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Question:

Treatment of cyclopentanone with methyl lithium gives which of the following species?

Cyclopentanonyl anion

Cyclopentanonyl radical

Cyclopentanonyl cation

Cyclopentanonyl biradical

Solution:

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.