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Combinatorial Synthesis of Esters

The purpose of this experiment was to see which mixtures smelled like wintergreen.

The 8 esters and the reactants (alcohols and carboxylic acids) from which they will be
made are shown in Table 1. We checked the smell mixtures by using odor. Two, and only two, of the mixtures should smell like wintergreen (they contain methyl
salicylate) pinpointing one starting alcohol (methanol) and one acid (salicylic acid).
The first mixture that smelled like wintergreen involved the reaction of CA4 with AA and AB (2 esters will form). The second mixture that smelled like wintergreen involved the reaction of CA1, CA2, CA3, and CA4 with the other alcohol AB (4
esters will form).

CA means carboxylic acid and AB or AA means the alcohol.

See attached file for full problem description.

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All we've got to do is use a little bit of logic and we can identify which acid is salicylic acid and which alcohol is methanol.

This is what we are told: "The first mixture that smelled like wintergreen involved the reaction of CA4 with AA and AB (2 esters will form)." Therefore, we may conclude that CA4, i.e. carboxylic acid #4 must be salicylic acid. In other words, when we added CA4 (salicylic acid) to a mixture of the two alcohols, ...

Solution Summary

268 words describe how to identify the ester mixtures that will smell like wintergreen.

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