Lakshya JEE Advanced (2026)

ABHEDYA
Chemistry Haloalkanes & Haloarenes
Exercise -1 3. Select the correct statement for the given reaction.
Br
SINGLE CORRECT TYPE QUESTIONS Zn
CH3OH, D
Br
1. (a) The above reaction proceeds via a-elimination.
Major product. (b) It proceeds via b-elimination and the product is but-2-yne.
OH– (c) It proceeds via b-elimination and the product is but-2-ene.
(d) It proceeds by redox reaction.
The major product of the reaction is 4. Which is the correct reaction coordinate diagram for the
Ph following solvolysis reaction?
(a) (b) CH CH OH
3 3
Ph H 2O
CH3 CH3 +
Cl OH CH3
(c) H (d) H

Ph CH2 Ph

2. Which of the following reactions would give trans-alkene (a) (b)

as the main product?
Me Reaction coordinate Reaction coordinate

H Br
(I) NaI
Acetone
H Br
(c) (d)
Me
Meso-isomer Reaction coordinate Reaction coordinate
Me
5. Select incorrect statement amongst the following.
(II) H Br
NaI (a) SN1 reaction occurs in polar solvent.
Acetone
Br H Cl Cl

Me
() or racemate
(b) will react more readily than for SN1
Me

(III) H Br reaction.
NaI
Acetone
H Br
(c) H3CO— —CH2—Br will react more readily
Et
() or racemate
than HSO3 CH2Br for SN1 reaction.
Me
(IV) Br
H Br
Br
NaI
Acetone
Br H
(d) will react more readily than for SN1
··
Et
() or racemate N N
(a) (I) (b) (II) H
(c) (I), (III) (d) (II), (IV) reaction.

1
 6. Which of the following reactions does not take place by SN2
reaction? 10.

The major product of above reaction is obtained by which

(a) –
+ mechanism?
Na
(a) SN2 (b) E2 (c) E1cB (d) E1
O 11. Which of the following reaction will follow E1cB
(b) Cl NaI
elimination as major path?
Acetone
O Br
OTs (a) Alc.NaOH, D
NaI
(c) Acetone Br
(b) Alc.NaOH, D

O
(d) Br
NaI
O Acetone (c) CN Alc.NaOH, D

OTs Br Alc.NaOH, 
7. E1cB reaction is not possible in which of the following case? (d)
H
(a) C6H5—CH—CH3 Base

Br MULTIPLE CORRECT TYPE QUESTIONS

CN 12. Which of the following order of reactivity is/are correct for
the solvolysis in 50% aqueous ethanol.
(b) C6H5—CH—CH—CH3 Base
(a) Cl < Cl <
Å Cl
SR2
(c) O2N (b) Cl <
Cl

< Ph Cl
(d) Cl

—
(c) Cl < < Cl
Br Cl Br
8. SN1 reaction undergoes through a carbocation
—

< —
intermediate as follows: (d) <
H F
Slow+ −
R − X(aq.)  R (aq.) + X (aq.)
 13. + NaCN A (Major)
(1 mole)
H2O

fast
→ ROH(aq.) + H + (aq.) Br H
Major product of this reaction is
[R = t-Bu, iso – Pr, Et, Me] (X = Cl, Br, I) NC F H H
The correct statement(s) is/are: (a) (b)
I. The decreasing order of rate of SN1 reaction is t-BuX H H Br CN
> iso-PrX > MeX. H H H F
II. The decreasing order of ionisation energy is MeX > EtX (c) (d)
> t-BuX. F CN CN H
III. The decreasing order of energy of activation is t-BuX
14. SN1 & SN2 products are same in (excluding stereoisomers)
> EtX > MeX. Cl
(a) I & II are correct (b) I & III are correct
—

— —
(c) II & III are correct (d) I, II & III are correct (a) (b)
—
9. How many structural isomers with molecular formula Cl
—

C5H11Br yield only a single alkene on dehydrohalogenation

(c) (d) Ph—CH—CH—CH3
by alc. KOH?
—
—

(a) 3 (b) 2 CH3 Cl

—

(c) 4 (d) 5 Cl

2
 H H 20. When an organic compound is treated with AgNO3, a white
TsCl NaBr
15. Pyridine X Y. ppt is obtained, the compound may be
Cl
CH3 OH

X and Y are: (a)
H H H Br
(a) X = (b) Y = (b) CH3O— —CH2—Cl
CH3 OTs CH3 H
O
H H H
(c) —C—Cl
(c) X = (d) Y =
OTs CH3 Br
(d) CH3 – CH = CH – CH2 – Cl
16. Which of the following conditions are favourable for SN2
mechanism in an alkyl halide? Cl
(a) Strong nucleophile (b) High conc. of nucleophile 21. * NaOH, H2O
Product
395°C
(c) 3º alkyl halide (d) Polar protic solvent
17. A gem dichloride is formed in the reaction between
The product of the reaction is
(a) CH3CHO and PCl5 (b) CH3COCH3 and PCl5 * OH *
(c) CH2 = CH2 and Cl2 (d) CH2 = CHCl and HCl (a) (b)
18. Identify correct steps representing SN1 mechanism for the OH
cleavage of the following with HI.
Å * *
R – O – R' + HI R—O—R¢+I
(c) (d)
—

(a) CH3 CH3

(RDS)
22. CH3—C—CH2—Br C2H5OH
CH3—C—CH3 (major)
(b) (RDS) H OC2H5
Fast
(c) R + + I −   → RI Which is/are correct statement (s) about the given reaction?
(d) R + + I − 
slow (a) It is unimolecular nucleophilic substitution reaction.
(RDS)
→ R− I
(b) Major product is obtained by rearranged carbocation.
19. In which of the following reactions, aromatic product(s) is/
are formed? (c) It is a two step process.
Br (d) Rate of reaction depends on the concentration of alkyl
(a) 2AgBF4 halide and nucleophile.
Br 23. Which of the following is/are bimolecular nucleophilic
substitution?
CH3 O
2K (Metal)
(b) I NaOH
NaOH
CH3 (a) DMSO
(b) I
D

H Br
I
(c) AgBF4
HI
(c) NaOH
(d) OH
D

(d) t-
NO2

3
 24. Which of the following alkyl halides form a substitution 28. If Q is treated with HBr the product will be
product from SN1 reaction, that is different from SN2 reaction? (a) No reaction (b) ‘X’
CH3 Br (c) ‘P’ (d) An Isomer of P
29. The set of reagents (R) can be
(a) CH3—CH—CH—CH—CH3 (1) HCHO (2) H 2 O
(a)  →  →
CH3 (b) 
(1) CH3 MgBr (2) HCHO
→  (3) H 2 O
→ →
CH3 (c) 
(1) Mg / ether
 (2) CH3 CHO
→  (3) H 2 O
→ →

(b) CH3—CH2—C—CH—CH3 (d) 

(1) Mg / ether (2) (3) H 2 O
 → O
→

CH3 Br
CH3
30.
(c)
Cl
(d) All of these The product P in the above reaction is
H3 C
COMPREHENSION BASED QUESTIONS (a) C CH—Ph (b)
Comprehension (Q. 25 to 26): An organic compound ‘A’ with H3 C
molecular formula C5H9Br decolorises brown colour of bromine
water but does not rotate plane polarised light. ‘A’ on treatment (c) (d)
with HBr/ROOR forms C5H10Br2 which on further treatment with

NaOH (aq) gives the cyclic ether . MATCH THE COLUMN TYPE QUESTIONS
O 31. Match the Column–I (reaction) with Column–II
25. The starting compound ‘A’ is most likely to be (reaction intermediate) and select the correct answer using
Br the codes given below the lists.
(a) Br (b)
Column-I Column-II
(c) Br (d)
Br
26. Compound ‘A’ on treatment with HBr will produce
Alc. KOH / ∆
CF3—CHCl2 → CF2—CCl2 Transition
A. p.
state only
(a) An achiral dibromide.
(b) A racemic mixture. CH3
—

⊕
(c) A single pure enantiomer. H
→
B. CH3 — C — OH CH3 — C — CH2 q. Carbocation
(d) A meso dibromide.
—
—

CH3 CH3
Comprehension (Q. 27 to 30): Observe
aqueous acetone the following reactions
(Q)
and answer the questions. (2) alc.KOH
Br2 /hv
aqueous
(P) acetone C. CH3—CH2—Br  ∆
→ CH2—CH2 r. Carbanion
(1) (Q)
(2) (R)
Br2 /hv
(P)
(X) (1)
(R)
(X) CH2—CH2— OH
D. s. Free radical
27. The product Q is CH2—CH2— OH
aq.KOH / ∆
→ CH3 — C — CH2
—

(a) (b) CH3

OH (a) A → r; B → q; C → s; D → p
(c) (d) (b) A → q; B → r; C → q; D → p
OH
(c) A → r; B → q; C → p; D → q
(d) A → r; B → q; C → q; D → p

4
32. Match the following: INTEGER TYPE QUESTIONS
33. Which carbon atom will give fastest SN2 reaction in given
Column-I Column-II
compound?

COO
 (1)
CH3 CH 2 O
− H3N H
→ ∆
CH2

(2) CH2
A. p. E1
 (4)
(3) S H2C O OH
H3C
H H
H H

OH OH

34. Following compound when heated in ethanol, SN1 reaction

occur involving rearrangement of carbocation.
−
CH3 CH 2 O
→ Br
CH3 CH 2 OD
B. q. E2
C2H5OH
Heat SN1

In the major product, how many carbon atom are present in

the single largest ring?
moist Ag 2 O
 → 35. If trans-3-methylchlorocyclopentane is treated with KOH
solution, both SN2 and E2 occur simultaneously. How many
Br Ph total substitution and elimination products are formed in
C. r. E1cB
principle?

36. Consider the following reaction,

CH3
C2H5OH
CH3
Heat
O O Cl
alc.KOH
Br 
→
Br In principle, how many different alkenes are possible by the
above elimination reaction?
O
O
37. How many different dichlorides, including stereoisomers by
D. s. Ei Wurtz coupling reaction with etheral solution of sodium, can
give 1, 4-dimethyl cyclohexane?

38. How many different halides with molecular formula C7H15Cl

upon reduction with (C6H5)3SnH can give 2,4-dimethyl pentane?

39. Relative reactivity of secondary versus primary hydrogens in

free radical bromination of n-butane, if the ratio of 1-bromo
(a) A → s; B → q; C → p; D → r
to 2-bromobutane formed is 7 : 93 is x : 1. Find x.
(b) A → q; B → r; C → p; D → q
40. Rate law for substitution reaction of 2-bromobutane with OH −
(c) A → q; B → r; C → q; D → p in 75% ethanol and 25% water at 30°C is rate = 3.2 × 10–5
[2-bromobutane] [OH–] + 1.5 × 10–6 [2-bromobutane]. What
(d) A → p; B → q; C → r; D → s
percent of reaction take place by SN2 when [OH–]= 1M?

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 Exercise-2 5. Find the major product of the following reaction:

SINGLE CORRECT TYPE QUESTIONS

1. Arrange the following in decreasing order of SN2 reaction
CH3Cl CH3CH2Cl
(P) (Q)
(a) (b)

CH3CH2CH2Cl
(R) (S)
(a) P>Q>S>R
(b) P>Q>R>S (c) (d)
(c) S>R>Q>P
(d) S>Q>R>P
2. Arrange the following in decreasing order of SN1 reaction
MULTIPLE CORRECT TYPE QUESTIONS

1. Li Y 2, 7-dimethyloctane
6. 
2. CuI
→ X →

(a) S > R > Q > P (b) S > Q > R > P

(a)
(c) R > S > Q > P (d) P > Q > R > S
3. Consider the following sequence of reactions.

alc. KOH B H aq. KOH (b)

A → B 
2 6
→ C A 
∆
→C
C3H 6Cl2 H 2O 2 /OH
The compound A is: (c)

(a) (b) (d)

7. Which of the following halides undergo E2 elimination?

(c) (d)
(a)
4. Which of the following reactions is not feasible?

(a)
(b)

(b)

(c)
(c)

(d) (d)

6
 8. Point out the following incorrect Grignard synthesis: NUMERICAL ANSWER TYPE QUESTION

11. 3° Alcohol. Find

out value of ‘X’.
(a)

12. ,
(b)

(c)
Find out value of ‘X’.
13. Find out numbers of possible E1 products from for following
reaction.
(d)

9. Among the following pair of reactions in which pair second

reaction is more reactive than first for SN1 reaction?
(a) Me3C — Cl + H 2 O and Me3C — Br + H 2 O 14. How many substrate(s) will show rearrangements during
(b) Me3C — Cl + CH3OH and Me3C — Cl + H 2 O SN1 reaction
(c) Me3C — Cl + H 2 O and Me3C — Cl + H 2 O
(1M) (2M)

(d) Me3C — Cl + CH3SH and Me3C — Cl + CH3OH

, , ,
10. In which product formation takes place according to
Hofmann’s rule?

(a) ,

, ,

(b)

, ,
(c)

(d)

7
15. Find out number of reactions those proceed with retention of
configuration.
(e)

(a)

(f)

(b)

(g)

(c)

(h)
(d)

8
 Exercise -3 (Advanced/Olympiad) PASSAGE I
1. 0.450 gm of an aromatic organic compound (A) on ignition Rose oil is an essential oil obtained from the steam distillation
gives 0.905 gm of CO2 and 0.18 gm of H2O. 0.350 gm of plant material from roses. It contains a number of terpenes,
of (A) on boiling with HNO3 and adding AgNO3 solution one of which is geraniol, C10H18O (A). Upon oxidation, geraniol
gives 0.574 gm of AgCl. The vapour density of (A) is 87.5. can either give a ten-carbon aldehyde or a ten-carbon carboxylic
(A) on hydrolysis with Ca(OH)2 followed by reduction acid. Reaction with two moles of bromine gives a tetrabromide
with LiAlH4 gives compound (C). On heating (C) with (C10H18OBr4) (B). Geraniol reacts with HBr to give two bromides,
I2 and NaOH, iodoform is produced along with (D). With (C) and (D) of formula C10H17Br.
HCl, (D) gives a solid, which is more soluble in hot water When geraniol is vigorously oxidized, three products are obtained:
than in cold. Identify (A) to (D). Which of the following OH
is optically active? O O OH
(a) A (b) B HO O
(c) C (d) D O
O
2. An organic compound A has molecular formula C6H11Br. 4. Identify the structure of geraniol (A). How many –OH
A decolorizes brown colour of bromine water but it can’t
(alcoholic) groups are present in compound A?
be resolved into enantiomers. A on treatment with HBr
5. What is sum of locant positions in IUPAC name of geraniol
produces B(C6H12Br2) which is still non-resolvable. Also
(A).
A on treatment with HBr in presence of a peroxide (R2O2)
yields C-an isomer of B, but it is resolvable. B on heating 6. Identify the structure of compound B. How many total
with Zn-metal yields D(C6H12) which on treatment with substituents are present in structural formula of compound
ozone followed by hydrolysis of product in presence of B?
Zn-powder yield acetone as the only organic compound. 7. How many >C=C< double bonds are present in compounds
Also A on treatment with ethanolic KOH solution yields D?
E(C6H10) as only possible product. E on treatment with
8. Compounds C and D differ in position of
excess of HBr/R2O2 in cold produces isomeric F and G with (a) –CH3 (b) –Br (c) >C=C< (d) –OH
their molecular formula C6H12Br2, in which F is a meso
compound while G is resolvable. Also F on hydrolysis in
aqueous NaOH yield a diol C6H14O2 which on refluxing
PASSAGE II
with dilute H2SO4 yields the following compound (H). After passing 0.25 mol of hydrocarbon A over heated pumice
Identify structures of A to G. (950 K) in an iron pipe, compound B in yield of 80 % (i. e. 15.4 g)
and 2.4 dm3 of hydrogen, (295 K, 102 kPa) were obtained.
B and hydrogen are the only products. A mixture of chlorine
derivatives C, D, E, F and G is produced from B by reaction with
a chlorine in presence of a Lewis acid. Compounds C to G contain
each one halogen atom more than the preceding compound. For the
O
compounds C to F only one of the possible isomers is formed. In
(H) compound G there is no such preference and its three isomers G1,
How many compounds among (A), (B), (C), (D), (E), (F) G2 and G3 are found in the mixture: Compounds C to F racemize
& (H) are capable of stereo-isomerism? easily so that no optical isomerism occurs. However racemization
3. Upon treatment with Ag+ ions, an a-halo-ether undergo is difficult for G1, G2, and especially for G3.
substitution via SN-1 mechanism. Consider the following Information:
two reactants and explain why 1 produces a mixture of two - kortho > kpara in compound B.
possible stereoisomers while 2 provides only one. - Compounds D and F in one of their conformations have
a center of symmetry.
O O
9. Identify the structures of A, B, C, D, E, F, G1, G2 and G3.
O O Br How many chlorine atoms are present in one molecule of
Br
Ph Ph O G1?
(1) (2) 10. Explain the order of G1, G2, G3 according to their increasing
difficulty of racemization.

9
 Exercise -4 (PYQ's) 7. The following compound on hydrolysis in aqueous acetone
will give (2005, 1M)
1. What would be the major product in each of the following
reactions?

(2000, 2M)
2. The compound that will react most readily with NaOH to
form methanol is (2001, 1M)
(a) (CH3)4N+I– (b) CH3OCH3
(c) (CH3)3S+I– (d) (CH3)3Cl
3. An SN 2 reaction at an asymmetric carbon of a compound
always gives (2001)
(a) an enantiomer of the substrate
(b) a product with opposite optical rotation
(c) a mixture of diastereomers
(d) a single stereoisomer
4. Identify X, Y and Z in the following synthetic scheme and
write their structures
It mainly gives
(a) K and L
(b) only K
(c) L and M
(d) only M
(2002, 5M)
5. Identify the set of reagents/reaction conditions X and Y in 8. Match the following: (2006, 3M)
the following set of transformations– (2002, 3M)
Column-I Column -II

A CH 3 – CHBr – CD 3 on p E1 reaction
treatment with alc. KOH
(a) X = dilute aqueous NaOH, 20° C,Y = HBr/acetic acid, gives CH2 = CH – CD3 as
20°C a major product.
(b) X = concentrated alcoholic NaOH, 80°C, Y = HBr/acetic
acid, 20°C
B Ph – CHBr – CH3 reacts q E2 reaction
(c) X = dilute aqueous NaOH, 20°C, Y = Br2 /CHCl3, 0°C
faster than Ph – CHBr
(d) X = concentrated aqueous NaOH, 80°C, Y = Br2/CHCl3, – CD3
0°C
6. The product of following reaction is C Ph – CH2 – CH2 Br r E1 CB reaction
on treatment with
C 2H 5OD/C 2H 5O – gives
Ph – CD = CH 2 as the
major product.
(2003, 1M)

(a) C6H5OC2H5 D P h C H 2C H 2B r a n d s First order reaction

(b) C2H5OC2H5 PhCD2CH2 Br react with
same rate.
(c) C6H5OC6H5
(d) C6H5I

10
 9. The major product of the following reaction is (2008, 3M) 10. The total number of alkenes possible by dehydrobromination
of 3-bromo-3-cyclopentylhexane using alcoholic KOH is
(2011)
11. KI in acetone, undergoes SN 2 reaction with each P, Q, R
and S. The rates of the reaction vary as (2013 Adv.)

(a) (b)

(a) P>Q>R>S
(b) S>P>R>Q
(c) P>R>Q>S
(d) R>P>S>Q
(c) (d)

12. Match the chemical conversion in Column-I with the appropriate reagents in Column-II and select the correct answer using the
code given below the lists. (2013Adv.)
Column-I Column -II

P 1 (i) Hg(OAc)2; (ii) NaBH4

Q 2 NaOEt

R 3 Et-Br

S 4 (i) BH3; (ii) H2O2/NaOH

Codes
P Q R S
(a) 2 3 1 4
(b) 3 2 1 4
(c) 2 3 4 1
(d) 3 2 4 1

11
13. In the following monobromination reaction, the number of 16. In the following reaction, the major product is
possible chiral product(s) is (are)... (2014) (2015 Adv.)

14. The product of the reaction given below is (a) (b)
(2015 Adv.)

(c) (d)

17. For the following compounds, the correct statement(s) with
respect to nucleophilic substitution reaction is(are)
(2017 Adv.)

(a)

(a) Compound IV undergoes inversion of configuration
(b) (b) The order of reactivity for I, III and IV is : IV > I > III
(c) I and III follow SN1 mechanism
(d) I and II follow SN1 mechanism
18. List-I contains reactions and List-II contains major
products. (2018 Adv.)
(c)
List-I List-II
P 1

Q 2
(d)

R 3
15. Compound(s) that on hydrogenation produce(s) optically
inactive compound (s) is/are (2015 Adv.)
S 4

(a)
5

(b)

Match each reaction in List-I with one or more products in

(c) List-II and choose the correct option.
(a) P → 1, 5; Q → 2; R → 3; S → 4
(b) P → 1, 4; Q → 2; R → 4; S → 3
(c) P → 1, 4; Q → 1, 2; R → 3, 4; S → 4
(d) (d) P → 4, 5; Q → 4; R → 4; S → 3, 4

12
 Answer Key (Abhedya)

Exercise-1
1. (c) 2. (c) 3. (c) 4. (c) 5. (b) 6. (a) 7. (a) 8. (a) 9. (c) 10. (c)
11. (c) 12. (b,c) 13. (a,c) 14. (b,c) 15. (a,b) 16. (a,b) 17. (a,b,d) 18. (b,c) 19. (a,b,d) 20. (b,c,d)
21. (a,b) 22. (a,b,c) 23. (a,b,c,d)24. (a,b) 25. (c) 26. (b) 27. (d) 28. (c) 29. (d) 30. (b)
31. (c) 32. (b) 33. [1] 34. [6] 35. [5] 36. [8] 37. [7] 38. [4] 39. [20] 40. [96]

Exercise-2
1. (b) 2. (a) 3. (a, d) 4. (d) 5. (A) 6. (b, c) 7. (a, b) 8. (a, c) 9. (a, b, c)
10. (a, c, d) 11. (3) 12. (4) 13. (4) 14. (6) 15. (4)

Exercise-3 (Advanced/Olympiad)
1. (c) 2. [3] 4. [1] 5. [19] 6. [6] 7. [2] 8. (b,c) 9. [5]

Exercise-4 (PYQ's)
2. (a) 3. (d) 5. (b) 6. (a) 7. (a) 8. (A → q; B → q; C → r; D → p, s) 9. (A) 10. (5)
11. (b) 12. (a) 13. (5) 14. (a) 15. (b, d) 16. (d) 17. (a, d) 18. (b)

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