ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Studies on the Mechanism of the Chlorohydrination of OlefinsWe studied the rate-determining and the product-determining steps of the chlorohydrination of olefins with Cl2/H2O and HOCl. In competitive kinetic experiments with 3-ethylpent-2-ene and cyclohexene we determined the relative rate constants krel = 1,5 (with Cl2/H2O) and krel = ∞ (with HOCl). This shows that the rate-determining steps of the chlorohydrination with Cl2/H2O and with HOCl are different. In order to investigate the product-determining steps we determined the proportion of alkyl-(2-chloroethyl)-ethers 3 and ethylene chlorohydrine 2 in the reaction of ethylene with Cl2 and with HOCl in alcohol/water-mixtures. The proportion of both the reaction products 3/2 was independent of the chlorinating agent used. Also the proportion of MARKOVNIKOV and anti-MARKOVNIKOV products in the chlorohydrination of propylene with Cl2/H2O or HOCl was independent of the type of chlorinating agent. In the chlorohydrination of cyclohexene both agents (Cl2/H2O and HOCl) yielded only the trans-chlorohydrine. From the results obtained it may be concluded that the product-determining step of chlorohydrination is the same for both the chlorinating agents studied.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19823240204
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