Problem 1: The m- and p-substituted methyl benzoates listed in the table below were treated with NaOH in dioxane and water. The rate constants of saponification, k, are also listed in the table. Provide structural explanations for the trend observed in the rate constants by comparing the effects of the various substituerts on the rate constant. Include all necessary resonance structures in your discussion NaOH Dioxane/H20 35°C Na + CH3OH p- and m-substituted methyl benzoates k (M'min-1) Methyl p-nitrobenzoate 102 Methyl m-nitrobenzoate 63 Methyl m-chlorobenzoate Methyl m-bromobenzoate 9.1 8.6 Methyl benzoate 1.7 Methyl p-methylbenzoate Methyl p-methoxybenzoate Methyl p-aminobenzoate 0.98 0.42 0.06 ৪ =

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Problem 1: The m- and p-substituted methyl benzoates listed in the table below were treated with NaOH in
dioxane and water. The rate constants of saponification, k, are also listed in the table. Provide structural
explanations for the trend observed in the rate constants by comparing the effects of the various substituerts
on the rate constant. Include all necessary resonance structures in your discussion
NaOH
Dioxane/H20
35°C
Na
+ CH3OH
p- and m-substituted methyl benzoates
k (M'min-1)
Methyl p-nitrobenzoate
102
Methyl m-nitrobenzoate
63
Methyl m-chlorobenzoate
Methyl m-bromobenzoate
9.1
8.6
Methyl benzoate
1.7
Methyl p-methylbenzoate
Methyl p-methoxybenzoate
Methyl p-aminobenzoate
0.98
0.42
0.06
৪ =
Transcribed Image Text:Problem 1: The m- and p-substituted methyl benzoates listed in the table below were treated with NaOH in dioxane and water. The rate constants of saponification, k, are also listed in the table. Provide structural explanations for the trend observed in the rate constants by comparing the effects of the various substituerts on the rate constant. Include all necessary resonance structures in your discussion NaOH Dioxane/H20 35°C Na + CH3OH p- and m-substituted methyl benzoates k (M'min-1) Methyl p-nitrobenzoate 102 Methyl m-nitrobenzoate 63 Methyl m-chlorobenzoate Methyl m-bromobenzoate 9.1 8.6 Methyl benzoate 1.7 Methyl p-methylbenzoate Methyl p-methoxybenzoate Methyl p-aminobenzoate 0.98 0.42 0.06 ৪ =
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