Reactivity of Ketones: Do They React with Thio Alcohols?

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SUMMARY

Ketones react with thio alcohols, producing thioketals under acidic conditions. This reaction is significant in the context of carbonyl protection, where ketones can be converted into stable cyclic thioketals using 1,3-dithiopropane as a protecting group. The resulting thioketals are stable to basic conditions and can be easily deprotected using acid. This process is essential for chemists working with carbonyl compounds in synthetic applications.

PREREQUISITES
  • Understanding of ketone chemistry
  • Knowledge of thio alcohols and thiols
  • Familiarity with acetal and ketal formation
  • Basic principles of acid-base reactions in organic chemistry
NEXT STEPS
  • Research the mechanism of ketal and thioketal formation
  • Study the properties and applications of 1,3-dithiopropane in organic synthesis
  • Explore methods for deprotecting thioketals using acid
  • Learn about the stability of cyclic thioketals under various conditions
USEFUL FOR

Chemists, organic synthesis researchers, and students studying carbonyl chemistry who are interested in protective group strategies and the reactivity of ketones with thio alcohols.

chaoseverlasting
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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?
 
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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.
 

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