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

SN1 Reaction

Organic Chemistry

7. Substitution Reactions

SN1 Reaction

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6:36 minutes

Problem 109

Textbook Question

Two bromoethers are obtained from the reaction of the following alkyl dihalide with methanol. Draw the structures of the ethers.

Verified step by step guidance

Analyze the given alkyl dihalide structure: The molecule contains a cyclopentane ring with two chlorine atoms attached to adjacent carbons. One chlorine is on a wedge (indicating it is above the plane), and the other is on a dash (indicating it is below the plane). Additionally, there is a benzyl group attached to the cyclopentane ring.

Understand the reaction conditions: The reaction involves methanol (CH3OH), which acts as a nucleophile. Methanol can substitute the halide groups (chlorine atoms) via an SN2 mechanism, leading to the formation of ethers.

Consider the stereochemistry: Since the reaction proceeds via an SN2 mechanism, the stereochemistry at the carbon centers will invert. This means that the configuration of the carbon bonded to the chlorine will flip when the methanol replaces the chlorine.

Predict the products: Two bromoethers will be formed because the reaction can occur at either of the two carbons bearing chlorine. The first product will have methanol substituting the chlorine on the wedge, while the second product will have methanol substituting the chlorine on the dash. Both products will retain the benzyl group and the cyclopentane ring structure.

Draw the structures of the ethers: For each product, replace one chlorine atom with an OCH3 group (from methanol) while ensuring the stereochemistry is inverted at the substitution site. The remaining chlorine atom stays in its original position.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In this case, methanol acts as the nucleophile, attacking the carbon atom bonded to the halogen in the alkyl dihalide, leading to the formation of bromoethers.

Ethers

Ethers are organic compounds characterized by an oxygen atom connected to two alkyl or aryl groups. They are formed through the reaction of alcohols with alkyl halides, where the hydroxyl group of the alcohol replaces a halogen atom. Understanding the structure and properties of ethers is crucial for predicting the products of the reaction shown.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the reaction of the alkyl dihalide with methanol, the stereochemistry of the resulting bromoethers can vary depending on the configuration of the starting material and the mechanism of substitution, which can lead to different isomers.

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Related Practice

Textbook Question

Rank the following alkyl halides from most reactive to least reactive in an S_N1 reaction:

2-bromo-2-methylpentane, 2-chloro-2-methylpentane, 3-chloropentane, and 2-iodo-2-methylpentane.

Textbook Question

Which reaction would be faster, the one with DMSO as the solvent or the one with ethanol (EtOH)?

Textbook Question

a. Identify the substitution products that form when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.

b. Explain why the same products are obtained when 2-chloro-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.

Textbook Question

Explain why tetrahydrofuran can solvate a positively charged species better than diethyl ether can.

Textbook Question

In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a reaction like that in part (a) does not occur.

Textbook Question

Propose a mechanism for each reaction, showing explicitly how the observed mixtures of products are formed.

(e) 3-chlorobut-1-ene + AgNO₃, H₂O → but-2-en-1-ol + but-3-en-2-ol

Textbook Question

There were actually two possible products in the solvolysis reaction from Figure 21.10. Show both products. Which would you expect to be more stable? Why?

Open Question

Provide the mechanism and final products for the following reactions.

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