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A Primer to Mechanism in Organic Chemistry
It is now well over thirty years since my Guidebook to Mechanism in
Organic Chemistry first saw the light of day, and during that time a great
deal has happened in the teaching of chemistry, and not least in the teaching
of organic chemistry. There have been six significant revisions of the
Guidebook over this period of time and now, despite considerable pressure
to undertake a seventh, I have decided that the time has come for a new
departure.
There is no doubt that, over this thirty year span, the Guidebook
has-despite manful efforts to the contrary-become a good deal more
sophisticated; not merely in the topics considered, but also in the arguments
offered to explain them. I believe that there is now a real need for a simpler
book, and have, therefore, decided to go back to. square one and start all
over again. The Primer is a considerably simpler book, one that seeks to set
out the basic, underlying framework of organic reaction mechanisms,
illustrated-and I hope illumined-by the simplest of examples. This book
is not, I hasten to add, a "son-of-Guidebook"; I have sought to think through
the subject matter de novo, and the general arrangement is indeed now quite
different.
The basic premise of the book is that it is possible-at this level-to make
some sense out of the apparent overfacing complexity of organic chemistry
on the basis of three underlying axioms: that there are only three types of
reaction-substitution, addition and elimination; that these reactions involve
only three types of reagent-nucleophiles, electrophiles and radicals; and
that there are only two effects-electronic and steric-through which the
behaviour of a bond, or group, undergoing reaction, can be influenced by
the rest of the molecule.
There is no discussion of bonding that involves orbital theory, nor-in
formal terms-of chemical energetics: discussion of either would have taken
up more space than their inclusion would have justified in what is intended
to be, above all, a short and simple book. Satisfactory explanations can, at
this level, be provided without an absolute need for either topic, and their
consideration is, I believe, better left till a rather more sophisticated treatment
of the subject is possible, e.g. at the level of the Guidebook.
This opinion marks a considerable change on my part: thirty years ago I
would have regarded it as heretical! In the intervening time, however, I have
seen only too often how a student's on-going difficulty with the above topics
can actually get in the way of his or her acquiring a more desirable ability:
an instinctive "feel" for the likely course taken by organic reactions.
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