Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the correct alkene reactant that yields a 50:50 mixture of the given enantiomers upon reaction with (i) CH ₃ CO ₃ H and (ii) H ^+, H ₂ O . Reactant (i) CH ₃ CO ₃ H (ii) H ^+, H ₂ O +
Correct answer
3
Step-by-step solution
The given reaction conditions—treatment with a peroxyacid ( CH ₃ CO ₃ H ) followed by acidic hydrolysis ( H ^+ , H ₂ O )—result in the anti-dihydroxylation of an alkene. Let's analyze the stereochemistry of the given products. The products are a pair of enantiomers of 3-methylpentane-2,3-diol, drawn in Fischer projections. In these projections, the main carbon chain is vertical. Notice that the two newly added hydroxyl ( -OH ) groups are on opposite sides of the carbon backbone (one is on the left, the other is on