Acidic S trength & Basic S trength 23

EXERCISE # O-II
1. Write decreasing order of basic strength of following :
– – – –
(i) (a) CH3 (b) NH2 (c) OH (d) F
AB0049
– – – –
(ii) (a) F (b) Cl (c) Br (d) I
AB0050
(iii) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (in H2O)
AB0051
(iv) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (Gas phase)
AB0052

(v) (a) R–NH2 (b) Ph–NH2 (c) R C NH 2

||
O

AB0053

O
(vi) (a) (b) (c)
NH NH N

Me

AB0054

NH2 NH2

(vii)(a) (b) (c)

NH
AB0055

N N N
(viii) (a) (b) (c)
O2N Me F
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AB0056

NH2 NH2 NH2 NH2

(ix) (a) (b) (c) (d)

Cl CH 3 H
NH3

AB0057

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24 JEE-Chemistry
2. Write decreasing order of basic strength of following :

(i) (a) CH3–CH2– N H 2 (b) CH3–CH= NH (c) CH3–C N

AB0058

(ii) (a) CH 3 C NH 2 (b) CH3–CH2– NH 2 (c) CH 3 C N H 2 (d) NH 2 C N H 2

|| || ||
O NH NH

AB0059
NH2
(iii) (a) (b) (c)
N N
H AB0060

NH2 NH2 NH2 NH2

(iv) (a) (b) (c) (d)

NO2 CN OMe NH2

AB0061

NH2 NH2 NH2

NO2
(v) (a) (b) (c)
NO2
NO2
AB0062
NH2 NH2
Me Me
(vi) (a) (b)
Me Me
N N
O O O O
AB0063
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O
NH–C–CH3 NH2 NH–CH2–CH3

(vii)(a) (b) (c)

AB0064

(viii) (a) (b) (c) (d)

AB0065

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 Acidic S trength & Basic S trength 25

(ix) (a) (b) (c) (d)

AB0066
3. Select the strongest base in following compound :
O S
(i) (a) (b) (c) (d)
N N N N
H H H
AB0067

NH2

(ii) (a) (b) (c) (d)

NH
N N
H AB0068

N
(iii) (a) (b) (c) (d)
N N N N

H H CH3 Et

AB0069
Ph H Me
+
N¯Li N N N

(iv) (a) (b) (c) (d)

AB0070
4. Arrange the following compound in decreasing order of their basicity.
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(i) (a) H2C = CHNa (b) CH3CH2Na (c) CH3CH2ONa (d) HC CNa
AB0071

(ii) (a) NH2 (b) CH2 – NH2 (c) NH2 (d) C – NH2
NO2 O
AB0072
(iii) (a) HO¯ (b) NH3 (c) H2O (d) HSO4¯
AB0073

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26 JEE-Chemistry
5. Correct decreasing order of basic strength -

NH2 NH2 NMe2

N N H–N N
H–N
N
H
(I) (II) (III)

Of following compound -
(A) III > II > I (B) II > I > III (C) I > II > III (D) III > I > II
AB0074
6. Consider the following bases:
(I) o-nitroaniline (II) m-nitroaniline (III) p-nitroaniline
The decreasing order of basicity is:
(A) II > III > I (B) II > I > III (C) I > II >III (D) I > III > II
AB0075
7. Consider the basicity of the following aromatic amines:
(I) aniline (II) p-nitroaniline (III) p-methoxyaniline (IV) p-methylaniline
The correct order of decreasing basicity is:
(A) III > IV > I > II (B) III > IV > II > I (C) I > II > III > IV (D) IV > III > II > I
AB0076
8. Which one of the following is least basic in character?

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

AB0077
9. In each of the following pair of compounds, which is more basic in aqueous solution?
Give an explanation for your choice:
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(a) CH3NH2 or CF3NH2

AB0078

(b) CH3CONH2 or H2N NH2

AB0078
(c) CH3CH2CH2NH2 or CH3CN
AB0078
(d) C6H5N(CH3)2 or 2,6-dimethyl-N-N-dimethylaniline
AB0078

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 Acidic S trength & Basic S trength 27

10. Choose the member of each of the following pairs of compunds that is likely to be the weaker base.
(a) H2O or H3O+
AB0079
(b) Cl¯, SH¯
AB0079
(c) F¯, OH¯, NH¯,
2 CH¯3
AB0079
(d) HF, H2O, NH3
AB0079
(e) OH¯, SH¯, SeH¯
AB0079
11. Explain which compound is the weaker base.

(a) or

AB0080
(b) CH2 = CH – CH = CH – CH2– or CH2 = CH – CH2–
AB0080
COO¯ COOH
(c) | or |
COOH COOH
AB0080

(d) or

AB0080
12. Arrange the basic strength of the following compounds.
(a) OH¯ CH3COO¯ Cl¯
(i) (ii) (iii)
AB0081
(b) CH C¯ CH2 = CH¯ CH3CH 2¯
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(i) (ii) (iii)

AB0082
(c) CH2 = CHCH2NH2 CH3 CH2 CH2 NH 2 CH C – CH2NH2
(i) (ii) (iii)
AB0083

(d)

(i) (ii) (iii)

AB0084

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28 JEE-Chemistry
13. Arrange the following compounds in order of increasing basicity.
(a) CH3NH2, CH3 NH 3 , CH3NH¯
AB0085
(b) CH3O¯, CH3NH¯, CH3CH¯2
AB0085
14. Which of the following is most basic :
N N
N N N
N N
(A) (B) (C) (D)
N

AB0086
15. Basicity order of N in following compound is :
CH3 CH3
O
Nb
H2N– C– CH 2 CH2 – NH – C– CH 3
c
NH
a
N
CH3 d CH3

(A) b > d > a > c (B) a > b > d > c (C) a > b > c > d (D) a > c > b > d
AB0087
16. The conjugate base of serotonin (used as tranquilisers) is given as follows :
CH2–CH2–NH2
–
O

••
N
H
How many basic groups present in following compound ?
AB0088
17. The structure of saccharin is given as follows :
O
C
NH [Provided N is the donor atom in all cases]
S
O O
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How many following compounds are more basic than saccharin ?

O
C
(i) CH3– C – NH2 (ii) H2N– C – NH 2 (iii) CH3 – C – NH2 (iv) N–H
C
NH NH O
O
CH2–NH2
(v) (vi) N

AB0089

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 Acidic S trength & Basic S trength 29

EXERCISE # S-I
1. In given reaction Gas liberated is/are

O O–H
C
14
NaHCO3

SO3H

(A) CO2 & SO3 (B) SO3 & 14CO2 (C) 14CO2 only (D) SO2 only
AB0090
2. Arrange marked atom in decreasing order of acidic strength
2
H O
3 1
H N–H

(A) 1 > 2 > 3 (B) 3 > 2 > 1 (C) 2 > 1 > 3 (D) 2 > 3 > 1
AB0091
3. Column - I Column-I
OH

(A) (P) React with NaOH

OH

(B) (Q) React with NaHCO3

OH

(C) (R) React with NaH

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NO2

OH
NO2
(D) (S) React with Na

NO2
(T) React with NaNH2
AB0092

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30 JEE-Chemistry
4. Compound which can give effevescences with NaHCO3
OH O OH
COOH
(i) (Salicylic acid) (ii) (Squaric acid)
O OH
SO3H OH
O2N NO2
(iii) (Benzene sulphonic acid) (iv) (Picric acid)

NO2
OH
(v) Ph–CH=CH–COOH (cinnamic acid) (vi)

OH CH2–OH OH OH
NO2
(vii) (viii) (ix) (x)
NO2
NO2
AB0093
5. Statement-1 : For the given two compounds-I is more acidic than compounds-II.

NO2 CN
H3C C H3 H3C CH3

OH OH
(I) (II)

and
Statement-2 : Due to presence of –CH3 group at ortho positions to –NO2 ; the plane of –NO2
deviates, w.r.t plane of ring.
(A) Statement-1 is True, Statement-2 is True ; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True ; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
AB0094

6. Statement 1 : is more basic than

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O N O O
N
(I) H
(II)

and
Statement 2 : Lone pair electrons on nitrogen in compound (I) does not participate in resonance.
(A) Statement-1 is True, Statement-2 is True ; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True ; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
AB0095

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 Acidic S trength & Basic S trength 31

7. Match Column-I with Column-II.

Column - I (Facts) Column - II (Reasons)
(A) Guanidine H 2 N–C–N H 2 is example (P) Resonance stabilisation of conjugate acid
of strong base N H of strong base.
(B) Carbanion stability C Cl 3 C F3 (Q) Due to s-character of central atoms
(C) Alkyne is more acidic than alkene (R) Due to d-orbital resonance
(D) Acidity : (S) Due to formation of aromatic anion

< (T) Stability of conjugate base due to more

number of identical resonating structure

AB0096
8. Match Column-I with Column-II.
Column - I (Compounds) Column - II (pKa)

(A) H O F (P) 7.15

(B) H O Cl (Q) 10.14

(C) H O NO2 (R) 9.98

(D) H O C H3 (S) 9.38

(T) pKa is more than phenol

AB0097
(Comprehension) (Q.9 to Q.11)
Observe the following feasible reactions :
COOH ONa COONa OH

(i) + +

NO 2 NO 2
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OH ONa
NO2 NO2
(ii) + NaHCO3 + H2CO3

NO 2 NO 2
ONa OH

(iii) + H2CO3 + NaHCO3

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32 JEE-Chemistry
Answer the following question :
9. Which of the following is the correct order of acidic strength.
COOH OH OH COOH OH OH
NO2 NO2
(A) > > H2CO3 > (B) > > > H2CO3

NO 2 NO 2
COOH OH OH
NO2
(C) > H2CO3 > > (D) None

NO 2
AB0098
10. Which of the following compound does not react with NaHCO3

OH OH OH COOH

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

NO 2
CH3 NO2 NO2

AB0099
11. Identify the feasible reactions
COOH COONa

(A) + NaHCO3 + H2O + CO2

NH2 NHNa

(B) + NaHCO3 + H2O + CO2

OH ONa
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(C) + NaHCO3 + H2O + CO2

COONa COOH COOH COO¯

(D) + +

NO2 NO2

AB0100

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 Acidic S trength & Basic S trength 33

12. Identify the non-feasible reaction

••
(A) CH3–C CH + NH¯2 CH3—C C + NH3

(B) CH3CH2—OH + NaH CH3CH2ONa + H2

(C) CH3—OH + NaOH CH3ONa + H2O
(D) HC CH + NaOH HC CNa + H2O
AB0101
13. Select the number of compounds in which deprotonation gives aromatic anion :
O
O O
HO–CH2 O
O
HN NH H
(A) (B) HO (C) (D)
O O HO OH N O
Barbituric acid Ascorbic acid |
(Vitamin-C) H AB0102

Paragraph for Questions 14 and 15

Aqueous
Layer
(Salt - B)
Aqueous
OH Organic Layer
NaOH

Aqueous
COOH NaHCO3
Organic
Layer
Aqueous Layer (Compound - C)
(Salt - A)
Mixture of
3-compounds
in hexane
14. Identify salt 'A' ?
– + – +
O Na COO Na +
– Na

(A) (B) (C) (D) All of these

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AB0103
15. Identify compound 'C' ?
OH COOH OH

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

COOH
AB0103