Questions: What is the expected major product for the following reaction? 1. Hg(OAc)2, H2O / 2. NaBH4, NaOH OH + enantiomer + enantiomer

Transcript text: What is the expected major product for the following reaction? $\square \frac{\text { 1. } \mathrm{Hg}(\mathrm{OAc})_{2}, \mathrm{H}_{2} \mathrm{O}}{\text { 2. } \mathrm{NaBH}_{4}, \mathrm{NaOH}}$ OH + enantiomer + enantiomer

Solution

Solution Steps

Step 1: Oxymercuration

The first step is the oxymercuration of the alkene. The Hg(OAc)₂ and water add to the double bond, following Markovnikov's rule. This means the -OH group adds to the more substituted carbon of the double bond. A mercurinium ion intermediate is formed, which is then opened by water.

Step 2: Reduction

The second step is reduction with NaBH₄ (sodium borohydride) and NaOH. This step replaces the mercury acetate group with a hydrogen atom. The stereochemistry of this step is not relevant as the carbon to which the mercury was added is not chiral.

Step 3: Identifying the product

The final product is a Markovnikov addition of water across the double bond. This corresponds to structure II in the image. Because the carbon to which the hydroxyl group adds becomes a chiral center, the reaction creates a racemic mixture.

Final Answer: ii

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