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- May 17, 2008
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Hey everyone,
I've been reviewing Orgo and I'm having some trouble understanding how a strong nucleophile can be a weak base. Chad provides a list of these strong nucleophiles but weak bases: CN, N3, Cl, Br I, SH, SR (all negatively charged ions).
I don't understand conceptually how something could be a good nucleophile but a weak base (I understand the difference between nucleophiles and bases and why something can be a good base but a bad nucleophile, but the opposite condition does not make any sense to me).
Related to this, I also was curious why the halide anions are weak bases to begin with: for example, they are weaker bases than H2O, despite having a negative charge. According to Chad's CARDIO method of ranking bases, a negative charge should be a sign of a strong base, but that doesn't seem to be the case here. I understand that HI, HBr, HCl, etc are all strong acids so the conjugate bases are weak, but again conceptually I do not understand why they are weak bases given their negative overall charge. Are they subject to some weird super stability because of their filled octet?
I've been reviewing Orgo and I'm having some trouble understanding how a strong nucleophile can be a weak base. Chad provides a list of these strong nucleophiles but weak bases: CN, N3, Cl, Br I, SH, SR (all negatively charged ions).
I don't understand conceptually how something could be a good nucleophile but a weak base (I understand the difference between nucleophiles and bases and why something can be a good base but a bad nucleophile, but the opposite condition does not make any sense to me).
Related to this, I also was curious why the halide anions are weak bases to begin with: for example, they are weaker bases than H2O, despite having a negative charge. According to Chad's CARDIO method of ranking bases, a negative charge should be a sign of a strong base, but that doesn't seem to be the case here. I understand that HI, HBr, HCl, etc are all strong acids so the conjugate bases are weak, but again conceptually I do not understand why they are weak bases given their negative overall charge. Are they subject to some weird super stability because of their filled octet?