4) An undergraduate researcher, James, was given the task of removing a t-butyl ether from thetyrosine derivative A to release the free phenol. James looked up a standard t-butyl ether removalprocedure and ran the reaction. Instead of getting the desired product, B, he got a high yield of C.Show a reaction mechanism that explains why James did not get the desired product. Make sureyour mechanism explains why James only got the ortho product.AHO.NHACNHACOBnOBnHONHACF3C OHOBnDCM, r.t.B 0% yieldC 99% yield

The proposed reaction mechanism explains why James obtained the ortho product (C) instead of the…

Answered: 4) An undergraduate researcher, James,…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 39MP

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1. The molecule below is ascorbic acid, also known as vitamin C. a. As drawn below, ascorbic acid is shown as a diketone. An enol tautomer of ascorbic acid exists and is how the molecule is usually drawn. Draw the enol tautomer of ascorbic acid. b. Show the mechanism for tautomerization under basic conditions from the ketone to the enol. c. Ascorbic acid has a pK₂ of 4.6 which is more similar to that of a carboxylic acid than an alcohol. Which H is most acidic in ascorbic acid? d. Explain why Vitamin C is so acidic. OH OH ascorbic acid OH
complete the reaction by adding reagents or prodcts Please provide only typed answer solution no handwritten solution needed allowed

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