The Sn2 reaction involves the treatment of a substituted phenol with 1-bromopropane under basic...

Question:

The Sn2 reaction involves the treatment of a substituted phenol with 1-bromopropane under basic conditions to synthesize an aryl ether. You will then repeat this synthesis in the presence of an equimolar amount of 2-bromopropane. Provide an electron-pushing mechanism that explains the role of 2,6-dimethylphenol in its SN2 reaction. A sample of 5 mmol of 2,6-dimethylphenol is required for the reaction. Calculate the mass (g) of the substituted phenol required for this reaction.

Aryl Ether synthesis by alkylation of Phenol

The Williamson synthesis of aryl ether involves the nucleophilic substitution of an alkyl halide with a phenolate ion acting as the nucleophile.

This phenolate ion is generated from the corresponding phenol by treatment with a base.

Answer and Explanation:

The Williamson synthesis proceeds via Bimolecular Nucleophilic Substitution mechanism ({eq}S_{N^2} {/eq}). The mechanism has been summarized for the reaction between 2,6-dimethylphenol and bromopropane with Sodium Hydride playing the role of base.

{eq}\text{The relative molecular mass of 2,6-dimethylphenol =} 122.07\ amu. \text{Thus, 5 mmol of this reagent weighs =} 0.005\times 122.07 = 610\ mg. {/eq}


Explore our homework questions and answers library

Support