Mechanism of the hydroxyiodination of 2-butenoic acid
โ Scribed by Stanley D. Furrow
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- English
- Weight
- 267 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0538-8066
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โฆ Synopsis
Aqueous iodination of trans-2-butenoic acid proceeds via hydrolysis of 12 to form HOI and I-, then rapid addition of HOI across the double bond to form the iodohydrin product. In the presence of iodate to keep iodide concentration low, the reaction proceeds a t a conveniently measurable rate. The rate for the addition reaction
where [H+] and [IO;] are total concentrations used to prepare the solution.
๐ SIMILAR VOLUMES
The acid-catalyzed hydrolysis mechanisms of maleamic (4-amino-4-0~0-2-butenoic) acids were studied using AM1 method. The reaction proceeded mainly in two steps: (1) nucleophilic attack of the undissociated carboxyl group on the adjacent aminocarbonyl carbon via a zwitterionic intermediate; and ( 2 )
Szinzmavy. The rates of the acid-catalysetl hydrolysis < I f a serics of hryi-2,2,2-trifluorocliazocthanes Ia-d havc been mcasured in dioxan/\vatcr/HC104. Thc results arc well corrclatetl with the Hanznzett equation when up substituent constants are used ( @ = -1.74 and er, = -1.75). Kinetic solven