Which Hydrogen Will the Base Extract?

• utsav55
In summary, the purpose of extracting a base is to separate it from the rest of the solution for further purification or analysis. Factors such as pKa value, solvent choice, and presence of other ions can affect the strength of a base that can be extracted. The choice of solvent is crucial, as it should be immiscible with the aqueous solution, have a lower density than water, and have appropriate polarity and hydrogen bonding ability. Multiple bases can be extracted simultaneously if they have different pKa values and can be selectively deprotonated. Controlling the pH of the solution is important as it can impact the solubility and extraction of the base, as well as other compounds in the solution.
utsav55

Homework Statement

See the pic (I know, its not clear but still).

Homework Equations

The compound is reacting with a base. The pic shows the alpha hydrogen taken out by the base.
Why in both the compounds that alpha H is taken out which is not near Chlorine. Why not the H which is near the halogen?

Think about inductive vs. resonance effects. Which one has a greater influence? What is the "pKa of acetophenone" vs "pKa of chloroacetone"? Those are good google terms...

The base will extract the alpha hydrogen because it is more acidic due to the presence of the adjacent carbonyl group. This makes it easier for the base to remove the hydrogen atom and form a more stable enolate intermediate. The hydrogen atom near the halogen may not be as acidic and therefore, will not be extracted by the base. Additionally, the presence of the halogen may also hinder the base from accessing the hydrogen atom.

What is the purpose of extracting a base?

The purpose of extracting a base is to separate it from the rest of the solution in order to isolate and purify it for further use or analysis.

What factors affect the strength of a base that can be extracted?

The strength of a base that can be extracted is affected by its pKa value, as well as the solvent used for extraction and the presence of any other ions or molecules in the solution.

How does the choice of solvent affect the extraction of a base?

The choice of solvent can greatly impact the extraction of a base. A solvent that is immiscible with the aqueous solution and has a lower density than water is ideal for extracting a base. Additionally, the solvent's polarity and ability to form hydrogen bonds with the base will also affect the extraction process.

Can multiple bases be extracted at the same time?

Yes, multiple bases can be extracted at the same time if they have different pKa values and can be selectively deprotonated by the solvent used for extraction.

What is the importance of controlling the pH of the solution during extraction?

Controlling the pH of the solution is important during extraction because it can affect the protonation or deprotonation of the base, and therefore its solubility and ability to be extracted. Additionally, the pH can also impact the extraction of other compounds in the solution.

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