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Amines as Bases

Arrange the f...

Question

Arrange the following:

(i) In the decreasing order of the $p K_{b}$ values
$C_{2} H_{5} N H_{2}, C_{6} H_{5} N H C H_{3}, (C_{2} H_{5})_{2} N H$ and $C_{6} H_{5} N H_{2}$

(ii) In increasing order of basic strength:
$C_{6} H_{5} N H_{2}, C_{6} H_{5} N (C H_{3})_{2}, (C_{6} H_{5})_{2} N H a n d C H_{3} N H_{2}$

(iii) In increasing order of basic strength:
(a) Aniline, p-nitroaniline and p-toluidine
(b) $C_{6} H_{5} N H_{2}, C_{6} H_{5} N H C H_{3}, C_{6} H_{5} C H_{2} N H_{2}$

(iv) In decreasing order of basic strength in gas phase :

$C_{2} H_{5} N H_{2}, (C_{2} H_{5})_{2} N H, (C_{2} H_{5})_{3} N a n d N H_{3}$

(v) In increasing order of boiling point:

$C_{2} H_{5} O H, (C H_{3})_{2} N H, C_{2} H_{5} N H_{2} .$

(vi) In increasing order of solubility in water :

$C_{6} H_{5} N H_{2}, (C_{2} H_{5})_{2} N H, C_{2} H_{5} N H_{2} .$

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Solution

(i) $C_{6} H_{5} N H_{2} > C_{6} H_{5} N H C H_{3} > C_{2} H_{5} N H_{2} > C_{2} H_{5} N H_{2} > (C_{2} H_{5})_{2} N H$

(ii) $C_{6} H_{5} N H_{2} < C_{6} H_{5} N (C H_{3})_{2} < C H_{3} N H_{2} < (C_{2} H_{5})_{2} N H$

(iii) (a) p-nitroaniline < aniline < p-toluidine

(b) $C_{6} H_{5} N H_{2} < C_{6} H_{5} N H C H_{3} < C_{6} H_{5} C H_{2} N H_{2}$

(iv) $(C_{2} H_{5})_{3} N > (C_{2} H_{5})_{2} N H > C_{2} H_{5} N H_{2} > N H_{3}$ .

(v) $(C H_{3})_{2} N H < C_{2} H_{5} N H_{2} < C_{2} H_{5} O H .$

(vi) $C_{6} H_{5} N H_{2} < (C_{2} H_{5})_{2} N H < C_{2} H_{5} N H_{2} .$

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Q. Arrange the following
(i) In decreasing order of the

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C_{2} H_{5} N H_{2}, C_{6} H_{5} N H C H_{3}, (C_{2} H_{5})_{2} N H

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(ii) In increasing order of basic strength:

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