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

7. Substitution Reactions

Substitution Comparison

Organic Chemistry

7. Substitution Reactions

Substitution Comparison

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Problem 28a

Textbook Question

For each solvent, indicate the most likely substitution reaction to take place.
(a)

Verified step by step guidance

Analyze the solvent structure provided in the image. The solvent shown is dimethoxyethane (DME), which is an aprotic solvent.

Understand the role of the solvent in substitution reactions. Aprotic solvents favor SN2 reactions because they do not stabilize the nucleophile, allowing it to remain reactive.

Consider the mechanism of SN2 reactions. SN2 reactions involve a single-step process where the nucleophile attacks the electrophilic carbon and displaces the leaving group simultaneously.

Evaluate the conditions under which SN2 reactions are favored. These include a strong nucleophile, a primary or secondary alkyl halide, and an aprotic solvent like DME.

Conclude that in the presence of dimethoxyethane (DME), the most likely substitution reaction to take place is an SN2 reaction due to the solvent's properties and its ability to support a strong nucleophile.

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Key Concepts

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

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule by a nucleophile. These reactions can occur via two main mechanisms: SN1, which is a two-step process involving carbocation formation, and SN2, which is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. The choice of mechanism often depends on the structure of the substrate and the nature of the nucleophile.

Solvent Effects on Reaction Mechanisms

The choice of solvent can significantly influence the rate and mechanism of nucleophilic substitution reactions. Polar protic solvents stabilize ions and favor SN1 mechanisms by stabilizing the carbocation intermediate, while polar aprotic solvents enhance the nucleophilicity of the nucleophile and favor SN2 mechanisms. Understanding the solvent's properties is crucial for predicting the outcome of substitution reactions.

Leaving Group Ability

The ability of a leaving group to depart from a substrate is a critical factor in nucleophilic substitution reactions. Good leaving groups, such as halides or sulfonate esters, can stabilize the negative charge they acquire upon leaving, facilitating the reaction. Conversely, poor leaving groups can hinder the reaction, making it essential to evaluate the leaving group's strength when predicting the reaction pathway.

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