Determining relative strengths of bases (6C 17)

[Nathan Nakaguchi 1G]

How does one determine which base is stronger than the other. For example, in 6C 17 we are given BrO- and C17H19O3N (morphine). My answer would be that BrO- is more basic because it has a full negative charge to pull in protons compared to morphine's possible lone pairs (I haven't attempted to create a lewis structure). In general how does one tackle a question like this?

[SGonzales_3L]

Yes, you're right. BrO^- is the stronger base. Looking at charge is one way of figuring out which is a stronger acid/base. It might help to also look at bond lengths--for the halogen acids, the longer the bond length, the stronger the acid. Strong acids also have stable conjugate bases so it is a good idea to consider the stability of the conjugate base as well.

[Nick Saeedi 1I]

BrO- has a negative charge so it is more likely to be a proton acceptor than morphine making it a stronger base.