General Organic Chemistry

Chemistry
Practice
Sheet
General Organic Chemistry

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IIT JEE | MEDICAL | MHT - CET
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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.
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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)
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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)
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Ex.22 The most unlikely representation of resonance Sol. [C]

structures of p-nitrophenoxide ion is - NO2
– 
O – + O – + O – CH3 NH2 NO2–C NH2
O
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
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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]
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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 CH  3
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)
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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
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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 II > III (B) II > I > III
(C) III < II > I (D) II < III II > (B) III < II I CH3
(C) CH3 – C – CH = CH2
CH3
(D) CH3 – C = CH2
CH3
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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
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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
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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 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 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
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Questions
based on Nucleophilicity & Leaving group
Q.56 Which of the following has the highest

nucleophilicity -
(A) F– (B) OH–
(C) CH 3 (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–
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LEVEL # 2
Q.7 In the anion HCOO–, the two carbon-oxygen
Q.1 Which of the following belongs to +  group
bonds are found to be equal length. What is the
(A) —OH (B) —OCH3
reason for it -
(C) —COOH (D) —CH3 (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
structures
(A) – F > – Cl > – Br > – I
(C) the electronic orbitals of carbon atom are
 
(B)  N R 3   N H 3   NO 2 hybridized
(D) the anion of obtained by removal of proton
(C) –OCH3 > – OH > – NH2
from the acid molecule
(D) > – C  CH > H
Q.8 Which of the following resonance structures is
Q.3 Which of the statement is not correct? the major contributor to the resonance hybrid ?
(A) – NH2 is ortho-para directing group  ..
CH3 – CH2 – C H – O
.. CH 3
(B) – CHO is meta directing group
(I)
(C)  CCl 2 is an electrophile 
  CH3 – CH2 – CH = O
.. CH 3

(D) – O

H is (– M) group
(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 -
(a) CH3–CH2–Cl
Q.5 Heterolysis of propane will yield -
(b) CH2=CH–Cl
 
(A) C H 3 and C 2 H 5 radicals
(c) C6H5– Cl
(B) CH 3 and CH 3CH 2 ions Arrange C–Cl bond length of these compounds
(C) CH 3 and CH3CH 2 ions in decreasing order -
(A) a > b > c (B) a > c > b
(D) CH 3 and CH 3CH 2 ions
(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 CH 3 C HCH 3 is less stable than -
(B) bonds only at vinylic position 
(A) (CH3)3 C+ (B) CH 3CH 2 C H 2
(C) bonds at allylic and nonallylic position

also (C) CH 3 C H 2 (D) CH 3
(D) – I effect
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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
H 2N 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) C 6 H 5  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), CH 3  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
(C) Nitrite ion (D) Sulphite ion
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OH Q.25 Arrange the following in increasing of pH
OH OH
NO2
value
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 (D) II < III II > III
CH 3 CH 2 COOH (C) III > II 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 
(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
Q.30 Stability of following radical is
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CH3 CH2•  
(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) I > IV > II > III (B) IV > III > II > I
(A) II > III > II > IV (B) III > II > I > IV (C) I > II > IV > III (D) I > II > III > IV
(C) III < II (CH3)2NH > CH3NH2 > NH3
CH3 NO2 OH
(B) (CH3)2NH > (CH3)3N > CH3NH2 > NH3
(C) (CH3)2NH > CH3NH2 > (CH3)3N > NH3
(D) (CH3)2NH > CH3NH2 > NH3 > (CH3)3N
(I) (II) (III) (IV)
(A) IV < III < II I > II > IV (A) pyrrole < pyridine < Me3N < Et3N
(B) pyridine < pyrrole < Et3N < Me3N
Q.32 Increasing order of the stability is (C) pyrrole < Et3N < Me3N < pyridine
CH3CH=CH2 CH3CH2CH=CH2, (D) Me3N < Et3N < pyridine < pyrrole
I II
CH3 Q.39 Give the correct order of decreasing basicity of
CHCH=CH2 (CH3)3CCH=CH2
CH3 the following compounds,
III IV C6H5NH2 (C6H5)2NH (C6H5)3N C6H11NH2
(A) I > II > III > IV (B) I > III > II > IV I II III IV
(C) I > IV > III > II (D) IV > III > II > I (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 -
Q.40 The correct order of stability of the following
(A) RO– > OH– > CN– > RCOO– > NO3–
carbocations is -
(B) NO3– > CN– > RCOO– > RO– > OH–  
(A) CH 3CH 2 C H 2 > CH 2  CH – C H 2 >
(C) OH > CN > RCOO > NO3 > RO
– – – – –
 
(D) NO3– > CN– > RCOO–  RO– > OH– CH2= CH C HCH 3 > CH2=CH C (CH3)2
 
(B) CH2= CH C H 2 > CH 3CH 2 C H 2 >
Q.34 COO electrophilic substitution  
CH 2  CH C(CH 3 ) 2 > CH2 = CH C HCH 3
occurs at  
(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 ? > CH3CH2– C H 2 > CH2 = CH C H 2
(A) CH3NH2 (B) CH3Cl
(C) CH3CN (D) CH3OH Q.41 The order of reactivity of the following
Q.36 Arrange acidity of given compounds in alcohols towards concentrated HCl is -
decreasing order in gas phase
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OH O
(1) (3)
F F H–N C–N(C2H5)2
OH , (2)
II
I N
OH
Ph OH CH3
, (A) 1
III IV (B) 2
(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
(B) (CH3)2C = CH2 > CH3CH = CH2 > CH3CH = CH—CH2—CH2—CH(CH3)2 are
CH2 = CH2 > CH2 = CHCO2H represented by alphabets. Arrange them in
(C) CH2 = CH2 > CH3CH = CH2 > decreasing order of reactivity towards radical
CH2 = CHCO2H > (CH3)2C = CH2 substitution :
(D) CH3CH = CH2 > CH2 = CHCO2H > (A) c > a > e > d > f > b
(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) III > II > I (B) I > II > III (A) Br
(C) II > I > III (D) I > III > II
COOH (B) CH=CH–CH2Br
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.45 Which type of hybrid orbitals do C and N use Q.50 Arrange the following in Decreasing of their
in the formation of C–N bond in pyrrole? basic nature.
:NH NH2
(A) sp2 and sp2 (B) sp2 and sp3

(C) sp and sp3 (D) sp and sp2 N N
Q.46 Weakest base among the following is: H
I II III
(A) NH (B) NH NH
(A) I > II > III (B) II < III I (D) II > I > III
Q.47 Which nitrogen in LSD is most basic
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LEVEL # 3
Single correct type Questions (I) ClCH2COOH (II) CH3CH2COOH
Q.1 Which of the following statements is not true (III) ClCH2CH2COOH (IV) (CH3)2CHCOOH
about the resonance contributing structures of a
resonance hybrid - (V) CH3COOH
(A) Contributing structures contribute to the (A) V < II < IV < I < III
resonance hybrid in proportion of their
(B) IV < II < V < III < I
energies
(C) III < I < IV < II < IV
(B) Equivalent contributing structures make
the resonance very important (D) V < IV < II < I < III
(C) Contributing structures represent
hypothetical molecules having no real Q.6 Which of the following molecules can behave
existence both as a nucleophile and an electrophile?
(D) Contributing structures are less stable than
(A) CH3NH2 (B)CH3Cl
the resonance hybrid
(C) CH3CN (D) CH3OH
Q.2 Among the given compounds, the one which is
least basic is - Q.7 Which of the following shows the correct order
of decreasing acidity -
(A) (B)
N N (A) PhCO2H > PhSO3H > PhCH2OH > PhOH
H H (B) PhSO3H > PhOH > PhCH2OH > PhCH2OH
(C) (D) (C) PhCO2H > PhOH > PhCH2OH > PhSO3H
N N
(D) PhSO3H > PhCO2H > PhOH > PhCH2OH
Q.3 Which of the following is the weakest

nucleophile - Q.8 Which of the following correctly shows the
(A) C2H5 O– (B) C2H5S– order of decreasing basicity -
(C) CH3 COO– (D) CO32– (A) Aniline > o-nitroaniline > p-nitroaniline >
m-nitroaniline
Q.4 Which of the following compounds on gentle (B) Aniline > p-nitroaniline > o-nitroaniline >
heating will undergo facile homolytic bond
m-nitroaniline
cleavage ?
(C) Aniline > m-nitroaniline > p-nitroaniline >
O CH3
(A) CH3–C–O–C–CH3 o-nitroaniline
CH3 (D) o-Nitroaniline > p-nitroaniline > aniline >

(B) (CH3)3 C—O—C(CH3)3 m-nitroaniline
(C) C6H5 —C(CH3)3
(D) (CH3)3C—O—O—C(CH3)3
Q.5 Give the correct order of increasing acidity of Q.9 (I) NH2
the following compounds -
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+ +
(II) CH3O NH2 (A) CH3CHCH2 > FCH2CH2CH2 >
F
+ +
(III) NO2 NH2 CH3CH2CH2 > CH3OCH2
+ + +
(B) CH3OCH2 > CH3CH2CH2 > FCH2CH2CH2
NH2
(IV) +
> CH3CHCH2
NO2
F
The correct order of decreasing basicity of the
+ + +
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
+ +
FCH2CH2CH2 > CH3OCH2
Q.10 Give the correct order of increasing acidity of
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 CH2 = CH– > HC  C– > OH–
+
< CH3CH2
(B) CH3CH2– > HC  C– > CH2 = CH– > OH–
+ + +
(B) CH3CH2CH2 < CH3CH2 < CH3OCHCH3
(C) CH3CH2– > OH– > HC  C– > CH2 = CH–
+
< CH3OCH2
(D) OH– > HC  C– > CH2 = CH– > CH3CH2–
+ + +
(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
Q.16 The correct order of decreasing

Q.13 The correct order of increasing stability of the hyperconjugative effect of the following
compounds is -
following carbocations is -
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(A) CH3CH=CH2 > CH3CH2CH=CH2 > CH3 +

(A) CH3CH•2 (B) CH
(CH3)2 CHCH=CH2 CH3
+
(B) (CH3)2 CHCH=CH2 > CH3CH=CH2 > (C) CH3CH=CH2 (D) (CH3)3C–CH2
CH3CH2CH=CH2
(C) (CH3)2 CHCH=CH2 > CH3CH2CH=CH2 > Passage based Questions
Passage :
CH3CH=CH2
Hyperconugation describes the orbital interaction
(D) CH3CH2CH=CH2 > CH3CH=CH2 > between the -system and the adjacent -bond of
(CH3)2 CHCH=CH2 the substituent group (s) in organic compounds.
Hyperconjugation is also called as Baker and
Q.17 Arrange the following compounds in the order Nathan effect. The necessary and sufficient
condition for the hyperconjugation are :
of increasing rate of reaction with HCl -
(i) Compound should have at least on sp2-
CH=CH2
hybrid carbon of either alkene, carbocation
(I) (II) CH3CH = CH2
or alkyl free radical.
CH=CH2 (ii) -carbon with respect to sp2-hybrid carbon
(III) should have at least one hydrogen.
CH3O Hyperconjugation are three types :-
(IV) CH2 = CH2 (i) (C–H), -conjugation
(ii) (C–H), positive charge conjugation
(A) IV < II < I < III (B) III < IV < II < I
(iii) (C–H), odd electron conjugation
(C) III CH3O CH2 > H H
H
+ + 
CH2 > CH3–CH2 HC=CH–CH2
+ + H
(B) CH3O CH2 > CH3 CH2 >
+ +
H

CH2 > CH3–CH2
H–C=CH–CH2
+ + H
(C) CH2 > CH3O CH2 >
Number of resonating structures due to
+ + hyperconjugation = (n + 1 ) where n is number
CH3 CH2 > CH3–CH2
of -hydrogen . Greater is the number of such
+ + forms, more is the stability of species under
(D) CH3O CH2 > CH2 >
consideration.
+ +
CH3–CH2 > CH3 CH2 Q.21 Hyperconjugation is possible in which of the
following species ?
Q.19 Among the following alkenes 
1-butene cis-2-butene trans-2-butene (A) CH 3 – C H 2 (B) C6H5–CH3
I II III CH3
the order of decreasing stability is - (C) CH2=CH2 (D) CH3–C–CH=CH2
(A) II > I > III (B) III > I > II
CH3
(C) I > II > II (D) III > II > I
Q.20 Which of the following cannot exhibit
hyperconjugation -
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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.
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ANSWER KEY
LEVEL # 1
Q.No. 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
Q.No. 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
Q.No. 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
Q.No. 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
Q.No. 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
Q.No. 41 42 43 44 45 46 47 48 49 50
Ans. C B C A A D B A D B
LEVEL # 3
Q.No. 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
Q.No. 21 22 23 24 25 26 27 28 29 30
Ans. B C B A A D A B B C
||Page 22||

General Organic Chemistry

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General Organic Chemistry

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Chemistry

General Organic Chemistry

Ex.10 The weakest acid among the following -

NH2  CH3 NO2

Ex.21 The compound that is most reactive towards

 – COOH, & –NO2 group are deactivating

Ex.22 The most unlikely representation of resonance Sol. [C]

Sol. [A] Ex.29 Which one of the following chlorides gives

basicity ? (D) CH3 –C–OH ; CH3–C=OH

(D) Reverse of (C) I II

Q.27 Select the most stable carboncation among the

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

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

Q.44 Carbon free radicals are -

Q.51 Which of the following statements are correct

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

Q.56 Which of the following has the highest

Q.57 Arrange the following nucleophiles in the order

Q.58 Correct order of leaving group tendency -

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

Q.60 Which of the following is the strongest

Q.6 Carbocations may be stabilised by - 

(C) NF3 (D) NH3

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

Q.44 , pKa value of the compound

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

Q.47 Which nitrogen in LSD is most basic

Q.3 Which of the following is the weakest

CH3 (D) o-Nitroaniline > p-nitroaniline > aniline >

Q.16 The correct order of decreasing

(A) CH3CH=CH2 > CH3CH2CH=CH2 > CH3 +

Q.24 Statement-I : Tertiary carbocations are

inductive effect due to additional alkyl group

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