In addition to organic halides, alkyl tosylates react with organocuprates (R2CuLi) to form coupling products R–R′. When 2° alkyl tosylates are used as starting materials (R2CHOTs), inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with (CH3)2CuLi. b. a.

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Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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In addition to organic halides, alkyl tosylates react with organocuprates (R₂CuLi) to form coupling products R–R′. When 2° alkyl tosylates are used as starting materials (R₂CHOTs), inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with (CH₃)₂CuLi.

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Step 1

Species containing copper-carbon bonds are known as organocuprate reagents. The reaction involves these reagents acting as nucleophile and reacts with alkyl tosylate to form coupling products and contains new C-C bond. Inversion of product takes which results in the formation of stereogenic centre and the addition of alkyl group will be from another side.

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