Strong Base and Strong nucleophile

[nwu]

I have the list compounds for a strong base/ but weak Nu and vice versa.

But I am having trouble making a list of compounds that are both Strong Nu and Strong bases. So far I only have two compounds NaOH and alkoxides (provided they are not bulky). I was thinking of adding amidogen, NH2- to the list. It is a very strong base, but I'm not sure if it is a strong Nu. My instinct would say yes, but reading online, people seem to say that NH2- would much rather act as a base than Nu.

So would NH2- count as SB and Strong Nu?

Also if there are other SB and Strong Nu that I am missing, let me know.

Thanks

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[nwu]

Sorry, one last question. Can anyone explain why NaN3 or sodium azide is a strong nu but a weak base. Specifically, I don't understand why it is a weak base. In general, I think of stability when it comes to weak bases. Weak bases are more stable and can distribute the electrons and so are not reactive. When I look at NaN3, it cannot form a stable resonance structure and in its current state it has a significant degree of separation of charge. It makes it seem like it is very unstable thus reactive and so a SB.

 

[SN2ed]

Thread closed. These types of questions belong in the MCAT Study Q&A forum only.