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.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations

Section11.SE: Something Extra

Problem 34MP: Reaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2Nâ‰¡C, along with the...

See similar textbooks

Similar questions

Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.
is steric hinderance not an issue here? why when reacting with KOC(CH3)3 does it yield 2-isopropyl-1-pentene and it yields 2,3-dimethyl-2hexene here?
Q3. For the following reactions, predict the products, mechanism and name all the products 4.2-hexene + chlorine gas5.Halogenation of cyclohexane in the presence of light and catalyst6.Sulfonation of Cyclobutane with oleum 7.Addition of HBr to methylcyclopropane
Predict the major products formed when 2- methyl-1-butene reacts with: H2, Pt/25°C. Show the reaction mechanism the given alkene reactions
For each compound, give the product(s) expected from (1) HgSO4>H2SO4@catalyzedhydration and (2) hydroboration–oxidation. cyclodecyne
Q3. For the following reactions, predict the products, mechanism and name all the products obtained Catalytic hydrogenation of cycloalkenes. Reduction of cyclohexanone with Zinc amalgam (Zn/Hg alloy) in concentrated hydrochloric acid Addition of CH2I2 in an alkene in the presence of Zn-Cu 2-hexene + chlorine gas Halogenation of cyclohexane in the presence of light and catalyst Sulfonation of Cyclobutane with oleum Addition of HBr to methylcyclopropane
The HCo(CO)4complex can catalyze the isomerization of pure cis-2-butene to a mixture of cis-2-butene, trans-2-butene, and 1-butene. Propose a mechanism. Carefully show the process using wedges and dashes to indicate stereochemistry of each intermediate.
Predict the major products formed when 2- methyl-1-butene reacts with: H2O, H+. Show the reaction mechanism of the given alkene reactions
2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.
25 g of n-butyl alcohol were brominated to obtain 30 g of n-butyl bromide. The yield of the product obtainedcalculation. Show all reaction mechanisms and clear reaction. (Molecular weights,CH3CH2CH2CH2OH = 74 g mol; (CH3CH2CH2CH2Br = 138 g \ mol)
5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.
Reaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2Nâ‰¡C, along with the nitrile CH3CH2Nâ‰¡N, as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.