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

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

Organic Chemistry

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

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4:44 minutes

Problem 63c

Textbook Question

Silver-assisted solvolysis of bromomethylcyclopentane in methanol gives a complex product mixture of the following five compounds. Propose mechanisms to account for these products.
(c)

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Step 1: Recognize the reaction type. The silver-assisted solvolysis of bromomethylcyclopentane in methanol involves a nucleophilic substitution reaction (SN1 mechanism) facilitated by AgNO3. Silver ion (Ag+) helps remove the bromide ion (Br−) by forming AgBr, which is insoluble and drives the reaction forward.

Step 2: Formation of the carbocation intermediate. The bromide ion leaves, forming a cyclopentylmethyl carbocation. This carbocation is stabilized by hyperconjugation and inductive effects from the cyclopentane ring.

Step 3: Consider rearrangements. The carbocation intermediate may undergo hydride or alkyl shifts to form a more stable carbocation. In this case, the cyclopentylmethyl carbocation could rearrange to form a tertiary carbocation, which is more stable.

Step 4: Nucleophilic attack by methanol. Methanol (CH3OH), acting as a nucleophile, attacks the carbocation to form an ether product. Depending on the carbocation formed, methanol can attack at different positions, leading to a mixture of products.

Step 5: Proton transfer. After methanol attacks the carbocation, a proton is transferred to stabilize the product. This step completes the formation of the ether products, which include variations depending on the carbocation rearrangements and positions of attack.

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Key Concepts

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

Silver-Assisted Solvolysis

Silver-assisted solvolysis involves the use of silver salts, such as AgNO3, to facilitate the nucleophilic substitution of a leaving group (like Br) in an organic compound. In this reaction, the silver ion helps to stabilize the leaving group, promoting the formation of a carbocation intermediate, which can then react with the solvent (methanol) to form various products.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution mechanisms, primarily SN1 and SN2, describe how nucleophiles replace leaving groups in organic molecules. SN1 involves a two-step mechanism where the leaving group departs first, forming a carbocation, followed by nucleophilic attack. In contrast, SN2 is a one-step mechanism where the nucleophile attacks the substrate simultaneously as the leaving group departs, leading to a concerted reaction.

Product Mixture Formation

The formation of a complex product mixture in reactions like the one described is often due to multiple pathways available for the carbocation intermediate. Depending on the stability of the carbocation and the nature of the nucleophile (methanol in this case), various rearrangements and substitutions can occur, leading to different structural isomers and products, such as ethers and alcohols.

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Related Practice

Textbook Question

Make models of the following compounds, and predict the products formed when they react with the strong bases shown.

Textbook Question

Make models of the following compounds, and predict the products formed when they react with the strong bases shown.

(d)

Textbook Question

Propose mechanisms for the following reactions. Additional products may be formed, but your mechanism only needs to explain the products shown.

(c)

Textbook Question

Silver-assisted solvolysis of bromomethylcyclopentane in methanol gives a complex product mixture of the following five compounds. Propose mechanisms to account for these products.

(b)

Textbook Question

Silver-assisted solvolysis of bromomethylcyclopentane in methanol gives a complex product mixture of the following five compounds. Propose mechanisms to account for these products.

(d)

Textbook Question

Silver-assisted solvolysis of bromomethylcyclopentane in methanol gives a complex product mixture of the following five compounds. Propose mechanisms to account for these products.

(e)

Textbook Question

Draw the products of each of the following S_N2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

b. (3R,4R)-3-bromo-4-methylhexane + CH₃O⁻

Textbook Question

Which of the following compounds would react faster in an

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a. E1 reaction?

b. E2 reaction?

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