Alkaline Hydrolysis of an Ester Involves Initial Attack by Hydroxide

question 3

Multiple Choice

Alkaline hydrolysis of an ester involves initial attack by hydroxide ion on the carbonyl carbon.The presence of substituents on the aromatic ring of ethyl benzoate may be expected to increase/decrease the rate of hydrolysis of this ester.In what order should the five substituents below be arranged to represent the decreasing order of the rates of hydrolysis when these substituents are present in the para position of the aromatic ring in ethyl benzoate?

• A)-NO₂ > -H > -Cl > -CH₃ > -OCH₃
• B)-NO₂ > -Cl > -H > -CH₃ > -OCH₃
• C)-OCH₃ > -CH₃ > -Cl > -H > -NO₂
• D)-Cl > -NO₂ > -H > -OCH₃ > -CH₃
• E)-H > -Cl > -CH₃ > -OCH₃ > -NO₂

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