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

Leaving Group Conversions - Sulfonyl Chlorides

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions - Sulfonyl Chlorides

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Problem 25

Textbook Question

Predict the major product(s) of each of the following reactions.

Verified step by step guidance

Identify the type of reaction for each substrate and reagent pair. For example, reactions with NaOEt/EtOH typically involve elimination or substitution, while NaCN/THF suggests a nucleophilic substitution.

For reaction (a), the substrate is a tosylate, which is a good leaving group. NaOEt is a strong base/nucleophile, suggesting an E2 elimination reaction, leading to the formation of an alkene.

In reaction (b), the substrate is a tosylate, and NaCN is a good nucleophile. This suggests an SN2 reaction, where the cyanide ion will replace the tosylate group, forming a nitrile.

For reaction (c), the substrate is a tosylate, and NaN3 is a nucleophile. This indicates an SN2 reaction, where the azide ion will replace the tosylate group, forming an azide.

In reaction (d), the substrate is a tosylate, and the reagent is a bulky base (t-BuONa). This suggests an E2 elimination reaction, leading to the formation of an alkene, favoring the less substituted alkene due to steric hindrance (Hofmann product).

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the major products of reactions based on the stability of intermediates and the energy changes involved.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict how different compounds will react under various conditions. This knowledge is essential for determining the major products in organic reactions, as different functional groups can lead to distinct pathways and outcomes.

Regioselectivity and Stereoselectivity

Regioselectivity refers to the preference of a chemical reaction to occur at one location over another in a molecule, while stereoselectivity involves the preference for forming one stereoisomer over another. These concepts are vital for predicting the major products of reactions, as they influence the distribution of products based on the structure of the reactants and the conditions of the reaction.