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: