Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product formed in the following two-step reaction sequence.
Correct answer
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Step-by-step solution
The reaction of 1-methylcyclohexanol with H ₃ PO ₄ and heat ( ) is an acid-catalyzed dehydration. It proceeds via a stable tertiary carbocation intermediate. According to Saytzeff's rule, the elimination of a proton occurs preferentially from the adjacent carbon that yields the more highly substituted alkene. Thus, the major product is 1-methylcyclohexene. The subsequent reaction of 1-methylcyclohexene with OsO ₄ (osmium tetroxide) is a syn-dihydroxylation. This reagent adds two hydroxyl ( -OH ) groups across the d