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For both of the following questions, please indicate whether the arrows represent the movement of one electron or a pair of electrons!

For both of the following questions, please indicate whether the arrows represent the movement of one electron or a pair of electrons!

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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For both of the following questions, please indicate whether the arrows represent the movement of one electron or a pair of electrons!

### Reaction of Alkynes with Aqueous Acid in the Presence of Mercury(II) Sulfate Alkynes do not react directly with aqueous acid as do alkenes but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, meaning that the OH group adds to the more highly substituted carbon, while the hydrogen (H) adds to the less highly substituted carbon. The initial product is a vinyl alcohol, or enol, which then immediately rearranges to a more stable ketone through tautomerization. **Mechanism Steps:** 1. **Reagents and Reaction Conditions:** - Benzene alkyne reacts with water (H₂O), sulfuric acid (H₂SO₄), and mercury(II) sulfate (HgSO₄). 2. **Formation of the Enol:** - Involves Markovnikov addition where OH adds to the more substituted carbon atom. 3. **Tautomerization:** - The enol rearranges to form a more stable ketone. **Diagram Overview:** - The first diagram shows the reaction starting with an alkyne synthesized with benzene, proceeding to a ketone. - The conversion from one form to another is indicated using a rightwards arrow. - **Arrow-pushing Instruction:** Users are prompted to draw curved arrows to indicate electron movement within the step of the mechanism. **Detailed Mechanism with Mercury(II):** - In an additional diagram, there is an alkyne reacting with Hg²⁺ to form an interaction suggesting an organomercury intermediate. - Positive charges are indicated on certain atoms, showing the development of an intermediary transition state or intermediate. This series of reactions illustrates the complexities of alkyne chemistry, particularly in how they can be persuaded to react similar to alkenes through the aid of a catalyst, leading to important transformations in synthetic chemistry.
Transcribed Image Text:### Reaction of Alkynes with Aqueous Acid in the Presence of Mercury(II) Sulfate Alkynes do not react directly with aqueous acid as do alkenes but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, meaning that the OH group adds to the more highly substituted carbon, while the hydrogen (H) adds to the less highly substituted carbon. The initial product is a vinyl alcohol, or enol, which then immediately rearranges to a more stable ketone through tautomerization. **Mechanism Steps:** 1. **Reagents and Reaction Conditions:** - Benzene alkyne reacts with water (H₂O), sulfuric acid (H₂SO₄), and mercury(II) sulfate (HgSO₄). 2. **Formation of the Enol:** - Involves Markovnikov addition where OH adds to the more substituted carbon atom. 3. **Tautomerization:** - The enol rearranges to form a more stable ketone. **Diagram Overview:** - The first diagram shows the reaction starting with an alkyne synthesized with benzene, proceeding to a ketone. - The conversion from one form to another is indicated using a rightwards arrow. - **Arrow-pushing Instruction:** Users are prompted to draw curved arrows to indicate electron movement within the step of the mechanism. **Detailed Mechanism with Mercury(II):** - In an additional diagram, there is an alkyne reacting with Hg²⁺ to form an interaction suggesting an organomercury intermediate. - Positive charges are indicated on certain atoms, showing the development of an intermediary transition state or intermediate. This series of reactions illustrates the complexities of alkyne chemistry, particularly in how they can be persuaded to react similar to alkenes through the aid of a catalyst, leading to important transformations in synthetic chemistry.
**Alkyne Hydration with HgSO₄ as a Catalyst** Alkynes do not react directly with aqueous acid as alkenes do, but they will in the presence of mercury(II) sulfate (HgSO₄) as a Lewis acid catalyst. The reaction proceeds with Markovnikov regioselectivity where the OH group attaches to the more substituted carbon, while the hydrogen (H) attaches to the less substituted carbon. The reaction initially produces a vinyl alcohol, also known as an enol, which instantly rearranges to form a more stable ketone through tautomerization. **Mechanism Illustration:** 1. **Initial Structure**: A benzene ring is attached to an alkyne group (C≡CH). 2. **Reagents**: The reaction is carried out with water (H₂O), sulfuric acid (H₂SO₄), and mercury(II) sulfate (HgSO₄). 3. **Product**: The resulting compound is a ketone with the formula shown as a benzene ring attached to a C=O group, followed by a CH₃ group. 4. **Arrow-Pushing Instructions**: Displayed are basic arrow types for showing electron movement in mechanistic drawings. **Diagrams:** - **Reactant to Product Transformation**: The reactants transform from an alkyne to a ketone via an enol intermediate. - **Arrow-Pushing Diagram**: Demonstrates electron movement necessary for the conversion of a vinyl alcohol to a ketone. - **Tautomerization Step**: Illustrates the transition from an enol form to a ketone, highlighting the stability of ketones over enols due to resonance and hydrogen bonding. This educational content is designed to aid in understanding the mechanism of alkyne hydration using HgSO₄, including the transfer and stabilization of electrons during chemical transformations.
Transcribed Image Text:**Alkyne Hydration with HgSO₄ as a Catalyst** Alkynes do not react directly with aqueous acid as alkenes do, but they will in the presence of mercury(II) sulfate (HgSO₄) as a Lewis acid catalyst. The reaction proceeds with Markovnikov regioselectivity where the OH group attaches to the more substituted carbon, while the hydrogen (H) attaches to the less substituted carbon. The reaction initially produces a vinyl alcohol, also known as an enol, which instantly rearranges to form a more stable ketone through tautomerization. **Mechanism Illustration:** 1. **Initial Structure**: A benzene ring is attached to an alkyne group (C≡CH). 2. **Reagents**: The reaction is carried out with water (H₂O), sulfuric acid (H₂SO₄), and mercury(II) sulfate (HgSO₄). 3. **Product**: The resulting compound is a ketone with the formula shown as a benzene ring attached to a C=O group, followed by a CH₃ group. 4. **Arrow-Pushing Instructions**: Displayed are basic arrow types for showing electron movement in mechanistic drawings. **Diagrams:** - **Reactant to Product Transformation**: The reactants transform from an alkyne to a ketone via an enol intermediate. - **Arrow-Pushing Diagram**: Demonstrates electron movement necessary for the conversion of a vinyl alcohol to a ketone. - **Tautomerization Step**: Illustrates the transition from an enol form to a ketone, highlighting the stability of ketones over enols due to resonance and hydrogen bonding. This educational content is designed to aid in understanding the mechanism of alkyne hydration using HgSO₄, including the transfer and stabilization of electrons during chemical transformations.
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We have given two mechanisms and we have to draw the curved arrows for the steps of the mechanism. Organic compounds are the compounds that contain carbon and hydrogen atoms.

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