HW 6C.17 Which is the stronger base?
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HW 6C.17 Which is the stronger base?
How do we find out which base is stronger -- either BrO- or C17H19O3N -- without knowing the pKb value?
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Re: HW 6C.17 Which is the stronger base?
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.
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Re: HW 6C.17 Which is the stronger base?
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.
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Re: HW 6C.17 Which is the stronger base?
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.
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Re: HW 6C.17 Which is the stronger base?
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.
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Re: HW 6C.17 Which is the stronger base?
the textbook's answer says, "the smaller the pKb of a base, the stronger the base. pKb (morphine)= 5.79. pKb (BrO-)= pKw-pKa=14-8.69=5.31." This reasoning is confusing me because I don't know how they calculated pKb and pKa. Can anyone explain how they got those numbers?
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