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Identify the product in the reaction PhC...

Identify the product in the reaction `PhC-=CMe overset(H_3O^(+),Hg^(2+)?)rarr`

A

`PhCOCH_2CH_3`

B

`PhCH_2CH_2CHO`

C

`PhCOCOMe`

D

`PhCH_2COCH_3`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to identify the product formed when phenylacetylene (PhC≡CMe) reacts with mercuric ion (Hg²⁺) in the presence of hydronium ion (H₃O⁺). This reaction involves the addition of water across the triple bond, leading to the formation of a ketone. ### Step-by-Step Solution: 1. **Identify the Starting Material:** - The starting material is phenylacetylene, represented as PhC≡CMe, where Ph is the phenyl group (C₆H₅) and C≡C indicates a triple bond between carbon atoms. 2. **Understand the Reaction Conditions:** - The reaction occurs in the presence of H₃O⁺ (acidic conditions) and Hg²⁺ (mercuric ion), which acts as a mild oxidizing agent. 3. **Reaction Mechanism:** - The triple bond in phenylacetylene undergoes hydroboration-oxidation. The Hg²⁺ ion facilitates the addition of water across the triple bond. - The reaction proceeds through the formation of a vinyl cation intermediate after the addition of the mercuric ion. 4. **Formation of the Intermediate:** - The vinyl cation formed will be stabilized by the adjacent phenyl group (Ph). This intermediate can then react with water (from H₃O⁺) to form an enol. 5. **Tautomerization:** - The enol formed will undergo tautomerization to yield the corresponding ketone. In this case, the enol will convert to a ketone due to the stability of the carbonyl group. 6. **Final Product:** - The final product after tautomerization will be a ketone, specifically phenyl-2-propanone (PhC(=O)CH₂CH₃). ### Conclusion: The product of the reaction is **PhC(=O)CH₂CH₃**.
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