By C.H. Bamford and C.F.H. Tipper (Eds.)
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Additional info 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
54. The high negative value of p* indicates that the reaction is strongly accelerated by groups with electron-releasing inductive effects (negative u*). 5 powers of ten for each substitution of H by CH, in the alpha position. This strong inductive effect and the complete absence of steric hindrance can be taken as evidence for an A 1 mechanism [ 1771 -- R,C(OR’), + H,O+ R,C(OR’)OR’H+ R*C+-OR’ + H,O R,C(OR‘)OR’H+ + H, 0 R2C+-OR’ + R’OH (fast) (slow) R,C(OH;)OR’ - (fast) (+ H,O; several subsequent, relatively fast steps) R 2 C 0 + R‘OH + H 3 0 + The slow step is the formation of the resonance stabilized alkoxycarbonium ion, R, C+-OR’ * R2C=O+-R’.
2, p. 358) is given by Ho =-log ho = PKBH+- log([BH+]/ [ B l ) = log(aHfB/fB,+) (26) For a given solution, H, may be determined with the aid of spectrophotometric measurements of the neutralization ratio [BH'] /[B] of an indicator base B. According to the Zucker-Hammett hypothesis [ 841, experimental data of log h ( k = apparent first-order rate coefficient) are linearly dependent on H, for A1 reactions, viz. log h = -&, + const. (27) The coefficient 01 in eqn. 4 in most cases. For A2 reactions, a linear relationship between log k and H, is not expected, but h is supposed t o be directly proportional to the stoichiometric concentration of the strong acid  .
Cyclic acetals and ketals must be considered as special cases. They will be discussed separately in Sect. ) The hydrolyses of ortho- and para-hydroxy substituted 2-phenyl-1,3dioxanes provide an interesting special case with the rate equation [ 1781 Rate = kH[S][ H 3 0 + ] + h , [ S ] However, the rate coefficient h , refers to the acid catalyzed hydrolyses of the anions of the substrates rather than t o uncatalyzed reactions. IntraReferences p p . 89-95 46 TABLE 1 4 Solvent isotope effects in t h e acid catalyzed hydrolyses of acetals, ketals, and orthoesters Substrate I CH2,0/ Solvent Temp.