Reactivity of Ketones: Do They React with Thio Alcohols?

[chaoseverlasting]

Do ketones react with thio alcohols?

I was studying the protection of carbonyls through acetals, and in my notes, I'd written down that ketones don't react with monohydric alcohols. Do they react with thio alcohols?

 

[chemisttree]

Ketones do indeed react with alcohols. The product is a ketal under acidic conditions. Thiols react as well to produce thioketals. One protection group for ketones is 1,3-dithiopropane. The cyclic thioketal is the protected group stable to base and easily removed by acid.

 

[Blueshift5]

The reactivity of ketones with thio alcohols is a well-studied topic in organic chemistry. Generally, ketones do not react with monohydric alcohols, as you have noted in your studies. However, they do react with thio alcohols, also known as thiols, to form thioacetals. This reaction is known as the thioacetalization reaction and is commonly used for the protection of carbonyl groups in organic synthesis.

Thioacetals are important intermediates in various organic reactions and can be easily converted back to the corresponding carbonyl compounds under mild conditions. The reaction between ketones and thiols is typically catalyzed by acid or base, and the resulting thioacetals are stable under a wide range of reaction conditions.

It is worth noting that the reactivity of ketones with thiols is influenced by the structure of the ketone and the thiol. For example, bulky ketones and thiols may hinder the formation of thioacetals, while electron-withdrawing groups on the ketone can increase the rate of reaction. Additionally, the presence of other functional groups on the ketone or thiol may also affect the reaction.

In conclusion, while ketones do not typically react with monohydric alcohols, they do react with thio alcohols to form thioacetals. This reaction is an important tool in organic synthesis and can be used for the protection of carbonyl groups. Further studies on the reactivity of ketones with thio alcohols can provide valuable insights into the mechanism of this reaction and its potential applications in organic chemistry.