Which one of the following is the strongest base in aqueous medium :

(C_{2} H_{5})_{3} N

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C_{2} H_{5} N H_{2}

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N H_{3}

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(C_{2} H_{5})_{2} N H

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Solution

The correct option is C $(C_{2} H_{5})_{2} N H$
$+ I$ effect of $C_{2} H_{5}$ group increases electron density on $N$ and make it stronger base. So the order of basic strength would be $3^{o} > 2^{o} > 1^{o} > N H_{3}$ but in aqueous medium presence of hydrogen bonding and bulkier groups affect the basicity. In the $(C_{2} H_{5})_{3} N$ , alkyl groups hinder the attack of proton on $N$ . Therefore it become less basic. And due the additive effects of steric hindrance and induction $(C_{2} H_{5})_{2} N H$ is strongest base in aquous medium.

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Similar questions

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 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}

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}

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

C_{2} H_{5} N H_{2}, C_{6} H_{5} N H_{2}, N H_{3}, C_{6} H_{5} C H_{2} N H_{2}

and

(C_{2} H_{5})_{2} N H

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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