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Chapter 25: Problem 69

An ester forms from a carboxylic acid and an alcohol. $$\mathrm{RCO}_{2} \mathrm{H}+\mathrm{HOR}^{\prime} \longrightarrow \mathrm{RCO}_{2} \mathrm{R}^{\prime}+\mathrm{H}_{2} \mathrm{O}.$$ This reaction is superficially similar to the reaction of an acid with a base such as sodium hydroxide. The mechanism of the reaction can be followed by using the tracer \(^{18} \mathrm{O}\). This isotope is not radioactive, but other physical measurements can be used to detect its presence. When the esterifcation reaction is carried out with the alcohol containing oxygen-18 atoms, no oxygen-18 beyond its naturally occurring abundance is found in the water produced. How does this result affect the perception that this reaction is like an acid-base reaction?

Short Answer

Expert verified
The notion that the esterification reaction is like an acid-base reaction is affected by this finding, as it indicates that there isn't proton transfer from the carboxylic acid to the alcohol as in typical acid-base reactions. Consequently, the Oxygen-18 atoms in the alcohol don't move to the water, suggesting a different mechanism taking place.

Step by step solution

01

Understanding the reaction

Firstly, let's understand the esterification reaction, which is between a carboxylic acid and an alcohol, resulting in an ester and water. The general formula is \(\mathrm{RCO}_{2}\mathrm{H}+\mathrm{HOR}^{\prime} \longrightarrow \mathrm{RCO}_{2}\mathrm{R}^{\prime}+\mathrm{H}_{2} \mathrm{O}\). For the purpose of this experiment, an oxygen -18 atom is used as a tracer.
02

Comparing to an Acid-Base Reaction

In a typical acid-base reaction, a proton (H+) is transferred from the acid to the base. In this context, the acid is the carboxylic acid, and the alcohol can be considered the base. If it was a typical acid-base reaction, the Oxygen-18 found in the alcohol would have been transferred to the water formed in the reaction.
03

Extracting Information from the Results

However, the experiment shows that when the esterification is done with alcohol containing Oxygen-18, it's not found in the water, indicating that the oxygen in the water isn't coming from the alcohol.
04

Understanding the Implication

This means that the analogy made between this esterification reaction and the typical acid-base reaction is not wholly accurate because the esterification of a carboxylic acid and alcohol appears to not be following the model of proton transfer that characterizes acid-base reactions.

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