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

SN2 Reaction

Organic Chemistry

7. Substitution Reactions

SN2 Reaction

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5:00 minutes

Problem 55b

Textbook Question

How will the rate of each of the following S_N2 reactions change if it is carried out in a more polar solvent?
b.

Verified step by step guidance

Step 1: Understand the SN2 reaction mechanism. SN2 reactions are bimolecular nucleophilic substitution reactions where the nucleophile attacks the electrophilic carbon in a single, concerted step, leading to the displacement of the leaving group.

Step 2: Analyze the reaction provided. In this case, the nucleophile (NH3) attacks the electrophilic carbon attached to the leaving group (CH3SCH3+), resulting in the formation of CH3NH3+ and CH3SCH3.

Step 3: Consider the role of the solvent in SN2 reactions. Polar solvents can stabilize the charged transition state and intermediates. However, highly polar solvents may also stabilize the nucleophile, reducing its reactivity and slowing down the reaction rate.

Step 4: Evaluate the specific case. Since NH3 is a neutral nucleophile, a more polar solvent may stabilize the positively charged transition state (CH3SCH3+), potentially increasing the reaction rate. However, excessive stabilization of the nucleophile could counteract this effect.

Step 5: Conclude the impact of a more polar solvent. The rate of the SN2 reaction may increase slightly due to stabilization of the transition state, but the exact effect depends on the balance between nucleophile stabilization and transition state stabilization.

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Key Concepts

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

SN2 Mechanism

The SN2 (substitution nucleophilic bimolecular) mechanism involves a single concerted step where a nucleophile attacks an electrophile, leading to the simultaneous displacement of a leaving group. This reaction is characterized by a second-order kinetics, meaning the rate depends on the concentration of both the nucleophile and the substrate. Understanding this mechanism is crucial for predicting how changes in conditions, such as solvent polarity, will affect the reaction rate.

Polar Solvents

Polar solvents are solvents that have a significant dipole moment, allowing them to stabilize charged species and polar interactions. In the context of SN2 reactions, polar solvents can stabilize the transition state and the nucleophile, which can enhance the reaction rate. The choice of solvent is critical, as it can influence the solubility of reactants and the overall kinetics of the reaction.

Nucleophilicity

Nucleophilicity refers to the ability of a nucleophile to donate an electron pair to an electrophile during a chemical reaction. In SN2 reactions, stronger nucleophiles typically lead to faster reaction rates. The polarity of the solvent can affect nucleophilicity; in polar protic solvents, nucleophiles may be less reactive due to solvation effects, while in polar aprotic solvents, nucleophiles remain more reactive, thus influencing the overall rate of the reaction.

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Related Practice

Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following S_N2 reactions.

(c)

Textbook Question

For each pair, choose the nucleophile that would react most quickly in an S_N2 reaction (assume H₂O is the solvent).

(c)

Textbook Question

For each pair, choose the haloalkane that would react most quickly in an S_N2 reaction.

(c)

Textbook Question

In which solvent—ethanol or diethyl ether—would the equilibrium for the following S_N2 reaction lie farther to the right?

Textbook Question

How will the rate of each of the following S_N2 reactions change if it is carried out in a more polar solvent?

Textbook Question

Show all the products, including their configurations, that are obtained from the above reaction.

Textbook Question

You were told in [SECTION 7.11] that is best to use a methyl halide or a primary alkyl halide for the reaction of an acetylide ion with an alkyl halide. Explain why this is so.

Textbook Question

Would you expect acetate ion (CH₃CO₂⁻) to be a better nucleophile in an S_N2 reaction with an alkyl halide carried out in methanol or in dimethyl sulfoxide?

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How will the rate of each of the following SN2 reactions change if it is carried out in a more polar solvent?b.

Key Concepts

SN2 Mechanism

Polar Solvents

Nucleophilicity

Watch next

How will the rate of each of the following S_N2 reactions change if it is carried out in a more polar solvent?
b.