Content:
Chapter 1 Equilibrium additions to carbonyl compounds (pages 1–69): Yoshiro Ogata and Atsushi Kawasaki
Chapter 2 Oxidation of aldehydes and ketones (pages 71–156): Herbert S. Verter
Chapter three Enolization (pages 157–240): S. Forsen and M. Nilsson
Chapter four Oxocarbons and their reactions (pages 241–275): Robert West and Joseph Niu
Chapter five Mass spectrometry of carbonyl compounds (pages 277–341): J. H. Bowie
Chapter 6 Radiation chemistry of ketones and aldehydes (pages 343–394): Gordon R. Freeman
Read Online or Download The Carbonyl Group: Volume 2 (1970) PDF
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Extra resources for The Carbonyl Group: Volume 2 (1970)
Example text
Usually, the reaction does not occur in the presence of nucleophiles other than cyanide ion. If a mixture of benzaldehyde and a substituted benzaldehyde is treated with alkali cyanide, a mixed benzoin is formed171. A. Equilibria T h e formatioIi of cyanohydrin from benzaldehydes (reaction 45) has been studied extensively in view of the substituent effects on rates and equilibria. The rate and equilibrium of the reaction may be followed by determining HCN according to Romijn's method (titration with AgN0,-NH,SCN) 176-177.
A claim that this effect of alkyl groups is due to a ponderal effect lE5 rather than to hyperconjugation 186 was regarded as dubious since, except at quite low temperatures, there is no appreciable ponderal effect calculated by statistical mechanics on the basis of all vibrational fiequencies corresponding to the force constants and molecular geometries assumed by the aldehydes and cyanohydrins The dissociation constants 102K of cyclic ketone cyanohydrins in 96% ethanol at 22" vary with the number of ring carbons (n) as follows : l8I7.
The rate equation for reversible reactions (forward first-order and backward secondorder) should, however, be applied in the absence of the oxidizing agent. + H+ 'C' R 11';. R ' 2' 36 Yoshiro Ogata and Atsushi Kawasaki TABLE 7. Relative rates" for the decomposition of sodium bisulphite adducts of substitutcd benzaldehydes, in water at 20°210. 33 #-OH +C*24 H 0 0 k is the pseudo first-order rate constant in substrate, A reprcscnts the increment rclative to benzaldchyde. both decomposition paths in reaction (60) : u = kz[XH-] or u = kz[XH-] + k3[X2-] (611 klk3[XH-] + k-,[H+] + k3 The above rate law explains the observed dependency on [OH-]" (n 5 1).