Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

12. Alcohols, Ethers, Epoxides and Thiols

Silyl Ether Protecting Groups

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Silyl Ether Protecting Groups

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4:43 minutes

Problem 93a,b

Textbook Question

Show how each of the following compounds can be prepared from the given starting material. In each case, you will need to use a protecting group.
a.
b.

Verified step by step guidance

Step 1: Analyze the starting material and the target compound. The starting material contains a hydroxyl group (-OH) and an ester functional group. The target compound introduces a new hydroxyl group at a specific position, requiring selective reactivity.

Step 2: Protect the existing hydroxyl group in the starting material to prevent unwanted reactions. Use a protecting group such as a silyl ether (e.g., TBDMS-Cl) to temporarily mask the hydroxyl group.

Step 3: Perform the desired reaction to introduce the new hydroxyl group. This can be achieved through a selective reduction of the ester group using a reducing agent like DIBAL-H (Diisobutylaluminum hydride) to form an aldehyde intermediate, followed by further reduction to an alcohol using NaBH4 or LiAlH4.

Step 4: Remove the protecting group from the original hydroxyl group to restore its functionality. Use a mild acid or fluoride source (e.g., TBAF for silyl ethers) to deprotect the hydroxyl group.

Step 5: Verify the structure of the final compound to ensure it matches the target compound. Confirm that both hydroxyl groups are correctly positioned and the ester group has been converted to the desired alcohol.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Protecting Groups

Protecting groups are temporary modifications used in organic synthesis to prevent certain functional groups from reacting during a chemical reaction. They allow chemists to selectively modify other parts of a molecule without interference. After the desired reaction is completed, the protecting group can be removed to restore the original functional group.

Silyl Ethers

Silyl ethers are a class of protecting groups derived from silanes, commonly used to protect alcohols during chemical reactions. They are stable under a variety of reaction conditions and can be easily removed by hydrolysis or fluoride treatment. This makes them particularly useful in multi-step synthesis where selective reactivity is required.

Functional Group Interconversion

Functional group interconversion refers to the process of transforming one functional group into another through chemical reactions. This concept is crucial in organic synthesis as it allows chemists to create desired compounds by modifying existing structures. Understanding the reactivity and compatibility of different functional groups is essential for successful synthesis.

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Related Practice

Textbook Question

Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]

(a)

Textbook Question

Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]

(b)

Textbook Question

Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]

(c)

Textbook Question

Show how you would use a protecting group to convert 4-bromobutan-1-ol to hept-5-yn-1-ol.

Textbook Question

Show how each of the following compounds could be prepared from the given starting material. Each requires a protecting group.

Textbook Question

Show how a protecting group might be used to make these reactions successful.

(b)

Textbook Question

Show how a protecting group might be used to make these reactions successful.

(a)

Multiple Choice