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H(3)C-C-=CH overset(H(2)O,H(4)SO(4))unde...

`H_(3)C-C-=CH overset(H_(2)O,H_(4)SO_(4))underset(HgSO_(4))to underset(A)("intermediate") to underset(B)("product")`

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B

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Text Solution

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The correct Answer is:
To solve the problem, we need to understand the reaction of the alkyne with water in the presence of sulfuric acid and mercuric sulfate. The alkyne given is 1-butyne (H₃C-C≡CH). Let's break down the steps involved in the reaction to identify the intermediate (A) and the final product (B). ### Step-by-Step Solution: 1. **Identify the Reactants**: The reactant is 1-butyne (H₃C-C≡CH) and the reagents are H₂O, H₂SO₄, and HgSO₄. 2. **Formation of the Mercuric Ion Complex**: When 1-butyne reacts with HgSO₄, the mercuric ion (Hg²⁺) interacts with the triple bond. This leads to the formation of a non-classical carbocation intermediate. The reaction can be represented as: \[ H₃C-C≡CH + HgSO₄ \rightarrow \text{Non-Classical Carbocation} \] 3. **Nucleophilic Attack by Water**: The non-classical carbocation is then attacked by water (H₂O). The oxygen in water acts as a nucleophile and attacks the more substituted carbon of the carbocation. This results in the formation of an oxonium ion (protonated alcohol): \[ \text{Non-Classical Carbocation} + H₂O \rightarrow \text{Oxonium Ion} \] 4. **Deprotonation**: The oxonium ion is unstable and loses a proton (H⁺), leading to the formation of an enol: \[ \text{Oxonium Ion} \rightarrow \text{Enol (C=C-OH)} \] 5. **Tautomerization to Ketone**: The enol undergoes tautomerization to form a more stable keto form. In this case, the enol will convert to propan-2-one (acetone): \[ \text{Enol} \rightarrow \text{Keto (Propan-2-one)} \] 6. **Final Product**: The final product (B) is propan-2-one (acetone, CH₃COCH₃). ### Summary of A and B: - Intermediate (A): Non-Classical Carbocation - Product (B): Propan-2-one (Acetone)
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Ph-C -= C - CH_3 overset(HgSO_4)underset(H_2SO_4) to A ,

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Knowledge Check

  • Predict the correct intermediate and product in the following reaction. H_(2)-C=CH overset(H_(2)OH_(2)SO_(2)) underset(H_(2)SO_(4)) to underset((A)) ("intermediante") to underset((B)) ("product")

    A
    `A:H_(3) C- underset(SO_(4)) underset(|) (C)=CH_(2) B: H_(3)C- underset(O) underset(||)(C)-CH_(3)`
    B
    `A:H_(3) C- underset(OH) underset(|) (C)=CH_(2) B: H_(3)C- underset(O) underset(||)(C)-CH_(3)`
    C
    `A:H_(3) C- underset(OH) underset(|)(C)=CH_(2) B: H_(3)C- underset(SO_(4)) underset(||)(C)-CH_(2)`
    D
    `A:H_(3) C- underset(O) underset(|) (C)=CH_(2) B: H_(3)C-C-=H`
  • Predict the correct intermediate and product in the following reaction. H_(2)-C=CH overset(H_(2)OH_(2)SO_(2)) underset(H_(2)SO_(4)) to underset((A)) ("intermediante") to underset((B)) ("product")

    A
    `A:H_(3) C- underset(SO_(4)) underset(|) (C)=CH_(2) B: H_(3)C- underset(O) underset(||)(C)-CH_(3)`
    B
    `A:H_(3) C- underset(OH) underset(|) (C)=CH_(2) B: H_(3)C- underset(O) underset(||)(C)-CH_(3)`
    C
    `A:H_(3) C- underset(OH) underset(|)(C)=CH_(2) B: H_(3)C- underset(SO_(4)) underset(||)(C)-CH_(2)`
    D
    `A:H_(3) C- underset(O) underset(|) (C)=CH_(2) B: H_(3)C-C-=H`
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    A
    B
    C
    D
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