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

Chemistry Oct 05, 2020

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.

Expert Solution

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, two esters formed, right? And one of these esters was methyl salicylate, the one that smells like wintergreen. So far, therefore, we've identified CA4.

Next, we focus on identifying which alcohol is methanol.

We are told the following: "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)." We know that when alcohol AB is used with all four carboxylic acid, the wintergreen smell forms. Therefore, alcohol AB must be methanol.

Therefore, we can conclude that:

AB = methanol
AA = 1-propanol
CA4 = salicylic acid

We cannot determine the identify of the other 3 carboxylic acids.

Here would be the deconvolution table you could create (although, I think it's totally unnecessary, since we have already figured out the identify of methanol and salicylic acid).

AA AB

CA1 CA1-AA CA1-AB*
CA2 CA2-AA CA2-AB*
CA3 CA3-AA CA3-AB*
CA4 CA4-AA* CA4-AB*

The combinations that gave rise to wintergreen smell are highlighted with the asterisk. You can color these red if you'd like. Clearly, the combinations with asterisks intersect at CA4-AB. Therefore, CA4 and AB are the appropriate carboxylic acid and alcohol, respectively.

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