GOC

DPP-1
1. The inductive effect - 6. Which of the following groups has the
(A) implies the atom's ability to cause highest + I effect -
bond polarization (A) CH3 – (B) CH3CH2 –
(B) increases with increase of distance (C) (CH3)2 CH – (D) (CH3)3 C –
(C) implies the transfer of lone pair of 7. Maximum –I effect is exerted by the
electrons from more electronegative group
atom to the lesser electronegative (A) C6H5 – (B) – OCH3
atom in a molecule (C) Cl (D) NO2
(D) implies the transfer of lone pair of 8. Zero inductive effect is exerted by -
electrons from lesser electronegative (A) C6H5 – (B) H
atom to the more electronegative (C) CH3 – (D) Cl
atom in a molecule 9. Mesomeric effect takes part in -
2. Which among the given acid has lowest (A) Saturated system
pKa value - (B) Unsaturated system containing
(A) Chloroacetic acid (B) Bromoacetic acid conjugated double bond.
(C) Nitroacetic acid (D) Cyanoacetic acid (C) Unsaturated system containing non
conjugated double bond.
3. Arrange basic strength of the given
(D) A triple bond in a carbon chain
compounds in decreasing order -
(a) CH3–CH2–NH2 10. Arrange their Acidic strength

(b) CH2=CH–NH2 OH

(c) CHC–NH2 H2O C2H5OH

(A) a > b > c (B) a > c > b I II III

(C) c > b > a (D) b > c > a
(A) I > II > III (B) II > I > III

4. Consider following acid (C) III < II > I (D) II < III < I

ClCH2COOH, CH3COOH, CH3CH2COOH 11. Arrange the following in Increasing of their

basicity
I II III
Correct order of their pH value will be - HO–, CH3COO– Cl–

(A) III < II < I (B) I < II < III I II III

(C) I < III < II (D) II < I < III (A) III > II > I (B) III < II < I
(C) II < III < I (D) II < III > I
5. Which is most acidic compound –
(A) C2H5COOH (B) CH3CH2CH2COOH
(C) CH3COOH (D) HCOOH

1
12. Consider following benzyl alcohol 15. The order of stability of the following
CH2OH CH2OH resonating structures is -

O O O

CH2=CH–CH CH2–CH=C–H CH2–CH=CH
NO2
(I) (II) (III)
I II
(A) II > I > III (B) I > III > II
CH2OH CH2OH
(C) I > II > III (D) III > II > I
16. Most stable carbocation is -

OCH3 Cl  
(A) CH2=CH (B) CH2=CH–CH2
III IV 
Correct order of their Kb value is - (C) CH2 (D)  CH3
(A) III > IV > II > I (B) III > I > IV > II 17. Which of the following is most stable -
(C) I < II < III < IV (D) IV > II > I > III  
(A) CH3 (B) CH3– CH2
13. Which of the following pairs of structures  
(C) CH3–CH –CH3 (D) CH2=CH–CH2
do not represent resonating structures -
O OH 18. Which of the following is most stable
(A) CH3 – C – CH3 ; CH3 – C = CH2
carbocations -

 
(B) O ; O (A) CH3 (B) CH3– CH2
 O CH3
OH OH 

(C) CH3 – C – CH3 ; CH3 – C – CH3 (C) CH3–C (D) CH3–C– CH2

CH3

(D) CH3 –C–OH ; CH3–C=OH 19. Which of the following is least stable
O O carbocations -
 
14. Which of the following pairs represent (A) CH2=CH (B) CH3– CH2
resonating structures -  
(C) CH3 (D) PhCH2
(A) ClCH2CH=CHCH3 and CH2=CH–CH–CH3
Cl 20. Which of the following is most stable -

  .. (A) CH3 (B) CH3– C–CH3

(B) :CH2–NN: and CH2=N=N
CH3
(C) CH3–CN and CH3–N C
(C) F–C–F (D) Cl –C–Cl
(D) All the above
F Cl

2
 GOC
DPP-2
CH2 5. Arrange the following nucleophiles in the
CH2
order of their nucleophilic strength -
1. is more stable than
(A) HO– > CH3COO– > CH3O– > C6H5O–
NO2
(B) CH3COO– < C6H5O– < CH3O– < HO–
NO2
(C) C6H5O– < CH3COO– < CH3O– < HO
(I) (II)
(D) CH3COO– < C6H5O– < HO– < CH3O–
because
6. Which of the following carbocation is most
(A) 180 location of NO2 and CH2 in I
stable-
(B) –NO2 opperate both –I and –M in I.  
CH2 CH2
(C) –I in II is weaker than I
(D) Due to steric hinderance (A) (B)

2. Which of the following is most stable - CH3

 
(A) CH3 (B) CH2=CH CH2 CH2

(C) CH C (D) CH3–C C (C) (D)

3. Consider the following carbocations - OH NO2


(a) CH3O CH2 7. Which one of the carboanions is most
stable-

(b) CH2 CH2 CH2
NO2
 (A) (B)
(c) CH3 CH2
NO2
 
(d) CH3– CH CH2

CH2
2
The relative stabilities of these CN
(C) (D)
carbocations are such that-
(A) d < b < c < a (B) b < d < c < a CN

(C) d < b < a < c (D) b < d < a < c 8. Arrange stability of the given carbocations
in decreasing order –
4. Least stable carbanion is -  
 
CH2 CH2 CH2 CH2
(A) HCC (B)

(C) CH2=CH (D) CH3–CH2

OCH3 OH NH2 Cl

3
 I II III IV
.
(c) CH3–C–CH3 (d) CH3
(A) I > II > III > IV (B) III > II > I > IV CH3
(C) IV > I > II > III (D) II > III > I > IV (A) c > d > a > b (B) a > b > c > d
(C) c > b > d > a (D) c > b > a > d
9. In the anion HCOO–, the two carbon-
13. Correct order of stability is -
oxygen bonds are found to be equal
(A) CH2=CH2 > CH3–CH=CH2 >
length. What is the reason for it –
(CH3)2C=CH2
(A) the C=O bond is weaker than the C–
O bond (B) CH2=CH2 < CH3–CH=CH2 <

(B) the anion HCOO– has two resonating (CH3)2C=CH2

structures (C) CH2=CH2 < (CH3)2C=CH2 < CH3–
(C) the electronic orbitals of carbon CH=CH2
atom are hybridized (D) CH3–CH=CH2 < CH2=CH2 <
(D) the anion of obtained by removal of
(CH3)2C=CH2
proton from the acid molecule
14. Rank the following radicals in order of
OH OH OH
10. NO2 Decreasing stability -

NO2
NO2
I II III I II III IV
Arrange following phenol in increasing (A) III > II > I > IV (B) III > II < I < IV
order of Pka value - (C) II > III > II > IV (D) III < II < I < IV
(A) I < II < III (B) III < I < II 15. Arrange the Stability of following -
(C) III < II < I (D) I < III < II

11. What is the decreasing order of strength

I II III
of the bases,
(A) I < II < III (B) II < I < III
OH , NH2 , H–CC , CH3CH2 - (C) I < III < II (D) II < III < I
(I) (II) (III) (IV)
(A) IV > II > III > I (B) III > IV > II > I 16. Which of the following substituents will

(C) I > II > III > IV (D) II > III > I > IV decrease the acidity of phenol -
(A) –NO2 (B) –CN (C) –CH3 (D) –CHO
12. The stability of given free radicals in
decreasing order is -
. .
(a) CH3–CH2 (b) CH3–CH –CH3

4
 (A) CH3–CH2–CH–COOH
17. Hyperconjugation is possible in which of
Cl
the following species -
(B) CH3–CH–CH2–COOH
(A) CH3–CH2 (B) C6H5–CH3 Cl
CH3 (C) CH2–CH2–CH2–COOH
(C) CH2=CH2 (D) CH3–C–CH=CH2 Cl

CH3 (D) CH3–CH–CH2–COOH

Br
18. Which of the following carbonium ions
will show highest number of 20. Which is more acidic than phenol -

hyperconjugation forms - OH OH

  CH3
(A) CH3–CH2 (B) CH3–CH (A) (B)

CH3 OH
CH3 CH3 OH
(C) CH3–C  (D) CH3–CH2–C 
NO2
(C) (D) All the above
CH3 CH3

19. Which of the following substituted

carboxylic acids has the highest Ka value -

5
 GOC
DPP-3
1. Choose the most stable Carbocation (A) NH2 is a stronger base

(A) CH3–CH=CH–CH2 (B) CCl3 is more basic than CF3
 (C) NH2OH is less basic than NH3
(B) CH2=CH–CH–CH3
 (D) CHC is less basic than CH2=CH
(C) CH2=C–CH2–CH3
 7. Which one of the following is strongest
(D) CH2=CH–CH2–CH2
acid -
2. Which of the following effect does not (A) 2-chloropentanoic acid
stabilises carbanion - (B) 3-chloropentanoic acid
(A) – I effect (B) – M effect (C) 5-chloropentanoic acid
(C) Hyper conjugation (D) All the above (D) 4-chloropentanoic acid

3. Charge on carbon free radical is - 8. Which has localized ve charge -

(A) Zero (C) Positive  
NH3 CH2
(C) Negative (D) All of these
(a) (b)
4. Which of the following is not the
resonance contributor for phenoxide ion - 
O CH3 CH2
O

(A) (B) (c) (d) H2N – C = NH2
NH2

O O (A) a, d (B) a, c
(C) c, d (D) b, d
(C) (D)
 9. Most powerful leaving group in following–
(A) NH2 (B) HO
5. Most stable carbonium ion in the
(C) CH3 (D) F
following will be -
..
:O : :O :
(A)  (B)  . . (I)  (II)
10. H–C–OH.. H–C=OH
..
(C) CH2 (D)  .. 
:O : :O :
. . (III) . . (IV)
H–C–OH. . H–C–OH
.. ..
6. Which of the following is not correct 

statement - Increasing order of stability is–

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

6
 (C) III < IV < II < I (D) II < IV < III < I
15. In which compound delocalisation is not
11. Consider the following three halides - possible -
(A) CH3–CH2–Cl (A) 2-Butene (B) 1, 3-Butadiene

(B) CH2=CH–Cl (C) 1, 3, 5-Hexatriene (D) Benzene

(C) C6H5–Cl 16. Consider the following compound :

CH2=CH–CH=CH2
Arrange C–Cl bond length of these 1 2 3 4
compound in decreasing order - carbon-carbon bond length between C2
(A) A > B > C (B) A > C > B and C3 will be -
(C) C > B > A (D) B > C > A
(A) 1.54 Å (B) 1.3 Å
12. Arrange the following in increasing basic
(C) Less than 1.54 and greater than 1.33 Å
strength-
NO2
.. (D) 1.21 Å
(a) CH3NH2 (b) NO2–C–NH2
NO2 17. In pyridine ; Number of conjugated
(c) Cl–CH2–NH2 (d) I–CH2–NH2 N
..
(e) NH3 electrons are -

Correct answer is - (A) 6 (B) 8

(A) (a) < (b) < (c) < (e) < (d) (C) zero (D) 5

(B) (a) < (b) < (c) < (d) < (e) 18. Which is the decreasing order of acidity

(C) (b) < (c) < (d) < (e) < (a) in,

(D) (c) < (b) < (e) < (d) < (a) HCOOH (I), CH3COOH(II), CH3CH2COOH(III)

13. What is the correct increasing order of and C6H5COOH(IV) -

bond lengths of the bonds indicated as I, (A) I > II > III > IV (B) IV > III > II > I
II, III and IV in following compounds - (C) IV > I > II > III (D) I > IV > II > III
19. Consider the follownig carbocations -
II III IV  
(a) CH3–CH2 (b) CH2=CH
I  
(c) CH2=CH–CH2 (d) C6H5–CH2
(A) I < II < III < IV (B) II < III < IV < I Stability of these carbocations in
(C) IV < II < III < I (D) IV < I < II < III decreasing order is -

14. Most stable carbocation is - (A) d > c > a > b (B) d > c > b > a

  (C) c > d > b > a (D) c > d > a > b

(A) CH3–CH2 (B) CH2CHCl2
 
(C) CH2CH2Cl (D) CH2–CH2NO2

7
20. Consider the following compounds - (A) a > b > c > d (B) b > c > a > d
NH2 NH2 NH2 NH2 (C) d > a > c > b (D) d > a > b > c

NO2 Cl CH3
(a) (b) (c) (d)
Arrange these compounds in decreasing
order of their basicity :

8
 GOC
DPP-4
1. Which free radical is the most stable - 5. Which of the following is most stable
(A) C6H5–CH2 (B) CH2=CH–CH2 alkene ?
(C) CH3–CH–CH3 (D) CH3–C–CH3 H H
(A) C=C
CH3 H H

2. Which carbocation is the most stable - CH3 H

(B) C=C
  H H
CH2 CH2
C2H5 H
(C) C=C
H H
(A) (B)
CH3
CH H
(D) CH3 C=C
CH3 OH H H
 
CH2 CH2
6. Homolytic fission of a hydrocarbon will
(C) (D) liberate -
(A) Carbonium ions (B) carbanions
Cl NO2 (C) free radicals (D) carbenes
3. Electromeric effect - 7. Heterolytic fission of carbon-chlorine
(A) comes into play at the demand of bond produces -
attacking reagent (A) two free radicals
(B) involves displacement of electrons in (B) two carbonium ions
a sigma bond (C) two carbonions
(C) comes into play in the molecule (D) one cation and one anion
when at least one atom has unshared 8. In CH3CH2OH, the bond that undergoes
pair of electrons
heterolytic cleavage most readily is -
(D) involves the distortion of the electron
(A) C—C (B) C—O
cloud
(C) C—H (D) O—H
9. Which of the following is heterocyclic
4. Which statement is correct for
aromatic species ?
electromeric effect -
(A) It is a temporary effect (A) (B)
O
(B) It is the property of bond
(C) It takes place in presence of reagent,
i.e., electrophile or nucleophile (C) (D)
O N
(D) All are correct
H

9
10. The hybridisation of saturated carbanion (A) HOH (B) R–OH
is - (C) R–NH2 (D) All of these

(A) sp3 (B) sp2 17. Which is most acidic compound -

(C) sp (D) All of these COOH COOH

CH3
11. Carbanion of CH3 CH2 has geometry - (A) (B)
(A) Planar
COOH COOH
(B) Pyramidal
(C) Squar bipyramidal (C) (D)
CH3
(D) All of the above
CH3
•
12. Hybridisation of R – CH2 is - 18. Which is maximum acidic compound-
COOH
(A) sp3 (B) sp2
COOH
NO2
(C) sp (D) All of these (A) (B)
13. Which of the following statements are
COOH COOH
correct for nucleophile-
NH2 OMe
(A) All negatively charged species are (C) (D)
nucleophile
(B) Nucleophiles are Lewis bases
(C) Alkenes, alkynes, benzene and pyrrole 19. Which is most stable carbocation -
 
are nucleophiles C
(D) All are correct (A) (B)
14. Which among the following species is an
ambident nucleophile ? 
(C) CH2=CH–CH2 (D) 
(A) CH3–CH2 (B) CH2–CH2

•• 20. Which is most stable carbanion -

(C) CN (D) N H 3

15. Which of the following reaction CH2

intermediates are electrophilic in

(A) (B)
character -
(a) Carbocation (b) Carbanion
(C)
(c) Free radicals (d) Carbenes
(A) Only b (B) a and c
(D)CH2=CH–CH –CH=CH2
(C) a, c and d (D) a, b, c and d
16. Which of the following can behave as a
nucleophile -

10
 GOC
DPP-5
..
1. Which is most stable species - .. NH2
Me N Me
Me Me
(C) Me Me (D)

(A) (B) Me
OMe

5. Which is aromatic compound -

OMe
(C) (D) (A) (B)
OMe 

2. Which is most stable carbocation -

Me Me O NH
 

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


O

(C) (D) 6. Which of the following diene is most
stable -
Me Me
3. Which is correct stability order -
(A) (B)
(A) CH –C–O O Me Me
3

O Me Me
 
(B) CH2=CH–CH–CH3 CH2–CH=CH–CH3 (C) (D)
Me Me

CH2

(C) 7. Rank the hydrogen atoms according to
  their acidic strength
(D) CH2
H

4. Which is most basic compound – H H

.. ..
NH2 NH2
(A) Me Me (B) (A)  >  >  (B)  >  > 
Me Me (C)  >  >  (D)  >  > 

8. Consider the hydrogen atoms attached to

three different carbon atoms (labeled 1, 2

11
 & 3). Rank the attached hydrogen atoms in 12. CH2=CH–CH=CH2
order from most acidic to least acidic – 1 2 3 4
O O 3 The bond between C2 – C3 is shorter than
|| ||
single bond because -
O
1 2 (A) +I effect
(A) 1 > 2 > 3 (B) 2 > 1 > 3 (B) –I effect
(C) 2 > 3 > 1 (D) 3 > 2 > 1 (C) M effect
(D) Hyper conjugative effect
9. the most stable carbocation among the 13. Examine the following two structures for
following is - the anilinium ion and choose the correct
statement from the ones given below.
(A) 
 NH3 :NH3

(B)

I II
(C)  (A) II is not an acceptable canonical
structure because carbonium ions are
less stable than ammonium ion.
(D) 
(B) II is not an acceptable canonical
10. Arrange the Carbocations in decreasing structure because it is non-aromatic.
order of stability – (C) II is not an acceptable canonical

OH  OH structure because the nitrogen has 10


valence electrons

OH (D) II is an acceptable canonical structure
I II III
(A) I > II > III (B) I > III > II 14. Formic acid is considered as a resonance
(C) II > III > I (D) III > II > I hybrid of the four structure -

O O

11. Which nitrogen is protonated readily in H–C–OH H–C=OH
the guanidine ? I II
2 
NH2 O O
H–C–O–H H–C–O–H
NH C 
1 NH2 III IV
3
Which of the following order is correct for
(A) 1 (B) 2
the stability of the four contributing
(C) 3 (D) None of these
structures?

12
 (A) I > II > III > IV (B) I > II > IV > III 18. The correct order of increasing
(C) I < III < II < IV (D) I > IV > III > II dissociation
15. Most stable carbocation is: constant of the following compound is-
  OH OH
CH2 CH2
NO2
(A) (B)

C1 NO2 NO2 NO2

 I
 CH2 II
CH2
OH OH
(C) (D) NO2 NO2

OCH3
NO2
16. Which is most stable carbocation – NO2
  III
(A) (B) H3C–C–CH3 IV
C
CH3 (A) II < IV < I < III (B) IV < III < I < II
(C) IV < II < I < III (D) IV < I < II < III
CH3 CH3 19. Which of the following shows the correct
 
(C) C (D) H3C–C––C–C–CH3
order of decreasing acidity-
CH3 CH3 (A) PhCO2H > PhSO3H > PhCH2OH > PhOH
H3C–C–CH3 (B) PhSO3H > PhOH > PhCO2H > PhCH2OH

CH3 (C) PhCO2H >PhOH > PhCH2OH > PhSO3H

COOH (D) PhSO3H > PhCO2H > PhOH > PhCH2OH

20. Arrange the following in correct order of
17. , pKa value of the compound acidic strength-

X (I) CH3–NO2 (II) NO2–CH2–NO2

decreases if X is: (III) CH3–CH2–NO2 (IV) NO2–CH–NO2

NO2
(A) –NO2 (B) – NH2
(C) – OH (D) – OCH3 (A) IV > II > I > III (B) IV > II > III > I
(C) III > I > II > IV (D) III > I > IV > II

13
 ANSWER KEY DPP-01
1 2 3 4 5 6 7 8 9 10
A C A B D D D B B A
11 12 13 14 15 16 17 18 19 20
B D A B C D D C A D

ANSWER KEY DPP-02

1 2 3 4 5 6 7 8 9 10
B C A D D C A B B C
11 12 13 14 15 16 17 18 19 20
A D B A C C B C A C

ANSWER KEY DPP-03

1 2 3 4 5 6 7 8 9 10
B C A D C B A B D B
11 12 13 14 15 16 17 18 19 20
A C D A A C A D A C

ANSWER KEY DPP-04

1 2 3 4 5 6 7 8 9 10
A B A D B C D D C A
11 12 13 14 15 16 17 18 19 20
B B D C C D B B A A

ANSWER KEY DPP -05

1 2 3 4 5 6 7 8 9 10
C D D C C B B B A C
11 12 13 14 15 16 17 18 19 20
A C C A C C A C D A

14