We have seen that the alpha carbon atom of an enamine can function as a nucleophile in a Michael reaction, and in fact, enamines can function as nucleophiles in a wide variety of reactions. For example, an enamine will undergo alkylation when treated with an alkyl halide. Draw the structure of intermediate A and the alkylation product B in the following reaction scheme (J. Am. Chem. Soc. 1954, 76, 2029-2030): TSOH NH -H₂O A 1) CH₂I 2) H₂O+ B + NH Modify the given copy of the starting material to draw compound A. If needed, use the single bond tool to interconvert between double and single bonds.

We have seen that the alpha carbon atom of an enamine can function as a nucleophile in a Michael reaction, and in fact, enamines can function as nucleophiles in a wide variety of reactions. For example, an enamine will undergo alkylation when treated with an alkyl halide. Draw the structure of intermediate A and the alkylation product B in the following reaction scheme (J. Am. Chem. Soc. 1954, 76, 2029-2030): TSOH NH -H₂O A 1) CH₂I 2) H₂O+ B + NH Modify the given copy of the starting material to draw compound A. If needed, use the single bond tool to interconvert between double and single bonds.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.SE: Something Extra

Problem 69GP

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