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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3:32 minutes

Problem 19

Textbook Question

The solvolysis of 2-bromo-3-methylbutane potentially can give several products, including both E1 and products from both the unrearranged carbocation and the rearranged carbocation. Mechanisms 6-6 and 7-2 show the products from the rearranged carbocation. Summarize all the possible products, showing which carbocation they come from and whether they are the products of E1 or reactions.
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Verified step by step guidance

Step 1: Understand the solvolysis reaction mechanism. Solvolysis typically involves the substitution or elimination of a leaving group (in this case, bromine) in the presence of a solvent. For 2-bromo-3-methylbutane, the reaction proceeds via a carbocation intermediate, which can undergo rearrangement.

Step 2: Identify the initial carbocation formed. When the bromine leaves, the molecule forms a secondary carbocation at the 2-position. This carbocation is prone to rearrangement to form a more stable tertiary carbocation at the 3-position.

Step 3: Determine the products from the unrearranged carbocation. The secondary carbocation can undergo elimination (E1 mechanism) to form an alkene, specifically 2-methyl-2-butene. Alternatively, it can undergo substitution to form a solvolysis product, such as 2-methoxy-3-methylbutane if methanol is the solvent.

Step 4: Determine the products from the rearranged carbocation. The tertiary carbocation formed after rearrangement can also undergo elimination (E1 mechanism) to form alkenes, such as 2-methyl-2-butene and 2-methyl-1-butene. Additionally, it can undergo substitution to form solvolysis products, such as 3-methoxy-3-methylbutane if methanol is the solvent.

Step 5: Summarize the possible products. From the unrearranged carbocation, you get products like 2-methyl-2-butene (E1) and 2-methoxy-3-methylbutane (substitution). From the rearranged carbocation, you get products like 2-methyl-2-butene and 2-methyl-1-butene (E1) and 3-methoxy-3-methylbutane (substitution).

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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 the nucleophile. In the case of 2-bromo-3-methylbutane, the solvent (often water or alcohol) attacks the carbon atom bonded to the leaving group (bromine), leading to the formation of various products. This process can proceed via different mechanisms, including E1 and SN1, depending on the stability of the carbocation formed.

Carbocation Rearrangement

Carbocation rearrangement occurs when a carbocation intermediate shifts to a more stable form during a reaction. In the case of 2-bromo-3-methylbutane, the initial carbocation can rearrange to a more stable tertiary carbocation, which can lead to different products. Understanding the stability of carbocations is crucial for predicting the outcome of solvolysis reactions.

E1 Mechanism

The E1 mechanism is a type of elimination reaction that involves the formation of a carbocation intermediate followed by the loss of a proton to form an alkene. In the context of 2-bromo-3-methylbutane, the E1 pathway can yield alkenes from both the rearranged and unrearranged carbocations. The rate of the E1 reaction depends on the stability of the carbocation and the solvent used.

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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

Textbook Question

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

b. 1-bromo-1-methylcyclohexane + triethylamine(Et₃N:)

Textbook Question

Give the substitution and elimination products you would expect from the following reactions.

b. 1-iodo-1-phenylcyclopentane heated in ethanol

Textbook Question

Predict the major and minor elimination products of the following proposed reactions (ignoring any possible substitutions for now). In each case, explain whether you expect the mechanism of the elimination to be E1 or E2.

(b)

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.

a. 1−bromohexane + sodium ethoxide in ethanol

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