The basic character of ethyl amine, diethyl amine and triethyl amine in chlorobenzene is

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

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

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

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

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Solution

The correct option is A
$C_{2} H_{5} N H_{2} < (C_{2} H_{5})_{2} N H < (C_{2} H_{5})_{3} N$

In presence of chlorobenzene. hydrogen bonding is not possible between the protonated amine and the solvent and thus the stabilization factor (solvation effect) is absent. Hence basicity is explained on the basis of the number of electron releasing groups in an amine.

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Similar questions

Q. Point out the correct decreasing order of

p K_{b}

values of following amines:

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}

Q. Arrange the following in increasing order of their basic strength:

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

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 :

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

Arrange the following in increasing order of their basic strength:

(i) C₂H₅NH₂, C₆H₅NH₂, NH₃, C₆H₅CH₂NH₂ and (C₂H₅)₂NH

(ii) C₂H₅NH₂, (C₂H₅)₂NH, (C₂H₅)₃N, C₆H₅NH₂

(iii) CH₃NH₂, (CH₃)₂NH, (CH₃)₃N, C₆H₅NH₂, C₆H₅CH₂NH₂.

Q. Arrange the following in decreasing order of their basic strength:

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

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