Problem

Suggest a reasonable explanation for each of the following observations:(a)    The second-...

Suggest a reasonable explanation for each of the following observations:

(a)    The second-order rate constant k for saponification (basic hydrolysis) of ethyl trifluoroacetate is over 1 million times greater than that for ethyl acetate (25°C).


(b)   The second-order rate constant for saponification of ethyl 2,2-dimethylpropanoate, (CH3)3CC02CH2CH3, is almost 100 times smaller than that for ethyl acetate (30°C).


(c)    The second-order rate constant k for saponification of methyl acetate is 100 times greater than that for tert-butyl acetate (25°C).


(d)   The second-order rate constant k for saponification of methyl m-nitrobenzoate is 40 times greater than that for methyl benzoate (25°C).


(e)    The second-order rate constant k for saponification of 5-pentanolide is over 20 times greater than that for 4-butanolide (25°C).


(f) The second-order rate constant k for saponification of ethyl rrims-4-rm-butylcyclohexane- carboxylate is 20 times greater than that for its cis diastereomer (25°C).

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