By C.H. Bamford and C.F.H. Tipper (Eds.)

ISBN-10: 044440936X

ISBN-13: 9780444409362

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Additional resources for Decomposition of Inorganic and Organometallic Compounds: Homogeneous Decompostion of Hydrides, Decompostion of Inorganic Oxides and Sulphides; Halides and Derivatives; Metal Alkyls, Aryls, Carbonyls and Nitrosyls

Example text

The equilibrium of the reaction HOCH,CH,Cl+ H2O G CH2CH2 + H,O+ + C1\ / 0 is far on the side of ethylene chlorohydrin. The reaction can be driven to the right-hand side by addition of the equivalent amount of base. The rate of the reaction of the chlorohydrin with hydroxide ion is much faster than the rate of the reverse reaction in which chloride ion attacks ethylene oxide in the reversible process HOCH2CH,Cl+ OH- k CH2CH2 + C1- + H2O \ / 0 In the presence of a sufficiently high concentration of base, alkaline hydrolysis of ethylene oxide takes place aL : Z leads t o ethylene glycol, viz.

Furthermore, particular attention is given to the mechanism of hydrolysis of cyclic acetals and ketals. Second-order rate coefficients, k H (= rate/ [ S] [ H, 0 '1 ), for the hydrolyses of some typical acetals, ketals, and orthoesters in purely aqueous solutions are collected in Table 12. In a compilation of data from one single source [162], k , values can be found for the reactions of a large number of diethyl acetals and ketals in 50 % dioxane-water a t 25 " C . In more recent studies, k , values have been determined for the hydrolyses of substituted benzaldehyde diethylacetals [ 1631 and benzophenone diethylketal [164] in the same solvent (Table 13).

R 2 C = 0 + H,O+ R2COH++ Nu - R2COH+ + H,O R2C(OH)Nu There are many examples of acid catalyzed carbonyl addition reactions, such as formation of hydrates (R, C(OH), ), hemiacetals, hemiketals, cyanohydrins, bisulfite compounds, azomethines, oximes, hydrazones, etc. These important reactions are discussed in Vol. 11. If the substrate is a carboxylic acid, ester, or amide, addition of the nucleophile R’O- or R’OH (R’ = H or alkyl) to the intermediate in the first step is followed by elimination of the other nucleophile X (= OR”, OH, or NR; ) in one of the subsequent steps, viz.

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Decomposition of Inorganic and Organometallic Compounds: Homogeneous Decompostion of Hydrides, Decompostion of Inorganic Oxides and Sulphides; Halides and Derivatives; Metal Alkyls, Aryls, Carbonyls and Nitrosyls by C.H. Bamford and C.F.H. Tipper (Eds.)


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