When methyl iodide at 0.1 M concentration is allowed to...

When methyl iodide at $0.1 M$ concentration is allowed to react with sodium ethoxide at $0.1 M$ concentration in ethanol solution, the product ethyl methyl ether is obtained in good yield. Explain why the reaction is over much more quickly, but about the same yield of the ether is obtained, when the reaction is run with an excess $(0.5 M)$ of sodium ethoxide.

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Key Concepts

SN2 Reaction Mechanism

The SN2 (bimolecular nucleophilic substitution) mechanism is a one-step reaction where the nucleophile attacks the electrophilic carbon from the opposite side of the leaving group, leading to inversion of configuration. This mechanism is sensitive to steric hindrance and relies on a concerted process in which both the nucleophile and the substrate are involved in the rate-determining step.

Effect of Concentration on Reaction Rate

Reaction kinetics play a key role in bimolecular reactions, where the rate is proportional to the concentrations of both the nucleophile and the electrophile. By increasing the concentration of sodium ethoxide, the frequency of effective collisions rises, resulting in a faster reaction despite the overall yield being limited by the initial concentration of methyl iodide.

Stoichiometry of Reactants

Stoichiometry determines the maximum yield of a product in reactions involving a limiting reagent. In the given reaction, methyl iodide serves as the limiting reagent, so increasing the amount of sodium ethoxide speeds up the reaction without changing the ultimate yield of ethyl methyl ether, which is determined by the quantity of methyl iodide available.

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