Question
Asked Sep 18, 2019
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What product would you obtain if you evaporated the water from the NaOH layer prior to acidifying the layer?  (we are trying to extract p-tert-butylphenol; it is in aqueous solution with NaOH, which we used to extract it from a mixture dissolved in ether).  Prior to acidifying with HCl, it is ionic (phenoxide).

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Expert Answer

Step 1

Ether layer contains acetanilide (C6H5NHCOCH3) and p-tert-butylphenol (p-C4H9-C6H4OH). On the addition of sodium hydroxide to the mixture, p-tert-butylphenol gets soluble in NaOH solution whereas acetanilide is insoluble in NaOH solution.

Step 2

The solubility of p-tert-butylphenol in NaOH solution is due to the formation of sodium salt of p-tert-butylphenol. Water and sodium salt of p-tert-butylphenol is formed when a p-tert-butylphenol reacts with NaOH. The reaction is shown below.

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р-С, Н, -С,Н,ОН + NaOH —>р-С,Н,-С,Н,О' Na"+ Н,О

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Step 3

On the evaporation of water, the product left is the sodium salt of  p-tert-butylphenol (p-C4H9-C...

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p-C,H-CHNa' + H,O -H,0 p-C,H,-CH,O Na" 4

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