You now have enantiomerically pure diacid that will serve as a starting material.

You now have enantiomerically pure diacid that will serve as a starting material. Your task is to selectively convert only one of the carboxylic acid groups into an ester (We will refer to this product as a mono-ester).

It is not important which carboxylic acid group would be converted to an ester and what is the alkyl group you choose for your esters. Your goal is to find a way to synthesize it selectively and efficiently. Selectivity will be defined as the ratio between the two possible mono-esters.

For example, the ratio between mono-ethyl esters 1 and 2. Efficiency will be defined as the overall yield. The following alcohols will be available in the lab: 1-propanol, isobutyl alcohol, benzyl alcohol 1- phenyl-1-propanol.

Prelab assignment: You will need to submit a proposal during the first lab section that will be reviewed by your TAs. Your proposal should be typed and chemical structures must be created with a ‘chemical structure editor’ such as ChemDraw, ChemSketch, Chemdoodle, etc.

1. Design: Research the literature and come up with a synthetic plan to create a monoester of your choice with high efficiency and selectivity. This may require multiple steps.

2. Justification: Explain why do you believe your proposal will achieve high selectivity and efficiency. Be aware that references will add credibility to your argument. Don’t add a reference without summarizing the facts that you relay on.

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