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Chemistry · Ch 12 — Organic Chemistry – Some Basic Principles and Techniques

Fundamental Concepts in Organic Reaction Mechanism

12.7

Fundamental Concepts in Organic Reaction Mechanism

Every organic reaction begins with an organic molecule — called the substrate — and an attacking reagent. The substrate is the reactant that supplies the carbon atom for the new bond that forms. If both reactants supply carbon, the choice of which is called the substrate is arbitrary; you simply focus on the molecule whose transformation you are studying.

The general scheme is:

Substrate+Attacking Reagent⟶[Intermediate(s)]⟶Product(s)+Byproducts\text{Substrate} + \text{Attacking Reagent} \longrightarrow [\text{Intermediate(s)}] \longrightarrow \text{Product(s)} + \text{Byproducts}

During the reaction, at least one covalent bond — either between two carbon atoms or between carbon and another atom — is broken, and a new covalent bond is formed. The complete, step-by-step description of this process, including the movement of electrons, the energy changes during bond breaking and bond formation, and the rates at which reactants turn into products, is called the reaction mechanism.

Important

Understanding the mechanism of a reaction tells you why one product forms instead of another, and it gives you the power to design synthetic routes deliberately rather than by trial and error.

The rest of this section builds the principles that explain how these bond-breaking and bond-forming events actually occur. …