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

A pharmacology lab compares volatility of small molecules used as topical antiseptics. Samples are equilibrated at 1.00 atm, and the investigator wants the concept of intermolecular hydrogen bonding and dimerization to predict boiling points relevant to evaporation from skin. Which compound would be expected to have the highest boiling point?

Compounds: methanol (CH$_3$OH), ethanol (CH$_3$CH$_2$OH), acetone ((CH$_3$)$_2$CO), acetic acid (CH$_3$CO$_2$H).

A serine hydrolase in intestinal fluid catalyzes cleavage of an ester prodrug (RCO$_2$R') to a carboxylic acid (RCO$_2$H) and an alcohol (R'OH). The investigator is testing the concept of acyl-enzyme intermediate formation typical of esterases. Which enzyme mechanism is most consistent with the transformation observed?

Conditions: pH 7.4 buffer; no added strong acid/base; enzyme active site contains a Ser–His–Asp catalytic triad.