Is ethanol acidic enough to lead to elimination?
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The above is a picture of α,β-dibromohydrocinnamic acid (2,3-dibromo-3-phenylpropanoic acid). In the lab today I carried out an elimination reaction on this molecule using potassium carbonate giving the carbonate anion as a base. I thought about the mechanism and I initially thought that the base would attack the hydrogen on the leftmost carbon atom (out of the two with the bromine atom on it) as I thought that this would be the most acidic proton of those two carbon atoms because of resonance available with the aromatic ring. However, the proton on the carboxylate group is surely the most acidic.
The above is a picture of α,β-dibromohydrocinnamic acid (2,3-dibromo-3-phenylpropanoic acid). In the lab today I carried out an elimination reaction on this molecule using potassium carbonate giving the carbonate anion as a base. I thought about the mechanism and I initially thought that the base would attack the hydrogen on the leftmost carbon atom (out of the two with the bromine atom on it) as I thought that this would be the most acidic proton of those two carbon atoms because of resonance available with the aromatic ring. However, the proton on the carboxylate group is surely the most acidic.
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