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Ranking Compounds by Basicity

This document contains 10 multiple choice questions testing basic concepts of basicity and relative strengths of bases. The questions cover topics such as which functional groups confer the strongest basicity, how substituents on amines affect their pKB values, and ordering compounds by basicity based on factors like resonance, inductive effects, and hybridization state of nitrogen. An answer key is provided with short explanations of the reasoning behind each answer. The document serves as a knowledge assessment of fundamental acid-base concepts.

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Surya Prakash
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24 views4 pages

Ranking Compounds by Basicity

This document contains 10 multiple choice questions testing basic concepts of basicity and relative strengths of bases. The questions cover topics such as which functional groups confer the strongest basicity, how substituents on amines affect their pKB values, and ordering compounds by basicity based on factors like resonance, inductive effects, and hybridization state of nitrogen. An answer key is provided with short explanations of the reasoning behind each answer. The document serves as a knowledge assessment of fundamental acid-base concepts.

Uploaded by

Surya Prakash
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd

BASICITY

Q.1 Strongest base is :

(A)

C=NH

(B)

C=NH 2

(C)

C=O

(D)

C OH

Q.2 Maximum pK b value is of :


(A)

NHCH3

(B) (CH3CH 2) 2NH

(C) (CH3) 2NH

(D)

NH

Q.3 In the following compounds :

(I)
(II)
the order of basic nature is :

(III)

(A) IV > I > III > II


(C) II >I > III > IV

(B) III > I > IV > II


(D) I > III > II > IV

Q.4 pKb of amines X

NH

(A) CH3 < H < CF3 < NO2


(C) H < CH3 < NO2 < CF3

(IV)

is in order when X is :
2

(B) H < CH < CF < NO2


(D) CH3 < H < NO < CF
3

Q.5 Rank in order of decreasing base strength.


CH3CO 2
CH3 CH2 O
CH3SO 3
A

(A) C > A > B

(B) A > B > C

(C) B > A > C

(D) A > C > B

Q.6 Arrange the compounds shown below in order of decreasing basicity


(most basic first).
H 3CNH 2
I

II

III

(A) I > II > III > IV


(C) IV > II > III > I
(E) I > III > II > IV

IV

(B) IV > III > II > I


(D) III > II > I > IV
(F) None of these

Q.7 Using the inforation in the table below,


rank the amines, X, Y and Z, in order of decreasing base strength
(most basic first) :
Amine
pKa of conjugate acid
(A) X > Y > Z

X
5

Y
5

(B) Z > Y > X

Z
10

(C) Y > X > Z

(D) Z > X > Y

Q.8 Rank the following compounds in order of increasing basicity O


O
O
||
||
||
H3C C N H H3 N CH C O
H3C C O
I
II
III
(A) III < II < I
(C) II < III < I

(B) III < I < II


(D) I < II < III

Q.9 What is the order of basicity in gas phase.


R3N

R2 NH

RNH2

II

NH 3

III

(A) I > II > III > IV


(C) III > I > IV > II

IV

(B) I > III > II > IV


(D) IV > III > II > I

Q.10 What is the order of basicity


RC N

RCH=NH

RNH2

II

III

(A) I > II > III


(C) II > III > I

(B) III > II > I


(D) I > III > II

ANSWER KEY
[Link].
Ans.

1
A

2
D

3
D

4
A

5
C

6
E

7
B

8
B

9
A

10
B

SOLUTIONS (BASICITY)
Ans.1

..
H2 N
..
H2 N

..
C = NH

H2 N
..
H2 N

C = NH2

HN
..
H2 N

..
C NH2

H2 N

..
C NH2

H2 N

Resonance involving three equivalent contributing structures which


accounts for the large delocalisation and unusual stability of the
cation resulting in the enhanced basicity of the guanidine.
Ans.2 pKb

1
Basicity

delocalisation of electrons cloud

In (D) maximum delocalisation of lone pair of electron of nitrogen


takes place so it is least basic.
Ans.3 IV is lesser basic than II because lp of N take part in aromaticity in
IV but does take part in II. I & III more basic than II because in I
& III lp is present on sp3 hybridised N atom. While in II it is present
on sp2 "N" atom.
III < I as in III-I effect of oxygen decreases basicity.
Ans.4 pKb

1
Basicity

NO2, CF3 have M & I effect which decreases the basicity while
CH3 has +M & +I effect which increases the basicity.
NO2 (M, I) > CF 3 (M, I)
NO2

NH2 is least basic.

Note that CF 3 has reverse hyperconjugation.


Ans.5 No delocalisation of ve charge in B so it is most basic.
Delocalisation is more is (C) than in (A) so basicity of A > C.
Ans.6 I is most basic as there is no delocalisation of lone pair of nitrogen
amount of delocalisation of lone pair of nitrogen is in order.
IV > II > III
More the delocalisation, lesser is the basicity.
Ans.7 pKb = 14 pka
pKb =
pKb =
pKb

x
[14 (5)]
19

1
Basicity

y
(14 5)
9

z
(14 10)
4

Ans.8 Acidity of conjugate acids of following compounds are


H3 C C NH2 < CH3 C OH < H3N CH2 C OH
||
O

||
O

||
O

Stronger acid has weaker conjugate base


So.
III < I < II
Ans.9 In the gas phase, Inductive effect is controlling the basicity. More
the +I group, greater is the basicity.
Ans.10 RC

RCH= H

R H 2

sp
sp2
sp3
Electronegative order of hybridised Nitrogen atom.
sp > sp2 > sp3
Greater the electronegativity, lesser is the Basicity.

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