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.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter27: Biomolecules: Lipids

Section27.SE: Something Extra

Problem 47AP: Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV...

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