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Basic organic reactions
339 by W. McCrae, Heyden and Son Ltd., London, 1973, pp- xiii +216, price L3.60 (cloth), Lf -95 (paper).
Basic Organic Reactions, York and Rheine,
New
This book, in its paperback version, is a moderately attractive student text in terms of value for money. It aims to set out, in limited compass, the facts relating to the most useful synthetic organic reactions. There is undoubtedly a place for books of this type because the properfy increased attention given to mechanistic studies and instrumental methods in undergraduate courses, does not alter the catdinat position of synthetic activity in organic chemistry. Not merely does the preparation of speciafised structures to test theoretical predictions often set a sufficient preparative challenge, but the planning of a major synthetic attack on some natural molecule calls for the maximum exploitation of selective control over the course of reactions. Designing such a book presents massive probfems in selection and arrangement, particularly so in one of limited length. Dr. McCrae begins, as do others, with chapters of a general nature, and it is a weakness of his book that he devotes only about I.5 o/0of it to “General Concepts”. This means that his first chapter can say fittie that students would not already have learned elsewhere, and much.of that not very relevant to the chapters that follow. An elementary discussion of cyclohexane conformation seems out of place when one realises that the chapter on alkylations does not touch on the stereochemical problems important for total synthesis of steroids (the ClaisenMichael-Robinson reaction, incidentally, finds no mention at all). Similarly while the pyramidal shape of ammonia and its rapid inversion (p. 51) is important, it is not so in the context of this book. It is, incidentally somewhat misleading to comment (p. 7) that the conformational interconversion of a steroid is “not so as for cycfohexane (it certainly isn’t!) and downright readily accompfished” misleading to follow this up with the statement that the all-trans “conformation” (i.e. 5-P steroid) is more stable than the 5~ one. The book is happier when it gets down to listing reactions in six chapters, acyfation, alkylation, hatogenation, oxidation, reduction, rearrangements and misceffaneous. For each reaction there is an exposition of mechanism, some examples are quoted, references are given and some problems end each chapter. These are all pleasing features, the brief experimental recipes - reminiscent of “Hickinbottom” - could well have been omitted. No scheme of arrangement can piease everyone, but it is odd to see the Reformatsky reaction and the Grignard reaction in separate chapters (respectivefy alkylation and misceIfaneous~~ There was probably little to say about catalytic hydrogenation in the chapter on reduction, but it is again odd to see not even a token mention. Despite its failings the book is worth serious consideration at the cheaper price, it is a pity a fittfe more judgement could not have gone into its production. S. H. G.
Basic Organic Reactions, York and Rheine,
New
This book, in its paperback version, is a moderately attractive student text in terms of value for money. It aims to set out, in limited compass, the facts relating to the most useful synthetic organic reactions. There is undoubtedly a place for books of this type because the properfy increased attention given to mechanistic studies and instrumental methods in undergraduate courses, does not alter the catdinat position of synthetic activity in organic chemistry. Not merely does the preparation of speciafised structures to test theoretical predictions often set a sufficient preparative challenge, but the planning of a major synthetic attack on some natural molecule calls for the maximum exploitation of selective control over the course of reactions. Designing such a book presents massive probfems in selection and arrangement, particularly so in one of limited length. Dr. McCrae begins, as do others, with chapters of a general nature, and it is a weakness of his book that he devotes only about I.5 o/0of it to “General Concepts”. This means that his first chapter can say fittie that students would not already have learned elsewhere, and much.of that not very relevant to the chapters that follow. An elementary discussion of cyclohexane conformation seems out of place when one realises that the chapter on alkylations does not touch on the stereochemical problems important for total synthesis of steroids (the ClaisenMichael-Robinson reaction, incidentally, finds no mention at all). Similarly while the pyramidal shape of ammonia and its rapid inversion (p. 51) is important, it is not so in the context of this book. It is, incidentally somewhat misleading to comment (p. 7) that the conformational interconversion of a steroid is “not so as for cycfohexane (it certainly isn’t!) and downright readily accompfished” misleading to follow this up with the statement that the all-trans “conformation” (i.e. 5-P steroid) is more stable than the 5~ one. The book is happier when it gets down to listing reactions in six chapters, acyfation, alkylation, hatogenation, oxidation, reduction, rearrangements and misceffaneous. For each reaction there is an exposition of mechanism, some examples are quoted, references are given and some problems end each chapter. These are all pleasing features, the brief experimental recipes - reminiscent of “Hickinbottom” - could well have been omitted. No scheme of arrangement can piease everyone, but it is odd to see the Reformatsky reaction and the Grignard reaction in separate chapters (respectivefy alkylation and misceIfaneous~~ There was probably little to say about catalytic hydrogenation in the chapter on reduction, but it is again odd to see not even a token mention. Despite its failings the book is worth serious consideration at the cheaper price, it is a pity a fittfe more judgement could not have gone into its production. S. H. G.