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

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.26P: Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and...
icon
Concept explainers
Question

Please explain clearly on how to do these type of questions and what I need to know in order to do them. Thank you!

### 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.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Aromatic Compounds
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Chemistry for Today: General, Organic, and Bioche…
Chemistry for Today: General, Organic, and Bioche…
Chemistry
ISBN:
9781305960060
Author:
Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:
Cengage Learning
Macroscale and Microscale Organic Experiments
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:
9781305577190
Author:
Kenneth L. Williamson, Katherine M. Masters
Publisher:
Brooks Cole