DAILY PRACTICE PROBLEMS

Organic Chemistry [GOC-I] || DPP-4 || BATCH : DROPPER’S 2021 (MAINS & ADV)

1. Arrange the radicals in their decreasing order of stability.

(I) CH2

(II) CH

(III) C

(IV)

(A) III > II > IV > I (B) III > IV > II > I
(C) III > II > I > IV (D) II > III > IV > I
2. The decreasing order of relative basic strengths of following compounds/anions is :

N N N N
H H H CH3
I II III IV

(A) I > III > IV > II (B) III > II > IV > I
(C) IV > III > II > I (D) III > IV > I > II
3. Amongst the following compounds select the strongest acid/correct acidic strength order/correct option.

O
O – C – CH3 OH
(A) (B)
COOH C – O – CH3
(Aspirin) O
(Oil of winter green)
COOH COOH
(C) (D)
C – O – CH3 CH3
O (o-Toluic acid)
(o-Methoxycarbonyl benzoic acid)

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 H Me Me
H H H Me Me Me
N N N N

4.

NH2
(I) (II) (III) (IV)

Which of the following has more charge density on the ring than NH3 ?
(A) I (B) II, III, IV (C) III, IV (D) I, IV
5. In which set first is more stable than second

(A) CF3 CCl3 (B) HC C H2 C = CH (C) (D) (CH 3)3C CH3

6. The decreasing order of relative basic strengths of following compounds/anions is :

H3C II CH3
O N
NH2–C–CH2 CH2–NH–C–CH3
III NH
I
H3C N CH3
IV
(A) I > II > IV > III (B) II > IV> I > III (C) IV > II > I > III (D) IV > II > III > I
7. Match the following for basicity order:
Column – I Column – II

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8. How many of the given molecule(s) will show reverse hyperconjugation :

NH2
F OCH3

CCl3–CH=CH2 C C
F F CH3O OCH3
F OCH3
CCl3

OH
NH2 NH–CH3

F
F F F
C(OCH3)3 CHCl2
F

(A) 6 (B) 7 (C) 8 (D) 5

9. The following carbocation rearranges to

(A) (B)

(C) (D) None of above

10. Amongst the following compounds select the strongest acid/correct acidic strength order/correct option.

COOH COOH COOH COOH

H3 C CH3
(I) (II) (III) (IV)
H3 C CH3
NO2 NO2 NO2 SO3H

(A) IV > I > II > III (B) II > IV > III > I
(C) I > IV > II > III (D) IV > II > I > III
11. The most stable carbocation amongst the following is :

CH3 CH3 CH3 CH2

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

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12. Species which are more acidic than Triphenylmethane would be ?

N
N N
(I) (II) (III)
N N

(IV) CH3–CC–H (V)

(A) I, II and IV (B) I, II, III and IV (C) II and IV (D) I, II, III, IV and V
13. The most stable carbocation amongst the following is :
CH3
(A) CH3–O–CH2 CH2–CH–CH2

CH3
(B) CH3–O–CH2 CH2–C–CH3

CH3
(C) CH3–O–CH2 CH–CH–CH3

CH3
(D) CH3–O–CH CH2–CH–CH3

14. Amongst the following compounds select the strongest acid/correct acidic strength order/correct option.

COOH COOH COOH COOH

OH OH OH CH3
(I) (II) (III) (IV)

OH

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

15. The following carbocation rearranges to

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

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16. How many of given relations are correct :

N
O
(I) > > N > (Basic strength)
N N NH2
N O

O NO2
OH O OH O
O OH OH
(II) > > > (Acidic strength)
O O2N NO2 O OH
OH

Me
Me Me
(III) < < (Aromatic character)
Me Me
Me

O
(IV) Br > O Br > Br (Ease for SN2 reaction)

Ph
(V) < < < (Carbocation stability)
Ph

Cl F Cl Cl Cl Cl F
(VI) F> Cl > Cl > (Ease for EICB reaction)
Cl Cl Cl
F F Cl

(VII) > > > (Resonance energy)

S N N
O

(A) 2 (B) 3 (C) 4 (D) 6

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17. With respect to the compounds I – V, choose the correct statement(s) [JEE Advanced 2020]

(A) The acidity of compound I is due to delocalization in the conjugate base

(B) The conjugate base of compound IV is aromatic
(C) Compound II becomes more acidic, when it has a –NO2 substituent
(D) The acidity of compounds follows the order I > IV > V > II > III
18. Consider the following four compounds I, II, III and IV. [JEE Advanced 2020]

Choose the correct statement(s).

(A) The order of basicity is II > I > III > IV.
(B) The magnitude of pKb difference between I and II is more than that between III and IV.
(C) Resonance effect is more in III than in IV.
(D) Steric effect makes compound IV more basic than III.

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ANSWER KEYS DPP
1. (C)
2. (D)
3. (C)
4. (A)

Sol. Electron withdrawing power of –NR3 group increases upon increasing size of R-group.
5. (B,C)
6. (A)
7. (A)S; (B)P; (C)Q; (D)R
8. (C)
Cl Cl
Sol. (8) : Cl Cl CH=CH2 Cl–C=CH–CH2 so on.
Cl Cl

F F

F C F F C F so on.
F

OCH3 O–CH3
C C so on.
CH3O OCH3 CH3O OCH3
OCH3

NH2 NH2

so on.
Cl–C–Cl C Cl
Cl Cl
Cl

OH O–H

F F so on.
F F
F F

so on.
F F F F

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 NH2 NH2

C C so on.
H3CO OCH3 CH3O OCH3
OCH3
OCH3

NH–CH3 NH–CH3

Cl so on.
H C Cl C
H Cl
Cl

9. (C)
10. (D)
11. (C)
12. (D)

N N
Sol. Aromatic [Aromatic and strongest charge stabilization] pKa = –9
N N

[Aromatic]
CH3 – C  C – H sp – Carbon

[Both rings are aromatic]

13. (D)
14. (B)
15. (D)

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16. (B)

Sol. (3) Most basic upon H+ trapping.

N N
H
(Sponge base)
Bridgehead amides are basic.
Picric acid is most acidic.

(Most planar) (Most non-planar)

O
Br (Best for SN2).
Bridge head carbocations are unstable.
EIcb depends upon stability of carbanion.
Resonance energy is :-
Benzene > Thiophene > Pyridine > Pyrole > Furan.
17. (A,B,C)

Sol.

Correct order and acidity = IV > V > I > II > III (Decreasing acidity)
18. (C,D)
Sol. (III) is the weakest base due to the presence of three –NO2 group, which exert strong –M effect.

In compound (IV) group is thrown out of the plane of aromatic ring due to steric crowding by

–NO2 groups at ortho positions as a result of this lone pair of electron on N – atom does not participate
in resonance with aromatic ring and hence it acts as an aliphatic amine. So, (IV) is the strongest base.
Difference of pKa values is highest between (III) and (IV).
pKb; (I)  9.42; (II)  8.94, (IV)  4.60

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