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

10. Addition Reactions

Epoxide Reactions

Organic Chemistry

10. Addition Reactions

Epoxide Reactions

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5:42 minutes

Problem 64

Textbook Question

Propose a mechanism for the following reaction.

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Step 1: Protonation of the epoxide ring. The reaction begins with the acid catalyst (H2SO4) protonating the oxygen atom of the epoxide ring, making it more electrophilic and susceptible to nucleophilic attack.

Step 2: Ring opening of the epoxide. Water (H2O) acts as a nucleophile and attacks the more substituted carbon of the epoxide ring, leading to the opening of the ring and forming a carbocation intermediate.

Step 3: Carbocation rearrangement. The carbocation formed undergoes rearrangement to stabilize itself. This involves a hydride shift or alkyl shift to form a more stable tertiary carbocation.

Step 4: Deprotonation to form the alcohol. A water molecule removes a proton from the intermediate, resulting in the formation of the alcohol group at the site of the carbocation.

Step 5: Formation of the final product. The double bond is retained in the structure, and the final product is formed with the hydroxyl group and the alkene in the correct positions as shown in the product structure.

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Key Concepts

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

Acid-Catalyzed Hydration

Acid-catalyzed hydration is a reaction where water adds to an alkene in the presence of an acid, typically sulfuric acid (H2SO4). The acid protonates the alkene, forming a more stable carbocation intermediate, which then reacts with water to form an alcohol. This mechanism is crucial for understanding how alkenes can be converted into alcohols through hydration.

Carbocation Stability

Carbocation stability is a key concept in organic chemistry that refers to the relative stability of positively charged carbon species. Carbocations are stabilized by alkyl groups through hyperconjugation and inductive effects. Understanding the stability of different carbocations helps predict the major products of reactions involving carbocation intermediates, such as in the hydration of alkenes.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached, while the halide (or hydroxyl group in hydration) will attach to the carbon with fewer hydrogen atoms. This rule helps predict the regioselectivity of reactions involving alkenes, guiding the formation of the more stable product.

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Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H₂SO₄, H₂O

(k)

Textbook Question

There are two mechanisms by which each of the two enantiomers can form in the reaction shown in Figure 9.37. Show them.

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Textbook Question

Show an arrow-pushing mechanism for reactions 1–4 in Figure 9.37.

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Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

f. peroxyacetic acid in acidic water

Textbook Question

Predict the major products of the following reactions.

b. trans-hex-3-ene + peroxyacetic acid (CH₃CO₃H) in water

c. 1-methylcyclohexene + MMPP in ethanol

Textbook Question

Show how you would accomplish the following conversions.

b. cis-hex-3-ene to (d,l)-hexane-3,4-diol

Textbook Question

Predict the products of the following reactions.

(j)

(k)

(l)

Textbook Question

Triethylene glycol is one of the products obtained from the reaction of excess ethylene oxide and hydroxide ion. Propose a mechanism for its formation.

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