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Ph-C-=C-CH(2)-CH(3)-((Hg^(2+))/(D^(o+)))...

`Ph-C-=C-CH_(2)-CH_(3)-((Hg^(2+))/(D^(o+)))underset((D_(2)SO_(4))/(D_(2)O))toA`, `A` is

A

`Ph-underset(O)underset(||)C-CH_(2)-underset(D)underset(|)CH-CH_(3)`

B

`Ph-underset(O)underset(||)C-underset(D)underset(|)CH-CH_(2)-CH_(3)`

C

`Ph-underset(OH)underset(|)CD-CH_(2)-CH_(2)-CH_(3)`

D

`Ph-underset(O)underset(||)C-CD_(2)-CH_(2)-CH_(3)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given problem, we will follow the steps involved in the oxymercuration-demercuration reaction using the provided reactants and conditions. ### Step-by-Step Solution: 1. **Identify the Reactants**: The reactant is phenylacetylene (Ph-C≡C-CH₂-CH₃) treated with mercuric ion (Hg²⁺) in the presence of deuterated sulfuric acid (D₂SO₄) and deuterated water (D₂O). 2. **Oxymercuration Reaction**: The first step involves the oxymercuration of the alkyne. The mercuric ion (Hg²⁺) will add across the triple bond of phenylacetylene. This will lead to the formation of a cyclic mercurinium ion intermediate. 3. **Formation of the Intermediate**: The cyclic mercurinium ion will form where the mercury atom is bonded to one of the carbons from the triple bond, and the other carbon will have a positive charge. The structure will look like this: - Ph-C⁺(Hg)-C-CH₂-CH₃ 4. **Nucleophilic Attack**: The deuterated water (D₂O) will act as a nucleophile. The oxygen from D₂O will attack the more substituted carbon (the one bonded to Hg), leading to the opening of the cyclic structure. 5. **Formation of Product**: After the nucleophilic attack, we will have: - Ph-CH=CH(OD)-CH₂-CH₃ Here, the hydroxyl group (OD) is attached to the carbon that was initially bonded to mercury. 6. **Demercuration**: The next step is the demercuration, where the mercury group (Hg) is replaced by a hydrogen atom (or in this case, deuterium). This will lead to the final product: - Ph-CH=CH(OD)-CH₂-CH₃ 7. **Final Product**: The final product can be represented as: - Ph-CH=CH(OD)-CH₂-CH₃, which is an enol form with deuterium. ### Conclusion: The final product A is Ph-CH=CH(OD)-CH₂-CH₃.

To solve the given problem, we will follow the steps involved in the oxymercuration-demercuration reaction using the provided reactants and conditions. ### Step-by-Step Solution: 1. **Identify the Reactants**: The reactant is phenylacetylene (Ph-C≡C-CH₂-CH₃) treated with mercuric ion (Hg²⁺) in the presence of deuterated sulfuric acid (D₂SO₄) and deuterated water (D₂O). 2. **Oxymercuration Reaction**: ...
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