CHEMISTRY FOR NEET & AIIMS

SOLVED EXAMPLE
Ex.1 In the case homologous series of alkanes, which one of the following statements is incorrect
(A) The members of the series are isomers of each other
(B) The members of the series have similar chemical properties
(C) The members of the series have the general formula Cn H 2n  2 ,where n is an integer
(D) The difference between any two successive members of the series corresponds to 14 unit of relative atomic mass

Sol. (A) The difference between any two successive members of the homologous series – CH2 – i.e., the molecular
weight of every two adjacent members differ by 14. (CH2 = 12 + 2 = 14)

Ex.2 How many primary, secondary, tertiary and quaternary carbons are present in the following hydrocarbon
CH3  CH(CH 3 )  C(CH3 ) 2  CH 2  CH(CH 3 )  CH 2  CH3
Primary Secondary Tertiary Quaternary
(A) 6 2 2 1
(B) 2 6 3 0
(C) 2 4 3 2
(D) 2 2 4 3

1o
CH3
| 2o 3o 1o
1o 3o o 2o
Sol. (A) CH3  CH  C4  CH 2  CH  CH 2  CH 3
| | |
CH3 CH3 CH
o o 3
1 1 1o

1o  Primary 6, 2o  Secondary 2

3o  Tertiary 2, 4o  Quanternary1

Ex.3 The octane number of a sample of petrol is 40. It means that its knocking property is equal to the mixture of
(A) 40% n-heptane + 60% iso-octane (B) 40% petrol + 60% iso-octane
(C) 60% n-heptane + 40% iso-octane (D) 60% petrol + 40% iso-octane
Sol. (C) Octane number of fuel is the percentage of iso- octane in mixture.

Ex.4 Formation of 2-butene as major product by dehydration of 2-butanol is according to

(A) Markownikoff rule (B) Saytzeff rule
(C) Peroxide effect (D) Anti-Markownikoff rule
Sol. (B) CH 3  C H  CH 2  CH3  CH 3  CH  CH  CH3  H 2 O
| 2  Butene
OH
2  Butanol

According to this rule H atom goes from that - carbon which is less hydrogenated.

(i) X
Ex.5 CH 3 C  CCH 3   CH 3  C  C  CH 3 X in the above reaction is
(ii)H 2 O / Zn | |
O O
(A) HNO3 (B) O2 (C) O3 (D) KMnO4
(i)O
Sol. (C) CH3  C  C  CH3   CH3  C  C  CH3
(ii) Zn/ H O || ||
3

O O

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Ex.6 Which of the following is Friedel-Craft's reaction
(A) C6 H6  FeCl3  Cl2  C6 H5 Cl (B) C6 H 5 CHO  CH 3CHO  KOH  C6 H5 CH  CH  CHO

O
||
(C) C6 H 6  CH3 COCl  AlCl3  C6 H5  C  CH 3 (D) C6 H 5 OH  CHCl 3  KOH 
 Salicylaldehyde
Sol. (C) Friedel-craft's reaction
anhydrous AlCl3
CH3 COCl C6 H 6   CH3 COC6 H5  HCl
Acetyl chloride Benzene Acetophenone

Ex.7 Condition for maximum yield of C2H5Cl is

Dark
UV Light
(A) C2H6 (excess)  Cl2   (B) C 2 H 6  Cl 2  
Room temp.

UV Light UV Light
(C) C 2 H 6  Cl 2 (excess)   (D) C 2 H 6  Cl 2  
U.V.Light
Sol. (A) C2 H 6 (excess)  Cl 2   C 2 H 5 Cl  HCl
Ethyl chloride
(Major product)

Ex.8 When ethyl alcohol is heated with red phosphorus and HI, then which of the following is formed
(A) C2H6 (B) CH4 (C) C3H8 (D) C2H4
Red P
Sol. (A) CH3 CH 2  OH  2HI   CH3  CH 3  H 2 O  I2
Ethylalcohol Ethane

Ex.9 In the Fischer-Tropsch synthesis of petrol..... and ..... are used as the raw materials
(A) H2; CO (B) CH4 ; H2 (C) CH4 ; CH3OH (D) CH3OH ; CO
Sol. (A) Fischer-Tropsch process -
CO or Ni
CO  H2  H 2   Mixture of hydrocarbons  H2 O
Excess heat (Petrol)
Water gas

Ex.10 Which one of the following reactions is most suitable for the preparation of n-propyl benzene
(A) Friedel-Craft's reaction (B) Wurtz reaction
(C) Wurtz-Fittig reaction (D) Grignard reaction

Br

Sol. (C) Dry

CH3 – CH2 – CH2 – Br + + 2Na
ether
Propyl bromide

2NaBr + CH3 – CH2 – CH2

n–propyl benzene

Ex.11 Propane cannot be prepared from which reaction

B2 H6 HI
(A) CH3  CH  CH 2  
 (B) CH 3 CH 2 CH 2 I 
P

OH

Na
(C) CH 3CH 2 CH 2 Cl   (D) None of these
Sol. (A) Hydroboration of alkenes followed by hydrolysis in basic medium yield alcohols and not the alkanes.
B2 H 6
R  CH  CH2  (R  CH2  CH2 )3  B

OH
  R  CH 2  CH 2 OH

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Ex.12 The reaction
(CO  H 2 )
CH3 CH  CH 2  
 CH 3  CH  CH 3 is known as
H |
COOH
(A) Wurtz reaction (B) Koch reaction
(C) Clemmensen reduction (D) Kolbe's reaction
Sol. (B) Koch reaction : (Carboxylation of Alkene)
COOH
|
Water gas (CO  H 2 )
CH 3  CH  CH 2  o
 CH 3  CH  CH 3
400 C, H3 PO 4 Isobutyric acid

CH 3
|
Ex.13 The compound CH 3  C  CH  CH 3 on reaction with NaIO4 in the presence of KMnO4 gives

(A) CH 3CHO  CO 2 (B) CH3COCH3

(C) CH3COCH3 + CH3COOH (D) CH3COCH3 + CH3CHO
CH 3
|
NaIO
Sol. (D) CH3  C  CH  CH3 
KMnO
 CH 3 COCH 3  CH 3 CHO
4

Ex.14 In the reaction :

NH4 OH
HC  CH  2AgNO3  X  2NH 4 NO3  2H 2 O
'X' is
(A) Ag2C (B) Ag2C2 (C) AgC (D) AgOH
NH 4 OH
Sol. (B) HC  CH  2AgNO3 

Ag  C  C  Ag  2NH 4 NO3  2H 2 O

Ex.15 Naphthalene is a/an

(A) Ionic solid (D) Covalent solid (C) Metallic solid (D) Molecular solid
Sol. (D) Naphthalene is a molecular solid. If the crystals contains only individuals atoms; as in solid argon or krypton or
if they are composed of non polar molecules as in naphthalene, the only attraction between the molecules are the
London forces.

Ex.16 Which of the following is not aromatic

(A) Benzene (B) Naphthalene (C) Pyridine (D) 1,3,5 heptatriene
Sol. (D) A compound is said to be aromatic if it is planar and there is complete delocalization of  electrons, which is only
possilble if it is a conjugated cyclic system and number of electrons used in delocalization is (4n + 2). 1, 3, 5
heptatriene is not an aromatic compound because complete delocalization of  electrons, is not possible in it.

3, 5 Heptatriene

Ex.17 Acetylene reacts with HCN in the presence of Ba(CN)2 to yield

(A) 1, 1-dicyanoethane (B) 1, 2-dicyanoethane (C) Vinyl cyanide (D) None of these
Ba(CN )2
Sol. C) CH  CH  HCN   CH 2  CHCN
Acetylene Vinyl cyanide

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Ex.18 Write the products of the addition reaction
C = C + XY 
C–C |
(A) (B) X  C  C Y (C) C  C  (D) X – C – C – X
| | | |
X Y
Y
X
| |
(E) C  C
| |
Y
Sol. (A) Addition reaction means addition on double bond.

Ex.19 Formation of polyethylene from calcium carbide takes place as follows

CaC2  2H 2 O  Ca(OH) 2  C2 H 2
C2 H 2  H 2  C 2 H 4
n(C2 H 4 )  (CH 2  CH 2 )n
The amount of polyethylene obtained from 64.1 kg CaC2 is
(A) 7 kg (B) 14 kg (C) 21 kg (D) 28 kg

Sol. (D) CaC

64 g
2  2H 2 O  Ca(OH) 2  C2 H 2

C2 H 2  H 2  C2H 4
28g

64g of CaC2 gives 28g of ethylene

 64kg of CaC2 will give 28kg of polyethylene

Ex.20 Nitrobenzene can be prepared from benzene by using a mixture of conc. HNO3 and conc. H2SO4. In the nitrating
mixture,HNO3 acts as a
(A) Base (B) Acid (C) Reducing agent (D) Catalyst
NO2

Conc. H2SO4
Sol. (A) HNO3

Nitro benzene

Ex.21 A group which deactivates the benzene ring towards electrophilic substitution but which directs the incoming
group principally to the o- and p-positions is
(A) –NH2 (B) – Cl (C) – NO2 (D) –C2H5
Sol. (B) Electron accepting groups which make the substitution difficult are known of deactivating groups. the group or
substituent already present on the ring also decides the position of incoming group.
ortho and para directing groups are as follow
CH 3 , C2 H5 (R),  NH 2 , OH , halogens, (Cl, Br, I)

Ex.22 Which order is correct for the decreasing reactivity to ring monobromination of the following compounds
C 6 H 5 CH 3 , C 6 H5 COOH, C6 H 6 C6 H 5 NO 2
I II III IV
(A) I > II > III > IV (B) I > III > II > IV (C) II > III > IV > I (D) III > I > II > IV
CH3 COOH NO2

Sol. (B) > > >

Toluene Benzene Benzoic acid Nitro Benzene

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Ex.23 Benzene is obtained by

(A) Substitution of three acetylene molecules (B) Addition of three C2H2 molecules
(C) Polymerisation of three C2H2 molecules (D) Condensation of three C2H2 molecules
Sol. (C) Polymerisation

heat
3CH  CH  
o
Cu ,500 C

Ex.24 Toluene can be oxidised to benzoic acid by

(A) KMNO4 (B) K2Cr2O7 (C) H2SO4 (D) Both (A) and (B)

CH3 COOH

KMnO4 or K2Cr2O7
Sol. (B) + [O]

H 2SO4 / HgSO4
Ex.25 CaC2  H 2 O  A   B . Identify A and B in the given reaction
(A) C2H2 and CH3CHO (B) CH4 and HCOOH (C) C2H4 and CH3COOH (D) C2H2 and Ch3COOH
Sol. (A) Wohler reaction :
CaC 2  2H 2 O 
 C 2 H 2  Ca(OH) 2
dil. H 2 SO 4 / HgSO4
C H 
2 2 o
 [CH 2  CHOH]  CH 3 CHO
Acetylene 60 C Unstable Acetaldehyde

Ex.26 The compound X on reaction with HgSO4 + H2SO4 gives Y which on oxidation gives acetic acid. X is
(A) C2H2 (B) C2H4 (C) C3H4 (D) C4H6
HgSO KMnO
Sol. (A) CH  CH H 2 O   CH2  CH  OH 
4 4

Ethyne H SO 2 4 Vinyl alcohol

Oxidation
CH 3CHO   CH 3COOH
Acetic acid

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Exercise # 1 SINGLE OBJECTIVE NEET LEVEL

1. To which of the following four types does this 7. The most common type of reaction in aromatic
compounds is
reaction belong B  R  A  B  R  A
(A) Elimination reaction
(A) Unimolecular electrophilic substitution
(B) Addition reaction
(B) Bimolecular electrophilic substitution
(C) Electrophilic substitution reaction
(C) Unimolecular nucleophilic substitution (D) Rearrangement reaction
(D) Bimolecular nucleophilic substitution
8. The function of AlCl3 in Friedel-Craft's reaction is
2. An alkyl halide may be converted into an alcohol by (A) To absorb HCl
(A) Elimination (B) To absorb water
(B) Addition (C) To produce nucleophile
(C) Substitution (D) To produce electrophile
(D) Dehydrohalogenation
9. Which of the following can't be used in Friedal
Craft's reactions
3. CH3 CH2 – Cl (A) FeCl3 (B) FeBr2
(C) AlCl3 (D) NaCl
10. The nitration of a compound is due to the
(A) NO2 (B) NO3
The above reaction proceeds through
(A) Nucleophilic substitution (C) NO (D) NO 2
(B) Electrophilic substitution 11. Dehydrohalogenation of an alkyl halide is a/an
(C) Free radical substitution (A) Nucleophilic substitution reaction
(D) More than one of the above processes (B) Elimination reaction
(C) Both nucleophilic substitution and elimination
4. Geometry of reaction intermediate in SN1 reaction is
reaction
(A) Tetrahedral
(D) Rearrangement
(B) Planar
(C) Triangular bipyramidal 12. Addition of HCl to vinyl chloride gives 1, 1-
(D) None of these dichloroethane because of
(A) Mesomeric effect of Cl
CH3 CH3 (B) Inductive effect of Cl
| |

5. H 3 C  C  Br  KOH(Aq.)  H 3 C  C  OH  KBr (C) Restricted rotation around double bond

| |
CH3 CH3 (D) None of these
above reaction is 13. Formation of ethylene from acetylene is an example of
(A) SN1 (B) SN2 (A) Elimination reaction
(C) E1 (D) Both (A) and (B) (B) Substitution reaction
(C) Addition reaction
6. In electrophilic substitution reaction nitrobenzene is (D) Condensation reaction
(A) Meta-directing
14. Conversion of CH4 to CH3Cl is an example of which
(B) Ortho-directing
of the following reaction
(C) Para-directing
(A) Electrophilic substitution
(D) Not reactive and does not undergo any
(B) Free radical addition
substitution
(C) Nucleophilic substitution
(E) Non-selective
(D) Free radical substituion

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15. Following reaction, 23. Among the following the strongest nucleophile is
(CH 3 ) 3 CBr  H 2 O  (CH 3 )3 COH  HBr (A) C2H5SH (B) CH3COO–
(C) CH3NH2 (D) NCCH2–
is an example of
(A) Elimination reaction 24. The reaction
(B) Free radical substitution O O
? ?
(C) Nucleophilic substitution R–C + Nu  R – C + X, , is fastest
(D) Electrophilic substitution X Nu
when X is
16. Which is an electrophile
(A) Cl (B) NH2
(A) BCl3 (B) CH3OH
(C) OC2H5 (D) OCOR
(C) NH3 (D) AlCl4–
25. Elimination of bromine from 2-bromobutane results
17. The electrophile in the nitration of benzene is
in the formation of
(A) NO 2 (B) NO2 (A) Equimolar mixture of 1 and 2-butene
(C) NO+ (D) NO 2 (B) Predominantly 2-butene
(C) Predominantly 1-butene
18. The following compound will undergo electrophilic (D) Predominantly 2-butyne
substitution more readily than benzene
(A) Nitrobenzene (B) Benzoic acid 26. Examine the following statements pertaining to an
SN2 reaction
(C) Benzaldehyde (D) Phenol
(1) The rate of reaction is independent of the
19. Which is an electrophile concentration of the nucleophile
(A) AlCl3 (B) CN– (2) The nucleophile attacks the C– atom on the side
(C) NH3 (D) CH3OH of the molecule opposite to the group being
displaced
20. Strongest nucleophile is (3) The reaction proceeds with simultaneous bond
(A) RNH2 (B) ROH formation and bond rupture/cleavage
(C) C6H5O– (D) CH3O– Amongst the following which of the above were true
21. The major product obtained when Br 2/Fe is (A) 1, 2 (B) 1, 3
treated with (C) 1, 2, 3 (D) 2, 3
O
HN 27. What is the decreasing order of reactivity amongst
H3C CH 3 is the following compounds towards aromatic
electrophilic substitution
I. Chlorobenzene II. Benzene
O O III. Anilinium chloride IV. Toluene
HN HN
H3 C CH3 H3C CH 3 (A) I > II > III > IV (B) IV > II > I > III
(A) (B) (C) II > I > III > IV (D) III > I > II > IV
Br Br
28. Which of the following is not a Nucleophile ?
O O (A) AICI3 (B) (CH3)2 NH
HN HN
H3C H3C
(C) C2H5OH (D) H2O
CH 3 CH3
(C) (D)
Br Br 29. Which one of the following has maximum
nucleophilicity ?
22. Which one of the following is least reactive in a
nucleophilic substitution reaction (A) CH3 S  (B)
(A) CH3CH2Cl (B) CH2 = CHCH2Cl (C) Et3N (D)
(C) (CH3)3 C – Cl (D) CH2 = CHCl

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30. Which one of the following has minimum 34. Substitution reactions involve :
nucleophilicity ? (A) Cleavage of a s–bond and formation of a new
(A) (CH3)3CLi (B) NaNH2 s–bond
(C) CH3ONa (D) NaOH (B) Cleavage of two s–bond and formation of a
new p –bond
31. Which of the following is an electrophilic reagent ? (C) Cleavage of a p–bond and formation of two
(A) H2O (B) OH– new s –bond
+
(C) NO2 (D) None (D) None of these

32. Best leaving group is :

35. Which of the following reaction is a substitution
(A) F– (B) Cl– reaction ?
(C) Br– (D) I– Ni / H2
(A) CH2 = CH2    CH3–CH3
33. The correct order of leaving ability is : Zn
(B) CH 2– CH2  CH2 = CH2 + ZnBr2
(A) > H2O (B) > Br Br
 
(C) CH3 – I + OH  CH3 OH  I
(C) > (D) >
H
KCN
(D) CH3 – CHO  CH3 – C –OH
H
CN

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Exercise # 2 SINGLE OBJECTIVE AIIMS LEVEL

1. Which of the following alkyl halide is most reactive 5. What is the final product of reaction.
towards H2O ?
Na CH3 – CH2 – I
CH3 – C  CH     Product
(A)
(A) CH2=CH–CH2–CH3
(B) (B) CH3–CH2–CC–CH2–CH3
(C) CH  C – CH2  CH2  CH3
(D) CH3  C  C  CH2  CH3
(C)

H O
6. 2 ‘Y’ Product :
(D) AgNO 3

HCl / ZnCl2
2.     [X]

(A) (B)
Identify X and the mechanism of the reaction.
(A) CH3 – CH2 – CH2 – CH2 – Cl & SN1
(B) CH3 – CH2 – CH2 – CH2 – Cl & SN2
(C) CH3  CH  CH2  CH3 & SN1
| (C) (D)
Cl

(D) CH3  CH  CH2  CH3 & SN2

|
Cl
7. SN2 mechanism proceeds through intervention of :
HBr
3. CH 3 (CH 2 ) 2 CH 2 OH  X, (A) Carbonium ion (B) Transition state
1- butanol (C) Free radical (D) Carbanion
Identify X and the mechanism of the reaction
8. When the concentration of alkyl halide is tripled
(A) CH3 – CH2 – CH2 – CH2 – Br & SN1
(B) CH3 – CH2 – CH2 – CH2 – Br & SN2 and the concentration of ion is reduced to half,
(C) CH3  CH  CH2  CH3 & SN1 the rate of SN2 reaction increases by:
| (A) 3 times (B) 2 times
Br
(C) 1.5 times (D) 6 times
(D) CH3  CH  CH2  CH3 & SN2
| 9. The reaction
Br
O O
– –
PCl5 R–C + Nu R–C +X
4.  (X) , X is :
X Nu
is slowest when X is :
(A) (B)
O O
– –
R–C + Nu R–C +X
X Nu
(C) (D) (A) Cl (B) NH2
(C) OC2H5 (D) OCOCH3

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13. The correct order of reactivity of CH3MgBr with
O
|| following compounds will be :
NaNH2
10. CH 3–CH 2– C – OCH3  X, X is CH3–CHO, (1)

HCHO, (2)
O Ph–CHO (3)
||
(A) CH3–CH2– C – ONa (4)

O
|| (A) 2 > 1 > 4 > 3 (B) 4 > 3 > 1 > 2
(B) CH3–CH2– C – NH2 (C) 2 > 1 > 3 > 4 (D) 1 > 3 > 2 > 4

O 14. Which of the following is free radical addition

|| reaction ?
(C) CH 3– C – NH–CH3

(D) CH 3– CH2–NH2 (A) + NO 2

11. Which of the following reaction is SN2Ar reaction ? (B) CH2 = CH2 + HBr  CH3 –CH2 – Br
R 2O 2
  (C) CH3 – CH = CH2 + HBr   CH3 – CH2 –
(A) + Br +H CH2 –Br
(D) CH3 – CH = CH2 + HCl  CH3 – CH – CH3
CH3 CH3 |
NO2 Cl
 
(B) + NO2 +H 15. Which of the following reaction is an elimination
reaction ?
5 PCl
Cl OH (A) CH3 – CH2 – CH2 – OH   CH3 – CH2 –
CH2 – Cl
 
(C) + OH + Cl HCl
(B) CH3 – CH = CH2 

NO2 NO2
Alc . KOH
(C)   CH3 – CH = CH2
 
(D) Br + OH OH+ Br
(D) CH OH
3
  

12. The given reaction most likely occurs by which of

the following mechanism ? 16. The relative rate of acid catalysed dehydration of
following alcohols would be :

CH O
3 
  

(A) SN1 (B) SN2

(C) SN2Th (D) SN2Ar

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CH3
OH
20. In the given reaction :

Conc.H 2SO 4
  [X] as major product
[X] will be :

CH3 (A) CH2 (B) CH3

|
C – Ph
| CH3 CH3
OH (C) (D)

IV
21. Which of the following cannot undergo E2 reaction ?
(A) III > I > IV > II (B) III >IV > I > II
(C) I > III > IV > II (D) IV > III > I > II (A) (B)

17. 2-Chlorobutane on treatment with alcoholic KOH/

gives mainly (C) (D) none of these
(A) 2-Butene (B) 1-Butene
(C) 2-Butanol (D) 1-Butyne
22. Which of the following applies in the reaction,
alc.KOH
CH 3 CHBrCH 2 CH 3  
18. Major Product is : (i) CH3CH = CHCH3 (major product)
(ii) CH2 = CHCH2CH3 (minor product)
(A) Markovnikov's rule (B) Saytzeff's rule
(A) CH 3–C=CH–CH 3 (C) Kharasch effect (D) Hofmann's rule
CH 3
23. Bromination of alkanes involves
(B) CH 3–CH–CH=CH 2 (A) Carbanions (B) Carbocations
CH3 (C) Carbenes (D) Free radicals

(C) CH 2=C–CH 2–CH 3 24. Which of the following cannot undergo nucleophilic
substitution under ordinary conditions
CH 3 (A) Chlorobenzene (B) tert-butylchloride
OH (C) Isopropyl chloride (D) None of these

(D) CH3–CH–CH–CH3 25. Which of the following alkyl groups has the
maximum + I effect
CH3
(A) CH3– (B) (CH3)2CH–
(C) (CH3)3 – (D) CH3CH2 –
Alc. KOH
19. Ph   X 26. Correction reactivity order for EAR of following

compound is
CH3
Br Ph – CH = CH2 Ph – C = CH – CH
3
I
X is the total number of possible products in this II
Ph2C = CH – CH3 CH2 = CH – NO2
elimination reaction : IV
III
(A) 01 (B) 03 (A) IV > I > II > III (B) III > II > I > IV
(C) 02 (D) 04 (C) II > III > I > IV (D) II > III > IV > I

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31. In which of the following conpound the electrophile
27. CH = CH – COOH + Br2  A attack on o– and p– positions :
NO2 Cl
the number of chiral carbons in ‘A’ are
(A) 1 (B) 2 (A) (B)
(C) 3 (D) 4
COOH
dil/H SO CCl3
CH3 – CH = CH2 A 2 4

28.
BH HO (C) (D)
CH3– CH = CH2   2

OH B 6
–
2 2

Wrong statement about the product is

(A) A and B have the same functional group
(B) A and B are position isomers 32. Which of the following product will be obtained
(C) A and B show chain isomerism when neophentyle alcohol is treated with conc. HCl
(D) Mixed ether is the isomer of both A and B in presence of ZnCl2.
(A) t – butyl chloride (B) isobutylene
29. What is the chieft product obtained when n- (C) t– pentyl chloride (D) Neo pentyl chloride
butane is treated with bromine in the presence
of light at 130°C ?
33. The major product obtained from the heating of 3, 3-
(A) CH3 – CH2 – CH2 – CH2 – Br
dimethyl -2 - butanol with H2SO4 is
(B) CH3 – CH2 – CH – Br (A) 3, 3- dimethyl - 1 - butene
CH 3 (B) 2, 3- dimethyl - 1 - butene
(C) CH3 – CH – CH2 – Br (C) 2, 3- dimethyl - 1 - butene
CH3 (D) cis and trans isomers of product (2)

CH3 34. Arrange the following alkyl halides in decreasing order

(D) CH3 – C – CH2 – Br of the rate of elimination reaction with alcoholic KOH.
CH3
H
30. Which of the following is maximum reactive towards (A) CH3 – C – CH2 – Br (B) CH3– CH2 – Br
E.S.R. :– CH3
(C) CH3 – CH2 – CH2 – Br
(A) (B) (A) A > B > C (B) C > B > A
(C) B > C > A (D) A > C > B

(C) (D)

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Exercise # 3 PART - 1 MATRIX MATCH COLUMN

1. Match the column I with column II.

Column-I (reaction) Column-II (Mechanism)
CH 3 OH CH3 Cl
(A) C + SOCl2 C (p) SN1
Ph Ph
(+) H (+)
H

CH3 OH Cl
C Pyridine CH3
(B) + SOCl2 C (q) SN2
Ph H H 5C 6 H
(+) (–)
–
(C) (r) SNi
CH3
CH3 OH CH3 Cl
(D) C +HCl  C (s) E2
H5C6 (+) H C 6H 5 H
(±)

2. Match the column I with column II.

Column-I Column-II
(Substrate) (Relative rate of solvolysis in 50%
aqueous ethanol at 45°C)
(A) Cl (p) 7700
(B) Cl (q) 1
H3C
(C) (r) 91
H3C Cl
(D) Ph Cl (s) 1,30,000

3. Match the entries listed in Column I with appropriate entries listed in Column II.
Column-I Column-II
O
C 1. AlCl3
Cl 2. NaBH4

(A) 3. Conc. H2 SO4

(p) Electrophilic sustitution

H 2(1 atm) / Pd
CH2 100° C
(B) (q) A hydrocarbon is the final product

O
C
1. , AlCl3
Cl 2.NH2NH2, KOH
(C) (r) Aromaticity is destroyed

+
N2 Cl–
H 2O
(D) (s) Nucleophilic substitution

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Exercise # 3 PART - 2 ASSERTION & REASONING

These questions contains, Assertion and Reason. 10. Assertion : Ketone gives 2.4 - DNP test easily than
(A)Assertion is True, Reason is True ; Reason is aldehyde.
a correct explanation for Assertion Reason : Ketone is more reactive than aldehyde.
(B)Assertion is True, Reason is True ; Reason is
NOT a correct explanation for Assertion 11. Assertion : p-nitrophenol gives more electrophilic
(C)Assertion is True, Reason is False. substituted compound than m-methoxy phenol.
(D)Assertion is False, Reason is True. Reason : Methoxy group shows only negative I-
(E) Both Assertion and Reason are False. effect.

1. Assertion : Chloropropane has higher boiling point 12. Assertion : Rates of nitrationof benzene and
than chloroethane. hexadeuterobenzene are different.
Reason : Haloalkanes are polar molecules. Reason : C-H bond is stronger than C-D bond.
2. Assertion : Polar solvent slows down SN1 reaction. 13. Assertion : Major product obtained from FCR of
Reason : CH3–Br is less reactive than CH3Cl. benzene with n-butyl chloride is tert. Butyl benzene.
3. Assertion : Optically active 2-iodibutane on Reason : Intermediate 1° carbocation
treatment with NaI in acetone undergoes rearrangements in more stable 3° carbocation.
racemisation.
14. Assertion : When CH3Cl and AlCl3 are used in F.C.R.
Reason : Repeated Walden inversions on the the electrophile is Cl.
reactant and its product eventually gives a racemic
mixture. Reason : The first attack on benzene is of Cl.

4. Assertion : Free radical chlorination of n-butane 15. Assertion : The correct reactivity order towards
gives 72% of 2-chlorobutane and 28% of 1- sulphonation is – meta xylene > Toluene >
chlorobutane though it has six primary and four chlorobenzene > Nitrobenzene
secondary hydrogens. Reason : m-xylene has the highest electron density
Reason : A secondary hydrogen is abstracted more & hence most reactive.
easily than the primary hydrogen.
16. Assertion : Iodine monochloride (ICI) reacts with
5. Assertion : Boiling point of alkyl halide increases benzene in presence of a lewis acid such as anhyd.
with increasse in molecular weight. AlCl3 to give iodobenzene and not chlorobenzene.
Reason : Boiling point of alkylhalides are in the order Reason : Iodine is less electronegative than chlorine
RI > RBr > RCI > RF. in the reaction.
6. Assertion : Nucleophilic substitution reaction on an
17. Assertion : Vinyl halides can not be used in place
optically active alkyl halide gives a mixture of
enantiomers. of alkyl halides in friedal crafts alkylation.
Reason : Vinyl halides does not give electrophile
Reason : The reaction occurs by S 1 mechanism.z
N easily.
7. Assertion : Trans 2-butene gives recemic mixture 18. Assertion : If the hydrogen atoms of benzene are
when treated with Cl2. replaced by deuterium atoms then the reactivity of
Reason : Adddition of Cl2. benzene ring is decreased for ESR.
8. Assertion : Addition of HBr in presence of peroxide Reason : The bond strength of C-D is more than
on alkene is free radical adition. This reaction is not C-H and reaction depends on the bond strength
shown by HCl. of C-D and C-H.
Reason : Due to less bond energy of HCl than HBr,
19. Assertion : Benzyl chloride is more reactive than p-
homolysis of HCl can not occurs.
chloro toluene towards aqueous NaOH.
9. Assertion : Addition of CBrCl 3 in presence of Reason : The C-Cl bond in benzyl chloride is more
peroxides takes place faster to 2-ethyl-1-hexene than polar than C-Cl bond in p-chloro toluene.
to 1-octene.
Reason : Intermidiate free radical in case of 2-ethyl-
1-hexene is more stable.

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Exercise # 4 PART - 1 PREVIOUS YEAR (NEET/AIPMT)

1. Which one of the following is a free radical H H2

substitution reaction? [CBSE AIPMT 2003] (A) H3C C C C Cl
H
CH2Cl CH2NO2
(A) + AgNO2 H H2
(B) H3C C C C Cl
H
(B) CH3CHO + HCN CH3CH(OH)CN
H H2
CH3 CH2Cl (C) H3C C C C Cl
Boiling H
(C) + Cl2
H H2
(D) H 3C C C C Cl
CH 3 H
+ CH 3Cl
Anhy. AlCl3 6. In an SN 1 reaction on chiral centres there is
(D)
(A) 100 % racemisation
(B) inversion more than retention leading to partial
2. Which of the following reactions is an example of racemisation
nucleophilic substitution reaction? (C) 100% retention
[CBSE AIPMT 2009] (D) 100% inversion [CBSE AIPMT 2015]
(A) RX + KOH  ROH + KX
7. The correct statement regarding a carbonyl
(B) 2 RX + 2NA  R – R + 2NaX
compound with a hydrogen atom on its alpha-
(C) RX + H2  RH + HX carbon, is [NEET 2016, Phase I]
(D) RX + Mg  RMgX (A) a carbonyl compound with a hydrogen atom
3. Which one is most reactive towards nucleophilic on its alpha-carbon rapidly equilibrates with its
addition reaction? [CBSE AIPMT 2014] corresponding enol and this process is known
as aldehyde-ketone equilibration
O
(B) a carbonyl compound with a hydrogen atom
CHO on its alpha-carbon rapidly equilibrates with its
C CH3
(A) (B) corresponding enol and this process is known
as carbonylation
(C) a carbonyl compound with a hydrogen atom
CHO CHO on its alphs-carbon rapidly equilibrates with its
corresponding enol and this process is known
as keto-enol tautomerism
(D) a carbonyl compound with a hydrogen atom
(C) (D) on its alpha-carbon never equilibrates with its
corresponding enol
CH3 NO2 8. In the reaction
–
4. Which of the following organic compounds has same OH O Na+
hybridisation as its combustion (CO2) product? CHO
[CBSE AIPMT 2014] + CHCl3 + NaOH
(A) Ethane (B) Ethyne the electrophile involved is [NEET 2018]
(C) Ethene (D) Ethanol 
(A) dichloromethyl anion ( C HCl 2 )

5. Which of the following is the most correct electron (B) formly cation ( C HO )

displacement for a nucleophilic reaction to take (C) dichloromethly cation ( C HCl 2 )
place? (D) dichlorocarbene (:CCl2)
[CBSE AIPMT 2015]

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Exercise # 4 PART - 2 PREVIOUS YEAR (AIIMS)

1. Consider the reaction (A) II > IV > I > III (B) IV > II > III > I
CH3 (C) III > II > IV > I (D) IV > I > II > III
CH2 CH [2011]
CH CH3
OTs 6. SN2 reaction readily occurs in
CH3 (A) CH3CH2 – O – CH3
(CH3)3CO
CH CH CH CH3 CH3
t-BuOH
(major product) O
(B) CH3 C CH3
The correct explanation is
(A) the product is formed due to nucleophilic CH3
substitution (C) CH2  CH – CH2 – O – CH3
(B) the product is formed according to Saytzeff’s
rule (D) Ph – CH2 – O – CH2 – CH3 [2011]

(C) conjugated double bond product is formed due 7. pKa increases in benzoic acid when substituent “x”
to higher stability because of resonance is bonded at para-position, then “x” is
stabilization
(A) – COOH (B) –NO2
(D) (CH3)3CO– is a better leaving group. [2009]
(C) –CN (D) – OCH3 [2012]
2. In solvents like DMSO, acetonitrile, F– ion of
dissolved NaF is more reactive than in methyl 8. Lassaigne’s test for the detection of nitrogen fails
alcohol. Explain in [2015]
(A) CH3OH is more polar than DMSO and CH3CN (A) H2N – CO – NHNH2.HCl
(B) CH3OH is less polar than DMSO and CH3CN (B) NH2 – NH2.HCl
(C) Unsolvated F– ion is DMSO or CH3Cn acts more (C) C6H5 – NH – NH2.HCl
efficiently as nucleophile (D) C6H5CONH2
(D) –OH group is a better leaving group than F– 9. In the reaction [2017]
ion.
NaOH (A)  CO2 HCl
3. 2-Phenylethylbromide when heated with NaOEt, Phenol  140 (B), here B is
elimination takes place. No deuterium exchange takes
place when the reaction is carried out in C2H5OD (A) benzaldehyde (B) chlorobenzene
solvent. The mechanism will be [2009]
(C) benzoic acid (D) salicylic acid
(A) E1 elimination (B) E2 elimination
(C) E1CB elimination (D) E2 or E1cB. CHO
NH2 NH2 CH2 NH2 OH
10. Br2 / CCl4 [2018]
4.  
OCH3
OH
OCH3 CH3 Cl
(I) (II) (III) (IV) CHO CHO
The correct decreasing order of pKb is [2011] Br Br
(A) I > II > III > IV (B) III > IV > II > I
(C) II > III > IV > I (D) IV > II > I > III (A) (B)
OCH3 Br OCH3
5. The correct decreasing order of pKa is
OH OH
OH OH OH OH
CHO CHO
Br Br
OCH3 Cl
CH3 NO2 (C) (D)
OCH3 OCH3
(I) (II) (III) (IV) OH OH
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12. Assertion : SN2 reaction of an optically active aryl
CH3 halide with an aqueous solution of KOH always
gives an alcohol with opposite sign of rotation.
NaOH Reason :S N 2 reactions always proceed with
11.   [2018]
H Br S 2
N inversion of configuration. [2017]

C6H5
13. Assertion : [2018]

CH3 C6H5 O C2H5

Br
(A) OH (B)
H H OH
C6H5 CH3 HBr
   + C2H2OH
NO2
p-nitroethyl NO2
CH3 OH phenyl ether

Reason : due to formation of highly stable

(C) (D) carbocation.
H OH H C6H5
C6H5 CH3

ASSERTION AND REASON

In each of the following questions, two statement
are given one is assertion and the other is reason.
Examine the statement carefully and mark the correct
answer according to the instruction given below
(A) If both the assertion and reason are true and
reason explains the assertion
(B) If both the assertion and reason are true but
reason does not explain the assertion
(C) If assertion is true but reason is false
(D) If assertion is false but reason in true
(E) Both assertion & reason are false

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MOCK TEST
STRAIGTH OBJECTIVE TYPE
COCH2COH3
NaOH
1.   P
Br
D H
Which of the following statement is correct
O
COCH2COH3
(A) P = (B) P = C CH3
OH O
D H
H D O
O
(C) P = CH3 (D) P =

H DO H D
2. Br NaOH
 Product, Product is

OH
OH

(A) (B) (C) (D)

O O
OH OH
(i) CH3O
3. CH3 – CH2SH (ii) ethylene oxide
Product, Product is :

(A) CH3 – CH2 – S – CH2 – CH2 – OH (B) CH3  CH2 O

(C) CH3 – CH2 – O – CH2 – CH2 – OH (D)

4. Read the following road map carefully

CH3
Ph — CH2COH
K I 1-Phenyl-2-propanol III TsCl
S.R = + 33.02°

CH3 CH3
Ph—CH2CHOK + gas Ph—CH2—CHOTs
II EtOTs IV C2H5OK

CH3 CH3
Ph—CH2—CH—OC2H5 Ph—CH2—CH—OC2H5
ethyl–1–phenyl–2–propylether Ethyl–1–phenyl–2–propylether

(A) Both the ethers obtained by the two routes have opposite but equal optical rotation.
(B) One of the either is obtained as a recemic mixture.
(C) Step II & III both are SN2 reaction and both have inversion
(D) Step II has inversion but step III has retention.

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5 A compound A has the molecular formula C5HgCl. It does not react with bromine in carbon tetrachloride. On
treatment with strong base it produces a single compound B. B has a molecular formula C5H8 and reacts with
bromine in carbon tetrachloride. Ozonolysis of B produces a compound C which has a molecular formula C5H8O2.
Which of the following structures is that of A?
Cl Cl Cl

(A) Cl (B) (C) CH3 (D)

CH3
Me2SO4
6. PhOH NaOH
P, P is
(A) Ph–O–SO2OMe (B) PhOMe (C) PhOSO2OPh (D) PhMe

Br

EtO
7. Ph + Ph – CH2 – NH2   Product, Product is
O
OEt

(A) Ph (B) Ph NH Ph
O
O
Br

(C) Ph NH Ph (D) Ph NH Ph
OH
CH3
In the reaction conc.H2SO4
8 CH3   A. The product A is –
OH OH
CH3 CH3
(A) (B)
O CH3 CH3
CH3 CH3
(C) (D)
CH3
COCH3
O
CH3(CH2)6 H
TsCl KI, DMSO
9 C—OH   A   B (Major) ; ‘B’ has stereochemistry –
C2H5
(A) R (B) S (C) R, S both (D) None of these
10 (CH3)3CCl + (CH3)3CO –K+   Product
(A) SN Product will be more (B) E2 Product will be more
(C) both will be same (D) None of these
11 Neopentyl iodideis treated with aq. AgNO3 solution, a yellow precipitate is formed along with other compound which is
OH
(A) (CH3)3CCH2NO3 (B) (CH3)2C CH2CH3
NO3
(C) (CH3)3CCH2OH (D) (CH3)2C CH2CH3

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*
CH 2Cl
12 The major end product of the following reaction is aq.AgNO3
 
OH
H3C

CH3
*
CH2 — OH
* O
OH
(A) H3C (B) H3C

O
(C) H 3C * O (D) CH3

NO2 NO2

13 CH3 C C H
CH3  A; Product ‘A’ is
OH OH

CH3
NO2

O
(A) CH3 C C (B) NO2 C C NO2

O
CH3
NO2
CH3
CH3

(C) O2N C CH(OH) CH3 (D) None of these

NO2


14 The products of hydrolysis of H3 O
  , is
O O C2H5
(A) HOCH2CH2CH2CH2CHO + CH3CHO (B) HOCH2CH2CH2CH2CH2OH + CH3CHO
(C) HOCH2CH2CH2CH2CHO + C2H5OH (D) HOCH2CH2CH2CH2CH2OH + C2H5OH

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15 CH2 — OH A. The produt is :

CH2 — HSO4 CH2 CH3 CH3

(A) (B) (C) (D)

OH

16 The major product P of the following reactionis

NH2 CH3 CH3
CH CH CH NH2
Cl

NH2 NH2 CH3 CH3

CH3 CH3
(A) C CH2 CH NH2 (B) CH CH2 C NH2
OCH3 OCH3

NH2 CH3 CH3 NH2 CH3 CH3

(C) CH CH CH NH2 (D) CH CH C NH2
OCH3

O

H3 O
17 The product of following reaction is 14  
O
Ar

OH
O
14

(A) (B) 14 + ArOH

O
OH
Ar

OH O

(C) 14 + ArOH (D) 14 + ArOH

O O

18 H 2C
14
H  /H 2O18
CH 2  
O
Which can not be the product
14 14
H 2C CH2 CH2 CH2 CH CH2
(A) 18 (B) 18 (C) 18 2 18
(D) A and B both
OH OH OH OH OH OH

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CH3
19. Peroxide
Ph – CH = C – CH3 + HBr  (X)
‘X’ is
Br CH3 Br
(A) Ph – CH – CH – CH3 (B) Ph – CH2 – C – CH3
CH3
(C) Ph – CH2 – CH – CH3 – Br (D) Ph – CH = C – CH2 – Br
CH3 CH3

20. X (major) ‘A’ is

H+


CH3 OH
CH3

(A) (B) (C) (D)

CH3 CH3 CH3 CH3

CH2 CH2 CH3 CH3

21. Which alcohol produces turbidity with Lucas reagent most slowly
(A) 2-Butanol (B) t-Butyl alcohol (C) Isobutyl alcohol (D) Diphenylcarbinol

MATRIX - MATCH TYPE

22. Match the compounds/ions in Column I with their properties/reactions in Column II.
Column I Column II
(A) C6H5CHO (p) Gives precipitate with 2, 4 – dinitrophenylhydrazine
(B) CH3C  CH (q) Gives precipitate with AgNO3
(C) CN– (r) Is a nucleophile
(D) I– (s) Is involved in cyanohydrin formation

ASSERTION AND REASON TYPE

Read the following question and choose the correct answer
(A) Assertion is True, Reason is True, Reason is a correct explanation for Assertion.
(B) Assertion is True, Reason is True, Reason is not a correct explanation for Assertion.
(C) Assertion is True, Reason is Fasle.
(D) Assertion is False, Reason is True.

H2SO4 CH3 CH3 CH3

23 Assertion : (CH3)3 CCH (CH3)3CCH = CH2 + C=C + CH2=C
CH3 CH3 CH(CH3)2
OH
Reason : It follows Hofmann’s elimination by E2.

OH H2SO4
24 Assertion : CH3 Heat
CH 3 Ph
Ph
Reason : Elimination follows E1 mechanism.

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25 Assertion : Ethers are prepared from alcohols acid medium through SN1 or SN2 mechanisms depending upon nature
of alcohol.

Reason : ROH + H+ R – OH 2
+ slow +
R O R OH 2 R O R + H 2O 
 ROR + H O+
3
H H

slow
or R – OH + H+ R OH 2 R+ + H2O

H2O
R+O R R O+ R fast
R OR + H3O+
H H

OH


26 Assertion : H
 
OH OH

H+
Reason :
OH

+
etc.
+
H

27. Assertion : Primary benzylic halides are more reactive than primary alkyl halides towards S N 1 reaction.
Reason : Reactivity depends upon the nature of the nucleophile and the solvent.
28. Assertion : Vinylic halides are reactive towards nucleophilic substitution reaction.
Reason : Reactivity is due to the polarity of carbon-halogen bond.
29. Assertion : Aryl halides undergo electrophilic substitution less readily than benzene.
Reason : Aryl halide gives only meta product w.r.t. electrophilic substitution.
30. Assertion : Iodination of akanes is carried out by heat in presence of readucing agent.
Reason : Iodination of alkanes takepalce explosively.

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 REACTION MECHANISM

ANSWER KEY
EXERCISE - 1
1. D 2. C 3. C 4. B 5. A 6. C 7. C 8. D 9. D 10. D 11. B 12. D 13. C
14. D 15. C 16. A 17. A 18. D 19. A 20. D 21. A 22. D 23. A 24. A 25. B 26. D
27. B 28. A 29. D 30. D 31. C 32. D 33. C 34. A 35. C

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

EXERCISE - 3 : PART - 1
1. A  (r), B  (q), C  (s), D  (p)
2. A  (q), B  (r), C  (s), D  (p)
3. A  (p, q), B  (q, r), C  (p, q, s), D  (s)

PART - 2
1. B 2. C 3. A 4. A 5. B 6. A 7. E 8. C 9. A 10. E 11. E 12. E 13. E
14. E 15. A 16. A 17. A 18. E 19. A

EXERCISE - 4 : PART - 1
1. C 2. A 3. D 4. B 5. D 6. B 7. C 8. D

PART - 2
1. C 2. C 3. B 4. D 5. A 6. A 7. D 8. B 9. D 10. B 11. B 12. D 13. E

MOCK TEST
1. C 2. B 3. A 4. A 5. B 6. B 7. B 8. D 9. A 10. C 11. B 12. D 13. B
14. C 15. C 16. B 17. C 18. C 19. B 20. D 21. C 22. A  p, q, s; B  q; C  q, r, s; D  q, r
23. D 24. A 25. A 26. A 27. A 28. D 29. C 30. D

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