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

Chapter20: Carboxylic Acids And Nitriles

Section20.SE: Something Extra

Problem 27MP: Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen...

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Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.
How might you convert geraniol into either ethyl geranylacetate or geranylacetone?
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