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What is the likely problem with doing a diethyl ether/water extraction on the following reaction product to isolate product E in the diethyl ether layer? What is the reason for the problem? 1) NaBH₁/MeOH 2) Mild acid Hom HO Product E пион OH

What is the likely problem with doing a diethyl ether/water extraction on the following reaction product to isolate product E in the diethyl ether layer? What is the reason for the problem? 1) NaBH₁/MeOH 2) Mild acid Hom HO Product E пион OH

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
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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### Transcription for Educational Website **Question:** What is the likely problem with doing a diethyl ether/water extraction on the following reaction product to isolate product E in the diethyl ether layer? **Follow-up Question:** What is the reason for the problem? **Chemical Reaction:** The reaction involves a cyclic anhydride reacting in the following steps: 1. Sodium borohydride (NaBH₄) in methanol (MeOH) 2. Followed by a treatment with mild acid **Structural Diagrams:** - On the left: A cyclic anhydride is depicted with a six-membered ring and two ketone groups, symbolized by "O" double bonds at the top and bottom of the structure, and two ester linkages at the sides. - The reaction results in compound "Product E," shown as a hexahydroxylated ring structure with hydroxyl groups (OH) at four positions on a six-membered ring. It suggests a reduction and opening of the anhydride structure resulting in a polyol. **Explanation:** The problem with isolating Product E using diethyl ether/water extraction arises because Product E is highly polar due to multiple hydroxyl groups. This means it is more soluble in water than in the nonpolar diethyl ether, making it difficult to isolate in the ether layer. **Reason:** The polar nature of the hydroxyl groups in Product E leads to high aqueous solubility, which complicates the extraction process, as it will remain dissolved in the aqueous layer rather than the organic layer of diethyl ether.
Transcribed Image Text:### Transcription for Educational Website **Question:** What is the likely problem with doing a diethyl ether/water extraction on the following reaction product to isolate product E in the diethyl ether layer? **Follow-up Question:** What is the reason for the problem? **Chemical Reaction:** The reaction involves a cyclic anhydride reacting in the following steps: 1. Sodium borohydride (NaBH₄) in methanol (MeOH) 2. Followed by a treatment with mild acid **Structural Diagrams:** - On the left: A cyclic anhydride is depicted with a six-membered ring and two ketone groups, symbolized by "O" double bonds at the top and bottom of the structure, and two ester linkages at the sides. - The reaction results in compound "Product E," shown as a hexahydroxylated ring structure with hydroxyl groups (OH) at four positions on a six-membered ring. It suggests a reduction and opening of the anhydride structure resulting in a polyol. **Explanation:** The problem with isolating Product E using diethyl ether/water extraction arises because Product E is highly polar due to multiple hydroxyl groups. This means it is more soluble in water than in the nonpolar diethyl ether, making it difficult to isolate in the ether layer. **Reason:** The polar nature of the hydroxyl groups in Product E leads to high aqueous solubility, which complicates the extraction process, as it will remain dissolved in the aqueous layer rather than the organic layer of diethyl ether.
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