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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5:29 minutes

Problem 49c

Textbook Question

For each of the following reactions, identify the bonds that are broken and formed. Be sure to indicate whether the bond that is broken is a σ bond or a π bond.
(c)

Verified step by step guidance

Analyze the given reaction and identify the reactants and products. Look for changes in the connectivity of atoms to determine which bonds are broken and which are formed.

For each bond broken, determine whether it is a σ (sigma) bond or a π (pi) bond. Recall that σ bonds are single bonds formed by head-on overlap of orbitals, while π bonds are formed by the side-on overlap of p orbitals in double or triple bonds.

For each bond formed, similarly determine whether it is a σ bond or a π bond. New single bonds are σ bonds, while additional bonds in double or triple bonds are π bonds.

Write down the specific bonds broken and formed, including the atoms involved. For example, if a C-H bond is broken, note that it is a σ bond, and if a C=C bond is converted to a C-C bond, note that a π bond is broken.

Summarize the changes in bonding, clearly indicating the type of bond (σ or π) for each bond broken and formed. This will help in understanding the overall reaction mechanism and energy changes.

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Key Concepts

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

Types of Chemical Bonds

Chemical bonds can be classified into sigma (σ) and pi (π) bonds. Sigma bonds are formed by the head-on overlap of atomic orbitals, allowing for free rotation around the bond axis. In contrast, pi bonds result from the side-to-side overlap of p orbitals and restrict rotation. Understanding these bond types is crucial for analyzing reaction mechanisms and predicting the stability of intermediates.

Bond Breaking and Formation

In a chemical reaction, bonds in the reactants must break to allow for the formation of new bonds in the products. The process of bond breaking requires energy input, while bond formation releases energy. Identifying which bonds are broken and formed helps in understanding the overall energy changes and the reaction's feasibility.

Reaction Mechanisms

A reaction mechanism describes the step-by-step process by which reactants transform into products. It includes details about the breaking and forming of bonds, the intermediates formed, and the transition states. Analyzing the mechanism provides insights into the kinetics and thermodynamics of the reaction, which is essential for predicting the outcome of chemical transformations.

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Related Practice

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

Which of the follosing is the best synthesis of the given molecule?

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.

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