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Two Hundred Exercises in
Mechanistic Organic Chemistry

© GalChimia, S.L., 2004

Two Hundred Exercises in
Mechanistic Organic Chemistry

Gabriel Tojo Suárez
Profesor Titular de Química Orgánica
University of Santiago de Compostela



Learning the mechanistic basis of Organic Chemistry is like mastering chess. In this game, one
needs to know how to move the pieces before embarking in a match. Similarly, a student in
Organic Chemistry begins by learning a list of simple reactions. This allows at a later stage to
explain the complex mechanisms that intervene in many organic reactions and consist in a chain of
simple reactions operating in a sequential way.
This book is aimed at students who have completed a learning cycle of Organic Chemistry and
need to settle their mechanistic knowledge. One of these students should be able to solve each
problem in about half an hour. A bachelor of Organic Chemistry should be able to do it in about
ten minutes, while a professional Organic Chemist should consume less than two minutes.
There is no way to scientifically prove that a certain mechanism is correct. A mechanism can only
be proved wrong. Mechanisms admitted as correct are those that explain the experimental data and
have been able to resist all attempts at proving their falsehood. On the other hand, only a few
simple reactions have been studied in detail from the mechanistic point of view.
The reactions depicted in this book are complex, and none have been studied in detail.
Consequently, the proposed solutions represent the opinion of author. Proposing a reasonable
mechanism is more relevant than hitting the right one. Many exercises admit more than one
sensible mechanism and the proposed solutions represent reasonable, but not unique, answers.
No enterprise would meet an end if the goal is the perfection. It is better to make soon a good job
than never a perfect one. Many people wait for the perfect moment to have children in order to
give them the best possible education. Often the resulting delay causes them to be biologically
unable to be parents. Bearing in mind that having children is so satisfactory that it is worth even in
a very imperfect way, I have written this book. I hope to be able to be proud of this intellectual
offspring in spite of its deficiencies.

Santiago, May 20th 2002
Gabriel Tojo



A BBREVIATIONS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ...
Two Hundred Exercises in
Mechanistic Organic Chemistry
© GalChimia, S.L., 2004
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