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Combinatorial Synthesis of a Series of Esters

1. Why are the crude ester mixtures washed with aqueous NaHCO3?

2. You wish to test 9 esters for antitumor activity. One and only one of the 9 esters will actually have antitumor activity. You will prepare the esters from an alcohol and an acid as was done in the lab experiment here. However, you will prepare mixtures containing 1 alcohol and 3 acids or mixtures containing 1 acid and 3 alcohols. How many mixtures will you need to prepare to find the 1 antitumor compound? How many of these mixtures will exhibit antitumor activity? Hint: You should construct a deconvolution table similar to the one shown below.

3. If the experiment performed in question 2 gave exactly 3 mixtures with antitumor
activity, how many of the 9 esters would be antitumor agents?

Solution Preview

DECONVOLUTION TABLES AND MIXTURES OF CARBOXYLIC ACIDS AND ALCOHOLS TO PRODUCE ESTERS

(Please see the attached Word document for a nice rendition of these data. The deconvolution tables don't line up really well here in the text format. They look better in Word. They're also color coded and bolded in places to help you see what's going on.)

1. Why are the crude ester mixtures washed with aqueous NaHCO3?

Sodium bicarbonate (NaHCO3) is a base. It reacts with excessive carboxylic acid to neutralize the acid and remove it from the reaction, thus helping to purify the ester formed.

2. You wish to test 9 esters for antitumor activity. One and only one of the 9 esters will actually have antitumor activity. You will prepare the esters from an alcohol and an acid as was done in the lab experiment here. However, you will prepare mixtures containing 1 alcohol and 3 acids ...

Solution Summary

600 words explains why we wash crude ester, how to find the number of mixtures that will exhibit antitumor activity and how many will be antitumor agents.

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