Page 1 of 1

HW 6C.17 Which is the stronger base?

Posted: Thu Dec 05, 2019 12:28 am
by Charysa Santos 4G
How do we find out which base is stronger -- either BrO- or C17H19O3N -- without knowing the pKb value?

Re: HW 6C.17 Which is the stronger base?

Posted: Thu Dec 05, 2019 1:39 am
by Mashkinadze_1D
I believe for something like this we would need the pKb value but we can also use a rule of thumb that most compounds with N are going to be a weak base and also due to the negative charge on hypobromite we can figure it will be a stronger acid as this allows it readily accept a proton.

Re: HW 6C.17 Which is the stronger base?

Posted: Sat Dec 07, 2019 7:49 pm
by Jielena_Bragasin2G
You can also look at the stability of the conjugate acid to see which one is stronger. The more stable one will be the stronger base.

Re: HW 6C.17 Which is the stronger base?

Posted: Sat Dec 07, 2019 8:14 pm
by Eugene Chung 3F
We know that BrO- is stronger base since it has a negative charge. This means that when it accepts a proton H+, it will become neutral whereas for C17H19O3N, it will become positively charged. Neutral charge is more favorable.

Re: HW 6C.17 Which is the stronger base?

Posted: Sat Dec 07, 2019 8:21 pm
by Edmund Zhi 2B
BrO- is more likely to pick up a hydrogen because it is the conjugate base of a weak acid and equilibrium will be more likely to lie the left. This makes it a STRONGER base than C17H19O3N since it is considered a weak base and is not too likely (but still can) pick up a proton with the lone pair on nitrogen.