Mechanisms of Organic Reactions

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Chapter: Organic Chemistry : Mechanisms of Organic Reactions

A very common way for students to try to learn organic chemistry is to commit a vast amount of material to memory and then try to retrieve the correct information when it is needed.


MECHANISMS OF ORGANIC REACTIONS

A very common way for students to try to learn organic chemistry is to commit a vast amount of material to memory and then try to retrieve the correct information when it is needed. The organization of organic transformations around the chemistry of functional groups is an important tool in this learning pro-cess. Thus selected functional group transformations provide the initial body of knowledge that must be mastered. This is why organic chemistry students typ-ically carry around piles of study cards, each with a reaction written on it that is to be committed to memory. This time-honored exercise allows students to learn what happens during a particular functional group reaction. Even with the simplifications of the functional group approach, there are still large numbers of reactions to deal with. The task is to learn them and, at the same time, organize them into coherent patterns that allow them to be retrieved when needed.

As a consequence beginning students typically concentrate on the beginning and end of a chemical reaction, that is, what reactants are converted to what products. There is also the need to learn what reagents cause these conversions. Such knowledge is an indispensable first step in the study of organic chemistry. In addition to learning what happens, however, it is also very interesting and important to understand how and why these transformations proceed.

The objective of this enlightenment is to expand our knowledge base so that it is possible to make reasonable predictions about what might happen in a reaction for which there is little precedence. Furthermore, it allows us to make educated guesses as to how a reaction might respond to changes in the structure of the starting material, or reagents, or reaction conditions. This jump in logic, from learning what happens during a reaction to predicting what will happen in a new reaction, requires a very clear understanding of mechanistic principles and the means by which they can be determined.

As we have seen, the mechanism of a reaction is the stepwise process by which reactants are converted to products. Moreover most steps in a reaction mechanism involve the movement and redistribution of electrons in the reactants or intermediates until the electronic configuration of the product is obtained. The electronic changes which are often depicted by curved-arrow notation result in bond making and/or bond breaking needed to get from the reactant to the product.

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