Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide? tert-Butoxide is more nucleophilic because it is more basic. Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects. These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom. tert-Butoxide is more nucleophilic because tert-butanol has a larger acid dissociation value than methanol. tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 24E
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Which of the following correctly describes the relative nucleophilicities of methoxide
and tert-butoxide?
tert-Butoxide is more nucleophilic because it is more basic.
Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is
diminished by steric effects.
These alkoxides have essentially the same nucleophilicities since the negative
charge in both is localized on an oxygen atom.
tert-Butoxide is more nucleophilic because tert-butanol has a larger acid
dissociation value than methanol.
tert-Butoxide is more nucleophilic because it contains three methyl groups
which increase the charge on its oxygen by donating electron density.
Transcribed Image Text:Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide? tert-Butoxide is more nucleophilic because it is more basic. Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects. These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom. tert-Butoxide is more nucleophilic because tert-butanol has a larger acid dissociation value than methanol. tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density.
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