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

Previous problemNext problem

3:46 minutes

Problem 92b

Textbook Question

Starting with an alkyl halide, how could the following compounds be prepared?
b. 1-methoxybutane

Verified step by step guidance

Step 1: Identify the starting material. The problem specifies an alkyl halide as the starting material. For 1-methoxybutane, the alkyl halide should be 1-bromobutane or 1-chlorobutane, as these contain the butane backbone with a halogen at the first carbon.

Step 2: Choose the appropriate reaction mechanism. To prepare 1-methoxybutane, a substitution reaction (SN2 mechanism) is ideal because it involves the replacement of the halogen with a methoxy group (-OCH₃). SN2 reactions work well with primary alkyl halides like 1-bromobutane.

Step 3: Select the nucleophile. The nucleophile in this reaction will be methoxide ion (CH₃O⁻), which can be generated by dissolving methanol (CH₃OH) in a strong base like sodium hydroxide (NaOH) or sodium methoxide (NaOCH₃).

Step 4: Set up the reaction conditions. Combine the alkyl halide (e.g., 1-bromobutane) with the methoxide ion in an appropriate solvent, such as methanol. Ensure the reaction is carried out under conditions favoring the SN2 mechanism, such as a polar aprotic solvent and low steric hindrance.

Step 5: Allow the reaction to proceed. The methoxide ion will attack the carbon bonded to the halogen in a backside attack, displacing the halogen and forming 1-methoxybutane. After the reaction is complete, purify the product using techniques like distillation or extraction.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (such as chlorine, bromine, or iodine). They serve as versatile intermediates in organic synthesis, allowing for various reactions, including nucleophilic substitutions and eliminations. Understanding their reactivity is crucial for designing pathways to synthesize other compounds, such as ethers.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (like a halogen) in an alkyl halide with a nucleophile. This process can occur via two main mechanisms: SN1 (unimolecular) and SN2 (bimolecular). The choice of mechanism affects the reaction rate and stereochemistry of the product, which is essential for synthesizing compounds like 1-methoxybutane.

Ethers and Their Synthesis

Ethers are organic compounds characterized by an oxygen atom bonded to two alkyl or aryl groups. They can be synthesized through various methods, including the reaction of alkyl halides with alcohols or alkoxides. In the case of 1-methoxybutane, the synthesis involves the nucleophilic attack of methanol on an appropriate alkyl halide, highlighting the importance of understanding ether formation in organic chemistry.

Watch next

Master Drawing the SN2 Mechanism with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Which substitution reaction takes place more rapidly?

Textbook Question

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?

Textbook Question

What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?

Textbook Question

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

a. 2-methoxybutane

Textbook Question

2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is stereospecific—that is, the stereoisomers obtained as products depend on the stereoisomer used as a reactant. Recall that because 2-acetoxycyclohexyl tosylate has two asymmetric centers, it has four stereoisomers—two are cis and two are trans. Explain the following observations:

b. Both trans reactants form the same racemic mixture.

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.

b. The same experiment was done using isopropyl iodide instead of methyl iodide. Which reaction had the larger rate constant?

Textbook Question

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

Show more practices