Practicing Success
The decreasing order of the rate of the above reaction with nucleophiles (Nu-) a to d (a) PhO- (b) AcO- (c) OH- (d) CH3O- |
d > c > a > b d > c > b > a a > b > c > d b > d > c > a |
d > c > b > a |
The order of nucleophilicity of the oxyanions is as follows: (d) CH3O- > (c) OH- > (b) AcO- > (a) PhO- This order can be explained by the following factors: Size: The smaller the nucleophile, the more easily it can approach the electrophile and attack it. CH3O- is the smallest oxyanion, followed by OH-, AcO-, and PhO-. Charge: The more negative the charge on a nucleophile, the more nucleophilic it is. All of the oxyanions have a negative charge, but CH3O- has the most negative charge. Electronic effects: The presence of electron-withdrawing groups (such as the carbonyl group in AcO-) decreases the nucleophilicity of a molecule. PhO- also has an electron-withdrawing group, but it is not as strong as the carbonyl group. Therefore, the order of nucleophilicity of the oxyanions is (d) CH3O- > (c) OH- > (b) AcO- > (a) PhO-. This means that the reaction rate will be fastest with CH3O-, followed by OH-, AcO-, and PhO- in decreasing order of reactivity. |