What will be the result when ketone is added with ethylene glycol and TsOH?
When ketone is added with ethylene glycol (also known as 1,2-ethanediol) and TsOH (p-toluenesulfonic acid), a reaction called the acetal formation or ketal formation reaction takes place.
To understand the result of this reaction, let's break it down step-by-step:
1. First, the ketone reacts with ethylene glycol in the presence of a catalytic amount of TsOH. The TsOH behaves as an acid catalyst, which helps facilitate the reaction.
2. The oxygen of the ethylene glycol attacks the electrophilic carbonyl carbon of the ketone, forming a new bond.
3. At this point, a hemiacetal intermediate is formed. It contains an -OH group attached to the carbon atom, which was previously the carbonyl carbon of the ketone.
4. The reaction continues as another molecule of ethylene glycol reacts with the hemiacetal intermediate. The same process occurs, with the oxygen of ethylene glycol attacking the electrophilic carbon, forming another bond.
5. This results in the formation of an acetal or ketal product, depending on the number of ethylene glycol molecules added. If one molecule of ethylene glycol reacts, it forms a hemiacetal, and if two molecules react, it forms a fully formed acetal or ketal.
The product obtained from this reaction will be an acetal or ketal, with the specific structure dependent on the ketone used and the number of ethylene glycol molecules added. This reaction is often used to protect or mask carbonyl groups in organic synthesis, as acetal or ketal groups are more stable and less reactive than carbonyls.
To determine the specific product, it is necessary to know the structure of the ketone and the number of ethylene glycol molecules involved in the reaction.