Carboxylate: Difference between revisions

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→‎Resonance stabilization of the carboxylate ion: added transitional words for clarity
m (→‎Resonance stabilization of the carboxylate ion: added transitional words for clarity)
:[[File:Carboxylate-resonance-2D.png|400px|Equivalence of the resonance forms the delocalised form of a general carboxylate anion]]
 
This [[delocalization]] of the electron cloud means that both of the oxygen atoms are less strongly negatively charged; the positive proton is therefore less strongly attracted back to the carboxylate group once it has left; hence, the carboxylate ion is more stable. In contrast, an alkoxide ion, once formed, would have a strong negative charge on the oxygen atom, which would make it difficult for the proton to escape. Carboxylic acids thus have a lower [[pH]] than alcohols: the higher the number of protons in solution, the lower the pH.<ref>{{cite book | last1= Fox|first1= Marye Anne|last2= Whitesell|first2= James K. | year = 1997 | title = Organic Chemistry | edition = 2nd| publisher = Jones and Bartlett Publishers | location = Sudbury, MA| isbn = 0-7637-0178-5 }}</ref>
 
==Examples==
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