orgo q
Started by nixon13
NH2 is a base so it would pull off a Hydrogen! One thing I know is that it could be used in alkylation of alkynes
It is a general base, but can also be used for nucleophilic aromatic substitution through a benzyme mechanism.
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On a somewhat related tangent... is NaOC2H5 considered a strong base? Is OC2H5 a bad leaving group?
NaOC2H5 is a strong base! I'm not sure if it is considered a bad leaving group, but I don't think it's a good leaving group!
OC2H5 is similar to OH- but an even worse leaving group because the C2H5 is electron donating (on top of the negative charge on the Oxygen)...OH- is a bad leaving group...
That's what I thought....thanks
Straight from wikipedia..... (lability is the ability for a functional group to leave)
In room temperature water, the sequence of lability is:
Less lability
amine NH2−
methoxy CH3O−
hydroxyl HO−
carboxylate CH3COO−
F−
water
Cl−
Br−
I−
azide N3−
thiocyanate SCN−
nitro NO2
Greater Lability
NO3− is also weaker than F−.
NaNH2 is a very powerful base that can be used in almost all eliminations. It is a stronger base than even acetlyne anion and therefore can be used to alkylate an alkyne. Dunno if it is a stronger base than a grignard?? i wonder??
I doubt its stronger than grignard. An alkane has a pKa of 60, making its conjugate base, the grignard, very very strong.
Come to think of it you're right. That is why you can not alkylate an alkane.
