Frequently Asked Question

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Show the mechanism of reaction and give the Iupac name of all possible chlorides when 2,2-dimethyl-1-propanone reacts with Hcl

Accepted Answer

The reaction of 2,2-dimethyl-1-propanone (also known as pivalone) with HCl will not form chlorides. Instead, it will result in the formation of a hemiacetal. Here's why:
1. Mechanism: The reaction is an acid-catalyzed nucleophilic addition of HCl to the carbonyl group of the ketone. The hydrogen ion (H+) from HCl protonates the carbonyl oxygen, making the carbon more electrophilic. The chloride ion (Cl-) then attacks the electrophilic carbon, forming a hemiacetal.
2. Hemiacetal Formation: The product is a hemiacetal because it has an -OH and an -OR group attached to the same carbon. The -OR group is derived from the original ketone.
3. No Chloride Formation: There is no chloride substitution or elimination reaction occurring in this case. The chloride ion acts as a nucleophile, but it does not replace any other atoms in the molecule.
Therefore, the reaction of 2,2-dimethyl-1-propanone with HCl does not lead to the formation of any chlorides. It results in the formation of a hemiacetal.


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