 1
CN
29. In each of the following groups, which is the strongest (best)
24. Which of the following halides will be most reactive in SN2 nucleophile?
reaction and SN1 reaction, respectively?
Br
(I) (1) H3C – O–
I. Me
(2) O– in CH3OH
Br
(3) H3C – S–
II.
Me Me
(II) (1) OH–
Me (2) H2O in DMF
III. — –
—

Me (3) NH2
Br
(a) (I), (II) (b) (II), (I) O–

(III) (1)
(c) (I), (III) (d) (III), (I)
25. Which of the following compounds will give curdy
precipitate with AgNO3 solution? (2) in DMSO
Cl O–
(3) CH3O–
(a) (b) CH2 = CH – Cl
(a) I, 3; II, 3; III, 2 (b) I, 2 ; II, 1 ; III, 3
(c) I, 1 ; II, 2 ; III, 1 (d) I, 3; II, 1 ; III, 3

Cl Cl
ELIMINATION REACTION (E1/E2)
(c) (d)
30. I
EtOH
D
P (Major elimination product)

The product P is
26. Pick out the strongest substrate(s) for a SN1 reaction.
C6H5 Br (a) (b)
Br Br
C2H5 C6H5 Br
C6H5
(c) (d)
III. IV.
I. II.
(a) Only I (b) Only II 31. [X] the major elimination product among the following
(c) Only III (d) Only IV products is
27. During SN2 reaction, which statement is essential or correct? Br
(a) (R)-configuration of reactant essentially gives (S)- CH3OH
CH3 C—CH3 [X]
configuration of product. D

(b) Reactant having d-configuration essentially gives H

product having l- configuration of product. CH3
(c) Backside attack takes place on substrate atom having HC=CH2
leaving group.
(a) HC=CH2 (b)
(d) All of the above
CH3
28. Arrange the following three chlorides in decreasing order
CH3 CH3
towards SN1 reactivity.
(c) (d)
(1) Cl
CH3

3
32. Arrange the following in decreasing order of stability of their CH C C C2H5
C
transition state during elimination by a strong base: ,
Br
(d)

37. 1-Phenyl-2-chloropropane on treatment with alcoholic

Br Br
I II III caustic potash gives mainly
(a) II > I > III (b) II > III > I (a) 1-Phenylpropene
(c) I > III > II (d) I > II > III (b) 1-Phenylpropanol
33. Consider the following reaction sequence. (c) 3-Phenylpropene
CH3C ≡ CH  HCl
2 mole
aq. KOH
→ A 
heat
→ B. (d) 2-Phenylpropan-2-ol.
The products (A) and (B) respectively, are: 38. Major product of the reaction given below is
(a) CH3CH2CHCl2 and CH3CH2CHO
(b) CH3CCl2CH3 and CH3COCH3 alc. KOH
D
(c) CH3CCl2CH3 and CH3C ≡ CH Cl
(d) CH3CHClCH2Cl and CH3CH(OH)CH2OH

(a) (b)
Cl EtOH/
34. NaOEt
P (Major elimination product)

The product P is
(c) (d)

(a) (b)
39. Which one of the following substrate will be the most
reactive for E1 reaction?
Br
(c) (d)

—
(a)
—C—CH2—CH3

—
alc. KOH
35. (X) D
(major product)
Me
The reactant (X) is: (b) Ph—CH—CH2 —CH3
—

Br Br
Br
(a) (b) (c) Br – CH = CH – CH2 – CH3
Br
Me Me
— —

Br Br (d) CH =CH—C —C H
2 2 5

CH3
(c) (d)
HALOARENES AND POLY HALOGENATED
Me Me
Br Br COMPOUNDS
36. CH CH2 Alc. KOH NaNH2
X Y 40. Full name of is:
CH3CH2Br
X and Y are respectively
C C Br (a) 1, 1, 1-trichloro-2, 2-bis (p-chlorophenyl) ethane
C C C2H5
(a) (b) 1, 1-dichloro-2, 2-diphenyl trimethylethane
,
(c) 1, 1-dichloro-2, 2-diphenyl trichloroethane
C CH CH2 CH2 C CH (d) None of these
(b) , 41. When phenyl magnesium bromide reacts with t-butanol, the
product formed will be
CH2 , CH2 CH3 (a) Benzene (b) Phenol
CH
(c) (c) t-butyl benzene (d) t-butyl phenyl ether

4
42. Electrophile NO+2 attacks the following Exercise -2
CCl3 1. When the concentration of an alkyl halide is doubled and
the concentration of nucleophile is reduced to half, the rate
of SN1 increases by:
to give product:
CCl 3 (a) 3 times

NO 2 (b) 2 times
(a)
(c) 1.5 times

CCl 3
(d) 4 times

2. In SN1 reaction of an alkyl halide on chiral centres, there is:

(b) (a) 100 % racemization
NO 2 (b) Inversion more than retention leading to partial
CCl 3 racemization
(c) 100 % retention
(c)
(d) 100 % inversion

3. Ethylene glycol on reaction with PCl5 gives:

NO 2
(a) Ethylene dichloride
Cl2 C NO 2
(b) Ethyl chloride

(d) (c) 1, 1–Dichloroethane

(d) Oxirane
43. Which reagent can be used in the Friedel – Craft acylation
4. How many dichlorocyclohexane would be produced upon
reaction?
free radical chlorination of chlorocyclohexane?
(a) CH3COOCOCH3 (b) CH3COCl
(a) 4 (b) 6
(c) CH3CH2COCl (d) All of these
(c) 8 (d) 9
44. Nitration of chlorobenzene takes place at
5. Which of the following is SN2Ar reaction?
(a) o – Position (b) m –Position
Br
(c) p – Position (d) Both o– and p – positions Å
Å
(a) + Br +H
45. The antiseptic action of CHI3 is due to
(a) Iodoform itself
(b) Liberation of free iodine
(c) Partially due to iodine and partially due to CHI3 itself (b)
(d) None of the above
46. CCl4 is a well known fire extinguisher. However, after using
it to extinguish fire, the room should be well ventilated.
This is because
(a) It is inflammable at higher temperature.
(b) It is toxic. (c)
(c) It produces phosgene by reaction with water vapours at
high temperature.
(d) It is corrosive.
47. Aryl halides are less reactive towards nucleophilic
substitution reactions as compared to alkyl halides due to:
(a) The formation of less stable carbanion (d)
(b) Longer carbon halogen bond
(c) Inductive effect
(d) sp2–hybridized carbon attached to the halogen

5
6. Following are the curves for nucleophilic substitution 9. The oxidation of CHCl3 by air & light is prevented by adding
reaction: (a) CH3COOH
[T.S.]state
Transition
(b) C2H5OH
Potential energy (c) CH3CHO
(I) Reactant (d) CH3COOCH3
10. For the reaction CH3 CH(X) CH2 CH3
Product
alc.KOH

∆
→ CH3 – CH = CH – CH3 + CH2 = CH – CH2 – CH3
Reaction coordinate
[T.S.] state
Transition (a) CH3 – CH = CH – CH3 predominates.
(b) CH2 = CH – CH2 – CH3 predominates.
Potential energy

(c) Both are formed in equal amounts.

(II) Product (d) The product ratio depends upon the type of X.

Reactant 11. In the given pairs, which pair has the first compound more
reactive than second for SN1 reaction?
Reaction coordinate
Transition state-I
[T.S. I] (a) Cl CH2Cl
[T.S. II]state-II
Transition
Potential energy

(III)
Cl
(b)
Reactant
Product Cl
Reaction coordinate
(a) ‘I’ is potential energy diagram for SN2 reaction that takes
place with a negative potential energy change. (c) Cl Cl
(b) ‘II’ is potential energy diagram for SN2 reaction with a
positive potential energy change
(c) ‘III’ shows potential energy diagram for SN1 reaction Cl Cl
with large energy of activation for first (slowest) step
(d) All of the above
(d)
7. An optically active alkyl bromide X (C 6H 13Br) upon
treatment with ethanolic KOH solution forms two alkenes
Y and Z with their molecular formula (C6H12). Y and Z 12. Which of the following compound can not give SN1 reaction
are positional isomers. Z upon treatment with cold, dilute easily?
alkaline KMnO4 solution gives a meso-diol. Hence, X is Br
(a) 2-bromohexane Br
(b) 1-bromo-2,3-dimethyl butane
(c) 3-bromohexane (a) (b)
(d) 2-bromo-2,3-dimethyl butane
8. An organic compound X (C6H13Br) is optically active. X Br Br
on treatment with (CH3)3COK in (CH3)3COH gives Y
(C6H12), a major product. Y on treatment with Br2– CCl4 in
the presence of FeBr3 gives a dibromide which on further (c) (d)
treatment with NaNH2 gives C6H10 which is still optically
active. Hence, X and Y respectively are 13. Arrange these compounds in the order of increasing SN2
Br
(a) reaction rate:
and
O
Br
—

(b) and
—

—
—
—

Br Cl Br Cl Br
(c) and (I) (II) (III) (IV)
Br (a) III < I < II < IV (b) III < II < I <IV
(d) and (c) IV < III <I < II (d) III < IV < I < II

6
14. Which reactant reacts faster with NaI in DMSO? 19. Arrange the following compounds in the order of decreasing
CH2Cl rate of hydrolysis for SN1 reaction.
Cl
(I) —CH2—Br
(a) CH3 (b)

Cl CH2Cl (II) H3C— —CH2—Br

(c) (d)
(III) CH3—CH2— —CH2—Br

15. Rate of SN2 will be negligible in CH3

—
Br Br (IV) CH— —CH2—Br

—
CH3
(a) (b)
(a) II > III > IV > I (b) IV > III > II > I
(c) III > IV > II > I (d) I > II > III > I
Br 20. Which of the following reaction is not expected to give a
Br
satisfactory yield of alkyl iodide?
(c) (d) (a) CH3CH2OH + KI + H3PO4 →
Heat
(b) CH3CH2OH + Pl3  →
acetone
Me (c) CH3CH2Br + Nal  →
— —

HBr
16. Me—C—CH2—OH  → Major product (d) CH3CH2COOAg + I2  CCl4
heat
→
Me 21. Treatment of ammonia with excess ethyl chloride will give
The major product is: (a) Diethylamine
(b) Ethane
Me
Me (c) Methylamine
— —

Me
(a) C=C (b) Me—C—CH2—Br (d) Tetraethyl ammonium chloride
Me H 22. In the Hunsdiecker reaction, the compound
Me
Br Me—CH—CH—Me CH3
— —

(c) Me—C—CH —Me (d)

—

CH3—C—COOAg is heated with:

2
Me Me
Me
17. The reaction of SOCl2 on alkanols to form alkyl chlorides CH3
gives good yield because (a) CH3Br (b) Br2 in CCl4
(a) Alkyl chlorides are immiscible with SOCl2. (c) CH3Br + AgF (d) NaI + AgBr
(b) The other products of the reaction are gaseous and 23. In SN2 reaction, if we double the concentration of reactant
escape from reaction mixture.
(c) Alcohol and SOCl2 are soluble in water. and nucleophile both, the rate of SN2 reaction increases by:
(d) The reaction does not occur via intermediate formation (a) 2 times (b) 4 times
of an alkyl chloro sulphite. (c) 8 times (d) No change
18. Which compound undergoes hydrolysis by SN1 mechanism CH3
at the fastest rate? PCl5
24. H OH X
CH3 CH3 Br
C2H5
(a) (b) (S-2- Butanol)
Br
The product (X) is:
CH3 Br CH3 (a) S-2-Chlorobutane
(b) R-2-Chlorobutane
(c) (d) (c) Mixture of R and S-2-Chlorobutane
Br (d) 1-Chlorobutane

7
25. Which of the following compounds will show faster NO2
bimolecular SNAr reaction?
F Cl I
Br 29. EtONa(1 mol)
D

(a) (b) (c) (d) Cl

Cl

The product is
NO2 NO2 NO2 NO2 NO2 NO2
OH OH Cl
26. HBr
(A),
HBr
(B)
(a) (b)
D D
Cl
CH2OH OCH3
OEt OEt
The products (A) and (B) are respectively
NO2 NO2
OH OH

(a) &

(c) EtO (d) OEt

CH2Br OH Cl
OH OH Cl Cl

(b)
& 30. Ease of ionization to produce carbocation and bromide ion
under the treatment of Ag⊕ will be maximum in:
CH2Br Br O
OH Br
(a) (b)
&
(c)

Br
Br Br
CH2Br
Br Br

(d)
& (c) (d)

CH2Br OCH3
Br Br
27. Identify the reactants (X) and (Y) for the following reaction,
Cl
respectively.
(X) +(Y) NaNH 2
→ 4– Decyne 31.
2SbCl5
P
Alkyl halide Alkyne Cl
(a) CH3(CH2)4CH2 – Cl + CH3 – C ≡ CH The product P will be:
(b) CH3(CH2)2CH2 – Cl + CH3 – (CH2)2 – C ≡ CH
(c) CH3(CH2)2CH2 – Cl + CH3 (CH2)3 – C ≡ CH
(d) CH3– CH2– CH2 –Cl + CH3 (CH2)4 – C ≡ CH (a) 2– (b) 2+ 2SbCl6–
28. Which of the following compound give fastest SN2Ar
reaction?
Cl Cl
(c) (d) Ṃixture of (a) & (b)
NO2
(a) (b)
32. Which of the following reagent is best when Friedel-craft
NO2 Alkylation takes place?
Cl Cl (a) HO–
(c)
NO2 NO2
(d) (b) AlCl3 (anhyd.)
(c) AlCl3 (hydrated)
(d) All of these
NO2 NO2

8
 33. Give the order of decreasing reactivity towards an 38. Which one of the following compound is most reactive
electrophile. towards SN2 displacement?
CHCl2 CHF2 CH3 CH2Cl
(a) CH3CH2CH2CH2—Cl
(b) (CH)3C—Cl
, , , (c) (CH3)2CH—CH—CH3

(1) (2) (3) (4) Cl

(a) 1 > 2 > 3 > 4 (b) 4 > 1 > 3 > 2 (d) (CH3)2CH—CH2—Cl
(c) 3 > 4 > 1 > 2 (d) 3 > 2 > 4 > 1 39. Which of the following compound will undergo E2 elimination
34. Which of the following organic chlorides will not give a readily?
Friedel-Craft alkylation product when heated with benzene Cl
and AlCl3? H2O
(a) (CH3)3C—Cl (a) C C2H5
(b) CH2 = CHCH2—Cl
(c) CH3CH2—Cl
(d) C6H5—Cl
35. Which of the following statement does not correctly OH
−

describe E1 reactions of alkyl halides (RX)? (b) (CH3)3C — Br 

DMF
→
(a) Rearrangement is possible. −

(b) Rate = k [Base] [RX] (c) CH3CH(F)CH2CH3 →

OH

(c) Rate = k [RX] Br –

(d) The reaction occurs in two or more distinct steps. (d) C2H5O

36. Which of the following alkyl halide is most reactive towards CH3
reaction with CH3 –OH?
40. Select the correct one among the following statements:
CH2—Cl CH2—Cl
(a) Br will react less readily than
(a) (b) Br for E2 reaction.
(b) Cl will react more readily than Br
Cl CH3 for SN2 reaction.
CH2—Cl CH2—Cl
(c) Br will react more readily than
(c) (d)

CH2Br for SN2 reaction.

OCH3
37. The major product of following reaction is
(d) I will react more readily than I towards
SN2 reaction.
H 2O
Product
55°C
Br NH2
Br 41. NaNH2
liq.NH3
(a) (b)
OH The reaction is
OH
OH (a) ArSN1
OH (b) ArSN2
(c) Nucleophilic substitution via benzyne mechanism
(c) (d) (d) None of these

9
INTEGER TYPE QUESTIONS 44. The total number of alkenes possible by dehydrobromination
of 3-bromo-3-methylhexane using alcoholic KOH is
42. How many substances show rearrangement during SN1
reaction? 45. Rearrangement of carbon skeleton of substrate is possible
Br in how many of the following reactions?
EAS (Electrophilic aromatic substitution), electrophilic
Br addition on alkenes, free radical substitution of alkanes,
Cl SN1, SN2, E1, E2, E1cB, SN2Ar
46. How many different isomers of alkenes (including
(a) (b) (c) stereoisomers) upon catalytic hydrogenation adds one mole
of H2 to give the same product 2, 2, 3, 5-tertramethyl hexane?
Br
47. If 3-bromo-4-methyl hexane is treated with ethanolic KOH
solution, how many different alkenes would be formed?
Cl
CH3 48. Consider the following reaction.
(d) (e)
H2O2
+ HBr(excess)

How many different products would be formed?

49. Consider the following reaction and the major product.
(f) (g) (h)
+ HCl
Cl
If energy profile of the above reaction is drawn, how many
transition states would be observed?
Br
50. If a racemic mixture of 3-methyl-1-pentene is treated with
(i)
HCl, how many different chloropentane (important products
43. Among the following, X is the number of electrophiles and only) would be formed?
Y is the number of nucleophiles. Report your answer as
X Y .
(i) CH 3⊕ (ii) I –
(iii) NO⊕2 (iv) CH3

(v) NH

3
(vi) Br⊕

(vii) Cl (viii) H+
(ix) AlCl3 (x) CH3OH
⊕
(xi) CH 3 − C =O (xii) BH3

10
 Exercise-3 7.
SINGLE CORRECT TYPE QUESTIONS H2 /Catalytic Reduction
(A) (P)
1. During debromination of meso-2,3-dibromobutane,
with Zn dust/CH3COOH the major compound formed (a)
is
(a) n-butane (b) 1-butene
(b)
(c) cis-2-butene (d) trans-2-butene

2. Benzyl chloride (C6H5CH2Cl) can be prepared from

toluene by chlorination with
(a) SO2Cl2 (b) SOCl2 (c)
(c) PCl5 (d) NaOCl

3. A solution of (+) 2-chloro-2-phenylethane in toluene (d) NO2

racemises slowly in the presence of small amount of
SbCl5 due to the formation of
(a) Carbanion (b) Carbene 8. The reagent (s) for the following conversion:
(c) Free-radical (d) Carbocation
HC  CH is

4. An S reaction at an asymmetric carbon of a (a) alcoholic KOH

N2
compound always gives : (b) Alcoholic KOH followed by NaNH2
(c) aquesous KOH followed by NaNH2
(a) an enantiomer of the substrate
(d) Zn/CH3OH
(b) a product with opposite optical rotation
9. The following compound on hydrolysis in aqueous
(c) a mixture of diastereomers
acetone will give:
(d) a single stereoisomer

5. The number of isomer for the compound with

molecular formula C2BrCl FI is -
(a) 3 (b) 4
(c) 5 (d) 6

6. Identify the set of reagents/reaction conditions 'X' and

'Y' in the following set of transformations

(a) X = dilute aqueous NaOH, 20°C, Y= HBr/acetic

acid, 20°C
(b) X = concentrated alcoholic NaOH, 80°C; Y =
HBr/acetic acid, 20°
(c) X = dilute aqueous NaOH 20°, Y = Br2/CHCl3,
0°C
(d) X = concentrated alcoholic NaOH, 80°C; Y = It mainly gives
(a) K and L only (b) K only
Br2/CHCl3, 0°C
(c) L and M only (d) M only

11
10. The major product of the following reaction is (c)

PhSNa
⎯⎯⎯⎯⎯⎯⎯
dim ethylformamide
→ (d)

14. The product formed in the reaction

is :
(a) (b)

(a) (b)

(c) (d)
(c) (d)

15. The reaction

HBr
11. In the reaction ⎯⎯⎯
→ the Proceeds by the mechanism
(a) S 1 (b) S
N N2
product are
(c) S (d) S
Ni E2
(a) and H2
16. Which one of the following compounds most readily
undergoes substitution by SN2 mechanism?
(b) and CH3Br

(a)
(c) and CH3OH

(b)
(d) and CH3Br

(c)
12. If an alkyl halide CH3CH2CH2X goes for
dehydrohalogenation followed by addition of HX
will lead to formation of
(a) Same alkyl halide (d)
(b) Different Compounds
(c) An isomer
(d) An hydrocarbon 17. For the reaction

13. Which one of the following compounds most readily

undergoes substitution by SN2 mechanism?
(a) predominates
(b) predominates
(a) (c) Both are formed in equal amounts
(b) CH3CH2Cl (d) The product ratio depends on the halogen

12
 21. A compound 'A' formula of C3H6Cl2 on reaction with
18. The correct reactivity order of alcohols towards H–X alkali can give 'B' of formula C3H6O or 'C' of formula
will be C3H4. 'B' on oxidation gave a compound of the
(I) CH2 = CH – OH formula C3H6O2. 'C' with dilute H2SO4 containing
Hg2+ ion gave 'D' of formula C3H6O, which with
(II) bromine and alkali gave the sodium salt of C2H4O2.
Then 'A' is
(a) CH3CH2CHCl2
(III) CH3 – CH2 – OH
(b) CH3CCl2CH3
(Iv) CH3 – CH– CH3 (c) CH2ClCH2CH2Cl

OH (d) CH3CHClCH2Cl
(a) II > I > III > IV (b) IV > III > II > I
(c) II > IV > I > III (d) II > IV > III > I 22. Isobutyl magnesium bromide with dry ether and
absolute alcohol gives
19. Identify ‘Z’ in the following reaction series, (a) CH3 ⎯ CH ⎯ CH2 and CH3CH2MgBr

CH3.CH2CH2Br CH3
aq.NaOH Al O HOCl
⎯⎯⎯⎯→ (X) ⎯⎯⎯
2 3
⎯→ (Y) ⎯⎯⎯→ (Z) : (b) CH3 ⎯ CH ⎯ CH 2 ⎯ CH 2CH3 and
(a) Mixture of CH3 ⎯ CH ⎯ C 2 
  CH3
Cl OH
Mg (OH) Br
and CH 3 ⎯ CH ⎯ CH 2 (c) CH3 ⎯ CH ⎯ CH3 ,
| |
OH OH 
CH3
(b) CH3 ⎯ CH ⎯ C 2
  CH2 = CH2 and Mg(OH)Br
OH Cl (d) CH3 ⎯ CH ⎯ CH3 and CH3CH2OMgBr
(c) CH3 ⎯ CH ⎯ C 2 
  CH3
Cl OH
(d) CH3 ⎯ CH ⎯ C 2
  23. Following reaction is
Cl Cl

20. Which of the following undergoes hydrolysis most

easily
(a) E1 (b) S
N1
(a) (c) E2 (d) S
N2

24. Consider the following anions,

(b) O O
 
CF3 − S − O − C6 H 5 − S − O −
 
O O
(c) (I)
(II)

O

CH3 − C − O −
(d)
(IV)

13
 When attached to sp3– hybridized carbon, their (i) How many compounds give SN2 reaction on
leaving group ability in nucleophilic substitution treatment with NaSH?
reactions decreases in the order (ii) How many compounds give E2 reaction on
(a) I > II > III > IV treatment with alcoholic KOH?
(b) I > II > IV > III (iii) How many compounds do not react under either
(c) IV > I > II > III of the previous reaction conditions?
(d) IV > III > II > I
29. How many substrates will show rearrangement during
INTEGER TYPE QUESTIONS SN1 reaction?
25. O 3° Alcohol.
||
(1) 'Y 'RMgX
Cl — C — OC2 H5 ⎯⎯⎯⎯⎯→
NH Cl 4
Find out value of ‘Y’ ______.

26. Find out number of possible E1 products from

following reaction.

30. Find out number of reactions those proceed with

27. Identify number of substrate those can given SN1 and
retention of configuration.
SN2 reaction both.

(i)

(ii)

(ii)

28. Examine the ten structures shown below and select (iv)
those that satisfy each of the following condition.

(a) (b)

(c) (d) CH3 — I

(e) (f)

(g) (h)

(i) (j)

14
 Exercise -4 (a) (A) - (II), (B) - (I), (C) - (III), (D) - (IV)
(b) (A) - (III), (B) - (II), (C) - (IV), (D) - (I)
Classification & Nomenclature of (c) (A) - (IV), (B) - (II), (C) - (III), (D) - (I)
Haloalkanes and Haloarenes (d) (A) - (II), (B) - (I), (C) - (IV), (D) - (III)

1. Maximum number of isomeric monochloro derivatives 5. In the following given reaction ‘A’ is
which can be obtained from 2,2,5,5tetramethylhexane by CH3
chlorination is ___________. [24 Jan, 2023 (Shift-II)]
C CH2
2. The IUPAC name of ethylidene chloride is:
 [25 June, 2022 (Shift-I)] + HBr ‘A’
major
(a) 1-Chloroethene (b) 1-Chloroethyne
product
(c) 1,2-Dichlorethane (d) 1,1,-Dichlorethane
3. What is the IUPAC name of the following compound? [24 Jan, 2023 (Shift-I)]
CH3 1 (a) CH3
CH 3 Br
2 3 H
H 4
CH3 5 Br
[10 Jan, 2019 (Shift-II)] CH3
(b) Br
(a) 3-Bromo-1,2-dimethylbut -1-ene
(b) 3-Bromo-3-methyl-1,2-dimethylprop-1-ene
(c) 2-Bromo-3-methylpent-3-ene CH3
(c) Br
(d) 4-Bromo-3-methylpent-2-ene
CH3
Me thod s o f P rep a rat io n of
(d) CH3 CH3
Ha lo al kanes a n d H a lo a re n es Br
4. Match List-I with List-II
List-I List-II
6. Choose the correct statement regarding the formation of
carbocations A and B given.[17 March, 2021 (Shift-II)]
(A) (I) Fittig reaction ⊕
H3C–CH2–CH2–CH2 + Br
‘A’

Cl H3C–CH2–CH=CH2 + HBr
Wurtz Fittig
(B) (II) ⊕
+2Na → reaction H3C–CH2–CH–CH3 + Br
‘B’

(a) Carbocation A is more stable and formed relatively

at slow rate
Finkelstein
(C) (III)
reaction (b) Carbocation B is more stable and formed relatively
at faster rate
(c) Carbocation B is more stable and formed relatively
Sandmeyer at slow rate
(D) C2H5Cl + NaI → C2H5I + NaCl (IV)
reaction
(d) Carbocation A is more stable and formed relatively
[30 Jan, 2023 (Shift-I)] at faster rate

15
 7. Excess of isobutane on reaction with Br2 in presence of hydrolysis increases.
light at 125°C gives which one of the following, as the Reason (R): I– is a good nucleophile as well as a good
major product? [26 Aug, 2021 (Shift-I)] leaving group.
In the light of the above statements, choose the correct
CH3 answer from the options given below.

(a) CH3 – CH – CH2Br (b) CH3 – CH – Br [24 Jan, 2023 (Shift-I)]

(a) (A) is false but (R) is true.
CH2Br CH3 (b) (A) is true but (R) is false.
Br (c) Both (A) and (R) are true and (R) is the correct
explanation of (A).
(c) CH3 – CH – CH2Br (d) CH3 – C – CH2 – Br (d) Both (A) and (R) are true but (R) is NOT the correct
explanation of (A).
CH3 CH3
11. Decreasing order towards SN1 reaction for the following
Physical and Chemical Properties of compounds is:
Haloalkanes and Haloarenes Cl Cl Cl Cl

——

——

——
——
8. The graph which represents the following reaction is:

( C6 H5 )3 C − Cl  → ( C6 H 5 )3 C − OH
−
OH
Pyridine

[1 Feb, 2023 (Shift-II)]

—
—

—
NO2 OMe Cl
(a) (b) (c) (d)

(a) (b) [30 Jan, 2023 (Shift-II)]

(a) (a) > (c) > (d) > (b) (b) (a) > (b) > (c) > (d)
(c) (b) > (d) > (c) > (a) (d) (d) > (b) > (c) > (a)
12. Choose the halogen which is most reactive towards SN1
reaction in the given compounds(A, B, C & D)
 [8 April, 2023 (Shift-I)]
(c) (d) Br(a)
—

A.

9. The compound which will have the lowest rate towards Br(b)
nucleophilic aromatic substitution on treatment with OH– B. I(a) I(b)
is [25 Jan, 2023 (Shift-I)]
(a) (b)
C.
—

—Br(b)
—

Br(a)
Me
Br(b)
D.
Br(a)
(c) (d)
(a) A-Br(b) ; B-I(b) ; C-Br(b) ; D-Br(b)
(b) A-Br(a) ; B-I(a) ; C-Br(b) ; D-Br(a)
(c) A-Br(b) ; B-I(a) ; C-Br(a) ; D-Br(a)
10. Assertion (A): Hydrolysis of an alkyl chloride is a
slow reaction but in the presence of NaI, the rate of the (d) A-Br(b) ; B-I(a) ; C-Br(a) ; D-Br(a)

16
 13. Consider the following reaction that goes from A to B in 16. Identify the correct order for the given property for
three steps as shown below: [6 April, 2023 (Shift-II)] following compounds [29 Jan, 2023 (Shift-I)]

(A) Boiling Point: Cl < Cl < Cl

(B) Density: Br < Cl < I

Energy A
Step Step Step B Br Br
Br
I II III
(C) Boiling Point: Br < Br < Br
Reaction Coordinate
(D) Density: I< Br < Cl
Choose the correct
Number of Number of Rate Br Br
intermediates Activated determining
(E) Boiling Point: Cl > Cl
complexes step Cl >
(a) 3 2 II Choose the correct answer from the option given below:
(b) 2 3 II (a) ( B), (C) and (D) only (b) (A), (C) and (E) only
(c) 2 3 I (c) ( A), (C) and (D) only (d) (A), (B) and (E) only
(d) 2 3 III 17. Compound from the following that will not produce
precipitate on reaction with AgNO3 is:
Cl Nu Nu  [11 April, 2023 (Shift-II)]
14. (I)
MeO OMe
Br
(a)
Cl Nu Nu
(II)
Br
O2N O2N (b)
Where Nu = Nucleophile
Find out the correct statement from the options given
below for the above 2 reactions. (c) Br
 [11 April, 2023 (Shift-I)]
(a) Reaction (I) is of 2nd order and reaction (II) is of 1st
order (d) CH=CH–CH2–Br
(b) Reaction (I) and (II) both are of 2nd order
(c) Reaction (I) is of 1st order and reaction (II) is of 2nd 18. The correct order of reactivity of following haloarenes
order towards nucleophilic substitution with aqueous NaOH is:
(d) Reactions (I) and (II) both are of 1st order  [8 April, 2023 (Shift-II)]
15. 2-Methyl propyl bromide reacts with C2H5O– and gives Cl Cl
‘A’ whereas on reaction with C2H5OH it gives ‘B’. The (A) (B)
mechanism followed in these reactions and the products NO2
‘A’ and ‘B’ respectively are: [13 April, 2023 (Shift-I)] NO2
(a) SN2. A = iso-butyl ethyl ether; SN1, B = tert-butyl Cl Cl
ethyl ether (C) (D)
(b) SN1, A = tert-butyl ethyl ether; SN1, B = 2-butyl ethyl
ether OMe O2N NO2
(c) SN1, A = tert-butyl ethyl ether; SN2, B = isobutyl ethyl Choose the correct answer from the options given below:
ether
(a) A > B > D > C (b) C > A > D > B
(d) SN2, A = 2-butyl ethyl ether; SN2, B = Isobutyl ethyl
(c) D > C > B > A (d) D > B > A > C
ether

17
 19. Match List-I with List-II 22. For the reaction:
1-Bromopropane is reacted with reagents in List-I to give
product in List-II The correct statement is :

List-I - Reagent List-II - Product [6 April, 2023 (Shift-I)]

(a) The transition state formed in the above reaction is
(A) KOH (alc) (I) Nitrile
less polar than the localised anion.
(B) KCN (alc) (II) Ester
(b) The reaction can occur in acetic acid also.
(C) AgNO2 (III) Alkene
(c) The solvent used in the reaction solvates the ions
(D) H3CCOOAg (IV) Nitroalkane formed in rate determining step.
[13 April, 2023 (Shift-II)] (d) Br– can act as competing nucleophile.

(a) (A) - (IV), (B) - (III), (C) - (II), (D) - (I) 23. Identify the correct order of reactivity for the following
pairs towards the respective mechanism
(b) (A) - (III), (B) - (I), (C) - (IV), (D) - (II)
[10 April, 2023 (Shift-I)]
(c) (A) - (I), (B) - (II), (C) - (III), (D) - (IV)

(d) (A) - (I), (B) - (III), (C) - (IV), (D) - (II) Br

(A) Br
>
S N2
20. The major product formed in the Friedel-Craft acylation
of chlorobenzene is . [15 April, 2023 (Shift-I)]
Br
Br
(B) SN1 >
(a) (b)

Cl Cl

(C) Electrophilic substitution >

NO2
(c) (d)
Br
Br
(D) Nucleophilic substitution >
Chlorine is ortho/para directing, para is major.

21. The isomeric deuterated bromide with molecular formula NO2

C4H8DBr having two chiral carbon atoms is
Choose the correct answer from the options given below:
[25 Jan, 2023 (Shift-II)]
(a) 2-Bromo-1-deuterobutane (a) (A), (B) and (D) only
(b) 2-Bromo-2-deuterobutane (b) (A), (B), (C) and (D)
(c) 2-Bromo-3-deuterobutane (c) (A), (C) and (D) only
(d) 2-Bromo-1-deutero-2-methylpropane (d) (B), (C) and (D) only

18
 24. Number of moles of AgCl formed in the following reaction 28. Which one of the following compounds is inactive towards
is ________. [24 Jan, 2023 (Shift-I)]
SN1 reaction? [28 June, 2022 (Shift-I)]
Cl
Cl H3C
Cl AgNO3 C Cl
O * * (A) + X AgCl  (a) H C
3
H CH3
Cl
(b) Cl
25. Considering the below reactions, the compound ‘A’ and
compound ‘B’, respectively are: [29 July, 2022 (Shift-I)]
AgCN NaCN
‘A’ Cl ‘B’
(Major Product) C2H5OH–H2O C2H5OH–H2O (Major Product)
(c)
(a)
Cl
(b)
H3C
(c) C Cl
(d)
(d) H
26. Compound ‘A’ undergoes following sequence of
reactions to give compound ‘B’. The correct structure
(i) Cl2 , ∆
and chirality of compound ‘B’ is [where Et is – C2H5] 29. (A) 
(ii) CN −
→ 4-Bromophenyl acetic acid.
(iii)H 2 O/ H +
[29 July, 2022 (Shift-II)]
In the above reaction (A) is [28 June, 2022 (Shift-II)]
Br
(i) Mg, Et 2 O
B —
Br (ii) D2 O
(a)
Compound ‘A’
—

CH2CH3
(a) , Achiral
D Br
—

(b) (b)
, chiral
OD

—CH3
(c) chiral (c)
,
D
Br —
OD —
CH=CH2
(d) (d)
, Achiral
Br —
27. The major product in the reaction,
CH3 CH3 30. Two isomers (A) and (B) with molar mass 184 g/mol and
— —

— —

+ – elemental composition C, 52.2%; H, 4.9% and Br 42.9%

CH3—C—Cl + K O—C—CH3
? is gave benzoic acid and p-bromobenzoic acid, respectively
CH3 CH3 on oxidation with KMnO4. Isomer ‘A’ is optically active
and gives a pale yellow precipitate when warmed with
[25 June, 2022 (Shift-I)]
alcoholic AgNO3. Isomer ‘A’ and ‘B’ are, respectively
(a) t-Butyl ethyl ether (b) 2, 2 -Dimethylbutane [29 June, 2022 (Shift-II)]
(c) 2-Methylpent-1-ene (d) 2-Methylprop-1-ene

19
 CH2Br OCH3
CH3
(a) H3C—CHBr—C6H5 and
(c) O
CH2CH3
CH2Br C–NH2
CH3
(b) and

Br
CH2CH3
(d)

(c) H3C—CHBr—C6H5 and

Br
CH2CH3 32. In the given reaction,

(d) and H3C—CHBr—C6H5

(i) 2Mg, THF

(ii) Methyl benzoate
+
(iii) H2O/H

Br
‘A’ can be [25 June, 2022 (Shift-II)]

A
(a) Benzyl bromide
31.
Major Product (b) Bromobenzene
(c) Cyclohexyl bromide
(d) Methyl bromide
The major product of the above reaction is
Cl
[24 June, 2022 (Shift-I)]
OCH3
33. NaOH
P
H2O (Major Product)

Consider the above reaction, the number of p electrons

(a) present in the product ‘P’ is _____.
NH2 [24 June, 2022 (Shift-II)]
34. Given below are two statements:
Statement I: C2H5OH and AgCN both can generate
nucleophile.
Statement II: KCN and AgCN both will generate nitrile
nucleophile with all reaction conditions.
Choose the most appropriate option:
(b) [18 March, 2021 (Shift-II)]
(a) Both statement I and statement II are false.
(b) Statement I is false but statement II is true.
(c) Both statement I and statement II are true.
(d) Statement I is true but statement II is false.

20
35. Match List-I with List-II; 37. The correct order of reactivity of the given chlorides with
List-I List-II acetate in acetic acid is: [31 Aug, 2021 (Shift-I)]

(A) Cl (I) Wurtz CH3

+ –
N2Cl reaction
Cu2Cl2
+ N2
Cl Cl Cl CH3
(a) > >
(B) Cl (II) Sandmeyer
+ –
N2Cl reaction CH2Cl
Cu,HCl
CH3
+ N2
>

(C) Ether (III) Fittig

2CH3CH2Cl + 2Na  → CH3
C2H5–C2H5 + 2NaCl reaction
Cl Cl CH2Cl
(D) Ether (IV) Gatterman
2C6H5Cl + 2Na  → (b) > >
C6H5–C6H5 + 2NaCl reaction
[26 Feb, 2021 (Shift-II)]
Choose the correct answer from the option given below: CH3 CH3
Cl
(a) (A) - (II), (B) - (I), (C) - (IV), (D) - (III) >
(b) (A) - (III), (B) - (IV), (C) - (I), (D) - (II)
(c) (A) - (II), (B) - (IV), (C) - (I), (D) - (III)
(d) (A) - (III), (B) - (I), (C) - (IV), (D) - (II) Cl CH2Cl
36. What is A in the following reaction? (c) >
O
CH3

NK CH3 CH3 Cl
(i) Cl
> >
CH 2Br
O
A
(Major Product)
(ii) OH / H2O
CH3
[27 July, 2021 (Shift-II)]
CH2Cl Cl Cl
CH2 NH2
(a) (d) > >

O
CH3
NH CH2
(b) Cl CH3
>
O

(c) 38. The product formed in the first step of the reaction of
NH
Br

O CH – CH2 – CH – CH2 – CH3 – CH3 with excess Mg/Et2O

CH2 OH (Et = C2H5) is:
Br
(d) [24 Feb, 2021 (Shift-I)]

21
 (a) H3C – CH – CH – CH2 – CH – CH3 Cl Cl CH3 Cl

H3C – CH – CH2 – CH – CH2 – CH3 NO2 O2N NO2

CH2
(b) CH3 – CH
CH – CH3
NO2 NO2 NO2
(c) CH3 – CH2 – CH – CH2 – CH – CH3 (i) (ii) (iii) (iv)
(a) (iv) < (i) < (iii) < (ii)
CH3 – CH2 – CH – CH2 – CH – CH3
(b) (iv) < (iii) < (ii) < (i)
MgBr (c) (i) < (ii) < (iii) < (iv)
(d) CH3CH2 – CH – CH2 – CH – CH3 (d) (iv) < (i) < (ii) < (iii)
42. The correct decreasing order of densities of the following
MgBr
compounds is:
39. Presence of which reagent will affect the reversibility
of the following reaction, and change it to a irreversible Cl
reaction: (a) (b)
hv
CH + I 
 CH 3 I + HI
4 2 Reversible [27 July, 2021 (Shift-I)]
(a) HOCl
(b) Liquid NH3
Cl Br
(c) dilute HNO2
(d) Concentrated HIO3
40. What is the major product formed by HI on reaction with (c) (d)
H 3C CH Cl Cl
C CH2 ?
H 3C [25 July, 2021 (Shift-II)]
CH3  [24 Feb, 2021 (Shift-I)]
(a) (C) > (B) > (A) > (D) (b) (A) > (B) > (C) > (D)
CH3
(c) (D) > (C) > (B) > (A) (d) (C) > (D) > (A) > (B)
(a) CH3 – C – CH – CH3 43. The major product of the following reaction is
CH3 I CH3
CH3 Cl
NaOH
C2H5OH Major Product
(b) CH3 – C – CH – CH3

I CH3 [31 Aug, 2021 (Shift-II)]

(c) CH3 – CH – CH – CH2 – CH3 CH3

CH3 I CH3
CH3 (a) (b)
OH
(d) CH3 – C – CH – CH2I HO
CH3 H CH3
CH3
41. The correct order of the following compounds showing (c)
OH
(d)
increasing tendency towards nucleophilic substitution
reaction is: [24 Feb, 2021 (Shift-II)]

22
44. The major product (A) formed in the reaction given below 46. The major product in the following reaction is:
is [27 Aug, 2021 (Shift-II)] I
t-BuOH
CH3 CH2 CH CH2 Br Heat

CH3OH
+ CH3O → A [3 Sept, 2020 (Shift-II)]
(Major Product)
(a) (b)
CH3 CH2 CH CH2 OH
Ot-Bu
(c) (d)
(a)

47. The decreasing order of reactivity of the following organic

molecules towards AgNO3 solution is
CH3 CH2 CH CH2 OCH3
[4 Sept, 2020 (Shift-I)]
Cl
(b) Cl
(A) (B)

OMe
CH3 CH2 CH CH2Br (C) CH3CHCH3 (D) CH3CHCH2NO2

Cl Cl
(c) (a) (B) > (A) > (C) > (D) (b) (A) > (B) > (D) > (C)
(c) (A) > (B) > (C) > (D) (d) (C) > (D) > (A) > (B)
48. The mechanism of SN1 reaction is given as:
OCH3 –
– + – –
+ Y
CH3 CH2 C CH2 R–X → R X → R || X → R–Y + X
Ion pair Solvent
Separated ion
(d) pair

A student writes general characteristics based on the given

mechanism as: [3 Sept, 2020 (Shift-I)]
45. Consider the reaction sequence given below: (A) The reaction is favoured by weak nucleophiles.
(B) RÅ would be easily formed if the substituents are
bulky.
rate = k[t-BuBr]
(C) The reaction is accompanied by racemization.
(D) The reaction is favoured by non-polar solvents.
Which observations are correct?
(a) (B) and (D) (b) (A), (B) and (C)
Which of the following statements is true? (c) (A) and (C) (d) (A) and (B)
(a) Changing the concentration of base will have no 49. Among the following compounds, which one has the
effect on reaction (2) shortest C – Cl bond? [4 Sept, 2020 (Shift-II)]
(b) Changing the concentration of base will have no H3C Cl
effect on reaction (1) (a) H C Cl (b) CH
3
(c) Changing the base from OH to OR will have no CH3 CH2
effect on reaction (2)
HC Cl
(d) Doubling the concentration of base will double the (c) H3C – Cl (d)
rate of both the reactions [2 Sept, 2020 (Shift-II)] CH2

23
50. Which of the following compounds will form the Br Br

—
precipitate with aq. AgNO3 solution most readily?
[4 Sept, 2020 (Shift-II)] (a) OH
&
— O
N Br CH2Br
Br CH2Br

—
(a) O Br (b)
(b) OH
&
—
CH2Br O
OCH3
Br OH OH
N Br

—
(c)
N
(d) (c) Br
& —
—
CH2Br

51. In Carius method of estimation of halogen, 0.172 g of an OH OH

—
organic compound showed presence of 0.08 g of bromine.
Which of these is the correct structure of the compound? (d) Br
&
 [2 Sept, 2020 (Shift-I)] —
CH2Br
NH2 NH2
Br 54. The decreasing order or reactivity of the following
compounds towards nucleophilic substitution (SN2) is:
(a) (b)
CH2Cl

Br Br
(c) H3C—Br (d) H3C—CH2—Br
(I)
52. The major product obtained from E2–elimination of
3-bromo-2-fluoropentane is [2 Sept, 2020 (Shift-II)] CH2Cl
Br NO2

(a) CH3CH2—CH—CH = CH2 NO2

F (II)
CH2Cl
(b) CH3—CH = CH—CH— CH3
(c) CH3CH2CH = C — F

CH3 NO2
Br NO2
(III)
(d) CH3—CH2—C = CH— CH3 CH2Cl
53. In the following reaction sequence, structure of A and B
respectively will be
O 2N NO2
O
(IV)
HBr A Na (Intermolecular product)B
 Ether
[3 Sept, 2020 (Shift-II)]
—
CH2Br (a) (II) > (III) > (I) > (IV) (b) (III) > (II) > (IV) > (I)
[7 Jan, 2020 (Shift-II)] (c) (II) > (III) > (IV) > (1) (d) (IV) > (II) > (III) > (1)

24
55. For the following reactions, reaction is: [9 April, 2019 (Shift-I)]
Cl OMe Me CN

CH3  A    B C   D
(a) D < B < A < C (b) A < B < C < D
where,Z–= CH3CH2O–(A) or H3C—C—O– (B)
(c) D < A < C < B (d) B < C < A < D
CH3
59. Increasing order of reactivity of the following compounds
ks and ke are respectively, the rate constants for substitution for SN1 substitution is: [9 April, 2019 (Shift-II)]
ks
and elimination reactions and µ = , the correct option (A) CH2–Cl
ke
is _____. [7 Jan, 2020 (Shift-II)]
(a) mA > mB and ke (B) > ke (A)
(B) H3C Cl
(b) mA > mB and ke (A) > ke (B)
Cl
(c) mB > mA and ke (B) > ke (A)
(d) mB > mA and ke (A) > ke (B) (C) H3CO
56. Consider the following reactions, which of these Cl
reaction(s) will not produce Saytzeff product? (D)
cons. H 2 SO4
(a) (CH3)3CCH(OH)CH3  → (a) (B) < (C) < (D) < (A) (b) (A) < (B) < (D) < (C)
(b) (CH3)2CHCH(Br)CH3 
→ cons.KOH
(c) (B) < (A) < (D) < (C) (d) (B) < (C) < (A) < (D)
(CH ) O K ⊕
(c) (CH3)2CHCH(Br)CH3 
3 3
→ 60. The major product obtained in the given reaction is
CH3 O CH2 CH3
(d) (CH3)2C –CH2CHO  ∆
→ CH2 CH AlCl3
| Product
OH Cl
Which of these reaction(s) will not produce Saytzeff [10 April, 2019 (Shift-II)]
product? [7 Jan, 2020 (Shift-I)]
CH3 O CH CH3
(a) (b) and (d) (b) (c) only CH2 CH
(a)
(c) (a), (c) and (d) (d) (d) only
57. The decreasing order of reactivity towards dehydro­
CH3 O CH2
halogenation (E1) reaction of the following compounds is: CH2 CH = CH2
(b)
[8 Jan, 2020 (Shift-I)]
(A) Cl (B) Cl CH3 O

(c)
(C) (D)
Cl Cl CH3
(a) D > B > C > A (b) B > A > D > C CH3
(c) B > D > C > A (d) B > D > A > C
(d) CH3 O
58. The increasing order of reactivity of the following
compounds towards aromatic electrophilic substitution

25
61. Which one of the following is likely to give a precipitate 64. The major product of the following reaction is
with AgNO3 solution? [12 April, 2019 (Shift-II)]
(a) CH2 = CH – Cl
(b) CHCl3
(c) (CH3)3CCl
(d) CCl4

62. The major product of the following reaction is [12 Jan, 2019 (Shift-II)]
CH3
CH3CH2C=CH2
(1) Cl2/hv (a)
CO2CH2CH3
(2) H2O, 

Cl CO2CH2CH3
[8 April, 2019 (Shift-II)]
(b)
CH2OH CHCl2 CH3C=CHCH3

(a) (b)

Cl (c)
Cl

CO2H CHO

(c) (d)

(d)
Cl Cl

63. The major product ‘Y’ in the following reaction is:

Cl EtONa HBr 65. An ‘Assertion’ and a ‘Reason’ are given below. Choose
X Y
Heat
the correct answer from the following options:
[10 April, 2019 (Shift-II)] Assertion (A): Vinyl halides do not undergo nucleophilic
substitution easily.
(a) Reason (R): Even though the intermediate carbocation
Br is stabilized by loosely held p-electrons, the cleavage is
difficult because of strong bonding.
(b) HO [12 April, 2019 (Shift-II)]
(a) Both (A) and (R) are wrong statements.
Br (b) Both (A) and (R) are correct statements and (R) is the
(c)
correct explanation of (A).
(c) Both (A) and (R) are correct statements but (R) is not
(d) Br the correct explanation of (A).
(d) (A) is a correct statement but (R) is a wrong statement.

26
66. Which of the following potential energy (PE) diagrams O O
represents the SN1 reaction? [9 April, 2019 (Shift-II)]
(a) (b)

Br Br
(a) PE
O O
Progress of reaction (c) (d)

HO HO
69. Heating of 2-chloro-1-phenylbutane with EtOK/EtOH
(b)
PE gives X as the major product. Reaction of X with
Hg(OAc)2/H2O followed by NaBH4 gives Y as the major
Progress of reaction product. Y is [12 April, 2019 (Shift-II)]

(a) Ph
OH

(c) OH
PE
(b)
Ph
Progress of reaction
OH
(c)
Ph
(d)
PE
(d) Ph

Progress of reaction
70. Increasing rate of SN1 reaction in the following compounds is
67. The major product of the following reaction is I

CH3
CH3OH A.
CH3–C–CH CH3 →
H Br  [10 April, 2019 (Shift-I)] I
CH3 CH3 MeO
(a) CH3–C–CH2CH3 (b) CH3–C–CH=CH2 B.
OCH3 H
I
CH3 CH3
(c) CH3–C=CH CH3 (d) CH3–C–CH CH3
C.
H OCH3
68. The major product of the following reaction is: H3C
I

Br (1) KOH(aqueous) D.
(2) CrO3/H+
Br (3) H2SO4/D
H3CO
[10 April, 2019 (Shift-I)]
[9 Jan, 2019 (Shift-I)]
(a) (A) < (B) < (C) < (D) (b) (B) < (A) < (C) < (D)
(c) (B) < (A) < (D) < (C) (d) (A) < (B) < (D) < (C)

27
71. The major product of the following reaction is: [JEE Adv 2023]
(i) KOH alc. List-I List-II
CH3CH2CH—CH2
(ii) NaNH2
—

—
(P) (–)-1-Bromo-2-ethylpentane (I) Inversion of
Br Br in liq NH3
(single enantiomer) configuration
[12 Jan, 2019 (Shift-II)] aq. NaOH
SN2 reaction
(a) CH3CH=C=CH2
(Q) (–)-2-Bromopentane (single (II) Retention of
(b) CH3CH2CH—CH2 aq. NaOH
enantiomer) 2 reaction configuration
SN
—

NH2 NH2
(R) (–)-3-Bromo-3-methylhexane (III) Mixture of
(c) CH3CH=CHCH2NH2 (single enantiomer) enantiomers
aq. NaOH
(d) CH3CH2C≡CH SN1 reaction

72. In the following reactions, P, Q, R, and S are the major (S) (IV) Mixture of
products. [JEE Adv 2023] structural
Me H Me Br isomers
(Single enantiomer)
(i) Mg, dry ether
P aq. NaOH
(ii) H2O SN1 reaction

Cl (a) P → 1; Q → 2; R → 5; S → 3
(i) Mg, dry ether (b) P → 2; Q → 1; R → 3; S → 5
(ii) CO2, dry ehter (c) P → 1; Q → 2; R → 5; S → 4
Q
(iii) H3O
+
(d) P → 2; Q → 4; R → 3; S → 5
Cl
Polyhalogen Compounds
(i) Mg, dry ether
74. In the following halogenated organic compounds the one
(ii) CH3CHO, then H2O
R with maximum number of chlorine atoms in its structure
(iii) CrO3 is:  [31 Jan, 2023 (Shift-II)]
(a) Chloral
Cl
(b) Gammaxene
(i) ethanolic NaCN (c) Chloropicrin
(ii) H2/Ni (d) Freon -12
S
(iii) CHCl3/KOH,  75. Which of the following compounds is an example of
Cl
(iv) LiAlH4, then H2O Freon? [11 April, 2023 (Shift-II)]
(a) C2Cl2F2
The correct statement about P, Q, R, and S is
(b) C2HF3
(a) P is a primary alcohol with four carbons. (c) C2H2F2
(b) Q undergoes Kolbe’s electrolysis to give an eight- (d) C2F4
carbon product. 76. Which of the following is true about freons?
[24 Jan, 2023 (Shift-I)]
(c) R has six carbons and it undergoes Cannizzaro
(a) These are chlorofluorocarbon compounds
reaction.
(b) These are chemicals causing skin cancer
(d) S is a primary amine with six carbons.
(c) These are radicals of chlorine and chlorine monoxide
73. Match the reactions in List-I with the features of their
(d) All radicals are called freons
products in List-II and choose the correct option.

28
77. In the following reaction: OH

H 3C CH3
CH (b) , CH3COCH3
CCl3 OH
+ O2
OH

H 3C CH3
(c) , CH3COCH3
C O O H
H+
CCl3 H2O
A and B
OH
OH
[25 June, 2022 (Shift-I)] (d) , CH3COCH3
CH3

(a) , CH3COOH

29
 Answer Key (Manthan)

Exercise - 1
1. (d) 2. (d) 3. (c) 4. (a) 5. (a) 6. (c) 7. (c) 8. (a) 9. (a) 10. (d)
11. (b) 12. (a) 13. (c) 14. (d) 15. (a) 16. (a) 17. (d) 18. (a) 19. (a) 20. (a)
21. (c) 22. (d) 23. (b) 24. (c) 25. (d) 26. (d) 27. (c) 28. (b) 29. (a) 30. (b)
31. (c) 32. (a) 33. (b) 34. (b) 35. (b) 36. (d) 37. (a) 38. (a) 39. (a) 40. (a)
41. (a) 42. (b) 43. (d) 44. (d) 45. (b) 46. (c) 47. (d)

Exercise - 2
1. (b) 2. (b) 3. (a) 4. (d) 5. (c) 6. (d) 7. (c) 8. (d) 9. (b) 10. (d)
11. (c) 12. (c) 13. (a) 14. (b) 15. (c) 16. (c) 17. (b) 18. (b) 19. (a) 20. (d)
21. (d) 22. (b) 23. (b) 24. (b) 25. (a) 26. (a) 27. (d) 28. (c) 29. (a) 30. (b)
31. (b) 32. (b) 33. (c) 34. (d) 35. (b) 36. (d) 37. (b) 38. (a) 39. (d) 40. (d)
41. (c) 42. [6] 43. [75] 44. [5] 45. [3] 46. [7] 47. [6] 48. [3] 49. [3] 50. [5]

Exercise - 3
1. (c) 2. (a) 3. (d) 4. (d) 5. (d) 6. (b) 7. (b) 8. (b) 9. (a) 10. (a)
11. (d) 12. (c) 13. (b) 14. (b) 15. (b) 16. (b) 17. (d) 18. (d) 19. (b) 20. (d)
21. (a) 22. (d) 23. (d) 24. (b) 25. (3) 26. (3) 27. (6) 28. (i) 5; (ii) 5; (iii) 4 29. (6)
30. (4)

Exercise - 4
1. [3] 2. (d) 3. (d) 4. (d) 5. (d) 6. (b) 7. (b) 8. (c) 9. (d) 10. (c)
11. (c) 12. (b) 13. (b) 14. (c) 15. (a) 16. (b) 17. (a) 18. (d) 19. (b) 20. (a)
21. (c) 22. (a) 23. (b) 24. [2] 25. (c) 26. (c) 27. (d) 28. (c) 29. (c) 30. (c)
31. (d) 32. (b) 33. [2] 34. (d) 35. (c) 36. (a) 37. (a) 38. (d) 39. (d) 40. (b)
41. (c) 42. (c) 43. (d) 44. (d) 45. (b) 46. (d) 47. (a) 48. (b) 49. (b) 50. (c)
51. (a) 52. (c) 53. (d) 54. (b) 55. (a) 56. (b) 57. (a) 58. (c) 59. (c) 60. (c)
61. (c) 62. (d) 63. (c) 64. (b) 65. (d) 66. (d) 67. (a) 68. (a) 69. (c) 70. (b)
71. (d) 72. (b) 73. (b) 74. (b) 75. (a) 76. (a) 77. (c)

30