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

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Acid-Catalyzed Alkoxylation

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Acid-Catalyzed Alkoxylation

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4:16 minutes

Problem 66g

Textbook Question

What is the major product of each of the following reactions?
g.

Verified step by step guidance

Step 1: Analyze the given reaction conditions. The reactant is a substituted cyclohexene, and the reagents are H2SO4 (sulfuric acid) and CH3OH (methanol). This indicates an electrophilic addition reaction, where the alkene will react with the acidic medium and methanol to form an ether product.

Step 2: Identify the mechanism. The reaction proceeds via protonation of the double bond by H2SO4, forming a carbocation intermediate. The stability of the carbocation is crucial in determining the major product.

Step 3: Determine the most stable carbocation. The double bond in the cyclohexene will be protonated, and the carbocation will form at the more substituted carbon (due to hyperconjugation and inductive effects). In this case, the carbocation forms at the carbon adjacent to the ethyl group.

Step 4: Nucleophilic attack by methanol. Methanol (CH3OH) acts as a nucleophile and attacks the carbocation, forming a new bond between the oxygen atom of methanol and the carbocation center.

Step 5: Final step - deprotonation. The protonated ether intermediate loses a proton to regenerate the acidic medium (H2SO4), resulting in the formation of the major product, which is an ether with the methoxy group (-OCH3) attached to the more substituted carbon of the original double bond.

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Key Concepts

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

Electrophilic Aromatic Substitution (EAS)

Electrophilic Aromatic Substitution is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for understanding how substituents can modify the reactivity and properties of aromatic compounds. In the context of the given reaction, the aromatic ring undergoes substitution with a methoxy group, facilitated by the presence of sulfuric acid as a catalyst.

Reactivity of Aromatic Compounds

Aromatic compounds exhibit unique reactivity due to their stable resonance structures. The presence of electron-donating or electron-withdrawing groups on the aromatic ring can significantly influence the position and rate of substitution reactions. In this case, the alkyl groups attached to the benzene ring are electron-donating, which enhances the reactivity of the ring towards electrophiles, guiding the formation of the major product.

Role of Catalysts in Organic Reactions

Catalysts, such as sulfuric acid in this reaction, are substances that increase the rate of a chemical reaction without being consumed in the process. In electrophilic aromatic substitution, catalysts help generate a more reactive electrophile, facilitating the substitution process. Understanding the role of catalysts is essential for predicting the outcome of reactions and optimizing conditions for desired products.

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Related Practice

Textbook Question

a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

8. CH₃OH + H₂SO₄

b. With which reagents do the two alkenes react to form different products?

Textbook Question

How could the following compounds be prepared using an alkene as one of the starting materials?

Textbook Question

b. Which step is the rate-determining step?

Textbook Question

a. Propose a mechanism for the following reaction (show all curved arrows):

Textbook Question

How could the following compound be prepared using an alkene as one of the starting materials?

Textbook Question

Propose a mechanism for the following reaction (remember to use curved arrows to show the movement of electrons from the nucleophile to the electrophile):

Textbook Question

c. What is the electrophile in the first step?

d. What is the nucleophile in the first step?

Textbook Question

e. What is the electrophile in the second step?

f. What is the nucleophile in the second step?

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