Treatment of cyclopentanone [figure] with methyl lithium gives which of the following species ?
- Cyclopentanonyl radical
- Cyclopentanonyl biradical
- Cyclopentanonyl anion
- Cyclopentanonyl cation
Answer
(3) Cyclopentanonyl anion
Solution
Methyl lithium ( CH3 --Li +) behaves like a Grignard reagent: the CH3 part is a strong nucleophile.
It attacks the electrophilic carbonyl carbon and the π electrons of C=O move to oxygen ⇒ a tetrahedral alkoxide ion is formed:
[figure]
∴ The species formed is an anion (alkoxide of cyclopentanone, which on hydrolysis gives 1-methylcyclopentanol).
Answer: (3)