51 - Organic Chemistry | StudyQuestionHub

51

Question

How would you separate toluene ( $C_{6} H_{5} C H_{3}$ ), benzoic acid ( $C_{6} H_{5} C O_{2} H$ ), and aniline ( $C_{6} H_{5} N H_{2}$ ) by an extraction procedure?

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Answer

The mixture of benzoic acid, aniline, and aniline can be extracted with the help of water and dichloromethane.

1Acid-base reaction

The reaction in which the acid donates a proton to the base (accepts a proton) is termed as the acid-base reaction.

2Explanation

The mixture is composed of benzoic acid, aniline, and aniline. All are soluble in dichloromethane and water.

When an acid is added to the mixture, aniline (base) abstracts a proton to form a conjugate acid. So,

Insoluble – dichloromethane
Soluble – water

When a base is added to the mixture, the benzoic acid (acid ) loses a proton to form a conjugate base. So,

Insoluble – dichloromethane
Soluble – water

In the above-mentioned way, the mixture of benzoic acid, aniline, and aniline can be extracted.

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