Which compound will be extracted in organic layer?

In summary, the conversation discusses the difficulty in predicting which compounds would be extracted into which layer (organic vs. aqueous) using acids and bases. The speaker's predictions for three compounds are provided and their reasoning is described. However, the answers state that compounds (A) and (B) would be extracted into the organic layer, but (C) would not be. The conversation ends with speculation that this may be a pre-lab that has not been proof-read.
  • #1
vetgirl1990
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I'm having a lot of trouble predicting which compounds would be extracted into which layer (organic vs. aqueous) using acids and bases.

Using the solvents dichloromethane (which would form the organic layer) and sodium hydroxide (would form the aqueous layer along with water), I am asked to predict which of the following compounds would end up being extracted into the organic layer.

My predictions for the attached compounds:
(A) Would be extracted in the AQUEOUS layer.
NaOH would deprotonate the hydrogen (on the OH) from the bezoic acid, leaving a charged conjugate base.
Charged materials stay in the aqueous layer.

(B) Would be extracted in the AQUEOUS layer.
NaOH would deprotonate the hydrogen (on the OH) from the phenol, leaving a charged conjugate base.
Charged materials stay in the aqueous layer.

(C) Would be extracted in the ORGANIC layer.
NaOH attacks the NH3+ group, forming a neutral compound, and anionic dicyclohexane.
The neutral compound that forms would be extracted in the organic layer.

BUT my reasoning seems to be all wrong! The answers state that compounds (A) and (B) will be extracted into the organic layer, but (C) would not be. Why?
 

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  • #2
A)? Check. B)? Check. C)? Check.
This could be a "re-cycled" pre-lab that hasn't been proof-read --- who knows.
 
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  • #3
Bystander said:
A)? Check. B)? Check. C)? Check.
This could be a "re-cycled" pre-lab that hasn't been proof-read --- who knows.

Interesting, that's what I was thinking too... so is my reasoning above correct then? Regarding the base being able to deprotonate A and B to form a charged conjugate base; and neutralizing C to form a neutral compound?
 
  • #4
That's my take.
 
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1. What is an organic layer in chemistry?

An organic layer in chemistry refers to a layer of a liquid mixture that contains organic compounds, such as hydrocarbons or carbon-based molecules. This layer is usually separated from the aqueous layer in a liquid-liquid extraction process.

2. How is the organic layer determined in a liquid-liquid extraction?

The organic layer is determined by the relative solubility of the organic compounds in the mixture. Typically, nonpolar organic compounds will dissolve in the organic layer, while polar compounds will dissolve in the aqueous layer.

3. Can multiple compounds be extracted in the organic layer?

Yes, it is possible for multiple compounds to be extracted in the organic layer, depending on their solubility and the method of extraction used. In some cases, a specific solvent may be used to selectively extract a certain compound from a mixture.

4. How does the density of a compound affect its extraction in the organic layer?

The density of a compound does not necessarily determine its extraction in the organic layer. Instead, the relative solubility of the compound in the organic and aqueous layers will determine where it is extracted during the process.

5. How do I know which compound will be extracted in the organic layer?

The best way to determine which compound will be extracted in the organic layer is to consult a solubility table or perform a small-scale extraction experiment. It is also important to consider the polarity and functional groups of the compounds in the mixture.

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