SOLVED EXAMPLE

Ex.1 Most stable carbanion - Ex.6 Benzoic acid is less acidic than salicylic acid
(A) (CH3)3C– (B) (CH3)2CH– because of -
(A) Hydrogen bond (B) Inductive effect
(C) CH3CH2– (D) (C2H5)3C– (C) Resonance (D) none of these
Sol. [C] Sol. [D]
Primary carbanion is most stable It is due to ortho effect.
(sterric inhibition of resonance)
Ex.2 Which one of the following is strongest
acid - Ex.7 In a reaction of C6H5Y, the major product
(A) 2-chloropentanoic acid (>60%) is m-isomer, so the group Y is -
(B) 3-chloropentanoic acid (A) –COOH (B) –Cl
(C) 5-chloropentanoic acid (C) –OH (D) –NH2
(D) 4-chloropentanoic acid Sol. [A]
Sol. [A] –COOH have (–M effect)
2-chloropentanoic acid, due to more effective Ex.8 Which one of the following orders is correct
– I effect. regarding the –I effect of the substituents ?
(A) –NR2 < –OR > –F
Ex.3 The most stable carbanion is - (B) –NR2 > –OR > – F
(A) CH3CH2 CH 2 (B) CH3—CC– (C) –NR2 < –OR < –F
(D) –NR2 > –OR < –F
(C) CH3CH= CH (D) CH3— C =CH2
Sol. [C]
Sol. [B]
See series of –I effect.
When highly electronegative atom carry –ve
(–I effect  electronegativity)
charge than it is highly stable

Ex.4 Correct order of nucleophilicity - Ex.9 Which one of the following compounds will be
(A) CH3– < NH2– < OH– < F– most easily attacked by an electrophile ?
(B) F– < OH– <CH3– < NH2– Cl
(A) (B)
(C) OH– < NH2– < F– < CH3–
(D) F– < OH– < NH2– < CH3– CH3 OH
Sol. [D] (C) (D)
For same periods nucleophilicity  Basic
Strength. Thus if more E.N. atom consist –ve Sol. [D]
Charge than stability  & basic strength  –OH group show (+M) effect and also +M
There by nucleophilicity  effect is greater from (–CH3) group.

Ex.10 The weakest acid among the following -

Ex.5 Hydrogen bonding is maximum in - (A) CH3COOH (B) CH3CO2OH
(A) Ethanol (B) Diethyl ether (C) ClCH2COOH (D) CH3CH2COOH
(C) Ethyl chloride (D) Triethylamine
O
Sol. Due the presence of O–H bond.
Sol. [B] CH3–C–O–O–H peroxide is week acid.

ACME Study Point G.O.C [Link].816-817-3-819

Ex.11 The correct order of boiling point for primary Ex.14 Strongest acid out of the following -
(1º), secondary (2º) and tertiary (3º) alcohols is (A) CH3COOH (B) ClCH2COOH
(A) 2º > 1º > 3º (B) 3º > 2º > 1º (C) CH3CH2COOH (D) CH3)2CHCOOH
Sol. [B]
(C) 1º > 2º > 3º (D) 2º > 3º > 1º
Acidic strength  –I power of Cl group.
Sol. [C]
On increase branching surface area decrease, Ex.15 Increasing order of acid strength among
thus boiling point decrease. p-methoxyphenol, p-methylphenol, and
p-nitrophenol is -
Ex.12 Which of the following is most acidic ? (A) p-nitrophenol, p-methoxyphenol, p-methylphenol
(A) m-chlorophenol (B) benzyl alcohol (B) p-methylphenol, p-methoxyphenol, p-nitrophenol
(C) phenol (D) cyclohexanol (C) p-nitrophenol, p-methylphenol, p-methoxyphenol
(D) p-methoxyphenol, p-methylphenol, p-nitrophenol
Sol. [A] Sol. [D]
OH+ CH2–OH+  – 
OH OH OH

+
–I Cl –I
0 – NO2
OH OCH3 CH3
OH (+m) (+m) (–m)
(i) (ii) (iii)
+I + m (–OCH3) > + m (–CH3)
(i) < (ii) < (iii)
–I (Cl) > –  (–C6H5CH2)
 of acidic strength

Ex.13 Among the following the strongest base is - Ex.16 In the following compounds -
OH OH OH OH
(A) C6H5NH2 (B) p-NO2–C6H4NH2
(C) m–NO2–C6H4NH2 (D) C6H5CH2NH2
Sol. [D] NO2

NH2  CH3 NO2

NH2
(I) (II) (III) (IV)
0 –
The order of acidity is -
(A) III > IV > I > II (B) I > IV > III > I
(C) II > I > III > IV (D) IV > III > I > II
NO2 Sol. [D]
(–M)
0 – + 
OH OH OH OH
NH2 CH2–NH2

+
NO2
CH3 (–I) NO3
NO2
(–I) lone pair localised (+M) (–M)
(+I) Primary amine (III) (IV)
(I) (II)
Aromatic primary amine is more basic than
aniline. at meta position +m effect absent thus only –
Because lone pair delocalised. effect of –NO2 is taken in (III)
(IV) > (III) > (I) > (II)

ACME Study Point G.O.C [Link].816-817-3-819

Ex.17 Most powerful leaving group in following - Ex.20 Increasing order of basic strength of following
(A) NH2– (B) OH– (C) CH3– (D) F– compounds is
Sol. [D] C6H5NH2, (CH3)3N, (C6H5)2NH, C6H5NHCH3
Weak base are always better leaving group. (I) (II) (III) (IV)
(A) III < IV < I < II (B) III < I < IV < II
..
:O: :O:– (C) I < III < II < IV (D) II < IV < III < I
.. +
Sol. [B]
Ex.18 (I) H–C–OH
.. (II) H–C=OH
..
.. NH2 CH3
:O:–
+
:O:
.. .. CH3–N
(III) H–C–OH (IV) H–C–OH
.. ..
+ .. –
Increasing order of stability is - CH3
(A) I < III < II < IV (B) IV < III < II < I (a) lone pair delocalised lone pair localised
(C) III < IV < II < I (D) II < IV < III < I (I) (II)
Sol. [B] NH NH–CH3
(I)  have higher no of covalent bond
(II)  have complete octet
lone pair delocalised lone pair delocalised
(III)  more E.N. atom consist –ve charge (III) (IV)
Thus II is more basic.
Ex.19 Increasing order of acidity in para methyl (I), (b) Now than apply the theory of power of
chloro (II), amino (III), and nitro (IV) benzoic delocalisation which is highest in III, thus it is
acids is - least basic.
(A) III < II < I < IV (B) I < II < IV < III (c) 2° amine is more basic than 1°
(C) III < I < II < IV (D) II < I < III < IV
thus (IV) is more basic than (I) due to +  effect
Sol. [C] of –CH3 group.
 
COOH COOH  (III) < (I) < (IV) < (II)

Ex.21 The compound that is most reactive towards

electrophilic nitration is -
CH3 Cl (A) Toluene (B) Benzene
(i) (ii) (C) Benzoic acid (D) Nitrobenzene
Operating Sol. [A]
group  +m CH3 COOH NO2
 
COOH COOH

 – COOH, & –NO2 group are deactivating

thus they are less reactive towards
NH2 NO2 electrophile nitration then benzene.
(iii) (iv)  – CH3 group is activating thus it is most
operating reactive towards electrophilic nitration then
group  +m –m benzene.
+ m (CH3) < + m (NH2)
ACME Study Point G.O.C [Link].816-817-3-819
Ex.22 The most unlikely representation of resonance Sol. [C]
structures of p-nitrophenoxide ion is - NO2
– 
– CH3 NH2
O– + O O + O– NO2–C NH2
N N
NO2
(A) (B) + –

O– O  
Cl–CH2 NH2 I CH2–NH2
O + O O– + O
N N – –

(C) (D) 
– H–NH2

O– O 
Sol. [C] As magnitude of +ve charge  basic strength 
In III structure, outermost orbit of N-atom have
10 e–which is invalid condition for resonance, Ex.25 Arrange in increasing pKa
thus it most unlikely structure. (a) CH3CH2COOH
(b) CH3CH2CH2COOH
Ex.23 Consider the following three halides - (c) CH3COOH
(1) CH3–CH2–Cl Correct answer is-
(2) CH2=CH–Cl (A) (c) < (a) < (b) (B) (b) < (a) < (c)
(C) (a) < (c) < (b) (D) (b) < (c) < (a)
(3) C6H5–Cl
Sol. [A]
Arrange C–Cl bond length of these compound
in decreasing order - Ex.26 Arrange in increasing basic strength
(A) 1 > 2 > 3 (B) 1 > 3 > 2 (a) Cl – CH2 – COOH
(C) 3 > 2 > 1 (D) 2 > 3 > 1 (b) Cl – CH2 – CH2– CH2 – COOH
Sol. [A]
(c) Cl – CH2 CH2 COOH
Correct answer is-
Ex.24 Arrange the following in increasing basic
(A) (a) < (c)< (b) (B) (b) < (a) < (c)
strength - (C) (c) < (b)< (a) (D) (a) < (b) < (c)
NO2 Sol. [A]
(a) CH3NH2 (b) NO2–C–NH2
NO2 Ex.27 Which one of the carbanions is most stable?
(c) Cl – CH2 – NH2 (d)  – CH2 – NH2 

CH2 CH2
(e) NH3
NO2
Correct answer is - (A) (B)
(A) (a) < (b) < (c) < (e) < (d) NO2
(B) (a) < (b) < (c) < (d) < (e)  
CH2 CH2
(C) (b) < (c) < (d) < (e) < (a)
CN
(D) (c) < (b) < (e) < (d) < (a) (C) (D)

CN
ACME Study Point G.O.C [Link].816-817-3-819
Sol. [A] Ex.29 Which one of the following chlorides gives
 
 ++  ++ white precipitate with AgNO3 most readily -
CH2 CH2
NO2 (A) CH2=CH–CH2Cl
–M
–I (B) CH2=CH–Cl
–M (C) CH3–CH2Cl
NO2
 ++  ++ (D) (C6H5)2CH–Cl
CH2 CH2
Sol. [D]
CN
–M –M
O O
CN Ex.30 Compound: on removal of proton
1
Stability  , gives a carbanion. The most stable carbanion
Magnitude of ch arg e
should be
Thus, 1 is most stable. O O O O

(A)  (B) 
Ex.28 What is the correct increasing order of bond
O O
lengths of the bonds indicated as I, II, III and
IV in following compounds - (C)  (D) All the above
II III IV Sol.[C] In this case negatively charged carbon is
present between two electron attracting groups.
I
As such it is a stable carbanion.
(A) I < II < III < IV (B) II < III < IV < I
(C) IV < II < III < I (D) IV < I < II < III
Sol. [D]

ACME Study Point G.O.C [Link].816-817-3-819

 LEVEL # 1
Questions Questions
based on Hybridisation based on Inductive effect

Q.1 Which of the following orbital overlaps is Q.6 The inductive effect -
involved in the formation of the carbon–carbon (A) implies the atom's ability to cause bond
single bond in the molecule HCC–CH=CH2 polarization
(A) sp3–sp3 (B) sp2–sp3 (B) increases with increase of distance
(C) implies the transfer of lone pair of
(C) sp–sp2 (D) sp3–sp
electrons from more electronegative atom
to the lesser electronegative atom in a
Q.2 Which of the following species (I), (II), (III), molecule
(IV) has an sp2 hybridized carbon - (D) implies the transfer of lone pair of
CH 3 CH3 CH 3 . : CH 2 electrons from lesser electronegative atom
(I) (II) (III) (IV) to the more electronegative atom in a
molecule
(A) (I) only (B) (I) and (II) only
(C) (I) and (III) only (D) (I), (III) and (IV) Q.7 In which of the following compounds is
hydroxylic proton the most acidic ?
F
Q.3 Hybridisation of arrow headed 'C' is (A) (B) I
O O
H H
(A) sp2sp3 (B) sp3sp3 O O
(C) H (D) H
(C) sp2sp2 (D) sp3sp3d
F F

Q.4 Which of the following has a bond formed by Q.8 Decreasing – I power of given groups is -
overlap of sp–sp3 hybrid orbital ? (a) –CN (b) –NO2 (c) –NH2 (d) –F
(A) CH3–CCH (A) b > a > d > c (B) b > c > d > a
(C) c > b > d > a (D) c > b > a > d
(B) CH3–CH=CH–CH3
Q.9 Express in decreasing order of (+) -
(C) CH2=CH–CH=CH2
(a) CH3CH2 – CH2 – (b) CH3 –
(D) CHCH CH3 CH3
(c) CH3–C–CH2–CH3 (d) CH3–C–
CH3
Q.5 The maximum number of carbon atoms (e) CH3–CH–CH2–
arranged linearly in the molecule CH2CH3
CH3–CC– CH=CH2 is - Correct answer is -
(A) (c) > (d) > (e) > (a) > (b)
(A) 5 (B) 4 (B) (d) > (a) > (b) > (c) > (e)
(C) 3 (D) 2 (C) (a) > (b) > (c) > (d) > (e)
(D) (a) > (b) > (c) > (e) > (d)

ACME Study Point G.O.C [Link].816-817-3-819

Q.10 Which among the given acid has lowest pKa Q.15 Which of the following contain + M but - 
value - effect -
(A) Chloroacetic acid (A) O = CH – (B) – NO2
(B) Bromoacetic acid (C) – Cl (D) CH3 –
(C) Nitroacetic acid
(D) Cyanoacetic acid
Q.16 The meta-directing power of the groups –NH2,
–OCH3, –C6H5 and – NO2 follows the order
Q.11 Arrange basicity of the given compounds in
decreasing order - (A) –NH2 > –OCH3 > –C6H5 > –NO2
(a) CH3 – CH2 – NH2 (b) CH2 = CH – NH2 (B) –NO2 > –C6H5 > –OCH3 > –NH2
(c) CH  C – NH2 (C) –OCH3 > –NH2 > –C6H5 > –NO2
(A) a > b > c (B) a > c > b (D) –OCH3 > –NO2 > –NH2> –C6H5
(C) c > b > a (D) b > c > a
Q.17 Which of the following pairs of structures do
not represent resonating structures -
Q.12 Consider following acid
O OH
ClCH2COOH, CH3COOH, CH3CH2COOH
(A) CH3 – C – CH3 ; CH3 – C = CH2
I II III

Correct order of their pH value
(B) O ; O
(A) III < II < I (B) I < II < III

(C) I < III < II (D) II < I < III OH OH

(C) CH3 – C – CH3 ; CH3 – C – CH3
Q.13 Which is the correct order of increasing 

basicity ? (D) CH3 –C–OH ; CH3–C=OH

(A) CH3CH2CH3 < CH3CH2SH < CH3CH2OH O O
< CH3CH2NH2 Q.18 In which of the following structure the
(B) CH3CH2CH3 < CH3CH2OH < CH3CH2SH electrophilic attack of nitronium ion will place
it at m-position
< CH3CH2NH2 O– CF3 Cl NO2
(C) CH3CH2NH2 < CH3CH2SH < CH3CH2OH
< CH3CH2CH3
I II III IV
(D) CH3CH2CH3 < CH3CH2OH < CH3CH2NH2
(A) only IV (B) II and IV
< CH3CH2SH
(C) II, III, IV (D) only I

Questions
based on Mesomeric effect Q.19 Which of the following is the strongest
base -
Q.14 'M' effect is the resonance of - (A) (B)
(A)  electrons only N N
(B)  electrons only H
NH2
(C)  and  both
(C) (D)
(D) (+)ve and (-) charge. N
H
ACME Study Point G.O.C [Link].816-817-3-819
Q.20 Arrange in increasing order of basicity Q.25 Consider following benzyl alcohol
CH3NH2, (CH3)2NH, C6H5NH2, (CH3)3N CH2OH CH2OH
(A) (CH3)3N<(CH3)2NH < CH3NH2 < C6H5NH2
(B) Reverse of (A)
(C) C6H5NH2< (CH3)3N < CH3NH2 < (CH3)2NH NO2

(D) Reverse of (C) I II

CH2OH CH2OH
Q.21 Which of the following pairs represent
resonating structures -
(A) ClCH2CH=CHCH3 and CH2=CH–CH–CH3 OCH3 Cl
Cl III IV

Correct order of their Kb value is -
 ..
(B) :CH2–NN: and CH2=N=N (A) III > IV > II > I (B) III > I > IV > II
(C) CH3–CN and CH3–N C (C) I < II < III < IV (D) IV > II > I > III
(D) All the above
Questions
based on Hyperconjugation
Q.22 In following acid, the correct increasing order
of acidic strength acid Q.26 Greater reactivity of 'H' is explained on the basis
HCOOH, CH3COOH, C6H5COOH of -
(A) + M effect
I II III (B) conjugative effect
(A) I < II < III (B) II < I < III (C) Hyper conjugative effect
(C) III < II < I (D) II < III < I (D) – I effect

Q.27 Select the most stable carboncation among the

Q.23 Arrange their Acidic strength
following -
OH 
H2O CH3OH
(A)

II III 
I (B)
(A) I > II > III (B) II > I > III
(C) III < II > I (D) II < III < I (C) 

Q.24 Arrange the following in Increasing of their (D)


basicity
OH–, CH3COO– CI– Q.28 Which of the following molecule has longest
I II III C = C bond length ?
(A) CH2 = C = CH2
(A) III > II > (B) III < II < I (B) CH3–CH = CH2
(C) II < III < I (D) II < III > I CH3
(C) CH3 – C – CH = CH2
CH3
(D) CH3 – C = CH2
CH3

ACME Study Point G.O.C [Link].816-817-3-819

Q.29 Correct order of reactivity - Q.34 Shifting of electron of a multiple bond under
(A)CH2=CH2>CH3—CH=CH2>(CH3)2C=CH2 the influence of a reagent is called -
(B)CH2=CH2>CH3—CH=CH2 < (CH3)2C=CH2 (A) I–effect (B) M–effect

(C)CH2=CH2<(CH3)2C=CH2 < CH3—CH=CH2 (C) E–effect (D) T–effect

(D)CH3—CH=CH2<CH2=CH2< (CH3)2C=CH2
Questions
based on Bond fission
Q.30 Which one of the following compounds
undergoes nitration fast - Q.35 Homolytic fission of a hydrocarbon will
liberate :
(A) (B) (A) Carbonium ions (B) carbanions
(C) free radicals (D) carbenes

(C) (D)
Q.36 Heterolytic fission of carbon-chlorine bond
produces :
Questions (A) two free radicals
based on Electromeric effect
(B) two carbonium ions
Q.31 Which among the following statement is wrong (C) two carbanions
(A) Cl–C bond is shorter in CH2=CH–Cl than (D) one cation and one anion
that in CH3CH2–Cl
(B) CH2=CH–CH2+ is allylic carbocation Q.37 In CH3CH2OH, the bond that undergoes

(C) C=C bond in CH2= CH–Cl is shorter than heterolytic cleavage most readily is -
(A) C—C (B) C—O (C) C—H (D) O—H
in CH2=CH2
(D) Electromaric effect comes into play at the
Q.38 Which among the following statements are
demand of attacking reagents
correct ?
(1) Energy needed for homolytic bond fission
Q.32 Which statement is correct for electromeric
is less than that required for the heterolytic
effect -
bond fission
(1) It is a temporary effect
(2) Homolytic bond fission gives neutral
(2) It is the property of  bond species which is paramagnetic in character
(3) It takes place in presence of reagent, i.e., (3) Energy needed for heterolytic bond fission
electrophile or nucleophile is less than that required for the homolytic
(4) All are correct bond fission.
(4) Heterolytic bond fission takes place in non
Q.33 Which of the following exhibit electromeric polar solvents
effect - (A) Only 1 (B) 1 and 3
(A) alkanes (B) aldehydes (C) 1 and 2 (D) 1, 2 and 4
(C) alkyl halides (D) alkyl amines

ACME Study Point G.O.C [Link].816-817-3-819

Questions Q. 43 Following carbocation changes to more stable
based on Reaction Intermediate
carbocation:

Q.39 Which of the following statements is correct? CH2
(A) +  group stabilised carbocation

(A) CH2 (B)  CH3
(B) +  group destabilised carbocation
(C) –  group stabilised carbanion 
(C) CH3 (D)  CH2
(D) –  group destabilises stabilised caranion

Q.44 Carbon free radicals are -

Q.40 Which of the following statements is wrong ?
(A) Diamagnetic (B) Paramagnetic
(A) a tertiary free radical is more stable than a
(C) Ferromagnetic (D) Non magnetic
secondary free radical
(B) a secondary free radical is more stable than Q.45 Arrange stability of the given carbocations in
a primary free radical decreasing order :
   
(C) atertiary carbonium ion is more stable than CH2 CH2 CH2 CH2
a secondary carbonium ion
(D) a primary carbonium ion is more stable
than a secondary carbonium ion OCH3 OH NH2 Cl
I II III IV
Q.41 Consider the following carbanions - (A) I > II > III > IV
 
(B) III > I > II > IV
(a) CH3 – C H 2 (b) CH2 = C H (C) IV > I > II > III
 (D) II > III > I > IV
(c) CH  C
Correct order of stability of these carbanions in Q.46 The order of stability of the following
carbanion is :
decreasing order is -

 
(A) a > b > c (B) b > a > c 
R C H2
(C) c > b > a (D) c > a > b ( I)   IV
(A) I > II > III > IV (B) I > III > II > IV
Q.42 The stability of given free radicals in (C) IV > III > II > I (D) III > IV > I > II
decreasing order is -
 
Q.47 Which free radical is the most stable :
(a) CH3– C H 2 (b) CH3– C H –CH3 
(A) C6H5— C H 2

(c) CH3–C–CH3 (d) C H 3 
(B) CH2=CH— C H 2
CH3

(A) c > d > a > b (B) a > b > c > d (C) CH3— C H —CH3
(C) c > b > d > a (D) c > b > a > d (D) CH3–C–CH3
CH3

ACME Study Point G.O.C [Link].816-817-3-819

Q.48 Rank the following radicals in order of Questions
based on Organic Reagent
decreasing stability

Q.51 Which of the following statements are correct

for nucleophile :
I II III IV (A) All negatively carged species are
(A) III > II > I > IV nucleophile
(B) III > II < I < IV (B) Nucleophiles are Lewis bases
(C) II > III > II > IV (C) Alkenes, alkynes, benzene and pyrrole are
nucleophiles
(D) III < II < I < IV
(D) All are correct
Q.49 Reactivity of C—H bond (abstraction of H)
CH2=CH—H, CH3—H, CH3CH2—H Q.52 Which among the following species is an
ambident nucleophile ?
vinylic(i) methyl(ii)1° (III) 

(CH3)2CH—H (CH3)3C—H, (A) CH3– C H 2 (B) CH2=CH2

 ..
2°(IV) 3°(V) (C) CN (D) N H 3
(A) II < III < I < IV < V
(B) I > II > III > IV > V Q.53 Which of the following statements are correct
(C) I < II < III < IV < V for nucleophile -
(D) I < II < IV < III < V (A) All negatively charged species are
nucleophile
(B) Nucleophiles are Lewis bases
Q.50 Rank the following free radicals in order of (C) Alkenes, alkynes, benzene and pyrrole are
decreasing stability : nucleophiles
 (D) All are correct
(I) C6H5 C H C6H5
 Q.54 Which of the following reaction intermediates
(II) C6H5– C H –CH = CH2
are electrophilic in character ?

(III) CH3– C H –CH3 (a) Carbocation (b) Carbanion
(c) Free radicals (d) Carbenes

(IV) C6H5 – C H – CH3 (A) Only b (B) a and c

(C) a, c and d (D) a, b, c and d
(V) CH3CH = CHCH2 C H 2

(VI) CH3–CH2–C–CH3 Q.55 Which among the following compounds behave

CH3 both as an electrophile as well as a nucleophile:

(A) I > II > III > IV > V > VI (a) CH2=CH2 (b) CH2=CH– C H 2
(B) VI > V > IV > III > II > I O O
(C) I > II > IV > VI > III > V (c) CH3–C–CH3 (d) CH3–C–Cl
(D) I > IV > VI > V > II > III (A) Only a (B) a and b
(C) c and d (D) b, c and d

ACME Study Point G.O.C [Link].816-817-3-819

Questions
based on Nucleophilicity & Leaving group

Q.56 Which of the following has the highest

nucleophilicity -
(A) F– (B) OH–
(C) CH3 (D) NH 2

Q.57 Arrange the following nucleophiles in the order

of their nucleophilic strength -
(A) OH– > CH3COO– > –OCH3 > C6H5O–
(B) CH3COO– < C6H5O– < –OCH3 < OH–
(C) C6H5O– < CH3COO– < CH3O– < OH–
(D) CH3COO– < C6H5O– < OH–< CH3O–

Q.58 Correct order of leaving group tendency -

(A) – > Br – > Cl– > F–
(B) F– > Cl– > Br – > 
(C) Cl– > F – > Br – > –
(D) – > Cl– > Br – > F

Q.59 The nucleophilicities of CH3–, NH2–, OH– and

F– decrease in the order –
(A) CH3– > NH2– > OH– > F–
(B) OH– > NH2– > CH3– > F–
(C) NH2– > OH– > CH3– > F–
(D) CH3– > OH– > F– > NH2–

Q.60 Which of the following is the strongest

nucleophile -
(A) OH– (B) CH3OH
(C) CH3 S– (D) CH3O–

ACME Study Point G.O.C [Link].816-817-3-819

 LEVEL # 2
Q.1 Which of the following belongs to +  group Q.7 In the anion HCOO–, the two carbon-oxygen
(A) —OH (B) —OCH3 bonds are found to be equal length. What is the
(C) —COOH (D) —CH3 reason for it -
(A) the C=O bond is weaker than the C—O
bond
Q.2 Which of them is false for order of –I effect
(B) the anion HCOO– has two resonating
(A) – F > – Cl > – Br > – I structures
  (C) the electronic orbitals of carbon atom are
(B)  N R 3   N H3   NO2
hybridized
(C) –OCH3 > – OH > – NH2 (D) the anion of obtained by removal of proton
from the acid molecule
(D) > – C  CH > H

Q.3 Which of the statement is not correct? Q.8 Which of the following resonance structures is
the major contributor to the resonance hybrid ?
(A) – NH2 is ortho-para directing group
 ..
(B) – CHO is meta directing group CH3 – CH2 – C H – O
.. CH 3

(C)  CCl2 is an electrophile (I)



(D) – O

H is (– M) group   CH3 – CH2 – CH = O
.. CH 3

(II)
(A) I
Q.4 Among the following compounds, the strongest
(B) II
acid is -
(C) Both have equal contribution
(A) HC  CH (B) C6H6
(D) They are not resonance structures
(C) C2H6 (D) CH3OH
Q.9 Consider the following three halides -
Q.5 Heterolysis of propane will yield - (a) CH3–CH2–Cl
 
(A) C H 3 and C 2 H 5 radicals (b) CH2=CH–Cl

(B) CH3 and CH3CH2 ions (c) C6H5– Cl

Arrange C–Cl bond length of these compounds
(C) CH3 and CH3CH2 ions
in decreasing order -
(D) CH3 and CH3CH2 ions (A) a > b > c (B) a > c > b
(C) c > b > a (D) b > c > a
Q.6 Carbocations may be stabilised by -
(A) -bonds only at allylic position 
Q.10 The species CH3 C HCH 3 is less stable than -
(B) bonds only at vinylic position

(C) bonds at allylic and nonallylic position (A) (CH3)3 C+ (B) CH 3CH 2 C H 2
also 

(D) – I effect (C) CH 3 C H 2 (D) CH3

ACME Study Point G.O.C [Link].816-817-3-819

 (C) Nitrite ion (D) Sulphite ion
Q.11 Increasing order of electrophilic substitution for Q.16 Which one of the nitrogen containing
following compounds - compounds is an electrophile :
CH3 OCH3 CF3 (A) NH2—NH2 (B) NH2—OH

(C) NF3 (D) NH3

(I) (II) (III) (IV)

(A) IV < I < II < III (B) III < I < II < IV Q.17 Consider the following species
 
(C) I < IV < III < II (D) II < III < I < IV (a) O H (b) C H 3 – O
 
Q.12 Arrange in decreasing pKb - (c) C H 3 (d) N H 2
(a) F–CH2CH2COOH Arrange these nucleophilic species in their
(b) Cl–CH–CH2–COOH decreasing order of nucleophilicity -
Cl (A) c > d > b > a (B) b > a > c > d
(c) F–CH2–COOH (C) a > b > c > d (D) c > a > b > d
(d) Br–CH2–CH2–COOH
Correct answer is - Q.18 Which one of the following statements is not
(A) (b) > (d) > (a) > (c) correct for electrophile :
(B) (a) > (c) > (d) > (b) (A) Electron deficient species are electrophile
(C) (c) > (b) > (a) > (d) (B) Electrophiles are Lewis acids
(D) (d) > (b) > (a) > (c)
(C) All + ive charged species are electrophile
Q.13 The strongest base is - (D) AlCl3, SF6, IF7 and SO3 are electrophiles
H2N NH
(A) CH3–N–CH3 (B) C
Q.19 Which of the following is an electrophilic
CH3 NH2
reagent ?
(C) C6H5–N–C6H5 (D) CH3—NH—CH3
(A) H2O (B) OH–
C6H5
(C) NO2+ (D) none
Q.14 In which of the following cases, the
carbocation (I) is less stable than the Q.20 Consider the following carbanions :
carbocation (II) ? 
..
  (I) H3CO CH2
(A) C6 H5  C H 2 (I), CH 2  CH  C H 2 (II)
+ + 
..
CH2 CH2 (II) O2N CH2
(B) (I), (II)

..
  (III) CH2
(C) CH 2  C H(I), CH3  C H 2 (II)
  
(D) H 3C  C H 2 (I), CH 2  C H 2 (II) ..
(IV) H3C CH2
|
F
Correct decreasing order of stability is -
Q.15 Which among the following species is an (A) II > III > IV > I (B) III > IV > I > II
ambident nucleophile - (C) IV > I > II > III (D) I > II > III > IV
(A) Acetone (B) Cyanide ion
ACME Study Point G.O.C [Link].816-817-3-819
 OH Q.25 Arrange the following in increasing of pH
OH OH
value
NO2
Q.21 NH2 NH C6H5 NH2
NO2 NO2
(I) (II) (III)
Arrange following phenol in increasing order (I) (II) (III)
of pKa value (A) III > I > II (B) III < I < II
(A) I < II < III (B) III < I < II (C) III < II > I (D) II < III < I
(C) III < II < I (D) I < III < II
Q.26 Arrange in Increasing of basic strength
NH2 NHCH3 N(CH3)2
CH2COOH

CH2=CHCH2COOH
Q.22
(I) (II) (III)
(I) (II) (A) II < III < I (B) I > II > III
CH 3CH 2 COOH (C) III > II < I (D) I < II < III
(III)
Arrange following acid in decreasing order of 
Q.27 Electrophile N O 2 attacks the following
[H+] conc.
 
(A) I > II > III (B) II > III > I CCl3 NO2 NH3 O
(C) II > I > III (D) III > II > I

Q.23 Arrange Increasing order of their Ka value. (I) (II) (III) (IV)

oxalic acid, succinic acid, In which cases N O 2 will be meta-position :
I II
(A) II and IV (B) I, II and III
malonic acid, adipic acid
(C) II and III only (D) I only
III IV
(all dibasic)
Q.28 Arrange Decreasing order of basicity
(A) III < II < I < IV (B) II < III > I > IV 
(C) I > III > II > IV (D) II > I > III < IV Cl– RCOO– OH– RO– N H2
I II III IV V
Q.24 Arrange the following in Decreasing order of (A) I > II < III > IV < V
their pKa value (B) V > IV > II > III > I
CH2=CHCH2NH2, CH3CH2CH2NH2 , (C) I > II > III > IV > V
I II (D) V > IV > III > II > I
CHCCH2NH2
Q.29 Arrange the Stability of following
III
(A) I > II < III (B) II > I > III
(C) III > II > I (D) II < III < I
(I) (II) (III)
(A) I < II < III (B) II < I < III
(C) I < III < II (D) II < III < I

ACME Study Point G.O.C [Link].816-817-3-819

Q.30 Stability of following radical is Q.36 Arrange acidity of given compounds in
CH3 CH2• decreasing order in gas phase
 
  • (I) N H 4 (II) CH 3 – N H 3
CH2= C H , C H 2 CH=CH2
 
(III) (CH 3 ) 2 N H 2 (IV) (CH 3 ) 3 N H
I II III IV
(A) II > III > II > IV (B) III > II > I > IV (A) I > IV > II > III (B) IV > III > II > I
(C) I > II > IV > III (D) I > II > III > IV
(C) III < II < I < IV (D) I < IV < II < III

Q.37 Which of the following shows the correct order

Q.31 Increasing of the following for SE of decreasing basicity in aqueous medium ?
CH3 NO2 OH (A) (CH3)3N > (CH3)2NH > CH3NH2 > NH3
(B) (CH3)2NH > (CH3)3N > CH3NH2 > NH3
(C) (CH3)2NH > CH3NH2 > (CH3)3N > NH3
(I) (II) (III) (IV) (D) (CH3)2NH > CH3NH2 > NH3 > (CH3)3N
(A) IV < III < II < I (B) IV < III < I < II
(C) III < I < II < IV (D) III > I > II > IV Q.38 The correct order of increasing basicity is -
(A) pyrrole < pyridine < Me3N < Et3N
Q.32 Increasing order of the stability is (B) pyridine < pyrrole < Et3N < Me3N
CH3CH=CH2 CH3CH2CH=CH2, (C) pyrrole < Et3N < Me3N < pyridine
I II (D) Me3N < Et3N < pyridine < pyrrole
CH3
CHCH=CH2 (CH3)3CCH=CH2
CH3 Q.39 Give the correct order of decreasing basicity of
III IV the following compounds,
(A) I > II > III > IV (B) I > III > II > IV C6H5NH2 (C6H5)2NH (C6H5)3N C6H11NH2
(C) I > IV > III > II (D) IV > III > II > I I II III IV
(A) I > II > III > IV (B) IV > III > II > I
(C) IV > I > II > III (D) III > II > I > IV
Q.33 Decreasing order of Basicities -
(A) RO– > OH– > CN– > RCOO– > NO3– Q.40 The correct order of stability of the following
(B) NO3– > CN– > RCOO– > RO– > OH– carbocations is -
(C) OH– > CN– > RCOO– > NO3– > RO–  
(A) CH 3CH 2 C H 2 > CH 2  CH – C H 2 >
(D) NO3– > CN– > RCOO–  RO– > OH–  
CH2= CH C HCH 3 > CH2=CH C (CH3)2
 
Q.34 COO electrophilic substitution (B) CH2= CH C H 2 > CH 3CH 2 C H 2 >
 
occurs at CH 2  CH C(CH 3 ) 2 > CH2 = CH C HCH 3
(A) o/p of 1st ring (B) meta at 1st ring  
(C) CH 2  CH C(CH 3 ) 2 > CH2 = CH C HCH 3 >
(C) o/p at 2nd ring (D) meto of 2nd ring.
 
CH 2  CH C H 2 > CH 3CH 2 C H 2
Q.35 Which of the following molecules can behave  
(D) CH2= CH  C HCH 3 > CH 2  CH C(CH 3 ) 2
both as a nucleophile and an electrophile ?
 
(A) CH3NH2 (B) CH3Cl > CH3CH2– C H 2 > CH2 = CH C H 2
(C) CH3CN (D) CH3OH

ACME Study Point G.O.C [Link].816-817-3-819

Q.41 The order of reactivity of the following Q.47 Which nitrogen in LSD is most basic
alcohols towards concentrated HCl is -
OH O
(1) (3)
H–N C–N(C2H5)2
F (2)
F
OH , N
II
I
OH CH3
Ph OH
(A) 1
, (B) 2
III IV
(A) I > II > III > IV (B) I > III > II > IV (C) 3
(C) IV > III > II > I (D) IV > III > I > II (D) All are equally basic

Q.42 The relative rate of addition of HCl to the

following compounds follows the order - Q.48 Different hydrogens in
(A) CH2=CHCO2H > CH2 = CH2 > a b b c d e f
CH3CH = CH2 > (CH3)2C = CH2 CH3CH = CH—CH2—CH2—CH(CH3)2 are
(B) (CH3)2C = CH2 > CH3CH = CH2 > represented by alphabets. Arrange them in
CH2 = CH2 > CH2 = CHCO2H
decreasing order of reactivity towards radical
(C) CH2 = CH2 > CH3CH = CH2 >
substitution :
CH2 = CHCO2H > (CH3)2C = CH2
(A) c > a > e > d > f > b
(D) CH3CH = CH2 > CH2 = CHCO2H >
(CH3)2C = CH2 > CH2 = CH2 (B) f > b > a > c > d > e
(C) b > c > a > f > d > e
Q.43 The order of decreasing stability of the cations (D) a > b > c > d > e > f
  
CH 3 C HCH 3 CH 3 C HOCH 3 CH 3 C HCOCH 3
I II III Q.49 Which most readily reacts with AgNO3 to give ppt.:
is - (A) Br
(A) III > II > I (B) I > II > III
(C) II > I > III (D) I > III > II
(B) CH=CH–CH2Br
COOH

Q.44 , pKa value of the compound (C) Br

X
decreases if X is: (D) Br
(A) –NO2 (B) – NH2 (C) – OH (D) – OCH3
Q.50 Arrange the following in Decreasing of their
Q.45 Which type of hybrid orbitals do C and N use
in the formation of C–N bond in pyrrole? basic nature.
NH2
:NH

(A) sp2 and sp2 (B) sp2 and sp3

N N
(C) sp and sp3 (D) sp and sp2
H
Q.46 Weakest base among the following is: III
I II
(A) NH (B) NH NH (A) I > II > III (B) II < III < I
(C) III < II > I (D) II > I > III
(C) NH2 (D) N

ACME Study Point G.O.C [Link].816-817-3-819

 LEVEL # 3
Single correct type Questions Q.5 Give the correct order of increasing acidity of
Q.1 Which of the following statements is not true the following compounds -
about the resonance contributing structures of a (I) ClCH2COOH (II) CH3CH2COOH
resonance hybrid -
(A) Contributing structures contribute to the (III) ClCH2CH2COOH (IV) (CH3)2CHCOOH
resonance hybrid in proportion of their (V) CH3COOH
energies
(A) V < II < IV < I < III
(B) Equivalent contributing structures make
the resonance very important (B) IV < II < V < III < I
(C) Contributing structures represent (C) III < I < IV < II < IV
hypothetical molecules having no real (D) V < IV < II < I < III
existence
(D) Contributing structures are less stable than
Q.6 Which of the following molecules can behave
the resonance hybrid
both as a nucleophile and an electrophile?

Q.2 Among the given compounds, the one which is (A) CH3NH2 (B)CH3Cl
least basic is - (C) CH3CN (D) CH3OH

(A) (B)
N N Q.7 Which of the following shows the correct order
H H of decreasing acidity -

(C) (D) (A) PhCO2H > PhSO3H > PhCH2OH > PhOH
N N (B) PhSO3H > PhOH > PhCH2OH > PhCH2OH
(C) PhCO2H > PhOH > PhCH2OH > PhSO3H
Q.3 Which of the following is the weakest
nucleophile - (D) PhSO3H > PhCO2H > PhOH > PhCH2OH
(A) C2H5O– (B) C2H5S–
(C) CH3COO– (D) CO32– Q.8 Which of the following correctly shows the
order of decreasing basicity -
Q.4 Which of the following compounds on gentle (A) Aniline > o-nitroaniline > p-nitroaniline >
heating will undergo facile homolytic bond
m-nitroaniline
cleavage ?
(B) Aniline > p-nitroaniline > o-nitroaniline >
O CH3
(A) CH3–C–O–C–CH3 m-nitroaniline

CH3 (C) Aniline > m-nitroaniline > p-nitroaniline >

(B) (CH3)3 C—O—C(CH3)3 o-nitroaniline
(C) C6H5 —C(CH3)3 (D) o-Nitroaniline > p-nitroaniline > aniline >
(D) (CH3)3C—O—O—C(CH3)3 m-nitroaniline

ACME Study Point G.O.C [Link].816-817-3-819

 Q.13 The correct order of increasing stability of the
Q.9 (I) NH2
following carbocations is -
+ +
(II) CH3O NH2 (A) CH3CHCH2 > FCH2CH2CH2 >
F
(III) NO2 NH2 + +
CH3CH2CH2 > CH3OCH2
+ + +
(B) CH3OCH2 > CH3CH2CH2 > FCH2CH2CH2
NH2
(IV) +

NO2 > CH3CHCH2

The correct order of decreasing basicity of the F

+ + +
above compound is - (C) FCH2CH2CH2 > CH3OCH2 > CH3CH2CH2
+
(A) I > II > III > IV > CH3CHCH2
(B) II > I > IV > III F
(C) III > IV > II > I + +
(D) CH3CHCH2 > CH3CH2CH2 >
D) II > I > III > IV
F
+ +

Q.10 Give the correct order of increasing acidity of FCH2CH2CH2 > CH3OCH2

the following compounds -

Q.14 In which of the following does the C–H bond
(I) OH (II) OH
(shown by a thick line) have the least bond
dissociation energy -
(III) COOH (IV) CCH
(A) PhCH2 – H (B) Me3C–H
(A) II < I < IV < III (B) IV < II < I < III (C) Me2CH – H (D) Me – H
(C) I < II < IV < III (D) IV < I < II < III
Q.15 Which of the following shows the correct order
of stability -
Q.11 Select the correct order of basicity -
+ + +

(A) CH3CH2– > CH2 = CH– > HC  C– > OH– (A) CH3OCHCH3 < CH3OCH2 < CH3CH2CH2
+
(B) CH3CH2– > HC  C– > CH2 = CH– > OH– < CH3CH2
+ + +
(C) CH3CH2– > OH– > HC  C– > CH2 = CH– (B) CH3CH2CH2 < CH3CH2 < CH3OCHCH3
+
(D) OH– > HC  C– > CH2 = CH– > CH3CH2– < CH3OCH2
+ + +
(C) CH3CH2CH2 < CH3CH2 < CH3OCH2
+
Q.12 Which of the following substituents will < CH3OCHCH3
decrease the acidity of phenol - + + +
(D) CH3OCH2 < CH3OCHCH3 < CH3CH2
(A) –NO2 (B) –CN +
< CH3CH2CH2
(C) –CH3 (D) –CHO

ACME Study Point G.O.C [Link].816-817-3-819

Q.16 The correct order of decreasing Q.20 Which of the following cannot exhibit
hyperconjugative effect of the following hyperconjugation -
CH3 +
compounds is - (A) CH3CH•2 (B) CH
(A) CH3CH=CH2 > CH3CH2CH=CH2 > CH3
+
(CH3)2 CHCH=CH2 (C) CH3CH=CH2 (D) (CH3)3C–CH2
(B) (CH3)2 CHCH=CH2 > CH3CH=CH2 >
CH3CH2CH=CH2 Passage based Questions
Passage :
(C) (CH3)2 CHCH=CH2 > CH3CH2CH=CH2 >
Hyperconugation describes the orbital interaction
CH3CH=CH2 between the -system and the adjacent -bond of
(D) CH3CH2CH=CH2 > CH3CH=CH2 > the substituent group (s) in organic compounds.
(CH3)2 CHCH=CH2 Hyperconjugation is also called as Baker and
Nathan effect. The necessary and sufficient
condition for the hyperconjugation are :
Q.17 Arrange the following compounds in the order (i) Compound should have at least on sp2-
of increasing rate of reaction with HCl - hybrid carbon of either alkene, carbocation
CH=CH2 or alkyl free radical.
(I) (II) CH3CH = CH2 (ii) -carbon with respect to sp2-hybrid carbon
should have at least one hydrogen.
CH=CH2 Hyperconjugation are three types :-
(III) (i) (C–H), -conjugation
CH3O
(ii) (C–H), positive charge conjugation
(IV) CH2 = CH2
(iii) (C–H), odd electron conjugation
(A) IV < II < I < III (B) III < IV < II < I
(C) III < I < II < IV (D) I < II < III < IV The hyperconjugation may be represented as
H H

Q.18 Which of the following shows the correct order H–C–CH=CH2 H–C=CH–CH2
of decreasing stability - H H
+ + H
(A) CH3 CH2 > CH3O CH2 > 
HC=CH–CH2
+ +
CH2 > CH3–CH2 H
+ +
(B) CH3O CH2 > CH3 CH2 > H

+ + H–C=CH–CH2
CH2 > CH3–CH2 H
+ + Number of resonating structures due to
(C) CH2> CH3O CH2 > hyperconjugation = (n + 1 ) where n is number
+ + of -hydrogen . Greater is the number of such
CH3 CH2 > CH3–CH2 forms, more is the stability of species under
+ + consideration.
(D) CH3O CH2 > CH2 >
Q.21 Hyperconjugation is possible in which of the
+ + following species ?
CH3–CH2 > CH3 CH2

(A) CH 3 – C H 2 (B) C6H5–CH3
Q.19 Among the following alkenes
1-butene cis-2-butene trans-2-butene CH3
I II III (C) CH2=CH2 (D) CH3–C–CH=CH2
the order of decreasing stability is - CH3
(A) II > I > III (B) III > I > II
(C) I > II > II (D) III > II > I
ACME Study Point G.O.C [Link].816-817-3-819
Q.22 Which of the following carbonium ions will Q.25 Statement I : Allyl free radical is more stable
show highest number of hyperconjugation than simple alkyl free radical.
forms ? Statement II: The allyl free radical stabilized
  by resonance.
(A) CH 3 – C H 2 (B) CH3–CH
CH3 Q.26 Statement I : Nucleophiles attack the regions
CH3 CH3 of high electron density.
(C) CH3–C (D) CH3–CH2–C Statement II : Nucleophiles act as lewis
CH3 CH3 bases.

Q.23 Which of the following alkenes will show Q.27 Statement I : Heterolytic fission involves the
maximum number of hyperconjugation forms ? breaking of a covalent bond in such a way that
(A) CH2=CH2 both the electrons of the shared pair are carried
away by one of the atoms.
(B) CH3–CH=CH2
Statement II : Heterolytic fission occurs
(C) CH3–CH2–CH=CH2 readily in polar covalent bonds.
CH3
(D) CH3–C–CH=CH2 Q.28 Statement - 1 : Acetate ion is more stable
than phenoxide ion.
Statement based Questions Statement - 2 : Phenoxide ion has more
resonating structure than acetate ion
Each of the questions given below consist of
Statement – I and Statement – II. Use the Q.29 Statement I : In resonance delocalisation of 
following Key to choose the appropriate
electrons takes place
answer.
Statement II : In hyperconjucation
(A) If both Statement-I and Statement-II are
delocalisation of  electrons takes place
true and Statement-II is the correct
explanation of Statement-I.
(B) If both Statement-I and Statement-II are Q.30 Statement I : The Pka value of acetic acid is
true but Statement-II is not the correct lower than that of phenol.
explanation of Statement-I. Statement II : Phenoxide ion is more
(C) If Statement-I is true but Statement-II is resonance stabilized.
false.
(D) If Statement-I is false but Statement-II is
true.

Q.24 Statement-I : Tertiary carbocations are

generally formed more easily than primary
carbocations.
Statement II : Hyperconjugation as well as
-

inductive effect due to additional alkyl group

stabilize tertiary carbocations.

ACME Study Point G.O.C [Link].816-817-3-819

 LEVEL # 4
(Question asked in previous AIEEE & IIT JEE)

SECTION-A Q.5 Which of the following is the strongest base -

[AIEEE-2004]
Q.1 In the following benzyl/alkyl system
(A) NH2 (B) NHCH3
R – CH = CH2 or R

(R is alkyl group) (C) NH2 (D) CH2NH2

increasing order of inductive effect is - CH3
[AIEEE-2002]
(A) (CH3)3 C – > (CH3)2 CH – > CH3CH2— Q.6 The decreasing order of nucleophilicity among
(B) CH3CH2 – > (CH3)2 CH – > (CH3)3C — the nucleophiles [AIEEE-2005]
(a) CH3C–O– (b) CH3O–
(C) (CH3)2 CH – > CH3CH2 – > (CH3)3C—
O
(D) (CH3)3C – > CH3CH2 – > (CH3)2CH—
O
(c) CN– (d) H3C S–O–
Q.2 The correct order of increasing basic no. of the
O
bases NH3, CH3NH2 and (CH3)2NH is -
is -
[AIEEE-2003]
(A) (d), (c) , (b) , (a) (B) (a), (b), (c) , (d)
(A) NH3 < CH3NH2 < (CH3)2NH
(C) (c) , (b) , (a) , (d) (D) (b), (c) , (a) , (d)
(B) CH3NH2 < (CH3)2NH < NH3
(C) CH3NH2 < NH3 < (CH3)2NH
(D) (CH3)2NH < NH3 < CH3NH2 Q.7 Amongst the following the most basic
compound is - [AIEEE-2005]
Q.3 Rate of the reaction [AIEEE-2004-2005] (A) aniline (B) benzylamine
O O (C) p–nitroaniline (D) acetanilide
R–C + Nu R–C + Z
Z Nu Q.8 The increasing order of stability of the
is fastest when Z is - following free radicals is - [AIEEE 2006]
(A) Cl (B) NH2   
(A) (C6H5)3C < (C6H5)2C H < (CH3)3 C
(C) OC2H5 (D) OCOCH3 
< (CH3)2C H
  
Q.4 Consider the acidity of the carboxylic acids : (B) (C6H5)2 C H < (C6H5)3C < (CH3)3C
[AIEEE-2004] 

(a) PhCOOH < (CH3)2C H

  
(b) o – NO2C6H4COOH (C) (CH3)2C H < (CH3)3C < (C6H5)3C
(c) p – NO2C6H4COOH 
< (C6H5)2C H
(d) m – NO2C6H4COOH   
(D) (CH3)2C H < (CH3)3C < (C6H5)2C H
Which of the following order is correct ?

(A) a > b > c > d (B) b > d > c > a < (C6H5)3C
(C) b > d > a > c (D) b > c > d > a
ACME Study Point G.O.C [Link].816-817-3-819
Q.9 CH3Br + Nu–  CH3 – Nu + Br– Q.14 Consider thiol anion (RS) and alkoxy anion
(RO). Which of the following statement is
The decreasing order of the rate of the above
correct ? [AIEEE 2011]
reaction with nucleophiles (Nu–) A to D is 
(A) RS is less basic but more nucleophilic
[Nu– = (A) PhO–, (B) AcO–, (C) HO–, (D) CH3O] than RO
[AIEEE 2006] (B) RS is more basic and more nucleophilic
(A) D > C > B > A (B) A > B > C > D than RO
(C) B > D > C > A (D) D > C > A > B (C) RS is more basic but less nucleophilic than
RO
(D) RS is less basic and less nucleophilic than
Q.10 The correct order of increasing acid strength of
RO
the compounds [AIEEE 2006]
(a) CH3CO2H (b) MeOCH2CO2H Q.15 The correct order of acid strength of the
Me following compounds is : [AIEEE 2011]
(c) CF3CO2H (d) CO2H is A. Phenol
Me B. p-Cresol
(A) d < a < c < b (B) d < a < b < c C. m-Nitrophenol
(C) a < d < c < b (D) b < d < a < c D. p-Nitrophenol
(A) D > C > A >B (B) B > D > A > C
(C) A > B > D >C (D) C > B > A > D
Q.11 Which one of the following is the strongest
base in aqueous solution ? [AIEEE-2007]
Q.16 The non aromatic compound among the
(A) Trimethylamine (B) Aniline following is - [AIEEE 2011]
(C) Dimethylamine (D) Methylamine
(A) (B)

Q.12 Presence of a nitro group in a benzene ring : S

[AIEEE 2007] (C) (D)
(A) activates the ring towards electrophilic
substitution Q.17 Ortho-Nitrophenol is less soluble in water than
(B) renders the ring basic
p-and m-Nitrophenols because - [AIEEE 2012]
(C) deactivates the ring towards nucleophilic
(A) o-Nitrophenol shows Intramolecular H-
substitution
(D) deactivates the ring towards electrophilic bonding
substitution (B) o-Nitrophenol shows Intermolecular H-
bonding
(C) Melting point of o-Nitrophenol is lower
Q.13 Arrange the carbanions, (CH3)3 C , CCl3 , than those of m- and p –isomers.
(D) o-Nitrophenol is more volatile in steam
(CH3)2 C H , C6H5 CH 2 , in order of their than those of m- and p-isomers
decreasing stability - [AIEEE 2009] Q.18 A solution of (–) – 1 – chloro – 1 –
phenylethane in toluene racemises slowly in the
(A) (CH3)2 C H > CCl3 > C6H5 CH 2 > (CH3)3 C presence of a small amount of SbCl5, due to the
(B) CCl3 > C6H5 CH 2 > (CH3)2 C H > (CH3)3 C formation of –
[JEE Main 2013]
(C) (CH3)3 C > (CH3)2 C H >C6H5 CH 2 > CCl3
(D) C6H5 CH 2 > CCl3 > (CH3)3 C > (CH3)2 C H (A) carbocation (B) free radical
(C) carbanion (D) carbene

ACME Study Point G.O.C [Link].816-817-3-819

Q.19 Arrange the following compounds in order of (C) II is not an acceptable canonical structure
decreasing acidity : because the nitrogen has 10 valence
[JEE Main 2013] electrons
(D) II is an acceptable canonical structure
OH OH OH OH
Q.4 The kind of delocalization involving sigma
; ; ; bond orbitals is called [IIT - 1994]
(A) Inductive effect
Cl CH3 NO2 OCH3 (B) Hyperconjugation effect
(I) (II) (III) (IV)
(C) Electromeric effect
(A) III > I > II > IV (B) IV > III > I > II
(C) II > IV > I > III (D) I > II > III > IV (D) Mesomeric effect
Q.20 The order of stability of the following
carbocations :
Q.5 Most stable carbonium ion is - [IIT-1995]
[JEE Main 2013]
 (A) p-NO2 - C6H4 - +CH2
CH2
(B) C6H5+CH2
 
CH2=CH–CH2 ; CH3–CH2–CH2; is - (C) p-Cl - C6H4 - +CH2
I II (D) p-CH3O - C6H4 - +CH2
III
(A) I > II > III (B) III > I > II
(C) III > II > I (D) II > III > I Q.6 Arrange in order of decreasing trend towards SE
reactions, [IIT-1995]
SECTION-B Chlorobenzene , Benzene,
Q.1 Which one of the following has the smallest I II
heat of hydrogenation per mole ? [IIT-1993] Aniline chloride, Toluene
(A) 1-Butene (B) trans-2-Butene III IV
(C) cis-2-Butene (D) 1,3-Butadiene
Q.2 What is the decreasing order of strength of (A) II > I > III > IV (B) III > I > II > IV
bases ?   [IIT - 1993] (C) IV > II > I > III (D) I > II > III > IV
O H , NH 2 , H – C  C–, CH3– CH2
Q.7 In the following compounds - [IIT-1996]
(A) CH3 – CH2 > NH2 > H – C  C– > OH– OH OH
OH
(B) H – C  C– > CH3 – > CH2 > NH2 > OH– OH
(C) OH– > NH2 >H–C C– > CH3 – CH2
NO2
(D) NH2 >H–C C– > OH– > H 3C – CH2 CH3 NO2
(I) (II) (III) (IV)
Q.3 Choose the correct statement from the ones
The order of acidity is -
given below for two anilium in - [IIT-1993]
(A) III > IV > I > II (B) I > IV > III > II
+
NH3 NH3 (C) II > I > III > IV (D) IV > III > I > II
+
Q.8 In the following groups : [IIT-1997]
–OAc –OMe
(I) (II) I II
(A) II is not an acceptable canonical structure –OSO2Me –OSO2CF3
because carbonium ions are less stable than III IV
ammonium ions the order of leaving group ability is
(B) II is not an acceptable canonical structure (A) I > II > III > IV (B) IV > III > I > I
because it is non aromatic (C) III > II > I > IV (D) II > III > IV > I

ACME Study Point G.O.C [Link].816-817-3-819

Q.9 In the following compounds, the order of (A) If both assertion and reason are correct, and
basicity is - [IIT - 1997]
reason is the correct explanation of the
O
assertion
N N N N (B) If both assertion and reason are correct, but
reason is not correct explanation of the
H H
assertion
(I) (II) (III) (IV)
(C) If assertion is correct but reason is
(A) IV > I > III > II (B) III > I > IV > II
(C) II > I > III > IV (D) I > III > II > IV incorrect
(D) If assertion is incorrect but reason is
Q.10 Polarisation of electrons in acrolein may be
written as - [IIT-1998] correct
 
(A) C H 2 = CH – C H = O
  Q.14 Amongst the following, the most basic
(B) C H 2 = CH – CH = O
compound is - [IIT - 2000]
 
(C) C H 2 = C H – CH = O (A) C6H5NH2 (B) p-NO2 – C6H4NH2
 
(D) C H 2 = CH–CH = O (C) m-NO2 – C6H4NH2 (D) C6H5CH2NH2

Q.15 Which of the following alkenes will react

Q.11 The most unlikely representation of resonance fastest with H2 under catalytic hydrogenation
structure of p-nitrophenoxide ion is - conditions ? [IIT- 2000]
[IIT - 1999]
     R R R H
O–N=O O–N–O (A) (B)
H H R H
(A) (B)
R R R R
 (C) (D)
O O
   R H R R
O=N=O O–N=O

(C) (D) Q.16 Which of the following has the highest


 nucleophilicity ? [IIT - 2000]
O O – –
Q.12 An aromatic molecule will not - [IIT- 1999] (A) F (B) OH
(A) have 4n  electrons (C) CH2 (D) NH2
(B) have (4n + 2)  electrons
(C) be planar
(D) be cyclic Q.17 The correct order of basicities of the following
compounds is - [IIT - 2001]
Q.13 Read the following statement and explanation NH2 CH3 CH2NH2
and answer as per the option given below : CH3–C
NH2
[IIT-2000]
Assertion : Phenol is more reactive than 1 2
benzene towards electrophilic substitution O
reaction.
(CH3)2NH CH3CONH2
Reason : In the case of phenol, the
3 4
intermediate cabocation is more resonance
(A) 2 > 1 > 3 > 4 (B) 1 > 3 > 2 > 4
stabilised.
(C) 3 > 1 > 2 > 4 (D) 1 > 2 > 3 > 4

ACME Study Point G.O.C [Link].816-817-3-819

 HOOC O
Q.18 Identify the correct order of reactivity in
electrophilic substitution reaction of the (B)
following compounds -
CH3 Cl NO2

O 2N OH

OOC OH
1 2 3 4
(C)
[IIT - 2002]
(A) 1 > 2 > 3 > 4 (B) 4 > 3 > 2 > 1

(C) 2 > 1 > 3 > 4 (D) 2 > 3 > 1 > 4 O2N O
HOOC O
Q.19 Left to right sp2, sp2, sp, sp hybridization is
present in : [IIT - 2003] (D)
(A) H2C=CH–CN
(B) H2C=C=CH–CH3

(C) HCC–CCH O2N OH
(D) HCC–CH = CH2
 
H3N NH3
Q.20 Maximum dipole moment will be of - Q.22 z y
COOH
[IIT - 2003]
x
(A) CCl4 (B) CHCl3
Correct order of acidic strength is : [IIT-2004]
(C) CH2Cl2 (D) CH3Cl
(A) x > y > z (B) z > y > x
(C) y > z > x (D) x > z > y
HOOC OH

Q.23 Which of the following is least stable :

Q.21 when X is made to
[IIT - 2005]

H (A) CH3 – O  CH – C H – HC  CH 2
O2 N 
OH
 
react with 2 eq. of NaNH2 the product formed (B) CH 3 – O  CH – CH  HC  C H 2
will be - [IIT - 2003]  

OOC OH (C) CH 3 – O  C H – C H – HC  CH 2
 
(A) (D) CH 3 – O  HC  CH – C H  C H 2

 Q.24 Statement-1 : p-Hydroxybenzoic acid has a

O2N OH lower boiling point that o-hydroxybenzoic acid.
Because
Statement-2 : o-Hydroxybenzoic acid has
intramolecular hydrogen bonding. [IIT - 2007]

ACME Study Point G.O.C [Link].816-817-3-819

 (A) Statement-1 is True, Statement-2 is True ; H H
1 2 + 4 5
Statement-2 is a correct explanation for H3C–C–C–CH3
Statement-1
HO H CH3
(B) Statement-1, is True, Statement-2 is True;
Statement-2 is NOT a correct explanation (A) CH3 at C-4 (B) H at C-4
for Statement-1 (C) CH3 at C-2 (D) H at C-2
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1, False, Statement-2 is True
Q.25 Among the following, the least stable
resonance structure is - [IIT - 2007] Q.29 The correct stability order of the following
 

O 
O resonance structures is - [IIT-2009]

(A) N (B) N
 
+ – + –
 O O H2C=N=N H2C–N=N
 
(I) (II)



O 
O
 – + – +
(C)   (D) H2C–NN H2C–NN
N 
N
(III) (IV)
O O
  (A) (I) > (II) > (IV) > (III)
Q.26 Hyperconjugation involves overlap of the (B) (I) > (III) > (II) > (IV)
following orbitals - [IIT-2008] (C) (II) > (I) > (III) > (IV)
(A)  –  (B)  – p (D) (III) > (I) > (IV) > (II)
(C) p – p (D)  –  Q.30 The correct acidity order of the following is
[IIT-2009]
Q.27 The correct stability order for the following OH COOH
COOH
species is - [IIT-2008] OH

 

O  Cl CH3
(I) (II) (III) (IV)
(I) (II)

(A) (III) > (IV) > (II) > (I)
 (B) (IV) > (III) > (I) > (II)
O 
(III)  (IV) (C) (III) > (II) > (I) > (IV)
(A) (II) > (IV) > (I) > (III) (D) (II) > (III) > (IV) > (I)
(B) (I) > (II) > (III) > (IV)
(C) (II) > (I) > (IV) > (III) Q.31 In allene (C3H4), the type (s) of hybridization of
(D) (I) > (III) > (II) > (IV) the carbon atoms is (are) [IIT-2012]
(A) sp and sp3 (B) sp and sp2
Q.28 In the following carbocation, H/CH3 that is (C) only sp2 (D) sp2 and sp3
most likely to migrate to the positively charged
carbon is - [IIT-2009] Q.32 Which of the following molecules, in pure
form, is (are) unstable at room temperature ?

ACME Study Point G.O.C [Link].816-817-3-819

 [IIT-2012] (A)  p (empty) and * electron
delocalisations
(A) (B) (B)  * and  electron
delocalisations
O (C)  p (filled) and  electron
O
delocalisations
(C) (D) (D) p (filled)  * electron
delocalisations

Q.33 The hyperconjugative stabilities of tert-butyl

cation and 2-butene, respectively, are due to –
[JEE-Advance 2013]
Q.34 Among P, Q, R and S, the aromatic compound(s) is/are –
[JEE-Advance 2013]
(A) P (B) Q (C) R (D) S
Cl

AlCl
3  P

NaH
 Q

( NH ) CO
 
4 2
3  R
O O 100115º C

O
HCl

 S

Q.35 Match the chemical conversions in List-I with the appropriate reagents in List-II and select the correct
answer using the code given below the lists –
[JEE-Advance 2013]

List-I List-II
P. Cl 
 1. (i) Hg(OAc)2; (ii) NaBH4

Q. ONa 
 OEt 2. NaOEt
OH
R. 
 3. Et-Br

S. 
 4. (i) BH3; (ii) H2O2/NaOH

OH
Codes :

ACME Study Point G.O.C [Link].816-817-3-819

 P Q R S
(A) 2 3 1 4
(B) 3 2 1 4
(C) 2 3 4 1
(D) 3 2 4 1

ACME Study Point G.O.C [Link].816-817-3-819

 ANSWER KEY
LEVEL # 1
[Link]. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. C D C A B A D A A C A B A A C B A B A C
[Link]. 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40
Ans. B D D B B C C D A B C D B C C D D C A D
[Link]. 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans. C D B B B D A A C C D C D C C C D A A C

LEVEL # 2

[Link]. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. D D D D B A B A A A A C B C A C A C C A
[Link]. 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40
Ans. C A C B A D B D C D C A A C C D C A C C
[Link]. 41 42 43 44 45 46 47 48 49 50
Ans. C B C A A D B A D B

LEVEL # 3

[Link]. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. A B D D B C D C B B A C B A C A A B D D
[Link]. 21 22 23 24 25 26 27 28 29 30
Ans. B C B A A D A B B C

LEVEL # 4
SECTION – A
Qus. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. A A A D D D B D D B C D B A A D A A A C
SECTION – B
1.[D]

ACME Study Point G.O.C [Link].816-817-3-819

 7.[D] OH OH OH OH
 
CH2=CH—CH=CH2 CH2—CH= CH —CH2
1, 3-Butadiene
  NO2
CH3 NO2
CH2—CH= CH —CH2 (I) (II) (+H) (III) (—I) (IV)
+ (–I, –M)
–
CH2 CH CH CH2 
More stable anion than more acidic strength

Partial double bond character imparted 8.[B] O –M effect

+I
—O—C—CH3 —O CH3

 
(i) (ii)
 
2.[A] CH3— CH 2 > NH 2 > HC C > OH
1 O –M effect O (–M, – I)
Basicity  +I
E.N —O—S CH3 —O—S CF3
E.N strength [Csp 3  Csp 2  N  C  O  N] –M
sp sp O –M O
(iii) (iv)

3.[C] NH3 NH3 Valency = 5 Leaving group ability
Not atall possible
 9.[D]
–I O –I

(II) +I +I
(I)
N N sp2 N N
II is not an acceptable canonical structure (iv)
(i)
because the nitrogen has 10 valence electrons Pyridine H H
[i.e. valency = 5] (ii) (iii) Pyrole
[Due to aromaticity]
4.[B] Hyperconjugation effect [maxm delocalisation
of lone pair]

CH2 (minm basicity)
5.[D] 1
% s = 33 s  E.N, E.N 
Basicity

:OCH3 [Stabilises the carbocation] O O
[+M effect] (+M > –I) 
10.[D] CH2=CH—C—H CH2—CH=CH—CH
Cl(–I, +M) Acrolein
(Charge separation)
6.[C]

Chlorobenzone Benzene O=N=O
(i) (ii)
11.[C] Valancey of N atom = 5
– I effect [Not possible]

 O

NH3 Cl CH3 [+H effect]
12.[A] have 4n  electrons

Anilinium chloride Toluene

(iii) (iv)

ACME Study Point G.O.C [Link].816-817-3-819

 .. C
:O–H +M effect
H
13.[A] C
C H H
Phenol C H H
+Ieffect C max
CH2 NH2 Localised
14.[D] (C) (D)
(1° amine) lone pair 21.[C]

R R (most acidic H-atom)

(Unstable alkene due
15.[A] C C to steric hinderance) Carboxylic grp
H H HOOC OH [strong base]
Cis-isomer is more catalytic hydrogenated as it is 2 eq NaNH2
more adsorbed and the C = C double bond is will attack the
more activated. 2–acidic H-atoms

16.[C] CH 3 
O2N OH
nucleophilicity order
   –I 2nd most acidic
CH 3 > NH 3 > OH > F H-atom
+I ..
17.[B] CH3–C NH CH3CH2 NH2
NH2
(1) (2) 22.[D]
 
H3N NH3
+I .. O z y
CH3 NH –I effect
CH3—C— NH2
+I
(4) COOH carboxylic grap
CH3 m
max acidic H-atom
(3) x
18.[C] Distance factor operates
CH3(+H) Cl(+M < –I) NO2(–M, –I) with COOH in between Z and Y

..
 
23.[D] CH3—O—CH=CH—CH2—CH2
1 2 3 4
[incomplete octet]
19.[A] CH2 = CH — C  N
 [Octet rule is applied]
 sp2 sp2 sp sp  
In option (C) ; octet is incomplete but more
C H stable than (D) because
..
20.[D] ..  
C C CH3—O—CH—CH—CH=CH
.. 2
C C C C +M effect –M effect
C C e– with
drawing group
[ = 0]
(A) (B) wherees in option (D), no M effect is working.

ACME Study Point G.O.C [Link].816-817-3-819

 –
24.[A] HO O HO O +
C C H
.. ..
O      
H2C=N=N CH2–N=N CH2–N=N
<
(i) (ii) (iii)
complete octet. in complete octet Complete octet
OH B.P OH –ve charge on –ve charge on
electro-ve atom electro +ve atom
25.[A] Same charge will repell making it least stable more stable than (iii) ..
  

O CH2–N=N

N
 O (iv)
H incomplete octet

p-orbital  [–ve] charge on
H
26.[B] H—C—CH2 electropositive atom
H—C=CH2
less stable]
H H
Phenol Banzoic acid
Hyper conjugation includes the conjugation of 30.[A]
 bond [i.e. C—H bond] with adjacent atoms p- OH OH COOH COOH
orbital
+H
CH3 Cl [EWG] (III) CH3(+H)
+H 
..  (I) (II) (IV)
H3C O
..
27.[D] (+M effect) +H +H Benzoic acid is more acidic from phenol
(I) (II) –CH3 has +H effect
(+M with 6–H atom) (3–H atom)
– Cl has (–I > +M) i.e. it is EWG

.. Acidity order
O
..
+H H3C +M effect +H

(III) (IV)
31.[B] CH 2  C  CH 2
(2–H atoms)
(+M with 3–H atom)   
sp2 sp sp2
H H 32.[B,C]
28.[D] 1 2  5 4
O
H3C C—C3—C—CH3
+I effect and are antiaromatic
HO .. : H CH3
[+M effect]
Order of stability
H H
  aromatic > nonaromatic > Antiaromatic
CH3—C—CH—C—CH3

H–O CH3
33.[A] –  empty and  – * electron delocalization.

29.[B]

ACME Study Point G.O.C [Link].816-817-3-819

34. [A, B, C, D]
A = P Aromatic
B = Q Aromatic
C = R Aromatic
D = S Aromatic
 
P= Q=

OH


R = HO CH3 S=
Aromatic ions


35.[A] P – 2 [Elimination –E2]

Q – 3 [Williamson etherification]
R – 1 [OMDM]
S – 4 [HBO]

Cl NaOEt

 Et Br
ONa  OEt
OH
2 
 
Hg ( OAc) / NaBH
4

( 
i ) BH 3
( ii ) H 2O 2 / OH 

OH

ACME Study Point G.O.C [Link].816-817-3-819