3. When the following deuterium-labeled compound is treated with potassium tert-butoxide in DMF, a single product is observed. When the same substrate is heated in the presence of dilute potassium ethoxide in ethanol, a mixture of two products is formed. Provide the complete, detailed mechanism (curved arrows) for each reaction and label each reaction as E1 or E2. Note: deuterium is an isotope of hydrogen and can be treated similarly to hydrogen in chemical reactions but cannot be implied. D H KOET DMF ? D H dilute KOET EtOH ?+ ?

3. When the following deuterium-labeled compound is treated with potassium tert-butoxide in DMF, a single product is observed. When the same substrate is heated in the presence of dilute potassium ethoxide in ethanol, a mixture of two products is formed. Provide the complete, detailed mechanism (curved arrows) for each reaction and label each reaction as E1 or E2. Note: deuterium is an isotope of hydrogen and can be treated similarly to hydrogen in chemical reactions but cannot be implied. D H KOET DMF ? D H dilute KOET EtOH ?+ ?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter24: Carboxylic Acids & Derivatives

Section: Chapter Questions

Problem 16CTQ

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