HC CH + CH;CO,H H;SO4 HC-C-O-c=CH, HgSo, Acetylene Acetic Acid Vinyl acetate Acetylene reacts with acetic acid in the presence of H,SO, and HgSO, 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* 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. Diagram the mechanism on a separate sheet of paper, and then draw the structure of the product(s) of step 3.

HC CH + CH;CO,H H;SO4 HC-C-O-c=CH, HgSo, Acetylene Acetic Acid Vinyl acetate Acetylene reacts with acetic acid in the presence of H,SO, and HgSO, 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* 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. Diagram the mechanism on a separate sheet of paper, and then draw the structure of the product(s) of step 3.

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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Question

HC CH
CH3CO2H
H,SO,
H3C-C-O-C=CH2
H
HgSO,
Acetylene
Acetic Acid
Vinyl acetate
Acetylene reacts with acetic acid in the presence of H,SO4 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 Hg- and acetylene;
2. Addition of acetic acid to open the three-membered ring;
3. Proton transfer to solvent to give an organomercury vinyl ester3;
4. Addition of H to the alkene to form a carbocation;
2+
5. Expulsion of Hg²+
to form the alkene.
Diagram the mechanism on a separate sheet of paper, and then draw the structure of the product(s) of step 3.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Draw organic species only.
• Do not include counter-ions, e.g., Na, I, in your answer.

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