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Organic Chemistry Text Book (CHEM 3401 and 3402)

6.4 Mechanisms and Curved Arrows

Mechanisms of Organic Reactions

A detailed description of the changes in structure and bonding that take place in the course of a reaction, and the sequence of such events is called the reaction mechanism. A reaction mechanism should include a representation of plausible electron reorganization, as well as the identification of any intermediate species that may be formed as the reaction progresses. These features are elaborated in the following sections.

1. The Arrow Notation in Mechanisms

Since chemical reactions involve the breaking and making of bonds, a consideration of the movement of bonding ( and non-bonding ) valence shell electrons is essential to this understanding. It is now common practice to show the movement of electrons with curved arrows, and a sequence of equations depicting the consequences of such electron shifts is termed a mechanism. In general, two kinds of curved arrows are used in drawing mechanisms:

A full head on the arrow indicates the movement or shift of an electron pair:
A partial head (fishhook) on the arrow indicates the shift of a single electron:

The use of these symbols in bond-breaking and bond-making reactions is illustrated below. If a covalent single bond is broken so that one electron of the shared pair remains with each fragment, as in the first example, this bond-breaking is called homolysis. If the bond breaks with both electrons of the shared pair remaining with one fragment, as in the second and third examples, this is called heterolysis.

Bond-Breaking   Bond-Making

Other Arrow Symbols

Chemists also use arrow symbols for other purposes, and it is essential to use them correctly.

The Reaction Arrow

The Equilibrium Arrow

The Resonance Arrow

The following equations illustrate the proper use of these symbols:

For further information about the use of curved arrows in reaction mechanisms  Click Here.