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

Question

Quizplus · Accepted Answer

The tert-butoxide ion is bulkier than the methoxide ion due to the presence of three methyl groups around the oxygen atom, which creates steric hindrance. This reduces its ability to approach target molecules and decreases its nucleophilicity compared to methoxide.

Which of the Following Correctly Describes the Relative Nucleophilicities of Methoxide