Two researchers had the goal of synthesizing pentylcyclohexane from pent-1-ene. Their strategy was to convert pent-1-ene to pentan-2-one, and then add the cyclohexane ring via the alkylation reaction, shown below. Subsequent reduction would give their final product. 1. LDA, -78 °C 2. Br Unfortunately, the alkylation reaction did not give the desired product. Identify the most likely problem. O Treatment of the ketone with LDA would lead to formation of the more substituted thermodynamic enolate, leading to the wrong product. O LDA is a strong nucleophile, so it can attach the ketone, giving a 3° alcohol. O The resulting enolate can attack the Br. leading to bromination of the a-position. The enolate is also a strong base, so when reacting with a 2 alkyl halide an E2 elimination can take place.
Two researchers had the goal of synthesizing pentylcyclohexane from pent-1-ene. Their strategy was to convert pent-1-ene to pentan-2-one, and then add the cyclohexane ring via the alkylation reaction, shown below. Subsequent reduction would give their final product. 1. LDA, -78 °C 2. Br Unfortunately, the alkylation reaction did not give the desired product. Identify the most likely problem. O Treatment of the ketone with LDA would lead to formation of the more substituted thermodynamic enolate, leading to the wrong product. O LDA is a strong nucleophile, so it can attach the ketone, giving a 3° alcohol. O The resulting enolate can attack the Br. leading to bromination of the a-position. The enolate is also a strong base, so when reacting with a 2 alkyl halide an E2 elimination can take place.
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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