Video Solution: (a) Which is the stronger acid (CH3)3NH+ or (CH3)3PH+? ...

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Organic Chemistry / Element Effect / Problem #15909

(a) Which is the stronger acid (CH3)3NH+ or (CH3)3PH+?

Video Transcript

So now let's take a look at these two molecules and figure out which one of them is more acidic, guys the only difference between the two, right? Is that here we've got a nitrogen and here we've got phosphorus and they're bonded like this, they've got 3 methyls coming off and an extra hydrogen, positive charge, phosphorus is the exact same arrangement, right? So now my question is which one of them is more acidic? Well, guys there's a quick way we can figure this out, right? Let's go ahead and use our chem 7 and let's add our phosphorus, phosphorus is directly underneath our nitrogen, so that tells us it's much bigger than nitrogen and guys we know because of the atom effect that the bigger the atom is the more acidic, right? So, actually it turns out that our phosphorus is going to be the more acidic compound here. Alright guys, let me know if have any questions, if not, let's move on.