Which of the Following Correctly Describes the Relative Nucleophilicities of Methoxide

question 49

Multiple Choice

Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide?

• A)These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom.
• B)Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects.
• C)tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density.
• D)tert-Butoxide is more nucleophilic because it is more basic.
• E)none of the above

Understand the mechanism of enolization and the conditions under which it occurs.

Predict the reactivity of compounds towards enolates and understand the factors governing these reactions.

Apply knowledge of pKa values to predict the direction of equilibrium in acid-base reactions.

Understand the types of reactions that enols and enolates can undergo, including aldol and Claisen condensations, Michael addition, and alkylation.

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