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 33a

Textbook Question

Predict the product of the following substitution reactions, making sure to note whether a rearrangement should occur.
(a)

Verified step by step guidance

Step 1: Identify the type of substitution reaction. The presence of Na⁺SCH₃ indicates a nucleophilic substitution reaction, likely SN2 due to the strong nucleophile (SCH₃⁻) and polar aprotic solvent (THF).

Step 2: Analyze the substrate. The substrate is a cyclopentane ring with a secondary alkyl chloride. Secondary alkyl halides can undergo SN2 reactions, especially in polar aprotic solvents.

Step 3: Consider stereochemistry. SN2 reactions proceed via a backside attack, leading to an inversion of configuration at the carbon where substitution occurs. The chlorine is leaving, and SCH₃⁻ will replace it with inversion of stereochemistry.

Step 4: Check for rearrangements. Rearrangements are unlikely in SN2 reactions because the mechanism involves a single concerted step without carbocation intermediates.

Step 5: Predict the product. The product will be a cyclopentane ring with SCH₃ replacing the Cl group, and the stereochemistry at the substitution site will be inverted relative to the starting material.

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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 (like Cl) by a nucleophile (like SCH3). The mechanism can be either SN1 or SN2, depending on the substrate structure and reaction conditions. In this case, the cyclic structure suggests that the reaction may proceed via an SN2 mechanism due to steric considerations.

Rearrangement in Organic Reactions

Rearrangement refers to the structural reorganization of a molecule during a reaction, which can lead to different products. In nucleophilic substitution reactions, rearrangements can occur if a more stable carbocation can be formed. Understanding when and how rearrangements happen is crucial for predicting the final product of the reaction.

Solvent Effects in Organic Reactions

The choice of solvent can significantly influence the outcome of organic reactions. In this case, THF (tetrahydrofuran) is a polar aprotic solvent that stabilizes the nucleophile and facilitates the reaction. The solvent's properties can affect the reaction rate and the mechanism, making it an important factor to consider in predicting the product.

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