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Which is the wrong statement about oxyme...

Which is the wrong statement about oxymercuration `-` demercuration `?`

A

In the first step, oxymercuration occurs, `i.e.,` water and `Hg(Oac)_(2)`, add to the double bond.

B

In the second step, demercuratio occurs, `i.e., NaBH_(4)` reduces `(HgOAc)` group to hydrogen.

C

The net reaction is the addition of water according to Markovnikov's rule.

D

Rearrangement takes place

Text Solution

AI Generated Solution

The correct Answer is:
To determine which statement about the oxymercuration-demercuration reaction is wrong, we first need to understand the mechanism of this reaction. ### Step-by-Step Solution: 1. **Understanding the Reaction**: The oxymercuration-demercuration reaction involves the addition of water across a double bond in an alkene using mercuric acetate (Hg(OAc)₂) followed by reduction with sodium borohydride (NaBH₄). 2. **Markovnikov's Rule**: This reaction follows Markovnikov's rule, meaning that when water adds across the double bond, the hydroxyl group (OH) will attach to the more substituted carbon atom, while a hydrogen atom (H) will attach to the less substituted carbon atom. 3. **Mechanism Overview**: - The alkene reacts with mercuric acetate to form a cyclic mercurinium ion intermediate. - Water then attacks the more substituted carbon from the backside, leading to anti-addition. - The resulting product is a mercurial alcohol. 4. **Demercuration Step**: In the second step, sodium borohydride reduces the mercurial alcohol, replacing the HgOAc group with a hydrogen atom, thus forming the final alcohol product. 5. **Evaluating the Statements**: - **Statement A**: "In the first step, oxymercuration occurs, that is water and HgOAc add to the double bond." - This is correct. - **Statement B**: "In the second step, demercuration occurs, that means NaBH₄ reduces HgOAc group to hydrogen." - This is correct. - **Statement C**: "The net reaction is the addition of water according to the Markovnikov rule." - This is correct. - **Statement D**: "Rearrangement takes place." - This is incorrect because there is no carbocation formed in this reaction; instead, a cyclic intermediate is formed, which does not allow for rearrangement. 6. **Conclusion**: The wrong statement about the oxymercuration-demercuration reaction is **Statement D**.
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