ORGANIC CHEMISTRY FIITJEE CPP

Applications of Electronic Effect [45]

EXERCISE
ACIDIC NATURE OF COMPOUNDS
01. Check the feasibility of the following reactions:
(a) CH 3COOH  C6 H 5ONa  CH 3COONa  C6 H 5OH
(b) HCOOH  C6 H 5COONa  HCOONa  C6 H 5COOH
(c) CH 3COOH  CF3COOK  CH 3COOK  CF3COOH

COOH ONa OH
COONa

CH3 CH3
(d) + +

NO2 NO2

CF 3 CH3 CF3 CH3

H
(e) N
+
H +
N H N H + N
+
H
F 3C H H3 C F3C H3 C

(f) CH 3COOH  NaHCO3  CH 3COONa  CO2 ( )  H 2 O

(g) CH 3 SO3 H  NaHCO3  CH 3 SO3 Na  CO2 ()  H 2O

+
OH O Na

O2N NO2 O2 N NO2

CO2 + H2O
(h) NaHCO3 +
+

NO2 NO2

(i) CH 3  C  CH  NaNH 2  CH 3  C  C  Na   NH 3

(j) CH 3  CH 2 OH  NaOH  CH 3  CH 2O  Na   H 2O

(k) CH 3OH  NaOH  CH 3O  Na   H 2O

(l) CH 3C  CH  Na  CH 3C  C  Na   H 2

(m) CH 3C  CH  NaOH  CH 3C  C  Na   H 2O

OH +
O Na

(n) + NaOH + H2O

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Applications of Electronic Effect [46]

OH +
O Na

(o) + NaHCO3 + H2O + CO2

02. How many of the following will liberate CO2 on reaction with NaHCO3:
(a) HCl (b) H2SO 4 (c) HI (d) C6H 5SO 3H
(e) C6 H 5COOH (f) C 6H 5OH (g) CH 3COOH (h) CH 3SO 3 H
(i) CH 3 OH
03. Compare the acidic strength of numbered hydrogens in the following compound:
COOH COOH
II IV
I
HO 3S

III
HO

04. Which among the following has strongest acidic character:

(a) Cyclohexanol (b) 3-nitrocyclohexanol
(c) 4-methylcyclohexanol (d) 4-ethylcyclohexanol
05. Of the following acids, the strongest acid is:
(a) o-nitrobenzoic acid (b) p-nitrobenzoic acid
(c) m-nitrobenzoic acid (d) Benzoic acid
06. Which one of the following carboxylic acids is most acidic in character?
(a) o-methyl benzoic acid (b) m-methyl benzoic acid
(c) p-methyl benzoic acid (d) Benzoic acid
07. Which one of the following is most acidic?
(a) Phenol (b) 2-chlorophenol (c) 3-chlorophenol (d) 4-chlorophenol
08. Which one of the following is least acidic?
(a) Phenol (b) o-fluorophenol (c) m-fluorophenol (d) p-fluorophenol
09. Arrange acidity of given compounds in decreasing order:
O OH
COOH
O

(I) (II) (IV)

(III)

(a) I > II > III > IV (b) IV> III > II > I (c) III > II > I > IV (d) II > IV > III > I
10. Consider the hydrogen atoms attached to three different carbon atoms (labeled 1, 2 and 3).
Rank the attached hydrogen atoms in order from most acidic to least acidic:
O O
3
H 3C O CH3
2
1

(a) 2  1  3 (b) 1  2  3 (c) 2  3  1 (d) 3  2  1

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Applications of Electronic Effect [47]

11. Arrange the given compounds in decreasing acidity:
(I) CI–CH2–CH2–SH (II) Cl2CH–CH2–SH
(III) CI–CH2–CH2–OH (IV) CH3–CH2–OH
(a) IV > III > II > I (b) I > II > III > IV (c) I > II > IV > III (d) II > I > III > IV
12. Which one of the following is most acidic in character?
 
(a) (C 2H5 )2 NH  CH2  CH3 (b) (C 2H 5 )2 N H  CH2  CN
 
(c) (C 2H 5 )2 N H  CH2  CH2  CN (d) (C 2 H 5 )2 N H  CH2  CH 2  CH 2  CN

OH
(Y)
HO
13.
(W)

OH
(Z)
(X)
OH

Decreasing order of acidic strength of different (  OH) groups is:

(a) W  X  Y  Z (b) W  Z  X  Y (c) Z  W  X  Y (d) Z  X  W  Y
14. Which of the following is most acidic compound?

OH
OH OH OH

NO 2

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

NO 2
NO 2

15. Consider the following compound:

H O

O 1 N H
2
N
5
H N
3
N

O O
4
NH

The decreasing order of pKa values of the labelled nitrogen atoms in the above compound is:
(A) 3  2  1  4  5 (B) 4  3  2  1  5
(C) 3  4  2  1  5 (D) 5  1  2  4  3

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Applications of Electronic Effect [48]

OH
OH OH
16.
NO 2

NO2
NO 2
(I) (II) (III)

Arrange the above phenols in increasing order of pKa value:

(A) I  II  III (B) III  I  II (C) III  II  I (D) I  III  II

O
H H
H H S
17. H3C H
H
H3C H
S H
O
(P) (Q) (R) (S)

Arrange the above compounds in decreasing order of acidity:

(A) S  P  R  Q (B) P  S  Q  R (C) R  P  S  Q (D) P  Q  R  S
18. Arrange the following carboxylic acids in decreasing order of acidity:

COOH COOH COOH

COOH
H3C CH3

H3C CH3

NO2 NO2 SO3H

NO2
(P) (Q) (R) (S)

(A) P  Q  R  S (B) S  R  P  Q (C) S  Q  P  R (D) S  R  Q  P

19. Which two of the following H will participate in the reaction with Na for the given com-
pound:

COOH SO 3H
a
b

2 Na

OH c

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Applications of Electronic Effect [49]

20. Which three of the following H will participate in the reaction with Na for the given
compound:

CH c

d b
HO OH

3 Na
O2N

a
COOH

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