The Art of Problem Solving in Organic Chemistry
Teaches organic chemists structured and logical techniques to solve reaction problems and uses a unique, systematic approach.
Stresses the logic and strategy of mechanistic problem solving -- a key piece of success for organic chemistry, beyond just specific reactions and facts
Has a conversational tone and acts as a readable and approachable workbook allowing reader involvement instead of simply straightforward text
Uses 60 solved and worked-through problems and reaction schemes for students to practice with, along with updated organic reactions and illustrated examples
Includes website with supplementary material for chapters and problems: Miguel Alonso is a Professor of Organic and Ecological Chemistry at the Universidad de Los Andes in Venezuela. With over forty years of teaching experience, he has also led courses on these topics in the US, Europe, and Latin America. His previous research interest includes the theory and application of metal carbenoids in cyclopropanes and heterocycles, and currently, focuses on chemical ecology of tropical mountain ecosystems. Among his publications, Dr. Alonso has over 90 research articles, 5 book chapters, and 4 books including the first edition of The Art of Problem Solving in Organic Chemistry , published by Wiley.
The Art of Problem Solving in Organic Chemistry
The book you just opened is an entirely rewritten second edition of the homonymous title, published by Wiley Interscience years ago. Growing on the success of the first edition, a set of three chapters describing time-proven techniques of problem solving and organic chemistry concepts is compounded with a new collection of 60 solved advanced-level problems of organic reaction mechanism extracted from groundbreaking research.
Proposing hypothetical solutions and contrasting them against chemical soundness and experimental evidence constitute the fundamental line of reasoning. Perhaps there is no better way to get to the bottom of things organic and extract a most rewarding learning experience. This would not have been possible without first describing a set of concepts and strategies, old and new, of problem-solving analysis applied to organic reactions. Several examples and embedded problems dot these introductory chapters in the belief that Seneca's words were absolutely right: " Teaching by precept is a long road, but short and beneficial is the way of the example " (Epistulae, 6, 5).
As there seems to be no end to what organic chemistry and reaction mechanism can expand and achieve, a web page has been created to lodge a large and growing body of supplementary material associated with chapter and problem discussions: better illustrate the purpose behind this brief introduction, let me take you to the following setting. Imagine, for a moment, that you are sitting at one of those multiple-choice tests wondering where to jot your tick mark. The question might be this one: Equimolar amounts of toluene and hydrogen bromide yield a C7H7Br product with the aid of aluminum tribromide. Which is the reaction involved? Your choices are: A – Nucleophilic aromatic substitution; B – Addition; C – Rearrangement; D – Addition–elimination; E – Electrophilic aromatic substitution; F – Elimination; G – Substitution.
Your answer is likely to be ciphered in the very large storage of memorized information etched somewhere in your gray matter during class or reading and deposited effectively and recoverably in your brain. Then, you plunge head on into this ocean of memorized data to identify that tiny and highly specific string, match it with a particular preselected choice in your test and finally tick that box hoping for the best.
In this sort of test, thinking as far as reasoning proper is not there but at a very rudimentary level. You may have selected choice E as a topical answer. However, if you stop and think rather than match memories, you will soon discover a high degree of ambiguity in some of the choices: electrophilic aromatic substitution involves answers D and G, as well as bits of B and F, for example.
Now, change the situation a bit as you are presented with an organic reaction like that in Scheme P.1 and asked to provide a mechanistic explanation. No multiple choices or anything to tune your mind on any particular lecture; just you and a bare bones chemical transformation: a real-life situation in which researchers expected a standard O-acylation (product 2 ) but were surprised to find compound 3 coming out of the silica gel column as the only isolable material .
Your brain's attitude will undergo a virtual commotion as it deliberates in terms of intellectual logic, beginning by detecting and selecting the important issues, organizing the available data; then move on to heat up educated imagination to new highs, throw in the inevitable intuitive kink, and, oh yes, explore memory banks deep in that heavy gray mass up there in search for spectral interpretation and other reaction courses sufficiently resembling this one, if at all. Gradually a feasible mechani