NURTURE

IIT CHEMISTRY
ORGANIC CHEMISTRY

ACID & BASES

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333
 ACID & BASES

EXERCISE # I
1. Write correct order of acidic strength of following compounds:
O O
(i) (a) NO2–CH2–C–O–H (b) F–CH2–C–O–H
O O
(c) Ph2–CH2–C–O–H (d) CH3–CH2–C–O–H
O O
(ii) (a) CH3–CH2–CH–C–O–H (b) CH3–CH–CH2–C–O–H
F F
O
(c) CH2–CH2–CH2–C–O–H
F
O O
(iii) (a) Cl–CH2–C–O–H (b) Cl–CH–C–O–H
Cl
Cl O
(c) Cl–C–C–O–H
Cl
(iv) (a) CH3–CH2–O–H (b) CH3–CH–O–H
CH3
CH3
(c) CH3–C–O–H
CH3
(v) (a) (b) (c)
COOH COOH COOH
COOH COOH CH2–COOH
(vi) (a) (b) CH2 (c)
COOH COOH CH2–COOH
(vii) (a) H–F (b) H–Cl (c) H–Br (d) H–I
(viii) (a) CH4 (b) NH3 (c) H2O (d) H–F
(ix) (a) F–CH2–CH2–O–H (b) NO2–CH2–CH2–O–H

(c) Br–CH2–CH2–O–H (d) NH3 – CH2 – CH2 – O – H
(x) (a) CH3COOH (b) CH3CH2OH (c) C6H5OH (d) C6H5SO3H

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 1
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 ACID & BASES
2. Among the following pairs, which compound is stronger acid?
O O
(a) CH3CH3 or BrCH2NO2 (b) CH3–C–CH3 or CH3–C–CH2CN
OH OH SH OH

(c) or (d) or

O=C–CH3 CH3

3. Which of the following would you predict to be the stronger acid?

(a) Benzoic acid or para-nitrobenzoic acid
(b) CH3–CH2–CH2–OH or CH3–CH=CH–OH
(c) CH3–CH=CH–CH2–OH or CH3–CH=CH–OH

4. Arrange the given phenol & its derivative in their decreasing order of acidity:
(I) C6H5–OH (II) F OH (III) Cl OH(IV) O2N OH
Select the correct answer from the given code:
(A) IV > III > I > II (B) IV > II > III > I (C) IV > III > II > I (D) IV > I > III > II

5. Which one of the following is the most acidic?

(A) (B) (C) (D) CH2=CH–CH3

6. Which of the following is weakest acid?

COOH COOH COOH COOH
OH
(A) (B) (C) (D)
OH
OH

7. Arrange pH of the given compounds in decreasing order:

(1) Phenol (2) Ethyl alcohol (3) Formic acid (4) Benzoic acid
(A) 1 > 2 > 3 > 4 (B) 2 > 1 > 4 > 3 (C) 3 > 2 > 4 > I (D) 4 > 3 > 1> 2

8. Arrange acidity of given compounds in decreasing order:

(I) CH3–NH–CH2–CH2–OH (II) CH3–NH–CH2–CH2–CH2–OH

(III) (CH3 )3 N– CH2 – CH2 – OH
(A) III > I > II (B) III > II > I (C) I > II > III (D) II > I > III

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 2
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 ACID & BASES
9. Which of the following compounds on reaction with NaHCO3 gives CO2 gas?
O OH
O
OH
CH3CCOOH
O OH COOH
I II III
(A) I, II and III (B) I and III (C) II and III (D) I and II

10. Which pka belong to the given functional group in case of following amino acids :
COOH
(i) cysteine : HS 1.8, 8.3 & 10.8

NH3
(ii) glutamic acid : HO2C COOH : 2.19, 4.25, 9.67

NH3

11. Arrange the following sets of compounds according to increasing pKa ( =  log Ka)
OH OH

(a) , , cyclohexane carboxylic acid.

(b) 1-butyne, 1-butene, butane

(c) Propanoic acid, 3-bromopropanoic acid, 2-nitropropanoic acid
(d) Phenol, o-nitrophenol, o-cresol
(e) Hexylamine, aniline, methylamine

12. Write correct order of acidic strength of following compounds:

OH OH OH OH
NO2 NO2 O2 N NO2
(i) (a) (b) (c) (d)

NO2 NO2 NO2

OH OH OH

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

NO2 Cl CH3

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 3
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 ACID & BASES
OH
OH O OH OH
N
(iii) (a) O (b) O (c) (d)
N
O N
O O
O–H OH OH OH

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

OH OH OH
Cl
(v) (a) (b) (c)
Cl
Cl
O O
C–OH C–OH
CH3
(vi) (a) (b)

O O
O
C–OH C–OH
C–OH
NO2
(vii) (a) (b) (c)
NO2

N
O O

13. Select the strongest acid in each of the following sets :

OH OH OH OH

(i) (a) (b) (c) (d)

CH3 NO2 Cl NH2

OH OH OH OH

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

NO2 F CH3

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 4
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 ACID & BASES
OH OH OH OH
OMe
(iii) (a) (b) (c) (d)
OMe
OMe
OH OH OH OH
NO2 NO2
(iv) (a) (b) (c) (d)
NO2 NO2 NO2 NO2
NO2 NO2

14. The strongest acid is:

(A) HF (B) CH3CO2H (C) HF + SbF5 (D) H2S

15. The weakest acid (does not show acidic character) is:
(A) HC CH (B) CH2 = CH2 (C) Me3CH (D) Ph3CH

16. Select correct order regarding acidic strength of given compounds :

(1) o-methylbenzoic acid (2) m-methylbenzoic acid
(3) p-methylbenzoic acid (4) benzoic acid
(A) 1 > 2 > 3 > 4 (B) 4 > 3 > 2 > 1 (C) 1 > 4 > 2 > 3 (D) 3 > 2 > 4 > 1

Paragraph for Question 17 to 18

The most important condition for resonance to occur is that the involved atoms in resonating
structure must be coplanar or nearly coplanar for maximum delocalisation. If this condition
does not fulfil, involved orbitals cannot be parallel- to each other and as a consequence
delocalisation cannot occur. Bulky groups present on adjacent atoms inhibit the planarity of
atoms involved in resonance. This phenomenon is known as steric inhibition of resonance.
Steric inhibition of resonance has profound effect on
(1) Physical properties (2) Acidity and basicity (3) Reactivity of organic compounds

17. Arrange the following in the increasing order of basicity :

NH2 CH3–N–CH3 NH2 NH2

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

NO2
NO2
(A) I > II > III > IV (B) IV > III > II > I (C) II > I > IV > III (D) I > IV > III > II

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 5
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 ACID & BASES
18. Which of the following is most acidic :
COOH COOH COOH COOH

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

CH3
CH3 CH3

19. How many following compounds are more acidic than water ?
CO2H
(a) SO3H (b) HCl (c) CH3–CCH (d)
OH
OH
(e) (f) (g) (h)
NO2
(i) NaOH

20. How many of the following are incorrect order of pKa.

(A) HF < HCl < HBr < HI
F F F F
COOH COOH COOH
(B) > >
F F
F F F
OH OH OH

(C) > >

NO2
NO2
(D) HF < H2O < CH  CH < NH3 < CH2 = CH2

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 6
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 ACID & BASES

EXERCISE # II
1. Write increasing order of basic strength of fo1lowing compounds/species :
(i) (a) CH3– (b) NH2– (c) OH– (d) F–
(ii) (a) F– (b) CI– (c) Br– (d) I–
(iii) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (in H2O)
(iv) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (Gas phase)
(v) (a) R–NH2 (b) Ph-NH2 (c) R–C–NH2
O
O
(vi) (a) (b) (c)
NH NH N
Me
NH2 NH2

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

NH
N N N
(viii) (a) (b) (c)
O2N Me F
NH2 NH2 NH2 NH2

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


NH3 Cl CH3 H

2. Write increasing order of basic strength of following:

(i) (a) CH3–CH2–NH2 (b) CH3–CH2=NH (c) CH3–CN
(ii) (a) CH3–C–NH2 (b) CH3–CH2–NH2 (c) CH3–C–NH2 (d) NH2–C–NH2
O NH NH
NH2

(iii) (a) (b) (c)

N N
H

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 7
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 ACID & BASES
NH2 NH2 NH2 NH2

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

NO2 CN OMe NH2

NH2 NH2 NH2

NO2
(v) (a) (b) (c)
NO2
NO2

NH2 NH2
Me Me
(vi) (a) (b)
Me Me
N N
O O O O

O
NH–C–CH3 NH2 NH–CH2–CH3

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

NH2 NH2 NH2 NH2

CH3 NO2
(viii) (a) (b) (c) (d)

NH2 NH2 NH2 NH–CH3

CH3
(ix) (a) (b) (c) (d)
CH3
CH3

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 8
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 ACID & BASES
3. Select the strongest base in following compound:
O S
(i) (a) (b) (c) (d)
N N N N
H H H
NH2

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

NH N
N
H
N

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

H H CH3 Et
Ph H Me
– +
N Li N N N
(iv) (a) (b) (c) (d)

4. Arrange the following compound in decreasing order of their basicity.

(i) (a) H2C = CHNa (b) CH3CH2Na (c) CH3CH2ONa (d) HC CNa

(ii) (a) NH2 (b) CH2–NH2 (c) NH2(d) C–NH2

O2N O
(iii) (a) HO– (b) NH3 (c) H2O (d) HSO4–

5. 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

6. 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
H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 9
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 ACID & BASES
7. Which one of the following is least basic in character?

(A) N (B) N N–H (C) (D)

N N
H
H H

8. In each of the following pair of compounds, which is more basic ?

(a) CH3NH2 or CF3NH2
NH

(b) CH3CONH2 or H2N NH2

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

9. Choose the member of each of the following pairs of compounds that is likely to be the weaker
base.
(a) H2O or H3O+ (b) Cl–, SH–
(c) F–, OH–, NH2–, CH3– (d) HF, H2O, NH3
(e) OH–, SH–, SeH–

10. Which compound in given pair is the weaker base?

NH2 NH2

(a) or

NO2
(b) CH2–CH–CH=CH–CH2– or CH2=CH–CH2–
COO– COOH
(c) or
COOH COOH
OH OH
CH3 CF3
(d) or

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 10
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 ACID & BASES
11. Arrange the basic strength of the following compounds.
(a) OH– CH3COO– Cl–
(i) (ii) (iii)

(b) CHC– CH2=CH– CH3CH2–

(i) (ii) (iii)

(c) CH2=CHCH2NH2 CH3CH2CH2NH2 CHC–CH2NH2

(i) (ii) (iii)

NH2 NH–C6H5 NH2

(d)

(i) (ii) (iii)

12. Arrange the following compounds in order of increasing basicity.

(a) CH3NH2, CH3NH3, CH3NH– (b) CH3O–, CH3NH–, CH3CH2–

13. Which of the following is most basic :

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

14. Basicity order of N in following compound is :

CH3 CH3
O Nb
H2N–C–CH2 CH2–NH–C–CH3
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

15. Which of the following possess highest basic conjugate base?

COOH COOH COOH COOH

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

NO2
NO2 NO2
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 ACID & BASES
16. Which of the following compound has least pKb value :

(1) (B) (C) (D)

O O S S HN NH NH O

17. Which of the following order(s) is(are) correct.


(A)  >  > - Stability

NH NH
(B) > > - Basic Strength
H2N NH2
N
.. N

(C) <  <  - Stability

< 

(D) NaN H2 > NaOH > NaSH - Basic Strength

18. Which one of the following option is correct regarding basic strength:
NH2 O
> > >
(A) NH2 NH NH2 NH2 NH O O
N
NH2 NH2 NH2 NH2
CH3
(B) > > >
CH3
CH3
NH NH
NH NH NH N
(C) > > >
N O
H
NH NH H
O N O
(D) NH NH NH N
< < <

H.O. 92, Rajeev Gandhi Nagar, Kota (Raj.) Mob. 97831-97831, 70732-22177, Ph. 0744-2423333 12
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 ACID & BASES
19. The conjugate base of serotonin (used as tranquilisers) is given as follows:
CH2–CH2–NH2
O–

N
H
How many basic groups present in given compound?

20. The structure of saccharin is given as follows :

O
C
N–H
S
O O
How many following compounds are more basic than saccharin ?
O
C
(i) CH3–C–NH2 (ii) H2N–C–NH2 (iii) CH3–C–NH2 (iv) N–H
C
NH NH O
O
CH2–NH2
(v) (vi) N

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 ACID & BASES
EXERCISE # III
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

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

3. Column-I Column-II
OH

(A) (P) React with NaOH

OH

(B) (Q) React with NaHCO3

OH

(C) (R) React with NaH

NO2
OH
NO2
(D) (S) React with Na

NO2
(T) React with NaNH2

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 ACID & BASES
4. Compounds which can give effervescences with NaHCO3 are :

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

5. Statement-1 : For the given two compounds-I is more acidic than compounds-II.
NO2 CN
H3C CH3 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.

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 ACID & BASES

6. Statement 1 : O N O is more basic than N O

(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.

7. Match Column-I with Column-II.

Column-I (Facts) Column-II (Reasons)
(A) Guanidine is proton sponge (P) 3 equivalent structures of conjugate acid
— —
(B) Carbanion stability CCl3  CF3 (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 equivalent resonating structure

8. Match Column-I with Column-II.

Column-I (Compounds) Column-II (pKa)

(A) HO F (P) 7.15

(B) HO Cl (Q) 10.14

(C) HO NO2 (R) 9.98

(D) HO CH3 (S) 9.38

(T) pKa is more than phenol

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 ACID & BASES
(Comprehension) (Q.9 to Q.11)
Observe the following reaction which are feasible:
COOH ONa COONa ONa

(i) + +

NO2 NO2
OH ONa
NO2 NO2
(ii) + NaHCO3 + H2CO3

NO2 NO2
ONa OH

(iii) + H2CO3 + NaHCO3

Answer the following question :

9. Which of the following is the correct order of acidic strength?
COOH OH OH
NO2
(A) > > H2CO3 >

NO2
COOH OH OH
NO2
(B) > > > H2CO3

NO2
COOH OH OH
NO2
(C) > H2CO3 > >

NO2
(D) None
10. Which of the following compound does not react with NaHCO3
OH OH OH COOH

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

NO2
CH3 NO2 NO2
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 ACID & BASES
11. Identify the feasible reactions
COOH COONa

(A) + NaHCO3 + H2O + CO2

NH2 NHNa

(B) + NaHCO3 + H2O + CO2

OH ONa

(C) + NaHCO3 + H2O + CO2

COONa COONa COOH COO–

(D) + +

NO2 NO2

12. Identify the non-feasible reaction


—
(A) CH3–CCH + NH2– CH3 – C  C NH3

(B) CH3CH2–OH + NaH CH3CH2ONa + H2

(C) CH3–OH + Na CH3ONa + 1/2H2

(D) HCCH + NaOH HCCNa + H2OH

13. Select the number of compounds in which deprotonation gives aromatic anion :
O HO–CH2O O
H
(A) HN NH (B) HO
HO OH
O O Ascorbic acid
Barbituric acid (Vitamin-C)

O O

(C) (D)
N O
H
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 ACID & BASES
Paragraph for Questions 14 and 15
Aqueous
Layer
Organic Aqueous (Salt-B)
OH Layer NaOH

Aqueous Organic
COOH NaHCO3 Layer
Aqueous (Compound-C)
Layer
Mixture of
(Salt-A)
3-cornpounds
in hexane

14. Identify salt 'A' ?

ONa+ COONa+ 
Na

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

15. Identify compound 'C' ?

OH COOH OH

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

COOH
16. Which of the following reactions is/are feasible in forward direction.
(A) CH CH + Na 

(B) Paranitrophenol + Caustic soda 

(C) Carbonic Acid + Carbolic acid 

(D) Ethyl alcohol + Carbonic acid 


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 ACID & BASES
Answer Q.17, Q.18 and Q.19 by appropriately matching the information given in the three
columns of the following table.
Column 1, 2 and 3 contain starting materials, reagents and resonating structure of
product involving monoion only.

17. Which of the following represent CORRECT combination ?

(A) (III) (iv) (R) (B) (I) (ii) (P) (C) (II) (iii) (Q) (D) (IV) (iii) (S)

18. Which of the following CORRECT combination represent equivalent resonating structures ?
(A) (I) (ii) (R) (B) (III) (iv) (Q) (C) (II) (iii) (P) (D) (IV) (i) (S)

19. Which of the following represent INCORRECT combination ?

(A) (I) (iv) (R) (B) (III) (ii) (Q) (C) (IV) (i) (S) (D) (II) (iii) (P)

COOH OH OH
20. (a) H3C–SO3H (b) (c) (d)
CH3 CH3 NO2
OH
O OH CH2–OH
(e) (f) (g) (h)
O OH
NO2
(i) (j) OH
In above given compounds if
(i) Total number of compounds which gives CO2() on reacting with NaHCO3 = A
(ii) Total number of compounds which are soluble in aq. NaOH are = B
Then what would be the value of BA
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 ACID & BASES
EXERCISE-IV
1. Which of the following dipolar structure of the amino acid is considered more correct?
CH2COOH CH2COO–
+ +
(A) H3NCHCOO– (B) H3NCHCOOH (C) Both (D) None

2. Which of the nitrogen of histidine is first protonated?

 p

N NH3
CH2CHCOO–

N q
H
(A) α (B) β (C) p (D) q

3. Histidine, a heterocyclic amino acid has following structure at pH < 1.82,

+ +
HN NH3
CH2CHCOOH
N
H
At pH > 1.82 it should have which structure?
+ + + +
HN NH3 HN NH3
(A) CH2CHCOO– (B) + CH2CHCOOH
N N
H H2
+ +
HN NH2 N NH3
(C) + CH2CHCOOH (D) + CH2CHCOOH
N N
H H2

4. Alanine forms Zwitter ion which exists as (pKa for two acids is 4.62 and 9.13) :
(A) CH3–CHCOO in medium of pH = 7
NH3
(B) CH3–CHCOOH in medium of pH = 4
NH3
(C) CH3–CH–COO in a medium of pH = 13
NH2

(D) CH3–CHCOO in a medium of pH = 2
NH3

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 ACID & BASES
5. In aqueous solution at pH =7, glycine is present as :
(A) H3N+CH2COO– (B) H3N+CH2COOH (C) H2NCH2COO– (D) All of these

6. In aqueous solution, the basic character of amino acids is due to :


(A) –NH2 group (B) –NH3 group (C) –COOH group (D) –COO– group

NH2
– H+
7. OOCCHCH2COO– product
Product in the above reaction is :
NH2 NH2
(A) HOOCCHCH2COOH (B) HOOCCHCH2COO–
+
NH3
(C) –OOCCHCH2COO– (D) Any of the three

NH2
8. The principle species present in the solution of lysine H2N(CH2)4CHCOOH at pH 9 is:
(Given pka are 4.2, 8.1, 9.8)
+
NH3 NH2
+ +
(A) H3N(CH2)4CHCOOH (B) H3N(CH2)4CHCOO–
+ +
NH3 NH3
+
(C) H2N(CH2)4CHCOO– (D) H3N(CH2)4CHCOO–

9. At, pH = 7, following amino acid predominantly exist as:

(Given pka are 2.2 ,4.3, 8.9)

(A) (C)

(B) (D)

10. Which of the following compounds forms anion at pH=7 dominantly?

(A) Benzene sulphonic acid (B) Carbolic acid
(C) Cinnamic acid (D) Picric acid
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 ACID & BASES
EXERCISE # V (JEE MAIN)
1. Picric acid is – [AIEEE-2002]
COOH COOH OH COOH
NO2 NO2 NO2
(1) (2) (3) (4)
OH NH2
NO2

2. Which of the following speices acts both as bronsted acid & base - [AIEEE-2002]
– 
(1) NH3 (2) HO (3) HSO4 (4) 1 and 3 both

3. The correct order of increasing basic nature for the bases NH3, CH3NH2 and (CH3)2NH is-
[AIEEE-2003]
(1) CH3NH2 < NH3 < (CH3)2NH (2) (CH3)2NH2 < NH3 < CH3NH2
(3) NH3 < CH3NH2 < (CH3)2NH (4) CH3NH2 < (CH3)2NH < NH

4. Consider the acidity of the carboxylic acids- [AIEEE-2004]

(i) PhCOOH (ii) o-NO2C6H4COOH
(iii) p-NO2C6H4COOH (iv) m-NO2C6H4COOH
which of the following is the correct order of acidity-
(1) i > ii > iii > iv (2) ii > iv > iii > i (3) ii > iv > i > iii (4) ii > iii > iv > i

5. Which of the following is the strongest base – [AIEEE-2004]

(1) NH2 (2) NHCH3 (3) NH2 (4) CH2NH2

CH3

6. Among the following acids which has the lowest pka value- [AIEEE-2005]
(1) CH3CH2COOH (2) (CH3)2 CHCOOH (3) HCOOH (4) CH3COOH

7. Amongest the following the most basic compound is- [AIEEE-2005]

(1) p-nitro aniline (2) Acetanilide (3) Aniline (4) Benzylamine

8. What is the conjugate base of OH–? [AIEEE-2005]

2– –
(1) H2O (3) O2 (3) O (4) O

9. Among the following acids which has the lowest pKa value? [AIEEE-2005]
(1) HCOOH (2) CH3COOH (3) CH3CH2COOH (4) (CH3)2CH–COOH

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 ACID & BASES
10. The correct order of increasing acid strength of the compounds is: [AIEEE-2006]
Me
(a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d) CO2H
Me
(1) d < a < c < b (2) d < a < b < c (3) a < d < c < b (4) b < d < a < c

11. Which one of the following is strongest base in aqueous solution? [AIEEE-2010]
(1) Trimehylamine (2) Aniline (3) Dimethylamine (4) Methylamine

12. The correct order of increasing basicity of the given conjugated base (R=CH3) is : [AIEEE-2010]
— — — — — — — —
(1) RCOO  HC  C  NH2  R (2) RCOO  HC  C  R  NH2
— — — — — — — —
(3) R  HC  C  RCOO  NH2 (4) RCOO  NH2  HC  C  R

13. The strongest acid amongst the following compounds is ? [AIEEE-2011]

(1) CH3CH2CH(Cl)CO2H (2) ClCH2CH2CH2CCOOH
(3) CH3COOH (4) HCOOH

14. The correct order of acid strength of the following compounds: [AIEEE-2011]
A. Phenol B. p-Cresol C. m-Nitrophenol D. p-Nitrophenol
(1) C > B > A > D (B) D > C > A > B (C) B > D > A > C (D) A > B > D > C

15. In the following compounds: [JEE(Main)-2012]

O

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

N
H H H
the order of basicity is as follows:
(1) IV > III > II > I (2) II > III > I > IV (3) I > III > II > IV (4) III > I > II > IV

16. The most basic compound among the following is : [JEE(Main)-2012]

(1) Acetanilide (2) Benzylamine (3) p-Nitro aniline (4) Aniline

17. The order of basicity of amines in gaseous state is : [JEE(Main)-2013]

(1) 3° > 2° > NH3 > 1° (2) 1° > 2° > 3° > NH3
(3) NH3 > 1° > 2° > 3° (4) 3° > 2° > 1° > NH3
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 ACID & BASES
18. Arrange the following compounds in order of decreasing acidity : [JEE(Main)-2013]
OH OH OH OH

; ; ;

Cl CH3 NO2 OCH3

(I) (II) (III) (IV)
(1) II > IV > I > III (2) I > II > IIII > IV (3) III > I > II > IV (4) IV > III > I > II

19. The conjugate base of hydrazoic acid is : [JEE(Main)-2014]

(1) NH3– (2) N3– (3) N2– (4) N–3

20. Which of the following compounds will not be soluble is sodium bicarbonate ?
[JEE(Main)-2014]
(1) Benzene sulphonic acid (2) Benzoic acid
(3) o-Nitrophenol (4) 2, 4, 6-Trinitrophenol

21. Considering the basic strength of amines in aqueous solution, which one has the smallest pK b
value? [JEE(Main)-2014]
(1) (CH3)3N (2) C6H5NH2 (3) (CH3)2NH (4) CH3NH2

22. Among the following oxoacids, the correct deceasing order of acid strength is : [JEE(Main)-2014]
(1) HClO4 > HClO3 > HClO2 > HOCl
(2) HClO2 > HClO4 > HClO3 > HOCl
(3) HOCl > HClO2 > HClO3 > HClO4
(4) HClO4 > HOCl > HClO2 > HClO3

23. The correct decreasing order for acid strength is [JEE(Main)-2019]

(1) NO2 CH2 COOH > NCCH2COOH > FCH2 COOH > CICH2 COOH
(2) FCH2 COOH > NCCH2 COOH > NO2 CHCOOH > CICH2COOH
(3) NO2 CH2 COOH > FCH2 COOH > CNCH2COOH > CICH2COOH
(4) CNCH2 COOH> O2NCH2 COOH > FCH2COOH > CICH2 COOH

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 ACID & BASES
24. Arrange the following amines in the decreasing order of basicity: [JEE(Main)-2019]

(1) I > II > III (2) III > II > I (3) I > III > II (4) III > I > II

25. Which amongst the following is the strongest acid ? [JEE(Main)-2019]

(1) CHI3 (2) CHCI3 (3) CHBr3 (4) CH(CN)3

26. The increasing basicity order of the following compounds is : [JEE(Main)-2019]

CH2CH3
(A) CH3CH2NH2 (B) CH3CH2NH
CH3 CH3
(C) H3C–N–CH3 (D) Ph–N–H
(1) (D) < (C) < (B) < (A) (2) (A) < (B) < (D) < (C)
(3) (A) < (B) < (C) < (D) (4) (D) < (C) < (A) < (B)

27. The increasing order of the pKa values of the following compounds is : [JEE(Main)-2019]

(1) B < C < D < A (2) C < B < A < D

(3) D < A < C < B (4) B < C < A < D

28. In the following compound, [JEE(Main)-2019]

the favourable site/s for protonation is/are :-

(1) (a) (2) (a) and (d) (3) (a) and (e) (4) (b), (c) and (d)
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 ACID & BASES
29. The correct order for acid strength of compounds [JEE(Main)-2019]
CHCH, CH3–CCH and CH2=CH2
is as follows :
(1) CH  CH > CH2 = CH2 > CH3–C  CH
(2) HC  CH > CH3–C CH > CH2 = CH2
(3) CH3–C  CH > CH2 = CH2 > HC  CH
(4) CH3–C  CH > CH  CH > CH2 = CH2

30. The increasing order of the pKb of the following compound is: [JEE(Main)-2019]

(A) (B)

(C) (D)

(1) (A) < (C) < (D) < (B) (2) (C) < (A) < (D) < (B)
(3) (B) < (D) < (A) < (C) (4) (B) < (D) < (C) < (A)

31. In the following compounds, the decreasing order of basic strength will be : [JEE(Main)-2019]
(1) (C2H5)2NH > C2H5NH2 > NH3 (2) NH3 > C2H5NH2 > (C2H5)2NH
(3) (C2H5)2NH > NH3 > C2H5NH2 (4) C2H5NH2 > NH3 > (C2H5)2NH

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 ACID & BASES
EXERCISE # VI (JEE ADVANCE)
1. In the following compounds [IIT-JEE-1996]
OH OH OH OH

NO2
CH3 NO3
(I) (II) (III) (IV)
The order of acidity is-
(A) III > IV > I > II (B) I > IV > III > II (C) II > I > III > IV (D) IV > III > I > II
2. Although phenoxide ion has more number of resonating structures than benzonate ion, benzoic
acid is a stronger acid than phenol. Why ? [IIT-JEE-1997]
3. Amongst the following, the most basic compound is: [IIT-JEE-2000]
(A) C6H5NH2 (B) p–NO2–C6H4NH2
(C) m–NO2–C6H4NH2 (D) C6H5CH2NH2
4. The correct order of basicities of the following compounds is : [IIT-JEE-2001]
NH O
CH3–C CH3CH2NH2 (CH3)2NH CH3CNH2
NH2 , , ,
1 2 3 4
(A) 2 > 1 > 3 > 4 (B) 1 > 3 > 2 > 4 (C) 3 > 1 > 2 > 4 (D) 1 > 2 > 3 > 4
5. Statement–I : p-Hydroxybenzoic acid has a lower boiling point that o–hydroxybenzoic acid.
Because
Statement–II : o-Hydroxybenzoic acid has intramolecular hydrogen bonding. [IIT-JEE-2003]
(A) Statement-I is True, Statement-II is True; Statement-II is a correct explanation for Statement-I
(B) Statement-I is True, Statement-II is True; Statement-II is NOT a correct explanation for Statement-I
(C) Statement-I is True, Statement-II is False.
(D) Statement-I is False, Statement-II is True.
6. Match Ka values with suitable acid : [IIT-JEE-2003]
Ka Acid
(A) 3.3 × 10–5 (P) COOH

(B) 4.2 × 10–5 (Q) Me COOH

(C) 6.3 × 10–5 (R) Cl COOH

(D) 6.4 × 10–5 (S) MeO COOH

(E) 30.6 × 10–5 (T) O2N COOH

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 ACID & BASES
7. (a) Which of the following is more acidic and why ? [IIT-JEE-2004]
 
NH3 NH3

F
(I) (II)
HOOC
OH

2Moles NaNH2
8. O2N A. The product (A) will be: [IIT-JEE-2007]

CH
OH

HOOC OOC
O OH

(A) O2N (B) O2N

CH C
O OH

OOC HOOC
OH OH

(C) O2N (D) O2N

CH C
O O

9. The correct acidity order of the following is :

OH OH COOH COOH

Cl CH3
(I) (II) (III) (IV)
(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)
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 ACID & BASES
10. Amongst the following, the number of compounds soluble in aqueous NaOH is: [IIT-JEE-2010]
H3C CH3
N COOH OCH2CH3 OH
CH2OH

NO2 OH COOH

N
H3C CH3

11. Among the following compounds, the most acidic is: [IIT-JEE-2011]
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p–toluic acid

12. The carboxyl functional group (–COOH) is present in – [IIT-JEE-2012]

(A) piric acid (B) barbituric acid (C) ascorbic acid (D) aspirin

13. Identify the binary mixtures(s) that can be separated into the individual compounds, by
differential extraction, as shown in the given scheme – [IIT-JEE-2012]
NaOH(aq)
Compound 1 + Compound 2
Binary mixture containing
compound1 and compound 2
NaHCO3(aq)
Compound 1 + Compound 2

(A) C6H5OH and C6H5COOH (B) C6H5COOH and C6H5CH2OH

(C) C6H5CH2 and C6H5OH (D) C6H5CH2 and C6H5CH2COOH

14. The compound that does NOT liberate CO2, on treatment with aqueous sodium bicarbonate
solution, is – [JEE-ADVANCE-2013]
(A) Benzoic acid (B) Benzenesulphonic acid
(C) Salicylic acid (D) Cabolic acid (phenol)

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 ACID & BASES
15. Hydrogen boiling plays a central role in the following phenomena [JEE-ADVANCE-2013]
(A) Ice floats in water
(B) Higher Lewis basicity of primary amines that tertiary amines in aqueous solution
(C) Formic acid is more acidic than acetic acid
(D) Dimerisation of acetic acid in benzene

16. The correct order of acidity for the following compounds is : [JEE-ADVANCED-2016]
CO2H CO2H CO2H CO2H
HO OH OH

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

17. The order of basicity among the following compounds is [JEE-ADVANCED-2017]

NH NH2

H3C NH2 N NH HN N H3N NH

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

18. The correct order of acid strength of the following carboxylic acids is:[JEE-ADVANCED-2019]
O O
(I) H (II) H OH
OH H
O OH
(III) MeO (IV) H3C
OH O
(A) I > II > III > IV (B) I > III > II > IV (C) II > I > IV > III (D) III > II > I > IV

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 ACID & BASES
ANSWER KEY
EXERCISE # I
1. (i) a > b > c > d, (ii) a > b > c, (iii) c > b > a, (iv) a > b > c,
(v) c > b > a, (vi) a > b > c, (viii) d > c > b > a, (viii) d > c > b > a
(ix) d > b > a > c (x) d > a > c > b

2. (a) 2; (b) 2; (c) 1; (d) 1 3. (a) 2; (b) 2; (c) 2 4. (C) 5. (B)

6. (B) 7. (B) 8. (A) 9. (A)
COOH HO2C COOH
HS 1.8 4.25 2.19
10. (i) cysteine : 8.3
(ii) glutamic acid :
NH2 NH2
10.8 9.67
11. (a) 3 < 2 < 1; (b) 1 < 2 < 3 ; (c) 3 < 2 < 1; (d) 2 < l < 3; (e) 2 < 3 < l
12. (i) d > c > a > b, (ii) a > b > c, (iii) c > a > b > d, (iv) d > b > c > a,
(v) a > b > c, (vi) b > a (vii) c > a > b
13. (i) b, (ii) a, (iii) b, (iv) b 14. (C) 15. (C) 16. (C)
17. (C) 18. (B) 19. (4) 20. (C)

EXERCISE # II
1. (i) a > b > c > d, (ii) a > b > c > d, (iii) c > b > d > a, (iv) a < b < c < d,
(v) a > b > c, (vi) a > b > c, (vii) c > a > b, (viii) b > c > a,
(ix) c > d > b > a
2. (i) a > b > c, (ii) d > c > b > a, (iii) b > c > a, (iv) d > c > b > a,
(v) b > a > c, (vi) b < a, (vii) c > b > a, (viii) c < b < a < d
(ix) a < b < c < d
3. (i) d, (ii) b, (iii) a, (iv) a
4. (i) b > a > d > c, (ii) b > a > c > d, (iii) a > b > c > d
5. (A) 6. (A) 7. (A)
8. (a) i, (b) ii, (c) i, (d) ii 9. (a) 2 ; (b) 1 ; (c) 1 ; (d) 1 ; (e) 3
10. (a) 2; (b) 1; (c) 2; (d) 2 11. (a) 1 > 2 > 3 ; (b) 1 < 2 < 3 ; (c) 3 < 1 < 2 ; (d) 2 < 1 < 3
12. (a) 2 < 1 < 3 ; (b) 1 < 2 < 3 13. (C) 14. (B) 15. (D) 16. (C)
17. (A,D) 18. (C) 19. (3) 20. (6)

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 ACID & BASES
EXERCISE # III
1. (C) 2. (C)
3. (A)R, S, T; (B)P, R, S, T; (C)P, Q, R, S, T; (D)P, Q, R, S, T
4. (i), (ii) (iii) (iv), (v) (ix) 5. (D) 6. (A)
7. (A)P; (B)R; (C)Q; (D)S,T 8. (A)R ; (B)S; (C)P ; (D)Q,T
9. (A) 10. (A) 11. (A, D) 12. (D)
13. (A, B, C, D) 14. (B) 15. (C) 16. (A,B) 17. (D)
18. (C) 19. (A) 20. (2401)

EXERCISE # IV
1. (A) 2. (B) 3. (A) 4. (A,B,C) 5. (A)
6. (D) 7. (C) 8. (B) 9. (D) 10. (A,C,D)

EXERCISE # V (JEE-MAIN)
1. (3) 2. (4) 3. (3) 4. (4) 5. (4) 6. (3) 7. (4)
8. (3) 9. (1) 10. (2) 11. (3) 12. (1) 13. (1) 14. (2)
15. (3) 16. (2) 17. (4) 18. (3) 19. (2) 20. (3) 21. (3)
22. (1) 23. (1) 24. (4) 25. (4) 26. (4) 27. (3) 28. (4)
29. (4) 30. (3) 31. (1)

EXERCISE # VI (JEE-ADVANCE)
1. (D) 2. Benzoate has equivalent resonating structures 3. (D)
4. (B) 5. (D) 6. A(S); B(Q); C(P); D(R); E(T)
7. (II is most acidic) 8. (C) 9. (A) 10. (4) 11. (C)
12. (D) 13. (B, D) 14. (D) 15. (A, B, D)
16. (A) 17. (B) 18. (A)

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 IIT CHEMISTRY
NURTURE

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