Reaction mechanisms

Structure and reactivity in organic chemistry

Mark G Moloney 

Oxford, UK: Blackwell Publishing 2008 | 306pp | ?29.99 (SB) ISBN 9781405114516  

Reviewed by Ian Fleming 

Reading this book has taken me back 50 years to the lectures we had from Peter Sykes on organic reaction mechanisms, the same lectures that eventually became the substance of his famous book, the last edition of which, the 6th, came out in 1986. 

Mark Moloney’s is aiming for a similar audience: organic chemists needing, for whatever reason, to look again at their understanding of organic reactions in the hope of placing them on a firmer mechanistic basis. It also comes in at much the same level, and makes many of the same points, but with a lot of additional chemistry, some of which had not fully entered the mainstream of undergraduate courses during the lifetime of Peter’s book - cross-coupling, aromatic chromium tricarbonyl complexes, silyl protecting groups, chiral auxiliaries and catalysts, metathesis, and many more topics, showing how far this book takes the reader.

Does he do it as well as Peter? Yes, although with a rather less vivid use of metaphor - I well remember the steric effect of bromine atoms being likened to that of ’bloody great footballs,’ but I dare say that didn’t make it into his book. But then I have to confess that for years I and some of my colleagues waged a campaign to persuade Peter to change some of his explanations, to no avail, and I fear I might want to do the same with this book.

It relies heavily upon a basis of Lewis structures and Pauling’s ideas - hybrid orbitals and valence bond theory. From there it treads a sure and familiar path through the thickets, with MO theory getting a look in only when resonance offers no guidance. If this is how your students think of structures and reactions it will serve its purpose well for them.