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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7:44 minutes

Problem 33e,f

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

Verified step by step guidance

Step 1: Analyze the reaction conditions for part (e) (isobutyl iodide + KOH in ethanol/water). The presence of KOH in a polar protic solvent (ethanol/water) suggests that the reaction will likely proceed via an SN2 or E2 mechanism. Consider the nucleophilicity of OH⁻ and the structure of isobutyl iodide.

Step 2: For part (e), determine the most likely mechanism. Since OH⁻ is a strong nucleophile and the substrate (isobutyl iodide) is a primary alkyl halide, the reaction is more likely to proceed via an SN2 mechanism. Write the substitution reaction where OH⁻ attacks the carbon bonded to iodine, displacing the iodide ion (I⁻).

Step 3: For part (e), consider the possibility of elimination (E2). Since the substrate is a primary alkyl halide, elimination is less favored compared to substitution. However, if the reaction conditions were more basic or involved heat, E2 could compete. Write the elimination reaction where OH⁻ abstracts a β-hydrogen, forming a double bond and releasing I⁻.

Step 4: Analyze the reaction conditions for part (f) (isobutyl chloride + AgNO₃ in ethanol/water). The presence of AgNO₃ in a polar protic solvent suggests that the reaction will likely proceed via an SN1 mechanism. Ag⁺ can coordinate with the chloride ion, facilitating its departure and forming a carbocation intermediate.

Step 5: For part (f), determine the most likely product. The carbocation formed from isobutyl chloride is a primary carbocation, which is less stable. However, the reaction may proceed slowly via SN1, leading to substitution by the solvent (ethanol/water). Write the substitution reaction where ethanol or water acts as the nucleophile, attacking the carbocation to form the corresponding ether or alcohol product.

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Key Concepts

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

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule by a nucleophile. The two main types are SN1 and SN2 mechanisms. SN1 is a two-step process where the leaving group departs first, forming a carbocation, followed by nucleophilic attack. SN2 is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs, leading to a concerted reaction.

Elimination Reactions

Elimination reactions involve the removal of a small molecule (like water or hydrogen halide) from a larger molecule, resulting in the formation of a double bond. The two primary types are E1 and E2 mechanisms. E1 is a two-step process similar to SN1, while E2 is a concerted mechanism where the base abstracts a proton as the leaving group departs. The choice between substitution and elimination often depends on the reaction conditions and the structure of the substrate.

Solvent Effects in Organic Reactions

The choice of solvent can significantly influence the outcome of organic reactions. Polar protic solvents, like water and ethanol, stabilize ions and can favor SN1 and E1 mechanisms by stabilizing the carbocation intermediate. In contrast, polar aprotic solvents favor SN2 and E2 mechanisms by enhancing nucleophilicity. Understanding solvent effects is crucial for predicting reaction pathways and product distributions.

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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)

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

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.

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)

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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/waterf. isobutylchloride + AgNO3 in ethanol/water

Key Concepts

Nucleophilic Substitution Reactions

Elimination Reactions

Solvent Effects in Organic Reactions

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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