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Q.1 Strongest Base Is

1. The strongest base is guanidine (C=NH) due to resonance stabilization of the conjugate acid. 2. Amine (NH) has the highest pKb value and maximum delocalization of electrons. 3. The order of basicity from most to least is IV < II < III < I due to varying degrees of delocalization in the compounds. 4. The order of pKb values for amines from lowest to highest is CH3 < H < CF3 < NO2 due to inductive and resonance effects. 5. Ranking of basicity decreases in the order C > A > B due to differing degrees of delocalization in the conjugate acids.

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253 views4 pages

Q.1 Strongest Base Is

1. The strongest base is guanidine (C=NH) due to resonance stabilization of the conjugate acid. 2. Amine (NH) has the highest pKb value and maximum delocalization of electrons. 3. The order of basicity from most to least is IV < II < III < I due to varying degrees of delocalization in the compounds. 4. The order of pKb values for amines from lowest to highest is CH3 < H < CF3 < NO2 due to inductive and resonance effects. 5. Ranking of basicity decreases in the order C > A > B due to differing degrees of delocalization in the conjugate acids.

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Uday Prakash Sahu
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BASICITY Q.

1 Strongest base is :

(A)

C=NH

(B)

C=NH2

(C)

C=O

(D)

C OH

Q.2 Maximum pKb value is of : (A) NHCH3 (B) (CH3CH2)2NH (D) NH

(C) (CH3)2NH Q.3 In the following compounds :

(I) (II) the order of basic nature is : (A) IV > I > III > II (C) II >I > III > IV Q.4 pKb of amines X

(III)

(IV)

(B) III > I > IV > II (D) I > III > II > IV NH2 is in order when X is : (B) H < CH3 < CF3 < NO2 (D) CH3 < H < NO2 < CF3

(A) CH3 < H < CF3 < NO2 (C) H < CH3 < NO2 < CF3

Q.5 Rank in order of decreasing base strength. CH 3CO 2


A

CH 3 CH 2 O
B

CH3SO3
C

(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 IV

(A) I > II > III > IV (C) IV > II > III > I (E) I > III > II > 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 Z 10 (D) Z > X > Y

(B) Z > Y > X

(C) Y > X > Z

Q.8 Rank the following compounds in order of increasing basicity O || H3C C O I


O || H3C C N H

O || + H3 N CH C O III

II

(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. R 3N


I

R 2 NH
II

RNH2
III

NH 3
IV

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

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

Q.10 What is the order of basicity RC N


I

RCH=NH
II

RNH2
III

(A) I > II > III (C) II > III > I

(B) III > II > I (D) I > III > II

ANSWER KEY
Q.No. 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
.. H2N .. H2N .. C = NH

H+

.. H2N .. H2N

C = NH2

HN .. H2N

.. C NH2

.. H2N H2N

.. C NH2

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 delocalisation of electrons cloud Basicity

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 IV but does take part in & III lp is present on sp3 on sp2 "N" atom. III < I as in III-I effect Ans.4 pKb
1 Basicity

because lp of N take part in aromaticity in II. I & III more basic than II because in I hybridised N atom. While in II it is present of oxygen decreases basicity.

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

NO2

NH2 is least basic.

Note that CF3 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

y (14 5) 9

z (14 10) 4

1 Basicity

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 H2 2 sp sp sp3 Electronegative order of hybridised Nitrogen atom. sp > sp2 > sp3 Greater the electronegativity, lesser is the Basicity.

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