HC=CH Acetylene + CH3CO₂H Acetic Acid H₂SO4 HgSO4 H3C- -0-C=CH₂ H Vinyl acetate Acetylene reacts with acetic acid in the presence of H₂SO4 and HgSO4 to yield vinyl acetate, a monomer used in the production of poly(vinyl acetate). The reaction mechanism includes the following steps: 1. Formation of a bridged mercurinium ion intermediate between Hg²+ and acetylene; 2. Addition of acetic acid to open the three-membered ring; 3. Proton transfer to solvent to give an organomercury vinyl ester; 4. Addition of H* to the alkene to form a carbocation; 5. Expulsion of Hg²+ to form the alkene.
HC=CH Acetylene + CH3CO₂H Acetic Acid H₂SO4 HgSO4 H3C- -0-C=CH₂ H Vinyl acetate Acetylene reacts with acetic acid in the presence of H₂SO4 and HgSO4 to yield vinyl acetate, a monomer used in the production of poly(vinyl acetate). The reaction mechanism includes the following steps: 1. Formation of a bridged mercurinium ion intermediate between Hg²+ and acetylene; 2. Addition of acetic acid to open the three-membered ring; 3. Proton transfer to solvent to give an organomercury vinyl ester; 4. Addition of H* to the alkene to form a carbocation; 5. Expulsion of Hg²+ to form the alkene.
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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What is the structure of the product in step 4?
![**Acetylene Reaction Mechanism and Vinyl Acetate Synthesis**
**Chemical Equation:**
\[ \text{HC} \equiv \text{CH} + \text{CH}_3\text{CO}_2\text{H} \xrightarrow{\text{H}_2\text{SO}_4,\text{HgSO}_4} \text{H}_2\text{C} = \text{C(O)O}\text{CH}_3 \]
\[ \text{Acetylene + Acetic Acid} \rightarrow \text{Vinyl Acetate} \]
**Reaction Mechanism:**
Acetylene reacts with acetic acid in the presence of H\(_2\)SO\(_4\) and HgSO\(_4\) to yield vinyl acetate, a monomer used in the production of poly(vinyl acetate). The reaction mechanism includes the following steps:
1. **Formation of a bridged mercurinium ion intermediate between Hg\(^{2+}\) and acetylene:**
- This step involves the interaction of acetylene with Hg\(^{2+}\) forming a three-membered ring intermediate.
2. **Addition of acetic acid to open the three-membered ring:**
- Here, acetic acid opens the bridged mercurinium ion intermediate, leading to the formation of an organomercury intermediate.
3. **Proton transfer to solvent to give an organomercury vinyl ester:**
- A proton transfer occurs resulting in the creation of an organomercury vinyl ester.
4. **Addition of H\(^{+}\) to the alkene to form a carbocation:**
- A proton (H\(^{+}\)) is introduced to the vinyl ester, thereby forming a carbocation.
5. **Expulsion of Hg\(^{2+}\) to form the alkene:**
- The final step involves the removal of Hg\(^{2+}\), leading to the formation of the final alkene product, vinyl acetate.
**Diagram Instructions:**
- Students are instructed to diagram the mechanism on a separate sheet of paper.
- The structure of the product(s) of step 4 should be drawn.
**Guidelines:**
- Stereochemistry considerations are not required.
- Explicit drawing of hydrogen (H) atoms is unnecessary.
- Only organic species should be drawn.
- Counter-ions (e](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F3b49abb7-22b1-43f4-8ea9-ededd2a6e7a5%2F55d0bb8e-5963-4dbc-9f99-1c99aa4a1fdc%2F49fmv2n_processed.png&w=3840&q=75)
Transcribed Image Text:**Acetylene Reaction Mechanism and Vinyl Acetate Synthesis**
**Chemical Equation:**
\[ \text{HC} \equiv \text{CH} + \text{CH}_3\text{CO}_2\text{H} \xrightarrow{\text{H}_2\text{SO}_4,\text{HgSO}_4} \text{H}_2\text{C} = \text{C(O)O}\text{CH}_3 \]
\[ \text{Acetylene + Acetic Acid} \rightarrow \text{Vinyl Acetate} \]
**Reaction Mechanism:**
Acetylene reacts with acetic acid in the presence of H\(_2\)SO\(_4\) and HgSO\(_4\) to yield vinyl acetate, a monomer used in the production of poly(vinyl acetate). The reaction mechanism includes the following steps:
1. **Formation of a bridged mercurinium ion intermediate between Hg\(^{2+}\) and acetylene:**
- This step involves the interaction of acetylene with Hg\(^{2+}\) forming a three-membered ring intermediate.
2. **Addition of acetic acid to open the three-membered ring:**
- Here, acetic acid opens the bridged mercurinium ion intermediate, leading to the formation of an organomercury intermediate.
3. **Proton transfer to solvent to give an organomercury vinyl ester:**
- A proton transfer occurs resulting in the creation of an organomercury vinyl ester.
4. **Addition of H\(^{+}\) to the alkene to form a carbocation:**
- A proton (H\(^{+}\)) is introduced to the vinyl ester, thereby forming a carbocation.
5. **Expulsion of Hg\(^{2+}\) to form the alkene:**
- The final step involves the removal of Hg\(^{2+}\), leading to the formation of the final alkene product, vinyl acetate.
**Diagram Instructions:**
- Students are instructed to diagram the mechanism on a separate sheet of paper.
- The structure of the product(s) of step 4 should be drawn.
**Guidelines:**
- Stereochemistry considerations are not required.
- Explicit drawing of hydrogen (H) atoms is unnecessary.
- Only organic species should be drawn.
- Counter-ions (e
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