A Reaction of an Unknown Alkene with MCPBA in Dichloromethane

question 117

Multiple Choice

A reaction of an unknown alkene with MCPBA in dichloromethane followed by work-up with H₂O/H+ yielded, as the major product, a racemic mixture of (2S,3S) and (2R,3R) -3-methylpentan-2,3-diol. What is the specific structure of the alkene used in the reaction?

• A) (Z)-3-methylpent-2-ene
• B) (E)-3-methylpent- 2-ene
• C) 2-methylpent-2-ene
• D) 2,3-dimethylbut-2-ene
• E) none of the above