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How does ethylene glycol react with sodium hydroxide?
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+ Chemical reactions
+ Sodium hydroxide
+ Sodium
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+ Ethylene glycol
+ Organic chemistry
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Lily
How does ethylene glycol react with sodium hydroxide?
How does ethylene glycol react with sodium hydroxide?
Ethylene glycol, specifically 1,2 ethanediol, doesn’t react with sodium hydroxide to any significant extent.
With a pKa of 15.1 ethylene glycol is slightly more acidic than most primary alcohols such as ethanol or methanol; it is less acidic than water, which has an accepted pKa of 14.0 (the sometimes cited value of 15.7 at 25 C is generally accepted as incorrect).
What this means is…
Sodium hydroxide is the combination of the sodium ion, Na+, and the hydroxide ion, -OH.
Being as hydroxide ion is the conjugate base of water, in general terms its reaction with anything less acidic than water is unfavourable. If anhydrous sodium hydroxide is dissolved in pure ethylene glycol a small percentage of it will react to form a sodium glycolate (structure NaOCH2CH2OH; further reaction to NaOCH2CH2ONa is very unfavoured and would require a much stronger base such as sodium amide) and water. This water will then tend to hydrolyze the glycolate, reforming the starting components. Any additional water present during the reaction will hinder it even further.
How does ethylene glycol react with sodium hydroxide?
Ethylene glycol, specifically 1,2 ethanediol, doesn’t react with sodium hydroxide to any significant extent.
With a pKa of 15.1 ethylene glycol is slightly more acidic than most primary alcohols such as ethanol or methanol; it is less acidic than water, which has an accepted pKa of 14.0 (the sometimes cited value of 15.7 at 25 C is generally accepted as incorrect).
What this means is…
Sodium hydroxide is the combination of the sodium ion, Na+, and the hydroxide ion, -OH.
Being as hydroxide ion is the conjugate base of water, in general terms its reaction with anything less acidic than water is unfavourable. If anhydrous sodium hydroxide is dissolved in pure ethylene glycol a small percentage of it will react to form a sodium glycolate (structure NaOCH2CH2OH; further reaction to NaOCH2CH2ONa is very unfavoured and would require a much stronger base such as sodium amide) and water. This water will then tend to hydrolyze the glycolate, reforming the starting components. Any additional water present during the reaction will hinder it even further.
In an aqueous solution there is really no reaction besides the exchange of H+ ions between HOCH2CH2OH and H2O. Both have about the same acid strengths.
In an aqueous solution there is really no reaction besides the exchange of H+ ions between HOCH2CH2OH and H2O. Both have about the same acid strengths.
How does ethylene glycol react with sodium hydroxide?
Ethylene glycol, specifically 1,2 ethanediol, doesn’t react with sodium hydroxide to any significant extent.
With a pKa of 15.1 ethylene glycol is slightly more acidic than most primary alcohols such as ethanol or methanol; it is less acidic than water, which has an accepted pKa of 14.0 (the sometimes cited value of 15.7 at 25 C is generally accepted as incorrect).
What this means is…
Sodium hydroxide is the combination of the sodium ion, Na+, and the hydroxide ion, -OH.
Being as hydroxide ion is the conjugate base of water, in general terms its reaction with anything less acidic than water is unfavourable. If anhydrous sodium hydroxide is dissolved in pure ethylene glycol a small percentage of it will react to form a sodium glycolate (structure NaOCH2CH2OH; further reaction to NaOCH2CH2ONa is very unfavoured and would require a much stronger base such as sodium amide) and water. This water will then tend to hydrolyze the glycolate, reforming the starting components. Any additional water present during the reaction will hinder it even further.
How does ethylene glycol react with sodium hydroxide?
Ethylene glycol, specifically 1,2 ethanediol, doesn’t react with sodium hydroxide to any significant extent.
With a pKa of 15.1 ethylene glycol is slightly more acidic than most primary alcohols such as ethanol or methanol; it is less acidic than water, which has an accepted pKa of 14.0 (the sometimes cited value of 15.7 at 25 C is generally accepted as incorrect).
What this means is…
Sodium hydroxide is the combination of the sodium ion, Na+, and the hydroxide ion, -OH.
Being as hydroxide ion is the conjugate base of water, in general terms its reaction with anything less acidic than water is unfavourable. If anhydrous sodium hydroxide is dissolved in pure ethylene glycol a small percentage of it will react to form a sodium glycolate (structure NaOCH2CH2OH; further reaction to NaOCH2CH2ONa is very unfavoured and would require a much stronger base such as sodium amide) and water. This water will then tend to hydrolyze the glycolate, reforming the starting components. Any additional water present during the reaction will hinder it even further.
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In an aqueous solution there is really no reaction besides the exchange of H+ ions between HOCH2CH2OH and H2O. Both have about the same acid strengths.
In an aqueous solution there is really no reaction besides the exchange of H+ ions between HOCH2CH2OH and H2O. Both have about the same acid strengths.
More
VOTE