Skip to main content
Tweeted twitter.com/StackChemistry/status/911910925212569600
added 18 characters in body; edited tags; edited title
Source Link
orthocresol
  • 71.9k
  • 12
  • 249
  • 423

Trimethylsilanol vs tert-butanol pKa. Why trimethylsilanol is trimethylsilanol a stronger acid than tert-butanol?

WikipediaThe Wikipedia article about Trimethylsilanoltrimethylsilanol says the following:

Trimethylsilanol is a weak acid with a $\mathrm{p}K_\mathrm{a}$ value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol ($\mathrm{p}K_\mathrm{a}$ 19).

Why is it so? A silicon atom is more electropositive than a carbon atom, therefore the conjugatedconjugate base willshould be more destabilized by the +I effect of the $\ce{Si(CH3)3}$ group compared to the $\ce{t-Bu}$ group.

Trimethylsilanol vs tert-butanol pKa. Why trimethylsilanol is a stronger acid?

Wikipedia article about Trimethylsilanol says the following:

Trimethylsilanol is a weak acid with a $\mathrm{p}K_\mathrm{a}$ value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol ($\mathrm{p}K_\mathrm{a}$ 19).

Why is it so? A silicon atom is more electropositive than a carbon atom, therefore the conjugated base will be destabilized by +I effect of the $\ce{Si(CH3)3}$ group compared to $\ce{t-Bu}$ group.

Why is trimethylsilanol a stronger acid than tert-butanol?

The Wikipedia article about trimethylsilanol says the following:

Trimethylsilanol is a weak acid with a $\mathrm{p}K_\mathrm{a}$ value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol ($\mathrm{p}K_\mathrm{a}$ 19).

Why is it so? A silicon atom is more electropositive than a carbon atom, therefore the conjugate base should be more destabilized by the +I effect of the $\ce{Si(CH3)3}$ group compared to the $\ce{t-Bu}$ group.

improved formatting
Source Link
andselisk
  • 38.5k
  • 14
  • 133
  • 223

In the wikipedia article (https://en.wikipedia.org/wiki/TrimethylsilanolWikipedia article about Trimethylsilanol), it is written that "Trimethylsilanol is a weak acid with a pKa value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than says the one of alcohols like tert-butanol (pKa 19)."following:

Trimethylsilanol is a weak acid with a $\mathrm{p}K_\mathrm{a}$ value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol ($\mathrm{p}K_\mathrm{a}$ 19).

Why is it so? A silicon atom is more electropositive than a carbon atom, therefore the conjugated base will be destabilized by +I+I effect of the Si(CH3)3$\ce{Si(CH3)3}$ group compared to tert-Bu$\ce{t-Bu}$ group.

In the wikipedia article (https://en.wikipedia.org/wiki/Trimethylsilanol), it is written that "Trimethylsilanol is a weak acid with a pKa value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol (pKa 19)."

Why is it so? A silicon atom is more electropositive than a carbon atom, therefore the conjugated base will be destabilized by +I effect of the Si(CH3)3 group compared to tert-Bu group.

Wikipedia article about Trimethylsilanol says the following:

Trimethylsilanol is a weak acid with a $\mathrm{p}K_\mathrm{a}$ value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol ($\mathrm{p}K_\mathrm{a}$ 19).

Why is it so? A silicon atom is more electropositive than a carbon atom, therefore the conjugated base will be destabilized by +I effect of the $\ce{Si(CH3)3}$ group compared to $\ce{t-Bu}$ group.

In the wikipedia article (https://en.wikipedia.org/wiki/Trimethylsilanol) it, it is written that "Trimethylsilanol is a weak acid with a pKa value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol (pKa 19)." So, why

Why is it so? A silicon atom is more electropositive than a carbon atom, therefore the conjugated base will be destabilized by +I effect of the Si(CH3)3 group compared to tert-Bu group.

In the wikipedia article (https://en.wikipedia.org/wiki/Trimethylsilanol) it is written that "Trimethylsilanol is a weak acid with a pKa value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol (pKa 19)." So, why is it so? A silicon atom is more electropositive than a carbon atom, therefore the conjugated base will be destabilized by +I effect of the Si(CH3)3 group compared to tert-Bu group.

In the wikipedia article (https://en.wikipedia.org/wiki/Trimethylsilanol), it is written that "Trimethylsilanol is a weak acid with a pKa value of 11. The acidity is comparable to that of orthosilicic acid, but much higher than the one of alcohols like tert-butanol (pKa 19)."

Why is it so? A silicon atom is more electropositive than a carbon atom, therefore the conjugated base will be destabilized by +I effect of the Si(CH3)3 group compared to tert-Bu group.

Source Link
Loading