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For the following set of reaction sequences, predict the major products and propose a mechanism for its formation. ? 1) LDA 2) CH₂I ? Product A Product B 1) LDA 2) CH₂CH₂I

For the following set of reaction sequences, predict the major products and propose a mechanism for its formation. ? 1) LDA 2) CH₂I ? Product A Product B 1) LDA 2) CH₂CH₂I

Chemistry
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
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For the following set of reaction sequences, predict the major products and propose a mechanism for its formation. ů Step 1 1) LDA 2) CH₂CH₂I H₂C CH₂ →? Modify the given starting material to draw Product A. -CH₂ Product A Correct. The starting material is a ketone, which has two alpha positions, although they are equivalent because the ketone is symmetrical. Deprotonation at either location will lead to the same enolate ion. In the first step. LDA functions as a base and deprotonates the ketone to give an enolate. This enolate is then treated with ethyl iodide to give an SN2 reaction, thereby installing an ethyl group, Subsequent treatment with LDA (at low temperature), followed by methyl lodide, installs a methyl group at the other (less substituted) alpha position via the kinetic enolate. The net result is the installation of an ethyl group at one alpha position and the installation of alpha methyl group at the other a position. 1) LDA 2) CH₂I CH₂ Modify the given starting material to draw Product B. CH₂ ? Product B
Transcribed Image Text:For the following set of reaction sequences, predict the major products and propose a mechanism for its formation. ů Step 1 1) LDA 2) CH₂CH₂I H₂C CH₂ →? Modify the given starting material to draw Product A. -CH₂ Product A Correct. The starting material is a ketone, which has two alpha positions, although they are equivalent because the ketone is symmetrical. Deprotonation at either location will lead to the same enolate ion. In the first step. LDA functions as a base and deprotonates the ketone to give an enolate. This enolate is then treated with ethyl iodide to give an SN2 reaction, thereby installing an ethyl group, Subsequent treatment with LDA (at low temperature), followed by methyl lodide, installs a methyl group at the other (less substituted) alpha position via the kinetic enolate. The net result is the installation of an ethyl group at one alpha position and the installation of alpha methyl group at the other a position. 1) LDA 2) CH₂I CH₂ Modify the given starting material to draw Product B. CH₂ ? Product B
Step 2 Add curved arrows to draw step 1 of the mechanism. Save for Later Edit Drawing CH₂ CH₂ CH₂ CH₂ CH₂ CH₂ Attempts: 0 of 3 used Step 3 The parts of this question must be completed in order. This part will be available when you complete the part above. Step 4 The parts of this question must be completed in order. This part will be available when you complete the part above. Step 5 The parts of this question must be completed in order. This part will Submit As
Transcribed Image Text:Step 2 Add curved arrows to draw step 1 of the mechanism. Save for Later Edit Drawing CH₂ CH₂ CH₂ CH₂ CH₂ CH₂ Attempts: 0 of 3 used Step 3 The parts of this question must be completed in order. This part will be available when you complete the part above. Step 4 The parts of this question must be completed in order. This part will be available when you complete the part above. Step 5 The parts of this question must be completed in order. This part will Submit As
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