Cyclopentanonyl anion
Cyclopentanonyl radical
Cyclopentanonyl cation
Cyclopentanonyl biradical
Treatment of cyclopentanone with methyllithium gives cyclopentanonyl anion. Methyllithium (CH3Li) is a strong base and a nucleophile. The oxygen atom in cyclopentanone is electrophilic and will readily react with the nucleophilic methyl anion (CH3-) from the methyllithium. The methyl anion attacks the carbonyl carbon, resulting in the formation of a new carbon-carbon bond and the formation of an alkoxide ion. This alkoxide ion is the cyclopentanonyl anion. The reaction can be represented as follows:
[Image of reaction mechanism would ideally be included here showing the nucleophilic attack of CH3- on the carbonyl carbon of cyclopentanone, leading to the formation of the cyclopentanonyl anion and methane.]
In summary, the reaction is a nucleophilic addition to the carbonyl group, and the product is the cyclopentanonyl anion.