Why Does the Following Reaction Result in a Racemic Mixture

question 39

Multiple Choice

Why does the following reaction result in a racemic mixture of products?

• A)The acetic acid reagent is achiral.
• B)Once the tosylate ionizes, it leaves a planar carbocation that can be attacked with equal likelihood at either side.
• C)The key intermediate is achiral.
• D)Both the enantiomeric products are equal in energy.
• E)Neighboring group participation diminishes the selectivity of the reaction.

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