DAILY PRACTICE PROBLEMS

Organic Chemistry [GOC-I] || DPP-3 || BATCH : DROPPER’S 2021 (MAINS & ADV)

1. Select the following compounds:

Select correct statement(s) :

(A) (A) is aromatic, (C) is non aromatic (B) All of these are aromatic
(C) (B) and (C) are non aromatic (D) (B) is not aromatic
2. Ordinarily the barrier to rotation about a carbon-carbon double bond is quite high but in compound P double
bond between two rings was observed by NMR to have a rotational energy barrier of only about 20 cal.\mol.,
showing that it has lot of single bond charcter.
nC3H7

nC3H7

The reason for this is

(A) Double bond having partial triple bond charcter because of resonance
(B) Doule bond undergo flipping
(C) Double bond having very high single bond charcter because of aromaticity gained in both three and five
membered rings.
(D) +I effect of nC3H7 groups makes double bond having partial single bond charcter.

CH3 H
H3C + CH3 H + H
N N

3. Between and

(l) (ll)

(A) N(I) has more 's' character in N–CH3 bonds (B) N(II) has more 's' character in N–H bonds
(C) N(I) has less 's' character in N–CH3 bonds (D) None of these
4. The acid strength order is:

O OH OH
HO OH CH3 CH 3
C C

O OH O O

I II III IV

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

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5. The correct order of acidic strength is :
COOH COOH COOH COOH
OH OH OH CH3 CH3
(l) (ll) (lll) (lV)

OH
(A) III > IV > I > II (B) II > I > III > IV (C) II > III > I > IV (D) II > I > IV > III
6. Which one of the following reaction is not possible?
(A) CH3COONa + HCI  CH3COOH + NaCI
(B) CH3 –SO3 H + H – C  C – Na  CH3SONa + H – C  C – H
(C) R – C  C – H + PhONa  PhOH + R – C  C – Na
(D) H – C  C – H + NaH2  H – C  C – Na + NH3
7. Match the column-I with column-II & select correct option :
Column-I Column-II
(A) (P) Non aromatic

(B) (Q) Anti aromatic

(C) (R) Resonance

(D) (S) Aromatic

(A) I-P, R; II-P, R; III-Q, S; IV-P, Q (B) I-Q, R; II-Q, R; III-Q, R; IV-P
(C) I-P, R; II-Q, R; III-R, S; IV-Q, R (D) I-P, R; II-P, R; III-R, S; IV-P, R

8. OH

COOH (x)
OH

(z) HOOC
HO

COOH (y)

The correct acidic strength order of acidic hydrogen x,y and z is respectively.
(A) x > z > y (B) x > y > z (C) z > y > x (D) y > z > x
H
(p)
N NH(r)

9.
O N O

H
(q)

The correct basicity order of atoms p,q and r is :

(A) p > q > r (B) r > p > q (C) r > q > p (D) q > p > r

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10. The correct order of acid and basic strength for the following pair of compounds should be?

COOH COOH COOH COOH

CH3 CH3
Acid strength : and ; and

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

NH2 NH2 NH2 NH2

CH3 CH3
Basic strength : and ; and

(V) (VI) (VII) (VIII)

(A) I > II ; III > IV ; V > VI ; VII < VIII

(B) I < II ; III > IV ; V < VI ; VII > VIII
(C) I > II ; III > IV ; V > VI ; VII > VIII
(D) I < II ; III > IV ; V < VI ; VII < VIII
11. Observe the following reaction :

– +
O Na
COOH COONa OH

+ +

NO2
NO2
OH ONa

+ NaHCO3 + H2CO3

NO2 NO2

ONa OH

+ H2CO3 + NaHCO3

Which of the following is the correct order of acid strength :

COOH OH OH COOH OH OH

(A) > > H2CO3> (B) > > > H2CO3

NO2 NO2

COOH OH OH OH COOH OH

(C) > H2CO3 > > (D) > > > H2CO3

NO2 NO2

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12. Which of the following statements would be incorrect about this compound?
NO2
3

1 5
NO2 NO2
Br
(A) All three C – N bond are of same length
(B) C1 – N and C3 – N bonds are of same length but longer than C3 – N bond
(C) C1 – N and C5 – N bonds are of same length but longer than C3 – N bond
(D) C1 – N and C3 – N bonds are of different length but both are longer than C5 – N bond
13. Choose the incorrect statement:
(A) Salicylic acid (o–Hydroxybenzoic acid) is much stronger than its m-,p-isomers and benzoic acid itself.
(B) Acidity of salicylic acid is due to steric inbibition of resonance, as – OH group forces – COOH out of
the plane of ring
(C) The orbitals which are in the same plane take part in resonance
(D) All the resonating structures have real existence
14. Which statement among the followijng are corect?
(A) Hydration effect stabilises dimethyl ammonium ion more than trimethyl ammonium ion
(B) In chlorobenzene as there is no hydration effect so, trimethyl ammonium ion gets less stabillised than dimethyl
ammonium ion
(C) RCONH2 is feebly acidic with respect to RCOOH
(D) CH3 > NH2 > OH is the basicity order
15. Match the following
CH3

CH3
(A) N (p)  is more
CH3

CH3

Cl

+
(B) O 2N N=O –
(q)  is less
O

Cl
CH3

(C) O 2N NH2 (r) Larger C– N compared to C – NO2

CH3

CH3

CH3
(D) O2N N (s) Larger C – N bond largteer compared to aniline
CH3

CH3

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 HOOC OH

16. x mole NH2

Br
CH
2 –C
–H
OHC
Br

value of X used for complition of reaction will be :

17. In the following set of resonationg structures which sets have the second resonation structure more contributing
than first :

O O

I :
N N

+
OCH3 OCH3

II : +
NH2 NH2
+
O O

III :

N N
O O O O

IV : +
Cl Cl

18. Which of the following molecules, in pure form, is (are) unstable at room temperature [JEE 2012]

O O

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

19. Hydrogen bonding plays a central role in the following phenomena : [JEE Adv. 2014]
(A) Ice floats in water
(B) Higher lewis basicity of primary amines than tertiary amines in aqueous solutions
(C) Formic acid is more acidic than acetic acid
(D) Dimerisation of acetic acid in benzene

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20. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown in the figure.
[JEE Adv. 2014]

The correct order of their boiling point is

(A) I > II > III (B) III > II > I (C) II > III > I (D) III > I > II
21. The number of resonance structures for N is : [JEE Adv. 2015]

22. The correct order of acidity for the following compounds is : [JEE Adv. 2016]

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

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ANSWER KEYS DPP
1. (A)

2. (C) Sol.

3. (A)

4. (D) Sol.

System is aromatic in nature. So, to gain aromaticity H are easily released.

5. (B)
6. (C) Sol. Stronger acid displaces weak acid from its salt.
7. (D)

8. (A) Sol.

9. (B)

10. (B) Sol.

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11. (A) Sol. From first reaction

From second reaction

From third reaction Ka

Since a strong acid displaces a weak acid from its salt and forms its own salt.
12. (A,B,D)

13. (B,D) Sol. In salicylic acid, there is H-bonding in conjugate base.

14. (A,C,D)

15. (A)  s; (B)  r; (C)  p; (D)  q

Sol. Stearic inhibition of resonance cause no change in bond length.

16. (5) 17. (IV) 18. (B,C) 19. (A,B,D) 20. (B) 21. (9) 22. (A)

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