SN1 and SN2 are the two mechanisms of nucleophilic substitution reactions where SN1 involves only one molecule, and SN2 involves two. A nucleophile is described as reagents which donate their pair of electrons or share them with another atomic nucleus, or to form a new bond between itself. The process of what a nucleophile does in reaction is shown in figure 1. A substitution reaction is described as a chemical process where an atom or a functional group of a molecular chain is substituted by a different atom or functional group. These synthesis reaction mechanisms stand for “substitution, nucleophilic, unimolecular (SN1)/bimolecular (SN2)” mechanism.
Alkyl halides can be prepared from their corresponding alcohols through an acid catalysed substitution reaction known as the SN1 mechanism which stands for “substitution, nucleophilic, unimolecular” mechanism. A tertiary alcohol is one where the hydroxyl (OH-) function group is connected to a parent chain carbon atom which is also connected to 3 other carbon atoms which are used as the building blocks for the synthesis of natural products and pharmaceuticals. Tertiary alcohols only follow the route of unimolecular nucleophilic substitution (SN1) while secondary alcohols may also follow this mechanism. The rate determining step within the SN1 reaction mechanism is where the reaction follows first order kinetics, meaning the rate of reaction is dependent on the concentration of only one reactant, in this case, it is dependent upon the concentration of t-butanol. Under acidic conditions (the addition of sulfuric acid (H2SO4)) the mechanism of the SN1 reaction involves the rapid protonation of the alcohol, followed by the loss of water as the rate determining step.
Unlike SN1 reactions, the SN2 mechanism occurs all within a single step and is bimolecular reaction. The SN2 reaction mechanism is also referred to as “solvolysis”, which is a chemical reaction where the solvent, such as water or alcohol is one of the reagents and is present in large excess required for the reaction to proceed, in which only primary alcohols and potentially secondary alcohols follow the route of the SN2 reaction (specific for nucleophilic aliphatic substitution). The mechanism for the SN2 reaction relies on the concentrations of both reactants, for example in the following reaction, it requires a collision between a hydroxide ion and a methyl bromide molecule.
Chris Mylonas