Answer to Question #33557 in Organic Chemistry for Sumit

Question #33557
Arrange the following in increasing order of basic character and give reason. HO-, CH3CH2O-, (CH3)3CO-, CH3COO-
1
Expert's answer
2013-07-25T08:15:15-0400
CH3COO- < HO- < CH3CH2O- < (CH3)3CO-

It is usually explained by resonance stabilization of acetate anion and inductive destabilization of alcoholate anions: larger alkyl radical (tert-butyl) exhibits higher destabilization.

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