®

ORGANIC

CHEMISTRY
PRE-MEDICAL

NURTURE COURSE

Exercise

Reaction Mechanism-II
English Medium

® Reaction Mechanism - II
Pre-Medical

EXERCISE-I (Conceptual Questions) Build Up Your Understanding

ELECTROPHILIC ADDITION REACTION 7. The predominant product formed when
1. Correct reactivity order for EAR of following 3–methyl–2–pentene reacts with HOCl is
compounds is Cl OH
CH3 (1) CH3–CH2–C–CH–CH3
Ph–CH=CH2 Ph–C=CH–CH3 CH3
I II CH3 OH
Ph2C=CH–CH3 CH2=CH–NO2
(2) CH3–C—–CH–CH3
III IV
CH3
(1) IV > I > II > III (2) III > II > I > IV
(3) II > III > I > IV (4) II > III > IV > I Cl Cl
HC0160 (3) CH3–CH2–C–CH–CH3

®
2. The intermediate during the addition of HCl to
CH3
propene in the presence of peroxide is
• ⊕ OH
(1) CH3 CHCH2 Cl (2) CH3 CH – CH3
(4) CH3–CH2–C—–CH–CH3 HC0169
⊕ •
(3) CH3 – CH2 – CH2 (4) CH3 CHCH3 CH3 Cl
HC0161 8. Propene on addition with HI, gives

3. (1) CH3—CHI—CH3 (2) CH3—CH2—CH2I

CH=CH–COOH + Br2 → A
(3) CH3—CHI—CH2I (4) None of the above
3
the number of sp carbon atoms in 'A' are HC0170
(1) 1 (2) 2 (3) 3 (4) 4 9. What is the main product of this reaction?
HC0162 HCl( g)
CH3 – C ≡ CH 
Excess
→?
4. Which of the following alkene is most reactive for
Cl
acidic hydration ?
(1) ethene (2) propene (1) CH3–C=CH2
(3) 1–butene (4) 2–methyl propene (2) CH3–CH–CH2
HC0165 Cl Cl
OH
A Cl
5. → ; Reagent 'A' is (3) CH3–CH2–CH
CH3 CH3 Cl
Θ Cl
(1) BH3/THF + H2O2/ OH
(4) CH3–C–CH3
(2) H2O/H⊕
Cl
(3) Hg(OCOCH3)2/NaBH4
HC0171
(4) Cl2/aq. NaOH
HC0167 10. Propan–1–ol can be prepared from propene by

6. Which of the following alkenes on hydration (1) H2O/H2SO4

gives a tertiary alcohol ? (2) Hg(OAc)2/H2O2 followed by NaBH4

Θ
(1) 2–Butene (2) Isobutylene (3) B2H6 followed by H2O2/ OH
(3) Ethene (4) α–Butylene (4) CH3CO2H/H2SO4
HC0168 NHC0405

112

Reaction Mechanism - II ®
Pre-Medical
FREE RADICAL ADDITION REACTION ELECTROPHILIC SUBSTITUTION REACTION
11. Reaction of HBr with propene in the presence of 18. The strongest deactivating effect on aromatic ring is
peroxide gives (1) –CH2Cl (2) –OCH3
(1) 3–bromo propane (2) Allyl bromide (3) –CH3 (4) –CCl3
(3) n–propyl bromide (4) Isopropyl bromide AH0187
HC0179 19. Which of the following is maximum reactive
12. → "product". The product is
Isobutene HBr
H2O2
towards E.S.R. ?

(1) Isobutyl bromide (2) Tert. butyl bromide (1) (2)

(3) Tert. butyl alcohol (4) isobutyl alcohol
HC0180
(3) (4)
FREE RADICAL SUBSTITUTION REACTION
AH0188
13. Alkane reacts with which of the following halogens
20. Correct order of reactivity of following compound
in dark

®
(1) F2 (2) Cl2 (3) I2 (4) Br2 with an electrophile :-
(I) p—CH3—C6H4—CH3
NHC0406
(II) C6H5—CH3
14. The nitrating agent for the nitration of alkanes is:
(III) p—CH3—C6H4—NO2
(1) Conc. HNO3
(IV) p—O2N—C6H4—NO2
(2) Mixture of conc. HNO3 and conc. H2SO4
(1) I > II > III > IV (2) II > I > IV > III
(3) Acetyl nitrate
(3) III > II > I > IV (4) IV > III > II > I
(4) HNO3 vapours at high temperature
AH0189
HC0182
21. Toluene is more reactive than benzene towards
15. The chain propagating step is fastest in the reaction
electrophilic reagents due to :-
of an alkane with
(1) Inductive effect only
(1) Fluorine free radical
(2) Hyperconjugative effect only
(2) Chlorine free radical
(3) Both inductive as well as hyperconjugative effects
(3) Iodine free radical
(4) Strong mesomeric effect
(4) Bromine free radical
AH0190
HC0183
22. Nitration of benzene is
16. In the nitration of propane, the product obtained
(1) nucleophilic substitution
in maximum yield is
(2) nucleophilic addition
(1) 1–nitropropane (2) 2-nitropropane
(3) electrophilic substitution
(3) Nitroethane (4) Nitromethane
(4) electrophillic addition
HC0184
AH0191
17. What is the chief product obtained when
23. Consider the following compounds :
n-butane is treated with bromine in the presence
CH3
of light at 130°C ?
(1) CH3–CH2–CH2–CH2–Br (I) (II)
(2) CH3–CH2–CH–Br
OH NO2
CH3
(3) CH3–CH–CH2–Br (III) (IV)

CH3
Correct order of their reactivity in electrophilic
CH3 substitution reactions would be :-
(4) CH3–C–CH2–Br (1) I > II > III > IV (2) IV > III > II > I
CH3 (3) III > II > I > IV (4) III > IV > I > II

HC0186 AH0192

113

® Reaction Mechanism - II
Pre-Medical
24. The active species in the nitration of benzene is 30. 1–phenyl-2-chloropropane on treating with
(1) NO2+ (2) HNO3 alc. KOH gives mainly :
(3) NO3
–
(4) NO2– (1) 1-phenylpropene (2) 2-phenylpropene
AH0193 (3) 1-phenylpropan-2-ol (4) 1-phenylpropan-1-ol
NHD0408
25. The function of anhydrous AlCl3 in the Friedel
31. Arrange the following alkanols A, B and C in
craft's reaction
order of their reactivity towards acid catalysed
(1) To absorb water
dehydration:-
(2) To absorb HCl (A) CH3–CH–CH2– CH2–OH
(3) To produce electrophile
(4) To produce Nucleophile CH3
AH0194 OH
26. In which of the following compound the (B) CH3–C–CH2– CH3
electrophile attack on o– and p– positions ?
CH3
NO2 Cl
CH3 OH

®
(1) (2)
(C) CH3–CH—CH– CH3
COOH
CCl3 (1) A > B > C (2) B > A > C
(3) (4) (3) B > C > A (4) C > B > A
AE0228
AH0195 32. The major product in the following reaction is
ELIMINATION REACTION H+
CH2–OH ∆ ?
27. The reactivity of alkyl halides in E2 elimination
reactions follows the order CH3
(1) R–I < R–Br < R–Cl < R–F CH2
(1) (2)
(2) R–F < R–Cl < R–Br < R–I OH
(3) R–I > R–Cl > R–Br < R–F CH3 CH3
(4) R–I < R–Br < R–F < R–Cl (3) (4)
HD0223 HD0229
28. The unimolecular elimination involves formation of 33. Arrange the following alkyl halides in decreasing
(1) A free radical (2) A carbanion order of the rate of elimination reaction with
(3) A carbocation (4) A biradical alcoholic KOH.
HD0224 H
29. Which of the following alkyl bromides will eliminate
(A) CH3–C–CH2–Br (B) CH3–CH2–Br
HBr fastest ?
(1) Ethyl bromide (2) Propyl bromide CH3
(3) Isopropyl bromide (4) t-Butyl bromide (C) CH3–CH2–CH2–Br
NHD0407 (1) A > B > C (2) C > B > A
(3) B > C > A (4) A > C > B
HD0231

EXERCISE-I (Conceptual Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 2 2 2 4 1 2 4 1 4 3 3 1 1 4 1
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 2 2 4 2 1 3 3 3 1 3 2 2 3 4 1
Que. 31 32 33
Ans. 3 3 4

114

Reaction Mechanism - II ®
Pre-Medical

EXERCISE-II (Previous Year Questions) AIPMT/NEET

AIPMT 2006 5. Which one of the following is most reactive
1. Nucleophilic addition reaction will be most favoured towards electrophilic attack ?
in : NO2 OH
O O
(1) (2)

(1) CH3CH2CH2–C–CH3 (2) CH3–C–CH3 Cl CH2OH

O O (3) (4)
(3) CH3–CH2–CH2–C–H (4) CH3–C–H
AH0241
CC0232 AIPMT 2009
AIPMT 2007 6. Benzene reacts with CH3Cl in the presence of
2. Predict the product ‘C’ obtained in the following anhydrous AlCl3 to form :-
reaction of 1-butyne : (1) Xylene
HCl HI
CH3–CH2–C≡CH  → B  
→C (2) Toluene

®
I (3) Chlorobenzene
(1) CH3–CH2–CH2–C–H (4) Benzylchloride
AH0243
Cl
I 7. Nitrobenzene can be prepared from benzene by
using a mixture of conc. HNO3 and conc. H2SO4.
(2) CH3–CH2–CH–CH2Cl In the mixture, nitric acid acts as a/an :-
I (1) Catalyst
(3) CH3–CH2–C–CH3 (2) Reducing agent
(3) Acid
Cl
(4) Base
(4) CH3–CH–CH2–CH2I
AH0244
Cl AIPMT 2010
HC0235 8. Which one is most reactive towards electrophilic
3. The order of decreasing rectivity towards reagent ?
electrophilic reagent for the following : CH3 CH3
(a) Benzene (b) Toluene
(c) Chloro benzene (d) Phenol OCH3 OH
(1) (2)
(1) b > d > a > c (2) d > c > b > a
(3) d > b > a > c (4) a > b > c > d CH3 CH3
AH0236
CH2OH NHCOCH3
AIPMT 2008 (3) (4)
CH3
4. AH0248
H3C–CH–CH=CH2 + HBr → A
9. The reaction of toluene with Cl2 in presence of
A (Predominantly) is : FeCl3 gives 'X' and reaction in presence of light
CH3 gives 'Y'. Thus, 'X' and 'Y' are :-
(1) CH3–C–CH2CH3 (1) X = Benzyl chloride,

Br Y = m–chlorotoluene
Br CH3 (2) X = Benzal chloride,
(2) CH3–CH–CH–CH3 Y = o–chlorotoluene
CH3 Br (3) X = m–chlorotoluene,
(3) CH3–CH–CH–CH3 Y = p–chlorotoluene
(4) X = o– and p–chlorotoluene
CH3
(4) CH3–CH–CH2–CH2Br Y = Trichloromethyl benzene
AH0249
HC0239
115

® Reaction Mechanism - II
Pre-Medical
10. Which one of the following compounds will be AIPMT 2014
most readily dehydrated ? 15. What products are formed when the following
O compound is treated with Br2 in the presence of
O OH
FeBr3 ?
(1) H3C (2) CH3
OH CH3

OH O
CH3
(3) CH3 (4) CH3
O OH CH3 CH3
HD0250 Br
(1) and
AIPMT Mains-2011
CH3 CH3
11. The order of reactivity of phenyl magnesium Br
bromide (PhMgBr) with the following compounds :-
CH3 CH3
CH3 CH3 Ph
C=O and C=O Br Br
C=O

®
H CH3 Ph (2) and
CH3 CH3
(I) (II) (III)
(1) I > II > III (2) III > II > I CH3 CH3
Br
(3) II > I > III (4) I > III > II (3) and
CC0257
CH3 CH3
AIPMT Pre.-2012 Br
12. In the following reaction: CH3 CH3
CH3
H O/H
CH3–C–CH=CH2 → 2
⊕
A + B (4) and
Major product Minor product CH3 Br CH3
CH3
Br
The major product is :-
AH0270
CH3 CH3
16. Which one is most reactive towards Nucleophilic
(1) H3C–C–—CH–CH3 (2) H3C–C–CH2–CH2 addition reaction?
CH3 OH CH3 OH CHO COCH3
(1) (2)
CH3 CH3
(3) H3C–C—CH–CH3 (4) H2C—C–CH2–CH3 CHO CHO

OH CH3 OH CH3 (3) (4)

HC0262
13. Among the following compounds the one that is CH3 NO2
most reactive towards electrophilic nitration is: CC0272
(1) Toluene (2) Benzene AIPMT 2015
(3) Benzoic Acid (4) Nitrobenzene 17. The reaction of C6H5CH=CHCH3 with HBr
AH0263 produces:-
NEET-UG 2013 (1) C6H5CH2CHCH3 (2) C6H5CH2CH2CH2Br
14. Which of the following compounds will not Br
undergo Friedal-Craft's reaction easily ? CH=CHCH3
(1) Toluene
(2) Cumene (3) (4) C6H5CHCH2CH3
(3) Xylene Br
(4) Nitrobenzene Br
AH0264 HC0277

116

Reaction Mechanism - II ®
Pre-Medical
Re-AIPMT 2015 F
F
18. In the reaction with HCl, an alkene reacts in (3) (4)
accordance with the Markovnikov's rule, to give a
product 1–chloro–1–methylcyclohexane. The
possible alkene is :- AH0300
CH2 CH3 23. The compound that will react most readily with
gaseous bromine has the formula
(1) (A) (2) (B) (1) C4H10 (2) C2H4 (3) C3H6 (4) C2H2
HC0301
CH3 24. Which of the following can be used as the halide
component for Friedel-Crafts reaction ?
(3) (A) and (B) (4) (1) Chloroethene (2) Isopropyl chloride
(3) Chlorobenzene (4) Bromobenzene
HC0279 AH0302
19. Which of the following is not the product of NEET(UG) 2017
25. Predict the correct intermediate and product in

®
dehydration of ? the following reaction :
OH
H2O, H2SO4
H3C–C≡CH HgSO4
Intermediate product
(A) (B)
(1) (2) (1) A : H3C–C=CH2 B : H3C–C=CH2
OH SO4
(2) A : H3C–C–CH3 B : H3C–C≡CH
(3) (4)
O
HD0283 (3) A : H3C–C=CH2 B : H3C–C–CH3
NEET-I 2016
OH O
20. In the reaction
(4) A : H3C–C=CH2 B : H3C–C–CH3
(1) NaNH2 / liq.NH3 (1) NaNH2 / liq.NH3
H–C≡CH X Y SO4 O
(2) CH3 CH2 Br (2) CH3 CH2 Br
CC0311
X and Y are :
NEET(UG) 2018
(1) X = 1-Butyne ; Y = 3-Hexyne
26. Which of the following carbocations is expected
(2) X = 2-Butyne ; Y = 3-Hexyne
to be most stable ?
(3) X = 2-Butyne ; Y = 2-Hexyne
NO2 NO2
(4) X = 1-Butyne ; Y = 2-Hexyne
⊕
HD0293 (1) (2)
21. Consider the nitration of benzene using mixed ⊕

conc. H2SO4 and HNO3. If a large amount of Y H Y H

KHSO4 is added to the mixture, the rate of NO2
nitration will be:- NO2
H
(1) faster (2) slower H ⊕
(3) (4)
(3) unchanged (4) doubled Y
Y ⊕
AH0296 GC0317
NEET-II 2016 NEET(UG) 2020
22. In the given reaction 27. Elimination reaction of 2-Bromo-pentane to form
HF
 → P pent-2-ene is:
+ 0°C
(a) β-Elimination reaction
the product P is :- (b) Follow Zaitsev rule
(c) Dehydrohalogenation reaction
(d) Dehydration reaction
(1) (2) (1) (a), (b), (d) (2) (a), (b), (c)
(3) (a), (c), (d) (4) (b), (c), (d)
HD0418
117

® Reaction Mechanism - II
Pre-Medical
NEET(UG) 2020 (COVID-19) NEET (UG) 2022 (Overseas)
28. Which of the following compound is most 32. The increasing order of reactivity of the following

reactive in electrophilic aromatic substitution ? compounds towards acid catalysed dehydration is

(a) CH3–CH2–OH
Cl NO2

(1) (2) (b) OH

OH
(c) CH3–CH–OH
(3) (4)
CH3
AH0419
29. Which of the following is a free radical
(d) CH3–C(CH3)2–OH
substitution reaction ?
Choose the correct answer from the options
(1) Benzene with Br2/AlCl3

®
given below :
(2) Acetylene with HBr
(1) (b) < (a) < (c) < (d) (2) (a) < (c) < (d) < (b)
(3) Methane with Br2/hv
(3) (c) < (a) < (b) < (d) (4) (b) < (c) < (a) < (d)
(4) Propene with HBr/(C6H5COO)2
AE0424
HC0421
NEET(UG) 2021 Re-NEET (UG) 2022
33. Given below are two statements : one is labelled
30. The major product of the following chemical
reaction is: as Assertion (A) and the other is labelled as
CH3 (C H CO)2O2 Reason (R).
CH–CH=CH2+HBr 6 5 ?
CH3 Assertion (A) : Chlorine is an electron
CH3 withdrawing group but it is ortho, para directing
(1)
CH3 CH–CH2–CH2–Br in electrophilic aromatic substitution.
CH3 Reason (R) :
(2) CH–CH2–CH2–O–COC6H5
CH3 Inductive effect of chlorine destabilises the
CH3 intermediate carbocation formed during the
(3) CH–CH–CH3
CH3 electrophilic substitution, however due to the
Br more pronounced resonance effect, the halogen

(4) CH3 stabilises the carbocation at ortho and para

CBr–CH2–CH3 positions.
CH3
HC0422 In the light of the above statements, choose the
NEET (UG) 2022 most appropriate answer from the options given
31. The incorrect statement regarding chirality is: below :
(1) The product obtained by SN2 reaction of (1) Both (A) and (R) are correct and (R) is the
haloalkane having chirality at the reactive correct explanation of (A)
site shows inversion of configuration,
(2) Both (A) and (R) are correct but (R) is not
(2) Enantiomers are superimposable mirror
images of each other. the correct explanation of (A)

(3) A racemic mixture shows zero optical (3) (A) is correct but (R) is not correct
rotation. (4) (A) is not correct but (R) is correct.
(4) SN1 reaction yields 1 : 1 mixture of both
AH0425
enantiomers.
HD0423
118

Reaction Mechanism - II ®
Pre-Medical
34. Which of the following reactions is not an
example for nucleophilic addition – elimination
reaction ?
(1) CH3CHO + NaHSO3

OH

CH3 C OSO2Na

(2) CH3CHO + NH2OH

CH3CH = N–OH+H2O

®
(3) CH3CHO+C6H5NHNH2

CH3CH=N–NHC6H5+H2O
(4) CH3CHO + NH3

CH3CH= NH + H2O
CC0426

EXERCISE-II (Previous Year Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 4 3 3 1 2 2 4 2 4 2 1 3 1 4 3
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 4 4 3 4 1 2 1 3 2 3 3 2 4 3 1
Que. 31 32 33 34
Ans. 2 1 1 1

119

® Reaction Mechanism - II
Pre-Medical

EXERCISE-III (Analytical Questions) Master Your Understanding

CH3 ⊕
D/H O O ⊕
1. CH3–CH–CH=CH2 
2
→ A; NO2
4. O–C  → Product is :-
A (major product) is
(1) CH3–CH–CHD–CH2–OH
O NO2
CH3
(1) O–C
(2) CH3–CH–CH–CH2–D
CH3 OH
O
(3) CH3–C(OH) CHDCH3
(2) O–C NO2
CH3
(4) CH3–C(OH) CH2–CH2–D
O
CH3

®
HC0337 (3) O2N O–C

C≡CH
2. Hydration of in presence of NO2
O
(4) O–C
H2SO4 / HgSO4 gives
COCH3
AH0341
(1)

CH2–CH2OH 5. p- nitro toluene on further nitration gives

(2)
CH3 CH3
CH2CH3 NO2
(3) (1) (2)
NO2
CH2CHO NO2 NO2
(4)
CH3 CH3
HD0339 NO2 NO2
3. Identify correct order of reactivity for electrophilic (3) (4)

substitution reaction of the following compounds :– NO2 NO2

Cl NO2 CH3 CHO
AH0342
(1) < < <
6. Which of the following reaction gives t-butyl
NO2 CH3 Cl NHCH3
benzene :
(2) < < < AlCl
(1) C6H6 + t–butyl chloride, 
3
→
Cl CHO NO2 CH3
HF
(2) C6H6 + (CH3)2C=CH2  →
(3) < < <
H SO
NO2 Cl CH3 NHCH3 (3) C6H6 + t–butyl alcohol 
2 4
→

(4) < < < (4) All of them

AH0340 AH0343

120

Reaction Mechanism - II ®
Pre-Medical
7. Halogenation of alkanes gives a mixture of ⊕
10. Electrophile NO2 attacks the following :
monohalo products. The ease of substitution
CCl3 NO2
follows the order
(I) (II)
(1) Tertiary H > primary H > secondary H
(2) Primary H < secondary H < tertiary H CHO O
(3) Primary H > secondary H > tertiary H (III) (IV)
(4) Secondary H > tertiary H < primary H
⊕
GC0344 in which cases NO2 will attack at meta position
8. Chlorination (1-mole) of toluene in the presence (1) II and IV (2) I, II and III
of light and heat followed by treatment with (3) III and IV (4) I only
aqueous NaOH gives AH0351
(1) o-cresol
+
H
(2) p-cresol 11. 
∆
→ X (major) 'A' is

®
CH3 OH
(3) 2, 4-dihydroxy toluene
CH3
(4) Benzyl alcohol
HC0346
(1) (2)
9. Which gives maximum yield of C2H5Cl CH3 CH3
hv, light
CH2 CH2
(1) C2 H6 + Cl2  → C2 H5 Cl + HCl
excess
(3) (4)
(2) C2 H6 + Cl2 hv
→ C2 H5 Cl + HCl CH3 CH3
light
excess CH2 CH3

(3) C2H6 + Cl2 hv

→ C2H5Cl HD0361
light

Dark
(4) C2H6+Cl2  → C2H5Cl + HCl
HC0347

EXERCISE-III (Analytical Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11
Ans. 4 1 4 3 1 4 2 4 2 2 4

121