Addition of alkali before extraction

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Adding alkali before extraction is crucial for the preparation of p-Toluidine because it helps to deprotonate the acidic components in the solution, converting them into their base form, which is more soluble in organic solvents like ether. This process enhances the separation of layers when ether is added, allowing for more efficient extraction. In an acidic pH, p-Toluidine, being an aromatic base, would exist primarily in its protonated form, making it less soluble in non-polar solvents like ether or hexane. Therefore, adjusting the pH to a more basic level prior to extraction increases the solubility of p-Toluidine in the organic phase, facilitating a more effective extraction process.
Taryn
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This is just a general question that I hope someone can answer.
Why do we add alkali before extraction rather than afterwards?
This is in the experiment I recently did, which was the preparation of p-Toluidine?
This was my main thought... that it helps to saturate the solution so that when ether is added the two layers form?

Any help on this question would be really helpful, just having a little bit of trouble finding something on the net.
 
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I assume that the pH of the crude material was acidic? Toluidine is an aromatic base. What will happen at acidic pH to this? In this form (acidic solution) do you think that it would be soluble in ether or hexane?
 

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