Microsoft Word - HW1.docx Fix the mistakes. Hydroxychloroquine has been in the news lately as an unproven treatment for the COVID-19 virus. A possible synthesis for hydroxychloroquine is shown below....

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Microsoft Word - HW1.docx Fix the mistakes. Hydroxychloroquine has been in the news lately as an unproven treatment for the COVID-19 virus. A possible synthesis for hydroxychloroquine is shown below. Several reactions will proceed as written. Several of the reactions contain mistakes. Clearly label reactions that work as “OK” and reactions that don’t as “Incorrect”. For the “incorrect” reactions, clearly draw what would actually happen. Hint: Three of the reactions definitely don’t work as shown below. The lab is investigating the isolation, synthesis, and biological activity of the following molecules. We have determined that we can convert compound D into compound E with either acid or base catalysis. Propose a mechanism for this transformation under both of these conditions. We have been unable to convert E into compound F. Propose a reason why this transformation is not favored. Fill in the boxes in the following scheme. Note: If you can’t determine the structure of the molecule with the NMR data, please use the molecule provided for partial credit.