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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3:46 minutes

Problem 33c

Textbook Question

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

Verified step by step guidance

Step 1: Identify the type of substitution reaction (SN1 or SN2). This depends on factors such as the structure of the substrate (primary, secondary, or tertiary), the strength of the nucleophile, and the solvent used. For example, tertiary substrates typically undergo SN1 reactions due to the stability of the carbocation intermediate.

Step 2: Analyze the substrate for the possibility of carbocation formation. If the reaction is SN1, the leaving group departs first, forming a carbocation. Check if the carbocation can undergo rearrangement to form a more stable carbocation (e.g., hydride shift or alkyl shift).

Step 3: Consider the nucleophile. In an SN1 reaction, the nucleophile attacks the carbocation to form the final product. In an SN2 reaction, the nucleophile directly attacks the substrate in a single step, leading to inversion of configuration at the stereocenter.

Step 4: Predict the product based on the mechanism. For SN1, if a rearrangement occurs, the nucleophile will attack the rearranged carbocation. For SN2, the nucleophile will attack the substrate without rearrangement, leading to a direct substitution.

Step 5: Verify stereochemistry and regiochemistry of the product. For SN2 reactions, ensure inversion of configuration at the stereocenter. For SN1 reactions, if the carbocation is planar, the nucleophile can attack from either side, leading to a racemic mixture if the product is chiral.

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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 involves a two-step process with a carbocation intermediate, and SN2, which is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. Understanding these mechanisms is crucial for predicting the products of substitution reactions.

Carbocation Stability

Carbocation stability is a key factor in determining the pathway of nucleophilic substitution reactions, particularly in SN1 mechanisms. Carbocations are positively charged species that can rearrange to form more stable structures, such as tertiary carbocations being more stable than secondary or primary ones. Recognizing the potential for rearrangement helps predict the final product of the reaction.

Leaving Groups

The effectiveness of a leaving group significantly influences the rate and outcome of substitution reactions. Good leaving groups are typically weak bases that can stabilize the negative charge after departure, such as halides or sulfonate groups. Identifying the leaving group in a reaction is essential for predicting whether a rearrangement will occur and what the final product will be.

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