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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3:55 minutes

Problem 30

Textbook Question

Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds by an S_N1 or S_N2 mechanism.
(a)

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Identify the substrate in the reaction. Determine whether it is primary, secondary, or tertiary, as this will influence the mechanism (S_N1 or S_N2).

Consider the nature of the nucleophile. Strong nucleophiles favor S_N2 reactions, while weak nucleophiles are more likely to participate in S_N1 reactions.

Evaluate the solvent used in the reaction. Polar protic solvents tend to stabilize carbocations and favor S_N1 mechanisms, whereas polar aprotic solvents favor S_N2 mechanisms by stabilizing the nucleophile.

Analyze the leaving group. A good leaving group is essential for both S_N1 and S_N2 reactions, but it is especially crucial for S_N1 reactions where the leaving group departs before the nucleophile attacks.

Based on the substrate, nucleophile, solvent, and leaving group, predict whether the reaction will proceed via an S_N1 or S_N2 mechanism and draw the expected product, considering stereochemistry if applicable.

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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 are fundamental in organic chemistry and can proceed via two main mechanisms: S_N1 and S_N2. Understanding the nature of the nucleophile, the substrate, and the leaving group is crucial for predicting the reaction outcome.

S_N1 Mechanism

The S_N1 mechanism is a two-step process where the leaving group departs first, forming a carbocation intermediate. This mechanism is favored in tertiary substrates due to carbocation stability and typically occurs in polar protic solvents. The reaction rate depends only on the concentration of the substrate, making it unimolecular.

S_N2 Mechanism

The S_N2 mechanism is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. This mechanism is favored in primary substrates and occurs in polar aprotic solvents. The reaction rate depends on both the substrate and nucleophile concentrations, making it bimolecular and leading to inversion of configuration at the reaction site.

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Related Practice

Textbook Question

Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds by an S_N1 or S_N2 mechanism.

(b)

Textbook Question

Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds by an S_N1 or S_N2 mechanism.

(c)

Textbook Question

Predict the product(s) of the following reactions.

(h)

Textbook Question

The benzylic bromide shown undergoes neither S_N1 nor S_N2 substitution reactions. Explain.

Textbook Question

Would you expect the following substitution reaction to proceed with inversion or racemization? Why?

Textbook Question

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

(a)

Textbook Question

Predict the product of the following substitution reactions, paying close attention to the stereochemical outcome of the reactions.

(f)

Textbook Question

Give a mechanism for the following substitution and elimination reactions.

(c)

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Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds by an SN1 or SN2 mechanism. (a)

Key Concepts

Nucleophilic Substitution Reactions

S_N1 Mechanism

S_N2 Mechanism

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Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds by an S_N1 or S_N2 mechanism.
(a)