Table of contents

1. A Review of General Chemistry(0)
2. Molecular Representations(0)
3. Acids and Bases(0)
4. Alkanes and Cycloalkanes(0)
5. Chirality(0)
6. Thermodynamics and Kinetics(0)
7. Substitution Reactions(0)
8. Elimination Reactions(0)
9. Alkenes and Alkynes(0)
10. Addition Reactions(0)
11. Radical Reactions(0)
12. Alcohols, Ethers, Epoxides and Thiols(0)
13. Alcohols and Carbonyl Compounds(0)
14. Synthetic Techniques(0)
15. Analytical Techniques:IR, NMR, Mass Spect(0)
16. Conjugated Systems(0)
17. Ultraviolet Spectroscopy(0)
18. Aromaticity(0)
19. Reactions of Aromatics: EAS and Beyond(0)
20. Phenols(0)
21. Aldehydes and Ketones: Nucleophilic Addition(0)
22. Carboxylic Acid Derivatives: NAS(0)
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides(0)
24. Enolate Chemistry: Reactions at the Alpha-Carbon(0)
25. Condensation Chemistry(0)
26. Amines(0)
27. Heterocycles(0)
28. Carbohydrates(0)
29. Amino Acids(0)
30. Peptides and Proteins(0)
31. Catalysis in Organic Reactions(0)
32. Lipids (0)
33. The Organic Chemistry of Metabolic Pathways(0)
34. Nucleic Acids(0)
35. Transition Metals(0)
36. Synthetic Polymers(0)

12. Alcohols, Ethers, Epoxides and Thiols

Silyl Ether Protecting Groups

12. Alcohols, Ethers, Epoxides and Thiols

Silyl Ether Protecting Groups: Videos & Practice Problems

Video Lessons Practice Worksheet

Silyl Ether Protecting Groups Practice Problems

20 problems

1PRACTICE PROBLEM

Show which bonds are broken and which bonds are formed during the following reaction. Also, indicate whether each of these bonds is a σ bond or a π bond.

Reaction showing bonds broken and formed in silyl ether protecting group formation.

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2PRACTICE PROBLEM

How would you synthesize the following compound using organic molecules with no more than three carbons? Hint: A protecting group will be required for the synthesis.

Chemical structure of a compound with hydroxyl groups and carbon chains.

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3PRACTICE PROBLEM

How would you synthesize the given compound using organic molecules with no more than three carbons and an alcohol-protecting group?

Chemical structure of a compound with an alcohol group for organic synthesis.

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4PRACTICE PROBLEM

How would you synthesize the following compound using organic molecules with no more than four carbons and an alcohol-protecting group?

Chemical structure of a compound with an alcohol group for synthesis discussion.

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5PRACTICE PROBLEM

Show the steps required to prepare the following compound from the provided starting material. Hint: A protecting group is needed.

Reaction steps to prepare a compound using a silyl ether protecting group.

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6PRACTICE PROBLEM

Show the steps required to prepare the following compound from the provided starting material. Hint: A protecting group is needed.

Chemical reaction steps for preparing a compound using silyl ether protecting groups.

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7PRACTICE PROBLEM

Illustrate the use of a protecting group in the synthesis of hex-4-yn-1-ol from 3-bromopropan-1-ol.

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8PRACTICE PROBLEM

Propose a reaction scheme that includes protecting groups to make the following reaction successful.

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9PRACTICE PROBLEM

Provide a reaction scheme that includes protecting groups for the following reaction to be successful.

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10PRACTICE PROBLEM

Which of the following is a common type of protecting group used for alcohols?

11PRACTICE PROBLEM

What is the role of TBDMS in the formation of silyl ethers?

12PRACTICE PROBLEM

In the formation of a silyl ether, what is the key step when reacting an alcohol with TBDMS chloride?

13PRACTICE PROBLEM

Why do silyl ethers act as effective protecting groups for alcohols in reactions involving other functional groups?

14PRACTICE PROBLEM

Which reagent is typically used to deprotect a silyl ether and regenerate the original alcohol?

15PRACTICE PROBLEM

In a synthesis involving both an esterification and a Grignard reaction, why might you choose to protect an alcohol as a silyl ether?

16PRACTICE PROBLEM

What is the primary reason for using silyl ethers in organic synthesis?

17PRACTICE PROBLEM

In the synthesis of complex pharmaceuticals, why are silyl ethers often employed?

18PRACTICE PROBLEM

Consider a sequence where an alcohol needs to be protected, reacted with a Grignard reagent, and then regenerated. Which of the following sequences correctly describes the process?

19PRACTICE PROBLEM

Why is a silyl ether considered a temporary protecting group for alcohols?

20PRACTICE PROBLEM

Given an alcohol and a ketone in a molecule, which order of reactions involving silyl ether protection would allow selective reduction of the ketone without affecting the alcohol?

Previous Topic: t-Butyl Ether Protecting Groups Next Topic: Sharpless Epoxidation

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