Consider the reaction of ethanoyl chloride with methanol shown below. What product(s) may you expect to be formed from the reaction?

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BlackTom AI · Accepted Answer

First, let's restate the scenario and the options to analyze the possibilities clearly.
Question: Consider the reaction of ethanoyl chloride with methanol. What product(s) may you expect to be formed from the reaction?
Answer options:
a. Product C only
b. All three products A, B and C
c. Product B only
d. Product A only
e. Mixture of products A and B

Now, examine each option in turn:
Option a: Product C only. This would imply that only product C is formed and that neither A nor B forms. In the reaction of an acyl chloride with an alcohol (here methanol), the typical outcome is nucleophilic acyl substitution where the alcohol attacks the carbonyl carbon to give an ester and HCl as a byproduct. Product C, as drawn, does not match the expected ester structure from methanol reacting with ethanoyl chloride, so this option misidentifies the expected major species.
Option b: All three products A, B and C. For esters formed from acyl chlorides and alcohols, the primary pathway is a single substitution producing one ester. The formation of multiple distinct products (A, B, and C) would require multiple competing reactions or rearrangements not supported by the straightforward acetyl chloride + methanol mechanism. Therefore, this option overcounts and is not consistent with a simple acyl chloride–alcohol reaction.
Option c: Product B only. Similar to option a, selecting only product B would imply a single, specific alternative to the typical ester; unless B represents the ester derived from methanol, this would still fail to correspond to the standard product of acetyl chloride with methanol. In most classic conditions, B would not be the sole product.
Option d: Product A only. Under standard conditions, ethanoyl chloride reacts with methanol to form methyl acetate (the ester), with HCl as the byproduct. This corresponds to a straightforward nucleophilic acyl substitution where the methoxide from methanol attacks the carbonyl carbon, displacing chloride, yielding the ester (Product A) as the primary organic product. This is the most consistent outcome with the known mechanism.
Option e: Mixture of products A and B. A mixture would require competing reaction pathways yielding both A and B in notable amounts. In the classic reaction of an acyl chloride with an alcohol like methanol, the dominant pathway is ester formation; without additional reagents or catalysts to produce alternate carbonyl-adduct products, a mixture is not the expected standard outcome.

In summary, the mechanism-driven expectation is that methanol acts as the nucleophile, acyl chloride undergoes nucleophilic acyl substitution, and methyl acetate (Product A) is formed predominantly with HCl as a byproduct. The other listed options either misidentify the product or imply additional products not supported by the straightforward reaction scheme.

CHM1052 - MUM S2 2025 Week 6: Preparation quiz

Consider the reaction of ethanoyl chloride with methanol shown below. What product(s) may you expect to be formed from the reaction?

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