Alcohols, Carboxylic Acids, and Acid Derivatives (5D) Practice Test

A researcher hydrolyzes an amide drug (RCONHCH3) in 0.10 M HCl at 37°C and observes slow conversion to carboxylic acid. In contrast, an analogous ester (RCOOCH3) hydrolyzes much faster under the same conditions. Which reasoning best accounts for the difference?

In an acid-catalyzed hydrolysis study of an ester (R–CO2R′) at pH 2.0, a student proposes that the key intermediate is a tetrahedral species formed after water attacks the carbonyl carbon. Concept probed: mechanistic intermediates in nucleophilic acyl substitution. Which description is most consistent with the structure of the tetrahedral intermediate formed immediately after nucleophilic attack (before collapse)?