Textbook Question 6C.17: Justification for Base Strength

[Sofia Lucido 3L]

For textbook question 6C.17 it asks: Which is the stronger base, the hypobromite ion BrO- or morphine, ? I said BrO- was the stronger base because it has a negative charge, but I was wondering if there was additional/stronger reasoning for why BrO- is a stronger base?

Thank you!

[reyvalui_3g]

If you compare the pKb values between hypobromite and morphine, you will find that the pKb value of hypobromite is lower than that of morphine. This means that hypobromite is a stronger base.

[Katherine_Douglas_1F]

If you don't have access to the pKb values, you can use logic to sort of figure out which one is the stronger base. Just as the stronger acids will lose H+ more easily and have more stable anions, stronger bases will gain H+ more easily and have less stable anions. Since BrO- is already negative, it will be more attracted to the H+ ions than C17H19O3N. It is also a less stable anion. All this means that BrO- would be the stronger base.