By Peter Sykes
A vintage textbook on mechanistic natural chemistry that is characterized quite through its readability, cautious number of examples and its common procedure that's designed to steer to a prepared realizing of the subject material. This guidebook is aimed sincerely on the wishes of the scholar, with an intensive knowing of, and provision for, the aptitude conceptual problems she or he is probably going to encounter.
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Additional info for A guidebook to mechanism in organic chemistry
5 Stereochemical criteria 51 The successful study of intermediates not only provides one or more signposts which help define the detailed pathway traversed by a reaction, the intermediates themselves may also provide inferential evidence about the transition states for which they are often taken as models (cf: p. 41 ). 5 Stereochemical criteria Information about the stereochemical course followed by a particular reaction can also provide useful insight into its mechanism, and may well introduce stringent criteria that any suggested mechanistic scheme will have to meet.
317) on the double bond. By contrast, the addition reactions exhibited by the carbon-oxygen double bond, in simple aldehydes and ketones, are usually nucleophilic in character (p. 204). An example is the basecatalysed formation of cyanohydrins in liquid HCN : Elimination reactions are, of course, essentially the reversal of addition reactions; the most common type is the loss of hydrogen and another atom or group from adjacent carbon atoms to yield alkenes (p. 246) : H \ I / C-C / I\ Br - -HBr \ / C=C / \ -H,O H \ 1 / OH 32 Structure, reactivity, and mechanism Rearrangements may also proceed via intermediates that are essentially cations, anions, or radicals, though those involving carbocations, or other electron-deficient species, are by far the most common.
Thus in the Cannizzaro reaction of benzaldehyde (p. 216), the question arises of whether the second hydrogen atom that becomes attached to carbon, in the molecule of phenylmethanol (benzyl alcohol, 48 Energetics, kinetics, and the investigation of mechanism 9) that is formed, comes from the solvent ( H 2 0 ) or from a secon molecule of benzaldehyde. Carrying out the reaction in D 2 0 is foun to lead to the formation of no PhCHDOH, thus demonstrating that the second hydrogen atom c z l d not have come from water, and must therefore have been provided by direct transfer from a second molecul of benzaldehyde.
A guidebook to mechanism in organic chemistry by Peter Sykes