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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2:36 minutes

Problem 31d

Textbook Question

Predict the product of the substitution reactions, paying attention to the stereochemical outcome.
(d)

Verified step by step guidance

Identify the type of substitution reaction: Determine whether the reaction proceeds via an SN1 or SN2 mechanism. This depends on factors such as the structure of the substrate (primary, secondary, or tertiary carbon), the strength of the nucleophile, and the solvent used.

Analyze the substrate: If the carbon attached to the leaving group is tertiary, the reaction is likely SN1. If it is primary or secondary, consider SN2 unless steric hindrance or other factors favor SN1.

Consider the stereochemical implications: For SN2 reactions, the nucleophile attacks the carbon opposite the leaving group, leading to an inversion of configuration (if the carbon is chiral). For SN1 reactions, a planar carbocation intermediate is formed, allowing the nucleophile to attack from either side, resulting in a racemic mixture if the carbon is chiral.

Predict the product: Replace the leaving group with the nucleophile. For SN2, ensure the stereochemistry is inverted. For SN1, consider both possible stereoisomers if the carbon is chiral.

Verify the reaction conditions: Ensure that the solvent, temperature, and other reaction conditions are consistent with the proposed mechanism and product formation.

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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 and SN2. The SN1 mechanism is a two-step process where the leaving group departs first, forming a carbocation intermediate, while the SN2 mechanism is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In substitution reactions, the stereochemical outcome is crucial, as it determines the configuration of the product. For example, SN2 reactions result in inversion of configuration at the chiral center, while SN1 reactions can lead to racemization due to the planar nature of the carbocation intermediate.

Leaving Groups

Leaving groups are atoms or groups that can depart from the parent molecule during a chemical reaction, facilitating nucleophilic substitution. A good leaving group is typically stable after departure, such as halides (e.g., Cl, Br, I) or sulfonate groups. The ability of a leaving group to stabilize its negative charge significantly influences the rate and mechanism of the substitution reaction.

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