what are some possible counterions for tert-butoxide and hydroxide ions? course hero

by Cristobal Bins 10 min read

Why is ethoxide more unstable than t-butoxide in water solution?

2- solvation effects, in water solution, the bulky t-Butoxide ion is more difficult to solvate which destabilizes it relative to ethoxide. Plastic surgeon shares one weird way to fill in wrinkles at home. Beverly Hills surgeon reveals at home fix (no creams needed).

Why is the O-H bond in tert-butyl alcohol stronger than ethanol?

In (CH3)3C-OH, the conjugate acid of the tert-butoxide ion, the +I effect on the alcoholic carbon is three times that in CH3-CH2-OH, the conjugate acid of the ethoxide ion which has only one methyl group. Therefore, the O-H bond in tert-butyl alcohol is less polar than that in ethanol, and the former should be a much weaker acid than the latter.

Is t-butoxide a suitable nucleophile?

However, t-butoxide despite being a strong base is sterically encumbered. Therefore, is it not a suitable nucleophile due to its bulk. It cannnot substitute—It eliminates in concerted step. For the same reaction, a smaller nucleophile does the job best.

Why is ethoxide a better nucleophile than hydroxide?

Because of more Lewis basicity of ethoxide due to more electron density on oxygen in ethoxide (inductive +I effect of ethyl group) as compared to hydroxide ion, ethoxide is better nucleophile. Here, in this case order of nucleophilicity and basicity is same but this is not always true (This is due to steric reasons, etc.