## Abstract Additional evidence for the occurrence of a rate determining proton transfer in the hydration of 1‐alkynyl ethers is afforded by the value of the solvent deuterium isotope effect, k/k = 1.7. The addition of water to 1‐ethoxy‐1‐propyne was investigated in a series of alcohol‐water mixtu
Mechanism of reactions of unsaturated ethers and thioethers III: Acid catalyzed addition of water to ethynyl ethers
✍ Scribed by E. J. Stamhuis; W. Drenth
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 504 KB
- Volume
- 80
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
The kinetics of the addition of water to ethynyl ethers in aqueous solution were investigated:
equation image
The reaction is general acid catalyzed. This indicates, that a proton transfer is the rate determining step of the reaction:
equation image
📜 SIMILAR VOLUMES
## Abstract Infrared analysis has shown that acid‐catalyzed hydration of ethylthioethyne in heavy water does not involve the uptake of deuterium in the initial compound. This confirms earlier evidence that protonation of the triple bond is the rate‐determining step. Values for the entropy of activ
## Abstract As in the formation of esters from alkyl ethynyl ethers with primary alkyl groups by addition of water, isopropyl and __tert__.‐butyl acetate are produced from isopropoxy‐ and __tert__.‐butoxyethyne. In addition, the latter ethers show formation of an acidic product and an olefin. A me
## Abstract The acid catalyzed addition of water to ethylthioethyne has been studied in aqueous solution. The reaction is general acid catalyzed and it is faster in H~2~O than in D~2~O. Substitution of a tertiary butyl group for the ethyl group results in a rate enhancement. The entropies of activa
## Abstract The position of the acetylenic hydrogen in the n.m.r. spectra of several acetylenic ethers and thioethers was measured in carbon tetrachloride, benzene and dioxan. 1‐Hexyne and 1,5‐hexadiyne were taken as reference compounds. The results prove the existence of a large charge shift in ac