Question:

Help with Separation of Acidic and Basic Substances question?

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I know that there needs to be an upper aqueous layer and an lower organic lower but have no idea which substances go in which layer and where you add in the NaOH. So any help with the following question would be greatly appreciated.

A convenient way of separating phenol from water-insoluble alcohols makes use of the fact that phenols are weakly acidic. Show a flow diagram to explain the separation of phenol from the neutral alcohol cyclohexanol by addition of NaOH. Both phenol and cyclohexanol are insoluble in water, but soluble in diethyl ether.

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  1. Since phenols are weakly acidic, the addition of NaON will make the sodium salt or sodium phenol.  This will be soluble in water, while the cyclohexanol will not.  If you then add diethyl ether, the cyclohexane will go into that layer (top layer) and the phenol as the sodium salt will stay in the aqueous layer (bottom layer).

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