Max Yield Phenolate Formation with Phenol

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Discussion Overview

The discussion revolves around the conditions under which phenol can form phenolate with maximum yield. Participants explore various factors influencing this reaction, including pH levels and the choice of base used in the process.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • One participant suggests that high pH is necessary for phenol to form phenolate, noting that phenol is a weak acid.
  • Another participant emphasizes the need for high pH and recommends adding excess strong base to achieve maximum yield.
  • A different participant acknowledges the weak acidic nature of phenol but seeks more specific circumstances for optimal phenolate formation.
  • One participant proposes using sodium hydride, a very strong base, instead of more commonly used bases like sodium or potassium hydroxide, particularly in tetrahydrofuran at low temperatures, to achieve extreme conditions for phenolate formation.

Areas of Agreement / Disagreement

Participants generally agree that high pH and the use of a strong base are important for maximizing phenolate yield, but there is no consensus on the specific conditions or the necessity of using particular bases.

Contextual Notes

Discussion includes varying assumptions about the strength of bases and the specific conditions required for optimal yield, which may depend on the reaction environment and other factors.

geo_alchemist
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under what circumstances phenol forms phenolate with max yield
 
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High pH - it is a weak acid.
 
I know it's a weak acid. I need to know circumstances of forming phenolate with max yield
 
High pH - add excess strong base.
 
I agree. If you are seeking extremes, you might want to add sodium hydride (a very strong base, not needed to prepare phenolate) instead of the commonly used sodium or potassium hydroxide in tetrahydrofuran under 10°C in a controlled manner.
 

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