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NEET CHEMISTRYAldehydes, Ketones and Carboxylic AcidsHard

Question

What is the product formed when cyclopentanone reacts with methyl lithium?

A

Cyclopentanonyl anion

B

Cyclopentanonyl cation

C

Cyclopentanonyl radical

D

Cyclopentanonyl biradical

Step-by-Step Solution

Methyl lithium (CH3LiCH_3Li) is an organolithium reagent which acts as both a strong nucleophile and a strong base.

  1. Nucleophilic Addition: Typically, CH3LiCH_3Li attacks the carbonyl carbon to form a tertiary alcohol (1-methylcyclopentanol) after hydrolysis. However, this product is not listed in the options.
  2. Acid-Base Reaction: Cyclopentanone possesses acidic α\alpha-hydrogens adjacent to the carbonyl group. Since CH3LiCH_3Li is a very strong base, it can abstract an α\alpha-proton from cyclopentanone.

Cyclopentanone+CH3−→Cyclopentanonyl Anion (Enolate)+CH4\text{Cyclopentanone} + CH_3^- \rightarrow \text{Cyclopentanonyl Anion (Enolate)} + CH_4

Given the options provided (Anion, Cation, Radical), the formation of the Cyclopentanonyl anion via the acid-base pathway is the correct answer expected in this context.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Aldehydes, Ketones and Carboxylic Acids. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAldehydes, Ketones and Carboxylic Acidsproductformedcyclopentanonereactsmethyl

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