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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7:26 minutes

Problem 13c

Textbook Question

Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second.
c. Show another S_N2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces 1-methoxybutane.

Verified step by step guidance

Step 1: Understand the SN2 reaction mechanism. SN2 reactions involve a single-step bimolecular nucleophilic substitution where the nucleophile attacks the electrophilic carbon, displacing the leaving group. The reaction rate depends on both the concentration of the nucleophile and the substrate.

Step 2: Identify the target product, 1-methoxybutane. This compound has a butane backbone with a methoxy (-OCH3) group attached to the first carbon. The goal is to produce this compound using a different alkoxide and alkyl bromide combination.

Step 3: Choose an alternative alkoxide nucleophile. Sodium ethoxide (NaOCH2CH3) can be used as the nucleophile, as it is a strong base and can participate in SN2 reactions. However, to ensure the formation of 1-methoxybutane, the alkoxide must be modified to match the desired methoxy group. Use sodium methoxide (NaOCH3) as the nucleophile.

Step 4: Select a different alkyl bromide substrate. Instead of 1-bromobutane, you can use methyl bromide (CH3Br) as the substrate. Methyl bromide is a good candidate for SN2 reactions due to its small size and lack of steric hindrance.

Step 5: Combine the chosen reactants. React sodium methoxide (NaOCH3) with methyl bromide (CH3Br) under appropriate conditions (e.g., polar aprotic solvent like acetone). The methoxide ion will attack the methyl carbon, displacing the bromide ion and forming 1-methoxybutane as the product.

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Key Concepts

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

SN2 Reaction Mechanism

The SN2 (substitution nucleophilic bimolecular) reaction is a type of nucleophilic substitution where a nucleophile attacks an electrophile, resulting in the simultaneous displacement of a leaving group. This mechanism involves a single concerted step, where the bond formation and bond breaking occur simultaneously, leading to an inversion of configuration at the carbon center. Understanding this mechanism is crucial for predicting the outcomes of reactions involving alkyl halides and nucleophiles.

Alkoxides as Nucleophiles

Alkoxides are strong nucleophiles derived from alcohols by deprotonation. They are characterized by the presence of an alkyl group attached to an oxygen atom with a negative charge. In SN2 reactions, alkoxides can effectively attack alkyl halides, such as 1-bromobutane, to form ethers like 1-methoxybutane. Recognizing the reactivity of different alkoxides is essential for designing alternative reactions that yield the same product.

Reactivity of Alkyl Halides

The reactivity of alkyl halides in nucleophilic substitution reactions is influenced by their structure, particularly the degree of substitution at the carbon atom bonded to the halide. Primary alkyl halides, like 1-bromobutane, are more reactive in SN2 reactions due to less steric hindrance, allowing easier access for the nucleophile. Understanding the reactivity patterns of various alkyl halides helps in selecting appropriate substrates for synthesizing desired products, such as 1-methoxybutane.

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Related Practice

Textbook Question

The rate of the reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of the reaction of methyl iodide with triethylamine was measured in the same solvent. The concentration of the reagents was the same in both experiments.

c. Which alkyl halide has the larger k_quinuclidine/k_{triethylamine} ratio?

Textbook Question

Starting with an alkyl halide, how could the following compounds be prepared?

c. butylmethylamine

Textbook Question

The reaction of an amine with an alkyl halide gives an ammonium salt.R3N amine + R'—X alkyl halide —> R3(N+)—R' X- ammonium salt The rate of this SN2 reaction is sensitive to the polarity of the solvent. 1. Draw an energy diagram for this reaction in a nonpolar solvent and another in a polar solvent. 2. Consider the nature of the transition state, and explain why this reaction should be sensitive to the polarity of the solvent. 3. Predict whether it will be faster or slower in a more polar solvent.

Textbook Question

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

c. 1-iodobutane

d. CH₃—(CH₂)₃—CN

Textbook Question

Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds.

e. CH₃—(CH₂)₃—C≡CH

f. CH₃CH₂—O—(CH₂)₃—CH₃

g. CH₃—(CH₂)₃—NH₂

Textbook Question

Show how each compound might be synthesized by the SN2 displacement of an alkyl halide.

e. H₂C=CH—CH₂CN

f. H—C≡C—CH₂CH₂CH₃

Textbook Question

Give two syntheses for (CH₃)₂CH—O—CH₂CH₃, and explain which synthesis is better.

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Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second.c. Show another SN2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces 1-methoxybutane.

Key Concepts

SN2 Reaction Mechanism

Alkoxides as Nucleophiles

Reactivity of Alkyl Halides

Watch next

Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second.
c. Show another S_N2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces 1-methoxybutane.