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C=CH H₂O: H₂O, H₂SO4 HgSO4 Draw curved arrows to show the movement of electrons in this step of the mechanism. H-OH C=CH 1 CH3 Hg HO: C=CH Hg H30

C=CH H₂O: H₂O, H₂SO4 HgSO4 Draw curved arrows to show the movement of electrons in this step of the mechanism. H-OH C=CH 1 CH3 Hg HO: C=CH Hg H30

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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### Image Transcription and Explanation for Educational Website #### Reaction Overview: 1. **Reaction**: The chemical reaction shown involves the transformation of a phenylacetylene into acetophenone. 2. **Reagents**: The reagents used in this reaction are water (H₂O), sulfuric acid (H₂SO₄), and mercuric sulfate (HgSO₄). 3. **Product**: The final product of this reaction is acetophenone. #### Mechanism: The reaction mechanism depicted includes the hydration of the alkyne. #### Step-by-Step Explanation: 1. **Initial Structure**: The starting material is phenylacetylene, represented with a triple bond between a carbon atom bonded to a phenyl group and another carbon atom. 2. **Reagents**: - **Water (H₂O)** - **Sulfuric Acid (H₂SO₄)** - **Mercuric Sulfate (HgSO₄)** 3. **Intermediate Step**: - **Formation of a Mercurinium Ion**: Water and mercuric sulfate assist in the formation of a mercurinium ion. The phenylacetylene coordinates with a mercury ion leading to the intermediate. - **Nucleophilic Attack**: A water molecule acts as a nucleophile, attacking the more substituted carbon of the mercurinium ion. - **Carbocation Formation**: The water attack leads to the formation of a carbocation intermediate. - **Transition to Enol**: Further water interaction leads to a hydroxyl group attaching to the carbon and a hydrogen bonding on the adjacent carbon. 4. **Final Product**: - The reaction results in the formation of acetophenone through tautomerization of the enol intermediate (not shown in this part of the mechanism). #### Diagrams: - **Top Reaction Scheme**: Shows the initial alkyne and final ketone product with reagents listed above the reaction arrow. - **Bottom Reaction Mechanism**: - **Left Diagram**: Phenylacetylene with coordinated mercury ion and a hydroxyl group attached to the adjacent carbon. Water is shown with lone pairs, positioned to form bonds. - **Right Diagram**: Intermediate formation where the hydroxyl group is now attached, and a positive charge remains on the mercuric ion. A hydronium ion (H₃O⁺
Transcribed Image Text:### Image Transcription and Explanation for Educational Website #### Reaction Overview: 1. **Reaction**: The chemical reaction shown involves the transformation of a phenylacetylene into acetophenone. 2. **Reagents**: The reagents used in this reaction are water (H₂O), sulfuric acid (H₂SO₄), and mercuric sulfate (HgSO₄). 3. **Product**: The final product of this reaction is acetophenone. #### Mechanism: The reaction mechanism depicted includes the hydration of the alkyne. #### Step-by-Step Explanation: 1. **Initial Structure**: The starting material is phenylacetylene, represented with a triple bond between a carbon atom bonded to a phenyl group and another carbon atom. 2. **Reagents**: - **Water (H₂O)** - **Sulfuric Acid (H₂SO₄)** - **Mercuric Sulfate (HgSO₄)** 3. **Intermediate Step**: - **Formation of a Mercurinium Ion**: Water and mercuric sulfate assist in the formation of a mercurinium ion. The phenylacetylene coordinates with a mercury ion leading to the intermediate. - **Nucleophilic Attack**: A water molecule acts as a nucleophile, attacking the more substituted carbon of the mercurinium ion. - **Carbocation Formation**: The water attack leads to the formation of a carbocation intermediate. - **Transition to Enol**: Further water interaction leads to a hydroxyl group attaching to the carbon and a hydrogen bonding on the adjacent carbon. 4. **Final Product**: - The reaction results in the formation of acetophenone through tautomerization of the enol intermediate (not shown in this part of the mechanism). #### Diagrams: - **Top Reaction Scheme**: Shows the initial alkyne and final ketone product with reagents listed above the reaction arrow. - **Bottom Reaction Mechanism**: - **Left Diagram**: Phenylacetylene with coordinated mercury ion and a hydroxyl group attached to the adjacent carbon. Water is shown with lone pairs, positioned to form bonds. - **Right Diagram**: Intermediate formation where the hydroxyl group is now attached, and a positive charge remains on the mercuric ion. A hydronium ion (H₃O⁺
**Image Transcription for Educational Purposes** The image depicts a two-step organic reaction mechanism involving the conversion of phenylacetylene to acetophenone. ### Reaction Overview 1. **Starting Material:** Phenylacetylene (C₆H₅C≡CH) 2. **Reagents:** Water (H₂O), Sulfuric Acid (H₂SO₄), Mercuric Sulfate (HgSO₄) 3. **Product:** Acetophenone (C₆H₅C(O)CH₃) ### Reaction Steps - **Top Half Mechanism:** - Phenylacetylene reacts in the presence of water, sulfuric acid, and mercuric sulfate to form acetophenone. This involves the addition of water across the triple bond to produce a ketone. - **Bottom Half Mechanism:** - Illustrates an intermediate step of the reaction: - The triple bond of phenylacetylene is converted to a single bond with an alcohol group and a positive charge on the adjacent carbon atom. - The intermediate has a structure C₆H₅C(OH)CH₂. - An adjacent hydronium ion (H₃O⁺) participates in this transformation. - The reaction leads to the formation of a carbonyl compound, with water as a by-product. ### Instruction The text instructs students to "Draw curved arrows to show the movement of electrons in this step of the mechanism." Curved arrows are used to depict the flow of electron pairs in the reaction mechanism, critical for understanding the electron movement during the formation of the intermediate and final product. This visual and instruction guide helps students understand alkyne hydration mechanisms resulting in ketone formation.
Transcribed Image Text:**Image Transcription for Educational Purposes** The image depicts a two-step organic reaction mechanism involving the conversion of phenylacetylene to acetophenone. ### Reaction Overview 1. **Starting Material:** Phenylacetylene (C₆H₅C≡CH) 2. **Reagents:** Water (H₂O), Sulfuric Acid (H₂SO₄), Mercuric Sulfate (HgSO₄) 3. **Product:** Acetophenone (C₆H₅C(O)CH₃) ### Reaction Steps - **Top Half Mechanism:** - Phenylacetylene reacts in the presence of water, sulfuric acid, and mercuric sulfate to form acetophenone. This involves the addition of water across the triple bond to produce a ketone. - **Bottom Half Mechanism:** - Illustrates an intermediate step of the reaction: - The triple bond of phenylacetylene is converted to a single bond with an alcohol group and a positive charge on the adjacent carbon atom. - The intermediate has a structure C₆H₅C(OH)CH₂. - An adjacent hydronium ion (H₃O⁺) participates in this transformation. - The reaction leads to the formation of a carbonyl compound, with water as a by-product. ### Instruction The text instructs students to "Draw curved arrows to show the movement of electrons in this step of the mechanism." Curved arrows are used to depict the flow of electron pairs in the reaction mechanism, critical for understanding the electron movement during the formation of the intermediate and final product. This visual and instruction guide helps students understand alkyne hydration mechanisms resulting in ketone formation.
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