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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2:53 minutes

Problem 63a

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.
(a)

Verified step by step guidance

Step 1: Recognize the reaction conditions. The reaction involves bromomethylcyclopentane undergoing solvolysis in methanol with silver nitrate (AgNO₃) under heat. Silver nitrate assists in the removal of the bromide ion (Br⁻), forming a carbocation intermediate.

Step 2: Identify the carbocation intermediate. The loss of Br⁻ generates a cyclopentylmethyl carbocation, which is a primary carbocation. This carbocation can undergo rearrangements or react directly to form products.

Step 3: Propose mechanisms for product formation. (a) The carbocation can lose a proton (H⁺) from the adjacent carbon to form cyclopentene via elimination. (b) Methanol (CH₃OH) can act as a nucleophile, attacking the carbocation to form methoxycyclopentane. (c) The carbocation can rearrange to form a cyclohexyl carbocation via a ring expansion, which can then lose a proton to form cyclohexene or react with methanol to form methoxycyclohexane.

Step 4: Explain the role of heat. Heat facilitates the solvolysis reaction and promotes carbocation rearrangements and elimination reactions, leading to the observed mixture of products.

Step 5: Summarize the product formation. The five products—cyclopentene, methoxycyclopentane, cyclohexene, methoxycyclohexane, and the rearranged ketone—are formed through a combination of nucleophilic substitution, elimination, and carbocation rearrangement mechanisms.

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Key Concepts

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

Solvolysis

Solvolysis is a type of nucleophilic substitution reaction where a solvent acts as a nucleophile, attacking a substrate to form new products. In this case, methanol (CH3OH) serves as the solvent that reacts with bromomethylcyclopentane. Understanding solvolysis is crucial for predicting the reaction pathway and the resulting product mixture.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution can occur via two primary mechanisms: SN1 and SN2. The SN1 mechanism involves a two-step process where the leaving group departs first, forming a carbocation intermediate, followed by nucleophilic attack. In contrast, the SN2 mechanism is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. Identifying which mechanism predominates is essential for predicting the products formed in this reaction.

Silver Ion Catalysis

Silver ions (Ag+) can facilitate nucleophilic substitution reactions by stabilizing the leaving group, in this case, bromide (Br-), thus promoting the formation of a carbocation. This catalytic effect can influence the reaction pathway and the distribution of products. Understanding the role of silver ions in this context is important for explaining the complexity of the product mixture resulting from the reaction.

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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.

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

Textbook Question

What products (including stereoisomers, if applicable) are formed from the reaction of 3-bromo-3-methylpentane:

b. with H₂O?

Textbook Question

Which of these reactions are likely to produce both elimination and substitution products?

a. 2-bromopentane + NaOCH₃

b. 3-bromo-3-methylpentane + NaOMe. (Me = methyl, CH₃)

c. 2-bromo-3-ethylpentane + NaOH

Textbook Question

For each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products.

c. chlorocyclohexane+NaOCH₃in CH₃OH

d. chlorocyclohexane + NaOC(CH₃)₃ in (CH₃)₃COH

Textbook Question

Deuterium (D) is the isotope of hydrogen of mass number 2, with a proton and a neutron in its nucleus. The chemistry of deuterium is nearly identical to the chemistry of hydrogen, except that the C―D bond is slightly (5.0 kJ/mol, or 1.2 kcal/mol) stronger than the C―H bond. Reaction rates tend to be slower if a C―D bond (as opposed to a C―H bond) is broken in a rate-limiting step. This effect on the rate is called a kinetic isotope effect. (Review PROBLEM 4-57)

a. Propose a mechanism to explain each product in the following reaction.

Textbook Question

Two stereoisomers of a bromodecalin are shown. Although the difference between these stereoisomers may seem trivial, one isomer undergoes elimination with KOH much faster than the other. Predict the products of these eliminations, and explain the large difference in the ease of elimination.

Textbook Question

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

(b) meso-1,2-dibromo-1,2-diphenylethane + (CH₃CH₂)₃N:

Textbook Question

Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.

e. isobutyliodide + KOH in ethanol/water

f. isobutylchloride + AgNO₃ in ethanol/water

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

Key Concepts

Solvolysis

Nucleophilic Substitution Mechanisms

Silver Ion Catalysis

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