GENERAL ORGANIC CHEMISTRY

Preface

As you have gone through the theory part that consists of given fundamental principles,
definitions, concepts involved and solved problems. After going through theory part it
becomes necessary to solve the unsolved problems based on the concepts given. To
solve this purpose we are providing exercise part that comprises of various exercises
based on the theory. By solving various kinds of problems you can check your grasp on
the topic and can determine whether you have been able to find optimum depth in relevant
topic or not.

Students are advised to solve the questions of exercises (Levels # 1, 2, 3, 4) in the same
sequence or as directed by the faculty members, religiously and very carefully.
Level # 3 is not for foundation course students, it will be discussed in fresher or target
courses.

Total No.of questions in General Organic chemistry are -

Level # 1 ....................................................................................... 60
Level # 2 ........................................ ........................................... 50
Level # 3 ........................................ ........................................... 30
Level # 4 ........................................ ........................................... 46

Total No. of questions .............................................................. 186

1
 LEVEL # 1
Questions
based on Hybridisation Q.7 In which of the following compounds is
hydroxylic proton the most acidic ?
Q.1 Which of the following orbital overlaps is F
involved in the formation of the carbon–carbon I O
(A) O (B)
single bond in the molecule HC  C – CH = CH2 H H
(A) sp3 - sp3 (B) sp2 - sp3 O O
(C) sp - sp2 (D) sp3 - sp (C) H (D) H
F F
Q.2 Which of the following species (I), (II), (III),
(IV) has an sp2 hybridized carbon -
Q.8 Decreasing – I power of given groups is -
CH3 CH3 CH3 . : CH2
(a) CN (b) NO2 (c) – NH2 (d) F
(I) (II) (III) (IV)
(A) b > a > d > c (B) b > c > d > a
(A) (I) only (B) (I) and (II) only
(C) (I) and (III) only (D) (I), (III) and (IV) (C) c > b > d > a (D) c > b > a > d

Q.3 Which of the following hydrocarbon groups Q.9 Express in decreasing order of (+ ) -
designated as I, II, III, IV and V has planar (a) CH3CH2 – CH2 –
geometry -
Phenyl Cyclohexyl Cyclopentyl Butyl Vinyl (b) CH3 –
I II III IV V
(A) IV (B) I and V
(c)
(C) II and III (D) II, III and IV

Q.4 Which of the following has a bond formed by

overlap of sp–sp3 hybrid orbital? CH3
|
(A) CH3 – C  CH CH3  C 
(B) CH3 – CH = CH – CH3 (d) |
(C) CH2 = CH – CH = CH2 CH3
(D) CH  CH

Q.5 The maximum number of carbon atoms (e) CH3  CH2  CH2 
arranged linearly in the molecule CH3 – C  |
C – CH = CH2 is - CH2  CH3
(A) 5 (B) 4
(C) 3 (D) 2 Correct answer is -
(A) (c) > (d) > (e) > (a) > (b)
Questions
based on Inductive effect (B) (d) > (a) > (b) > (c) > (e)
(C) (a) > (b) > (c) > (d) > (e)
Q.6 The inductive effect : (D) (a) > (b) > (c) > (e) > (d)
(A) implies the atom's ability to cause bond
polarization
Q.10 Which among the given acid has lowest pKa
(B) increases with increase of distance
(C) implies the transfer of lone pair of electrons value -
from more electronegative atom to the (A) Chloroacetic acid
lesser electronegative atom in a molecule (B) Bromoacetic acid
(D) implies the transfer of lone pair of electrons
from lesser electronegative atom to the (C) Nitroacetic acid
more electronegative atom in a molecule (D) Cyanoacetic acid

2
Q.11 Arrange basicity of the given compounds in
decreasing order - Q.17 —  CH2 — C — CH3 and CH2 — C — CH3
 || |
(a) CH3 – CH2 – NH2 (b) CH2 = CH – NH2 O  O –
   
(c) CH  C – NH2
(A) a > b > c (B) a > c > b are –
(C) c > b > a (D) b > c > a (A) resonating structures
(B) tautomers
Q.12 Consider following acid
(C) geometrical isomers
ClCH2COOH, CH3COOH, CH3CH2COOH
I II III (D) optical isomers
Correct order of theIr pH value.
(A) III < II < I (B) I < II < III Q.18 Identify the correct order of reactivity in
(C) I < III < II (D) II < I < III electrophilic substitution reactions of the
following compounds –
Q.13 W hich is the correct order of increasing
basicity ?
(A) CH3CH2CH3 < CH3CH2SH < CH3CH2OH
< CH3CH2NH2
(B) CH3CH2CH3 < CH3CH2OH < CH3CH2SH
< CH3CH2NH2
(A) a > b > c > d (B) d > c > b > a
(C) CH3CH2NH2 < CH3CH2SH < CH3CH2OH
< CH3CH2CH3 (C) b > a > c > d (D) b > c > a > d

(D) CH3CH2CH3 < CH3CH2OH < CH3CH2NH2

< CH3CH2SH Q.19 Which of the following is the strongest
base -

Questions
based on Mesomeric effect
(A) (B)

Q.14 'M' effect is the resonance of -

(A)  electrons only
(B)  electrons only
(C)  and  both (C) (D)
(D)(+)ve and (-) charge.

Q.15 Which of the following contain + M but - 

Q.20 Arrange in increasing order of basicity
effect -
CH3NH2, (CH3)2NH, C6H5NH2, (CH3)3N
(A) O = CH – (B) – NO2
(A)(CH3)3N<(CH3)3NH < CH3NH2 < C6H5NH2
(C) – Cl (D) CH3¯
(B) Reverse of (A)
Q.16 The meta-directing power of the groups –NH2, (C)C6H5NH2< (CH3)3N < CH3NH2 < (CH3)2NH
–OCH3, –C6H5 and – NO2 follows the order (D) Reverse of (C)
(A) –NH2 > –OCH3 > –C6H5 > –NO2
(B) –NO2 > –C6H5 > –OCH3 > –NH2
(C) –OCH3 > –NH2 > –C6H5 > –NO2
(D) –OCH3 > –NO2 > –NH2> –C6H5

3
Q.21 In the following compounds– Q.25 Consider following benzyl alcohol

H I II

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

The order of basicity is -
(A) IV > I > III > II (B) III > I > IV > II
(C) II > I > III > IV (D) I > III > II > IV III IV
Correct order of their Kb value Is
(A) III > IV > II > I (B) III > I > IV > II
Q.22 In following acid, the correct increasing order (C) I < II < III < IV (D) IV > II > I > III
of acidic strength acid
Questions
HCOOH, CH3COOH, C6H5COOH based on Hyperconjugation
I II III
(A) I < II < III (B) II < I < III Q.26 Greater reactivity of 'H' is explained on the
basis of -
(C) III < II < I (D) II < III < I
(A) + M effect
(B) conjugative effect
Q.23 Arrange theIr Acidic strength (C) Hyper conjugative effect
(D) - I effect

OH
Q.27 Hyperconjugation occur due to overlaping of-
(A)  M.O. with 's'
H2 O CH3 OH
(B) 'p' orbital with 
II III
(C)  M.O. with  M.O.
I
(D) None

(A) I > II > III (B) II > I > III Q.28 Which of the following properties cannot be
(C) III < II > I (D) II < III < I explained on the basis of hyperconjugation.
(A) Dipole moment of CH3 – NO2
(B) o-p directing character of – CH3 group.
Q.24 Arrange the following in Increasing of their
CH3
basicity |
OH–, CH3COO– CI– (C) Greater stability of CH3  C  CH
2
|
I II III CH3
(A) III > II > I (B) III < II < I
(D) Metadirecting character of CCl3 group.
(C) II < III < I (D) II < III > I

4
Q.29 Correct order of reactivity– Q.36 Heterolytic fission of carbon-chlorine bond
(A)CH2=CH2>CH3—CH=CH2>(CH3)2C=CH2 produces :
(B)CH2=CH2>CH3—CH=CH2 < (CH3)2C=CH2 (A) two free radicals
(C)CH2=CH2<(CH3)2C=CH2 < CH3—CH=CH2
(B) two carbonium ions
(D)CH3—CH=CH2<CH2=CH2< (CH3)2C=CH2
(C) two carbonions

Q.30 W hich one of the following compounds (D) one cation and one anion
undergoes nitration fast :
Q.37 In CH3CH2OH, the bond that undergoes
heterolytic cleavage most readily is :
(A) (B) (A) C—C (B) C—O (C) C—H (D) O—H

Q.38 Which among the following statements are

(C) (D) correct ?
(1) Energy neede for homolytic bond fission
is less than that required for the heterolytic
Questions
Electromeric effect bond fission
based on
(2) Homolytic bond fission gives neutral species
which is paramagnetic in character
Q.31 The formation of cyanohydrin from a ketone
is an example of– (3) Energy needed for heterolytic bond fission
(A) Electrophilic substitution is less than that required for the homolytic
(B) Nucleophilic addition bond fission.
(C) Nucleophilic substitution (4) Heterolytic bond fission takes place in non
(D) Electrophilic addition polar solvents
(A) Only 1 (B) 1 and 3
Q.32 Involves no displacement or shifting of
(C) 1 and 2 (D) 1, 2 and 4
electrons–
(A) Zeeman effect
(B) Inductive effect Questions
based on Reaction Intermediate
(C) Resonance
(D) Electromeric effect
Q.39 Which of the following statements is correct?
Q.33 Which of the following exhibit electromeric (A) +  group stabilised carbocation
effect – (B) +  group destabilised carbocation
(A) alkanes (B) aldehydes (C) –  group stabilised carbocation
(C) alkyl halides (D) alkyl amines (D) –  group destabilises stabilised
Q.34 Shifting of electron of a multiple bond under carbocation
the influence of a reagent is called -
(A) I - effect (B) M - effect
(C) E - effect (D) T - effect Q.40 Which of the following statements is wrong ?
(A) a tertiary free radical is more stable than
Questions a secondary free radical
based on Bond fission
(B) a secondary free radical is more stable
than a primary free radical
Q.35 Homolytic fission of a hydrocarbon will
(C) atertiary carbonium ion is more stable than
liberate :
a secondary carbonium ion
(A) Carbonium ions (B) carbanions
(C) free radicals (D) carbenes (D) a primary carbonium ion is more stable
than a secondary carbonium ion

5
Q.41 Consider the following carbanions - Q.46 The order of stability of the following carbanion
 
is :
(a) CH3 – C H2 (b) CH2 = C H

(c) CH  C
Correct order of stability of these carbanions 
in decreasing order is - RCH 2
(A) a > b > c (B) b > a > c
(C) c > b > a (D) c > a > b
(I) (II)
Q.42 The stability of given free radicals in
decreasing order is -
 
(a) CH3 – C H2 (b) CH3 – C H – CH3
 
(c) CH3 – C – CH3 (d) C H3
|
CH3
(III) (IV)
(A) c > d > a > b (B) a > b > c > d
(C) c > b > d > a (D) c > b > a > d (A) I > II > III > IV (B) I > III > II > IV
(C) IV > III > II > I (D) III > IV > I > II
Q.43 Which one of the carboanions is most stable?

Q.47 Which free radical is the most stable :

(A) C6H5—CH2 (B) CH2 CH—CH2
(A) (B)
(C) CH3—CH—CH3 (D) CH3—

Q.48 Rank the followIng radIcals in order of

Decreasing stability
(C) (D)

Q.44 Carbon free radicals are - I II III

(A) Diamagnetic (B) Paramagnetic IV
(C) Ferromagnetic (D) Non magnetic (A) III > II > I > IV (B) III > II < I < IV
(C) II > III > II > IV (D) III < II < I < IV
Q.45 Arrange stability of the given carbocations in
decreasing order :
Q.49 Reactivity of C—H bond (abstraction of H)
CH2=CH—H, CH3—H, CH3CH2—H
(III)

(CH3)2CH—H (CH3)3C—H,
2°(IV) 3°(V)
(A) II < III < I < IV < V
I II III IV (B) I > II > III > IV > V
(A) I > II > III > IV (B) III > II > I > IV (C) I < II < III < IV < V
(C) IV > I > II > III (D) II > III > I > IV (D) I < II < IV < III < V

6
Q.50 Rank the following free radicals in order of Q.54 Which of the following reaction intermediates
decreasing stability : are electrophilic in character ?
•
(I) C6H5 CHC6H5 (a) Carbocation (b) Carbanion
• (c) Free radicals (d) Carbenes
(II) C6H5– CH–CH = CH2 (A) Only b (B) a and c
• (C) a, c and d (D) a, b, c and d
(III) CH3– CH–CH3
•
(IV) C6H5 – CH – CH3 Q.55 Which among the following compounds behave
• both as an electrophile as well as a
(V) CH3CH = CHCH2 CH2 nucleophile:
• 
(a) CH2= CH2 (b) CH2 = CH – C H2
(VI) CH3  CH2  C CH3
|
O O
CH3
|| ||
(A) I > II > III > IV > V > VI (c) CH3  C  CH3 (d) CH3  C  Cl
(B) VI > V > IV > III > II > I (A) Only a (B) a and b
(C) I > II > IV > VI > III > V (C) c and d (D) b, c and d
(D) I > IV > VI > V > II > III
Questions Questions
based on Organic Reagent based on Nucleophilicity & Leaving group

Q.51 Which of the following statements are correct

Q.56 W hich of the following has the highest
for nucleophile : nucleophilicity –
(A) All negatively carged species are (A) F– (B) OH–
nucleophile
 
(B) Nucleophiles are Lewis bases (C) CH 3 (D) NH 2
(C) Alkenes, alkynes, benzene and pyrrole
are nucleophiles Q.57 Arrange the following nucleophiles in the order
of their nucleophilic strength –
(D) All are correct

(A) OH– > CH3COO– > OCH 3 > C6H5O–
Q.52 Which among the following species is an 
(B) CH3COO– < C6H5O– < OCH 3 < OH–
ambident nucleophile ?
(C) C6H5O– < CH3COO– < CH3O– < OH–

(A) CH3 – C H2 (B) CH2 = CH2 (D) CH3COO– < C6H5O– < OH–< CH3O

 •• Q.58 Correct order of leaving group tendency -

(C) C N (D) NH3
(A) – > Br – > Cl– > F–
(B) F– > Cl– > Br – > 
Q.53 In each of the following pairs of species which (C) Cl– > F – > Br – > –
species is an electrophile : (D) – > Cl– > Br – > F

•• ••
(A) NH3 and N F3 Q.59 The nucleophilicities of CH3–, NH2–, OH– and
F– decrease in the order -
I II (A) CH3– > NH2– > OH– > F–
•• •• (B) OH– > NH2– > CH3– > F–
(B) P H3 and P Cl3 (C) NH2– > OH– > CH3– > F–
I II (D) CH3– > OH– > F– > NH2–
(C) CH4 and CCl4
I II Q.60 W hich of the following is the strongest
nucleophile -
•• ••
(D) H2 O and C Cl2 (A) OH– (B) CH3OH
•• (C) CH3S– (D) CH3O–
I II

7
 LEVEL # 2
Q.1 Which of the following belongs to +  group Q.8 Which of the following resonance structures
(A)—OH (B)—OCH3 is the major contributor to the resonance
(C)—COOH (D)—CH3 hybrid ?

Q.2 Which of the following is the strongest - I 

group - CH3 – CH2 – C H – CH3
(A) – N+ (CH3)3 (B) – +NH3
+
(C) – S (CH3)2 (D) – F  CH3 – CH2 – CH = CH3
(A) I
Q.3 Which of the statement are correct?
(A) – NH2 is ortho-para directing group (B) II
(B) – CHO is meta directing group (C) Both have equal contribution
(D) They are not resonance structures
(C) CCl2 is an electrophile

 Q.9 Consider the following three halides -

(D) – OH is (– M) group
 (a) CH3 – CH2 – Cl
(b) CH2 = CH – Cl
Q.4 Among the following compounds, the strongest
acid is – (c) C6H5 – Cl
(A) HC  CH (B) C6H6 Arrange C–Cl bond length of these
(C) C2H6 (D) CH3OH compounds in decreasing order -
Q.5 Heterolysis of propane will yield – (A) a > b > c (B) a > c > b
(C) c > b > a (D) b > c > a
(A) H3 and 2H5 radicals

  Q.10 The species CH3 CHCH3 is less stable
(B) CH 3 and CH3CH 2 ions
  than -
(C) CH 3 and CH3CH 2 ions

 
(D) CH 3 and CH3CH 2 ions (A) (CH3)3 C+ (B) CH3 CH2 CH2

Q.6 Carbocations may be stabilised by - 

(C) CH3 CH 2 (D) CH3
(A) -bonds only at allylic position
(B) bonds only at vinylic position Q.11 Increasing order of electrophilic substitution
(C) bonds at allylic and nonallylic position for following compounds–
also
(D) - I effect

Q.7 In the anion HCOO–, the two carbon-oxygen

bonds are found to be equal length. What is
the reason for it –
(A) the C=O bond is weaker than the C—O (I) (II) (III) (IV)
bond
(B) the anion HCOO– has two resonating (A) IV < I < II < III (B) III < I < II < IV
structures (C) I < IV < III < II (D) II < III < I < IV
(C) the electronic orbitals of carbon atom are
hybridized
(D) the anion of obtained by removal of proton
from the acid molecule

8
Q.12 Arrange in decreasing pKb - Q.17 Consider the following species
(a) F – CH2 CH2 COOH
(a) (b)
(b) Cl CH  CH2 – COOH
| (c) (d)
Cl
Arrange these nucleophilic species in their
(c) F – CH2 – COOH decreasing order of nucleophilicity :
(d) Br – CH2– CH2 – COOH (A) c > d > b > a (B) b > a > c > d
Correct answer is- (C) a > b > c > d (D) c > a > b > d
(A) (b) > (d) > (a) > (c)
(B) (a) > (c) > (d) > (b)
Q.18 Which one of the following statements is not
(C) (c) > (b) > (a) > (d)
correct for electrophile :
(D) (d) > (b) > (a) > (c)
(A) Electron deficient species are electrophile
(B) Electrophiles are Lewis acids
Q.13 The strongest base is–
(C) All + ive charged species are electrophile
(D) AlCl3, SF6, IF7 and SO3 are electrophiles
(A) (B)
Q.19 Which of the following is an electrophilic
reagent ?
(C) (D) CH3—NH—CH3
(A) H2O (B) OH–
(C) NO2+ (D) none

Q.14 Which allylic carbocation is the most stable Q.20 Consider the following carbanions :
carbocation :
(I) H3CO (II) O2N
(A) CH3—CH CH—

(B) CH3—CH CH— (III) (IV) H3C

Correct decreasing order of stability is :

(C) C6H5 —CH CH—
(A) II > III > I > IV (B) III > IV > I > II
(C) IV > I > II > III (D) I > II > III > IV

(D) All have same stability

Q.15 Which among the following species is an

ambident nucleophile : Q.21
(A) Acetone (B) Cyanide ion
(C) Nitrite ion (D) Sulphite ion

Q.16 W hich one of the nitrogen containing I II III

compounds is an electrophile : Arrange following phenol in increasing order of
(A) NH2 —NH2 (B) NH2—OH Pka value
(C) NF3 (D) NH3 (A) I < II < III (B) III < I < II
(C) III < II < I (D) I < III < II

9
 
Q.27 Electrophile NO 2 attacks the following

Q.22 CH2=CHCH2COOH

I II
CH3CH2COOH
III I II III IV
Arrange following acid In decreasing order of 
In which cases cases NO 2 will be
[H+] conc.
(A) I > II > III (B) II > III > I meta-position :
(C) II > I > III (D) III > II > I (A) II and IV (B) I, II and III
(C) II and III only (D) I only
Q.23 Arrange Increasing order of their Ka value.
oxalic acid, succinic acid, Q.28 Arrange Decreasing order of basicity
I II CI— RCOO— OH— RO— NH —
2
malonic acid, adipic acid I II III IV V
III IV (A) I > II < III > IV < V
(all dibasic) (B) V > IV > II > III > I
(A) III < II < I < IV (B) II < III > I > IV (C) I > II > III > IV > V
(C) I > III > II > IV (D) II > I > III < IV (D) V > IV > III > II > I

Q.24 Arrange the following in Decreasing order of

Q.29 Arrange the Stability of following
theIr PKa value
CH2=CHCH2NH2, CH3CH2CH2NH2 ,
I II
CHCCH2NH2
III I II III
(A) I > II < III (B) II > I > III (A) I < II < III (B) II < I < III
(C) III > II > I (D) II < III < I (C) I < III < II (D) II < III < I

Q.25 Arrange the following in increasing of pH value Q.30 StabIlIty of followIng radIcal Is
NH C6H5

CH2= H, H2CH=CH2

I II III
I II III IV
(A) III > I > II (B) III < I < II
(A) II > III > II > IV (B) III > II > I > IV
(C) III < II > I (D) II < III < I
(C) III < II < I < IV (D) I < IV < II < III

Q.26 Arrange in Increasing of basic strength Q.31 Increasing of the following for SE

I II III I II III IV
(A) II < III < I (B) I > II > III (A) IV < III < II < I (B) IV < III < I < II
(C) III > II < I (D) I < II < III (C) III < I < II < IV (D) III > I > II > IV

10
Q.32 Increasing order of the stability is Q.39 Give the correct order of decreasing basicity
CH3CH=CH2 CH3CH2CH=CH2, of the following compounds,
I II C6H5NH2 (C6H5)2NH (C6H5)3N C6H11NH2
I II III IV
(CH3)3CCH=CH2 (A) I > II > III > IV (B) IV > III > II > I
(C) IV > I > II > III (D) III > II > I > IV
III IV
(A) I > II > III > IV (B) I > III > II > IV
(C) I > IV > III > II (D) IV > III > II > I Q.40 The correct order of stability of the following
carbocations is -
 
Q.33 Decreasing order of Basicities - (A) CH3 CH2 C H2 > CH2  CH  C H2 >
(A) RO– > OH– > CN– > RCOO– > NO3– 
(B) NO3– > CN– > RCOO– > RO– > OH– CH2  CHCHCH3 > CH2 = CHC(CH3)2
(C) OH– > CN– > RCOO– > NO3– > RO–
 
(D) NO3– > CN– > RCOO– RO– > OH– (B) CH2  CHC H2 > CH3 CH2 C H2 >
 
CH2  CHC (CH3 )2 > CH2  CHCHCH3
Q.34 electrophilic  
(C) CH2  CHC (CH3 )2 > CH2  CHCHCH3 >
substitution occurs at  
(A) o/p of 1st ring (B) meta at 1st ring CH2  CH C H2 > CH3 CH2 C H2
(C) o/p at 2nd ring (D) meto of 2nd ring.
 
(D) CH2  CH  C HCH3 > CH2  CH C(CH3 )2
Q.35 Which of the following molecules can behave  
both as a nucleophile and an electrophile ? > CH3 CH2  C H2 > CH2  CH C H2
(A) CH3NH2 (B) CH3Cl
(C) CH3CN (D) CH3OH Q.41 The order of reactivity of the following alcohols
towards concentrated HCl is -
OH
Q.36 Which of the following molecules has the
F ,
shortest carbon-carbon single bond length ? OH F
(A) CH2 = CH – C  CH
I II
(B) CH2 = CH – C  N
OH
(C) CH2 = CH – CH = O Ph OH
,
(D) CH2 = CH – CH  CH2
III IV
(A) I > II > III > IV (B) I > III > II > IV
Q.37 Which of the following shows the correct order
(C) IV > III > II > I (D) IV > III > I > II
of decreasing basicity in aqueous medium ?
(A) (CH3)3N > (CH3)2NH > CH3NH2 > NH3
Q.42 The relative rate of addition of HCl to the
(B) (CH3)2NH > (CH3)3N > CH3NH2 > NH3 following compounds follows the order -
(C) (CH3)2NH > CH3NH2 > (CH3)3N > NH3 (A) CH2=CHCO2H > CH2 = CH2 >
(D) (CH3)2NH > CH3NH2 > NH3 > (CH3)3N CH3CH = CH2 > (CH3)2C = CH2
(B) (CH3)2C = CH2 > CH3CH = CH2 >
Q.38 The correct order of increasing basicity is - CH2 = CH2 > CH2 = CHCO2H
(C) CH2 = CH2 > CH3CH = CH2 >
(A) pyrrole < pyridine < Me3N < Et3N
CH2 = CHCO2H > (CH3)2C = CH2
(B) pyridine < pyrrole < Et3N < Me3N
(D) CH3CH = CH2 > CH2 = CHCO2H >
(C) pyrrole < Et3N < Me3N < pyridine (CH3)2C = CH2 > CH2 = CH2
(D) Me3N < Et3N < pyridine < pyrrole

11
Q.43 The order of decreasing stability of the cations Q.48 Different hydrogens in
a b b c d e f
  
CH3 C HCH3 CH2 C HOCH3 CH3 C HCOCH3 CH3CH = CH—CH2—CH2—CH(CH3)2 are
represented by alphabets. Arrange them in
I II III decreasing order of reactivity towards radical
is - substitution :
(A) III > II > I (B) I > II > III (A) c > a > e > d > f > b
(B) f > b > a > c > d > e
(C) II > I > III (D) I > III > II
(C) b > c > a > f > d > e
(D) a > b > c > d > e > f
Q.44 What is the decreasing order of strength of
the bases, OH– (I), NH2– (II), H––C C– (III),
Q.49 Consider the following
CH3CH2– (IV) ?
(A) IV > II > III > I (B) III > IV > II > I
(C) I > II > III > IV (D) II > III > I > IV CH3CH2NH2 CH3 NH2

I II III
Q.45 In the following compounds, anisole (I),
Correct order of theIr basIc strength Is
benzene (II) and nitrobenzene (III), the ease of
(A) I < II < III (B) II > I > III
reaction with electrophiles is -
(C) III > II < I (D) II < III < I
(A) II > III > I (B) III > II > I
(C) II > I > III (D) I > II > III
Q.50 Arrange the following in Decreasing of their
basic nature.
Q.46 The decreasing order of nucleophilicity among
the nucleophiles -

(I)
I II III
(A) I > II > III (B) II < III < I
(II) CH3O–
(C) III < II > I (D) II > I > III
(III) CN–

(IV)

(A) I, II, III, IV (B) IV, III, II, I

(C) II, III, I, IV (D) III, II, I, IV

Q.47 The correct order of basicities of the following

compounds is–

CH3CH2NH2

(a) (b)

(CH3)2NH
(c) (d)
(A) b > a > c > d (B) a > c > b > d
(C) c > a > b > d (D) a > b > c > d
12
 LEVEL # 3
Single correct type Questions Q.6 Which of the following molecules can behave
both as a nucleophile and an electrophile?
Q.1 Which of the following statements is not true (A) CH3NH2 (B)CH3Cl
about the resonance contributing structures of (C) CH3CN (D) CH3OH
a resonance hybrid -
(A) Contributing structures contribute to the
Q.7 Which of the following shows the correct order
resonance hybrid in proportion of their
of decreasing acidity -
energies
(A) PhCO2H > PhSO3H > PhCH2OH > PhOH
(B) Equivalent contributing structures make the
resonance very important (B) PhSO3H > PhOH > PhCH2OH > PhCH2OH
(C) Contributing structures represent (C) PhCO2H > PhOH > PhCH2OH > PhSO3H
hypothetical molecules having no real (D) PhSO3H > PhCO2H > PhOH > PhCH2OH
existence
(D) Contributing structures are less stable than Q.8 Which of the following correctly shows the
the resonance hybrid order of decreasing basicity -
(A) Aniline > o-nitroaniline > p-nitroaniline >
Q.2 The numbers of  bonds and  bonds present m-nitroaniline
in a molecule of benzaldehyde are, respectively- (B) Aniline > p-nitroaniline > o-nitroaniline >
(A) 4 and 13 (B) 4 and 8 m-nitroaniline
(C) 4 and 14 (D) 8 and 10 (C) Aniline > m-nitroaniline > p-nitroaniline >
o-nitroaniline
Q.3 W hich of the following is the weakest (D) o-Nitroaniline > p-nitroaniline > aniline >
nucleophile - m-nitroaniline
(A) C2H5O – (B) C2H5S–
(C) CH3COO– (D) CO32–
Q.9 (I) (II)

Q.4 The length of the carbon–carbon single bond

of the compounds
(I) CH2 = CH – C  CH (III) (IV)
(II) CH  C – C  CH
(III) CH3 – CH = CH2 The correct order of decreasing basicity of the
(IV) CH2 = CH – CH = CH2 above compound is -
is expected to decrease in the order - (A) I > II > III > IV (B) II > I > IV > III
(A) III > II > I > IV (C) III > IV > II > I (D) II > I > III > IV
(B) I > III > II > IV
(C) III > IV > I > II Q.10 Give the correct order of increasing acidity of
the following compounds -
(D) II > IV > I > III

(I) (II)
Q.5 Give the correct order of increaseing acidity of
the following compounds -
(I) ClCH2COOH (II) CH3CH2COOH (III) (IV)
(III) ClCH2CH2COOH (IV) (CH3)2CHCOOH
(V) CH3COOH (A) II < I < IV < III (B) IV < II < I < III
(C) I < II < IV < III (D) IV < I < II < III
(A) V < II < IV < I < III (B) IV < II < V < III < I
(C) III < I < IV < II < IV (D) V < IV < II < I < III

13
Q.11 Select the correct order of basicity - Q.15 Which of the following shows the correct order
(A) CH3CH2– > CH2 = CH– > HC  C– > OH– of stability -
(B) CH3CH2– > HC  C– > CH2 = CH– > OH–
(A) < <
(C) CH3CH2– > OH– > HC  C– > CH2 = CH–
(D) OH– > HC  C– > CH2 = CH– > CH3CH2– <

Q.12 W hich of the following substituents will (B) < <

decrease the acidity of phenol -
(A) –NO2 (B) –CN <

(C) –CH3 (D) –CHO

(C) < < <

Q.13 The correct order of increasing stability of the

following carbocations is -
(D) < < <
(A) > >

> Q.16 The correct order of decreasing hyperconjugative

effect of the following compounds is -
(B) > > (A) CH 3 CH=CH 2 > CH 3 CH 2 CH=CH 2 >
(CH3)2 CHCH=CH2
> (B) (CH 3 ) 2 CHCH=CH 2 > CH 3 CH=CH 2 >
CH3CH2CH=CH2
(C) (CH3)2 CHCH=CH2 > CH3CH2CH=CH2 >
(C) > > CH3CH=CH2
(D) CH 3 CH 2 CH=CH 2 > CH 3 CH=CH 2 >
> (CH3)2 CHCH=CH2

Q.17 Arrange the following compounds in the order

(D) > > of increasing rate of reaction with HCl -

(I) (II) CH3CH = CH2

>

Q.14 In which of the following does the C–H bond

(III)
(shown by a thick line) have the least bond
dissociation energy -
(IV) CH2 = CH2
(A) PhCH2 – H (B) Me3C–H
(C) Me2CH – H (D) Me – H (A) IV < II < I < III (B) III < IV < II < I
(C) III < I < II < IV (D) I < II < III < IV

14
Q.18 Which of the following shows the correct order Hyperconjugation are three types :-
of decreasing stability -
(i) (C–H), -conjugation
(A) > > (ii) (C–H), positive charge conjugation
(iii) (C–H), odd electron conjugation
>
The hyperconjugation may be represented as

(B) > >

H H
|
> H – C – CH = CH2 H – C = CH – CH2
| |
H H
(C) > >
H
|
> H C = CH – CH2
|
H
(D) > >

>

H
Q.19 Among the following alkenes |
1-butene cis-2-butene trans-2-butene H – C = CH – CH2
I II III H
the order of decreasing stability is -
(A) II > I > III (B) III > I > II Number of resonating structures due to
(C) I > II > II (D) III > II > I hyperconjugation = (n + 1 ) where n is
number of -hydrogen . Greater is the number
Q.20 W hich of the following cannot exhibit of such forms, more is the stability of species
hyperconjugation - under consideration.

(A) CH3CH2 . (B)

Q.21 Hyperconjugation is possible in which of the
following species ?
(C) CH3CH = CH2 (D)
(A) CH –CH
3 2
Passage based Questions
(B) C6H5–CH3
Passage :
Hyperconugation describes the orbital (C) CH2=CH2
interaction between the -system and the
adjacent -bond of the substituent group (s) in CH3
|
organic compounds. Hyperconjugation is also (D) CH3 – C – CH = CH2
called as Baker and Nathan effect. The |
CH3
necessary and sufficient condition for the
hyperconjugation are :
(i) compound should have at least on sp2-
hybrid carbon of either alkene, carbocation
or alkyl free radical.
(ii) -carbon with respect to sp2-hybrid carbon
should have at least one hydrogen.

15
Q.22 Which of the following carbonium ions will Q.24 Statement I : Tertiary carbocations are
show highest number of hyperconjugation generally formed more easily than primary
forms ? carbocations.

(A) CH3–CH 2 Statement II: Hyperconjugation as well as
inductive effect due to additional alkyl group
 stabilize tertiary carbocations.
(B) CH3 – CH
| Q.25 Statement I : Allyl free radical is more stable
CH3 than simple alkyl free radical.
Statement II: The allyl free radical stabilized
CH3 by resonance.
|
(C) CH3 – C Q.26 Statement I : Nucleophiles attack the
|
CH3 regions of high electron density.
Statement II : Nucleophiles act as lewis
bases.
CH3
|
(D) CH3– CH2 – C Q.27 Statement I : Heterolytic fission involves the
| breaking of a covalent bond in such a way
CH3 that both the electrons of the shared pair are
carried away by one of the atoms.
Statement II : Heterolytic fission occurs
Q.23 Which of the following alkenes will show
readily in polar covalent bonds.
maximum number of hyperconjugation forms ?
(A) CH2 = CH2
Q.28 Statement I : tert-Butoxide is a stronger
(B) CH3 – CH = CH2 base than OH or C2H5 ion but is a much
poor nucleophile.
(C) CH3 – CH2 – CH = CH2 Statement II : A negatively charged ions is
always more powerful nucleophile than its
CH3 conjugate acid.
|
(D) CH3 – CH – CH = CH2
Q.29 Statement I : Formaldehyde is a planar
molecule.
Statement based Questions Statement II : Carbon atom in formaldehyde
is sp2-hybridized.
Each of the questions given below consist
of Statement – I and Statement – II. Use the
following Key to choose the appropriate Q.30 Statement I : The Pk a value of acetic acid
answer. is lower than that of phenol.
(A) If both Statement- I and Statement- II are Statement II : Phenoxide ion is more
true, and Statement - II is the correct resonance stabilized.
explanation of Statement– I.
(B) If both Statement - I and Statement - II
are true but Statement - II is not the
correct explanation of Statement – I.
(C) If Statement - I is true but Statement - II
is false.
(D) If Statement - I is false but Statement - II
is true.

16
 LEVEL # 4
(Questions asked in previous AIEEE & IIT-JEE)

SECTION-A Q.4 Rate of the reaction

Q.1 In the following benzyl/alkyl system [AIEEE-2004]

R – CH = CH2 or
R– +N  R – +
(R is alkyl group)
increasing order of inductive effect is –
is fastest when Z is -
[AIEEE-2002]
(A) Cl (B) NH2
(A) (CH3)3 C – > (CH3)2 CH –> CH3CH2— (C) OC2H5 (D) OCOCH3
(B) (CH3CH2 – > (CH3)2 CH –> (CH3)3C —
(C) (CH3)2 CH – > CH3CH2 –> (CH3)3C— Q.5 Consider the acidity of the carboxylic acids :
(D) (CH3)C – > CH3CH2 –> (CH3)2CH— [AIEEE-2004]
(a) PhCOOH
CH3 (b) o – NO2C6H4COOH
| (c) p – NO2C6H4COOH
Q.2 W hen – CH 3 , CH3  CH  & CH3  C  (d) m – NO2C6H4COOH
| | Which of the following order is correct ?
CH3 CH3 (A) a > b > c > d (B) b > d > c > a
groups are introduced on benzene ring then (C) b > d > a > c (D) b > c > d > a
correct order of their inductive effect is -
[AIEEE-2002] Q.6 Which of the following is the strongest base -
CH3 [AIEEE-2004]
|
(A) CH3 – > CH3  CH  > CH3  C  (A)
| |
CH3 CH3

CH3 (B)
|
(B) CH3  C  > CH3  CH  > CH3 –
| |
CH3 CH3 (C)

CH3
|
(C) CH3  CH  > CH3 – > CH3  C 
| | (D)
CH3 CH3

CH3
| Q.7 The decreasing order of nucleophilicity among
(D) CH3  C  > CH3 – > CH3  CH  the nucleophiles
| | [AIEEE-2005]
CH3 CH3
Q.3 The correct order of increasing basic no. of the
(a) CH3C  O  (b) CH3O–
bases NH3, CH3NH2 and (CH3)2NH is – ||
[AIEEE-2003] O
(A) NH3 < CH3NH2 < (CH3)2NH
(c) CN– (d)
(B) CH3NH2 < (CH3)2NH < NH3
is
(C) CH3NH2 < NH3 < (CH3)2NH
(A) (d), (c) , (b) , (a) (B) (a), (b), (c) , (d)
(D) (CH3)2NH < NH3 < CH3NH2 (C) (c) , (b) , (a) , (d) (D) (b), (c) , (a) , (d)

17
Q.8 The reaction Q.13 Which one of the following is the strongest
[AIEEE-2005] base in aqueous solution ?
[AIEEE-2007]
(A) Trimethylamine (B) Aniline
is fastest when X is – (C) Dimethylamine (D) Methylamine
(A) NH2 (B) Cl
(C) OCOR (D) OC2H5
Q.14 Presence of a nitro group in a benzene ring-
Q.9 Amongst the following the most basic compound [AIEEE 2007]
is– [AIEEE-2005] (A) activates the ring towards electrophilic
(A) aniline (B) benzylamine substitution
(C) p–nitroaniline (D) acetanilide
(B) renders the ring basic
Q.10 The increasing order of stability of the following (C) deactivates the ring towards nucleophilic
free radicals is – [AIEEE 2006] substitution
   (D) deactivates the ring towards electrophilic
(A) (C6H 5)3 C < (C 6H 5)2 C H < (CH3) 3 C <
substitution

(CH3)2 C H
   Q.15 Arrange the carbanions, (CH 3 ) 3 C , CCl3 ,
(B) (C6H 5)2 C H < (C 6H 5)3 C < (CH3) 3 C <
 (CH 3 ) 2 C H , C 6 H 5 C H2 , in order of their
(CH3)2 C H
   decreasing stability- [AIEEE 2009]
(C) (CH 3 ) 2 C H < (CH 3 ) 3 C < (C 6 H 5 ) 3 C <

(C6H5)2 C H (A) (CH3)2 CH > CCl3 > C6H5 C H2 > (CH3)3 C

  
(D) (CH3)2 C H < (CH3)3 C < (C6H5)2 C H < (B) CCl3 > C6H5 C H2 > (CH3)2 C H > (CH3)3 C


(C6H5)3 C (C) (CH3)3 C > (CH3)2 C H >C6H5 C H2 > CCl3

Q.11 CH3Br + Nu–  CH3 – Nu + Br– (D) C6H5 C H2 > CCl3 > (CH3)3 C > (CH3)2 C H
The decreasing order of the rate of the above
reaction with nucleophiles (Nu–) A to D is
[Nu– = (A) PhO–, (B) AcO–, (C) HO–, (D) CH3O] SECTION-B
[AIEEE 2006]
(A) D > C > B > A (B) A > B > C > D Q.1 Which one of the following has the smallest
(C) B > D > C > A (D) D > C > A > B heat of hydrogenation per mole ?
[IIT - 1993]
Q.12 The correct order of increasing acid strength of
(A) 1-Butene (B) trans-2-Butene
the compounds [AIEEE 2006]
(a) CH3CO2H (b) MeOCH2CO2H (C) cis-2-Butene (D) 1,3-Butadiene

Me
(c) CF3CO2H (d) CO2H is
Me
(A) d < a < c < b (B) d < a < b < c
(C) a < d < c < b (D) b < d < a < c

18
Q.2 What is the decreasing order of strength of Q.6 Arrange in order of decreasing trend towards
bases ? [IIT - 1993] SE reactions,
O H, N H2 , H – C  C–, CH3 – CH2 Chlorobenzene , Benzene,
I II
(A) CH3 – CH2 > NH2 > H – C  C– > OH– Aniline chloride, Toluene
III IV
(B) H – C  C– > CH3 – CH2 > NH2 > OH–
[IIT-1995]
(A) II > I > III > IV (B) III > I > II > IV
(C) IV > II > I > III (D) I > II > III > IV
(C) OH– > NH2 >H – C  C– > CH3 – CH2

(D) NH2 >H – C  C– > OH– > H3C – CH2 Q.7 In the following compounds -
[IIT - 1996]
Q.3 Choose the correct statement from the ones OH
given below for two anilium in - [IIT-1993] OH

+
NH3 NH3
CH3
I
+ II

(I) (II)

(A) II is not an acceptable canonical structure be-

cause carbonium ions are less stable than am-
monium ions
(B) II is not an acceptable canonical structure III IV
because it is non aromatic
(C) II is not an acceptable canonical structure The order of acidity is -
because the nitrogen has 10 valence elec- (A) III > IV > I > II (B) I > IV > III > II
trons (C) II > I > III > IV (D) IV > III > I > II
(D) II is an acceptable canonical structure
Q.8 In the following groups :
Q.4 The kind of delocalization involving sigma [IIT-1997]
bond orbitals is called [IIT - 1994] –OAc –OMe
(A) Inductive effect I II
(B) Hyperconjugation effect
–OSO2Me –OSO2CF3
(C) Electromeric effect
III IV
(D) Mesomeric effect
the order of leaving group ability is
(A) I > II > III > IV (B) IV > III > I > II
Q.5 Most stable carbonium ion is -
(C) III > II > I > IV (D) II > III > IV > I
[IIT-1995]
(A) p-NO2 - C6H4 - +CH2
(B) C6H5+CH2
(C) p-Cl - C6H4 - +CH2
(D) p-CH3O - C6H4 - +CH2

19
Q.9 In the following compounds, the order of basicity Q.13 An aromatic molecule will not -
is - [IIT - 1997] [IIT - 1999]
(A) have 4n  electrons
(B) have (4n + 2)  electrons
O (C) be planar
(D) be cyclic
N
N |
N N Q.14 Read the following statement and explanation
H
I II H and answer as per the option given below :
III IV
[IIT-2000]
(A) IV > I > III > II (B) III > I > IV > II Assertion : Phenol is more reactive than
(C) II > I > III > IV (D) I > III > II > IV benzene towards electrophilic substitution
reaction.
Q.10 The formation of cynohydrin from a ketone is Reason : In the case of phenol, the
an example of -
intermediate cabocation is more resonance
[IIT - 1998]
stabilised.
(A) Electrophilic addition
(A) If both assertion and reason are correct, and
(B) Nucleophilic addition
(C) Nucleophilic substitution reason is the correct explanation of the
(D) Electrophilic substitution assertion
(B) If both assertion and reason are correct, but
Q.11 Polarisation of electrons in acrolein may be reason is not correct explanation of the
written as- assertion
[IIT - 1998] (C) If assertion is correct but reason is
  incorrect
(A) C H2 = CH – C H = O (D) If assertion is incorrect but reason is
  correct
(B) C H2 = CH – CH = O
 
Q.15 Amongst the following, the most basic
(C) C H2 = C H – CH = O compound is - [IIT - 2000]
(A) C6H5NH2
 
(D) C H 2 = CH–CH = O (B) p-NO2 – C6H4NH2
(C) m-NO2 – C6H4NH2
Q.12 The most unlikely representation of resonance (D) C6H5CH2NH2
structure of p-nitrophenoxide ion is -
[IIT - 1999]
Q.16 Which of the following alkenes will react fastest
with H 2 under catalytic hydrogenation
conditions? [IIT- 2000]

(A) (B)
(A) (B)

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

20
Q.17 W hich of the following has the highest
nucleophilicity ?
[IIT - 2000]
–
(A) F (B) OH– Q.22 when X is made to
(C) CH3 (D) NH2

Q.18 The correct order of basicities of the following

compounds is - react with 2 eq. of NaNH2 the product formed
[IIT - 2001] will be:

[IIT - 2003]
CH3 CH2NH2

1 2
O
||
(CH3)2NH CH3CONH2
3 4
(A) 2 > 1 > 3 > 4 (B) 1 > 3 > 2 > 4 (A)
(C) 3 > 1 > 2 > 4 (D) 1 > 2 > 3 > 4

Q.19 Identify the correct order of reactivity in

electrophilic substitution reaction of the following
compounds-

(B)

[IIT - 2002]

(A) 1 > 2 > 3 > 4 (B) 4 > 3 > 2 > 1

(C) 2 > 1 > 3 > 4 (D) 2 > 3 > 1 > 4

Q.20 Left to right sp2, sp2, sp, sp hybridization is (C)

presnt in :
[IIT - 2003]
(A) H2C = CH – C  N
(B) H2C = C = CH – CH3
(C) HC  C – C  CH
(D) HC  C – CH = CH2

Q.21 Maximum dipole moment will be of :

[IIT - 2003]
(A) CCl4 (B) CHCl3
(D)
(C) CH2Cl2 (D) CH3Cl

21
Q.23 Order of rate of reaction of following compound Q.27 Among the following, the least stable
with phenyl magnesium bromide is : resonance structure is :
[IIT - 2004]
[IIT - 2007]
Ph–C–Ph Me–C–H
O O
I II (A)
Me–C–Me
O
III
(A) I > II > III (B) II > III > I
(C) III > I > II (D) II > I > III
(B)

Q.24

Correct order of acidic strength is : (C)

[IIT - 2004]
(A) x > y > z (B) z > y > x
(C) y > z > x (D) x > z > y
(D)
Q.25 Which of the following is least stable
[IIT - 2005]

(A) Q.28 Hyperconjugation involves overlap of the

+
O -
O following orbitals-
(B) CH3  O = CH  CH = HC  CH2
[IIT-2008]
(C) (A)  –  (B)  – p
(C) p – p (D)  – 
(D)
Q.29 The correct stability order for the following
Q.26 Statement-1 : p-Hydroxybenzoic acid has a species is-
lower boiling point that o-hydroxybenzoic [IIT-2008]
acid.
Because
Statement-2 : o-Hydroxybenzoic acid has O
intramolecular hydrogen bonding. (I) (II)
[IIT - 2007]
(A) Statement-1 is True, Statement-2 is True ;
Statement-2 is a correct explanation for
Statement-1 O
(III) (IV)
(B) Statement-1, is True, Statement-2 is True;
Statement-2 is NOT a correct explanation (A) (II) > (IV) > (I) > (III)
for Statement-1
(B) (I) > (II) > (III) > (IV)
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1, False, Statement-2 is True (C) (II) > (I) > (IV) > (III)
(D) (I) > (III) > (II) > (IV)

22
Q.30 In the following carbocation, H/CH3 that is most
likely to migrate to the positively charged car-
bon is - [IIT-2009]

H H
1 2 + 4 5
H3C––C––C––C––CH3

HO H CH3

(A) CH3 at C-4 (B) H at C-4

(C) CH3 at C-2 (D) H at C-2

Q.31 The correct stability order of the following

resonance structures is -[IIT-2009]

+ – + – – + – +
H2C=N=N H2C–N=N H2C–NN H2C–NN
(I) (II) (III) (IV)

(A) (I) > (II) > (IV) > (III)

(B) (I) > (III) > (II) > (IV)
(C) (II) > (I) > (III) > (IV)
(D) (III) > (I) > (IV) > (II)

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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 21 22 23 24 25
Ans. C D B A B A D A A C A B A A C B A B A C D D A B B
Q.No. 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50
Ans. C C A,C B B B A B C C D D C A,D D C D A B B D A A C C
Q.No. 51 52 53 54 55 56 57 58 59 60
Ans. D C B C C C B 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 A A,B D B A B B A A A C B C B,C,D C A B 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 B C A C C
Q.No. 41 42 43 44 45 46 47 48 49 50
Ans. C B C A D C D A D A

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 C D C 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 B B A B

LEVEL # 4
SECTION-A

Qus. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. A A A A D D D B B D D B C D B

SECTION-B

Q.No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. D A C B D C D B D B D C A A D A C B C A
Q.No. 21 22 23 24 25 26 27 28 29 30 31
Ans. D C B D A D A B D D B

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