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Fundamentals of Organic ChemistryChemistryAldehydes and Ketones

Identify the major product formed in the following reaction sequence:

Correct answer

2

Step-by-step solution

Lithium diisopropylamide (LDA) is a strong, bulky base that abstracts an acidic -hydrogen from cyclopentanone to form a lithium enolate. The enolate acts as a nucleophile and attacks methyl iodide ( CH ₃ I ) via an S_N2 mechanism, resulting in -methylation to form 2-methylcyclopentanone. Sodium borohydride ( NaBH ₄ ) in methanol is a reducing agent that reduces the ketone group of 2-methylcyclopentanone to a secondary alcohol. This yields 2-methylcyclopentanol as the final major product. Answer:

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