Conjugate base question

[jeep1010]

TBR states: "The weaker the conjugate base, the stronger the acid that is required to react with it"

I am having trouble understanding why this is. I figured that a weaker conjugate base means its more stable (less likely to react) and thus a strong acid needs to be present to cause a reaction.

Conversely, stronger the conjugate base means its less stable, and would need a weaker acid to cause a reaction?

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[aldol16]

A weak conjugate base means that its acid is strong. So something like HCl would have a weak conjugate base.

This question hinges on what a weak base is. A weak base doesn't want to deprotonate things. So if you have a weak base and a weak acid, which doesn't really want to donate a proton, then you don't really get a reaction. So say your friend has an iPhone you want. But you don't want that iPhone so much and your friend doesn't want to give it up either. So nothing really happens. In this case, you would need a friend who really wants to give up his or her iPhone - so much so that he/she is essentially just pushing it onto you. That's the only way the exchange would occur.