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

11. Radical Reactions

Radical Reaction

Organic Chemistry

11. Radical Reactions

Radical Reaction

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1:37 minutes

Problem 11b

Textbook Question

Show how the following compounds could be prepared from 2-methylpropane:
b. 2-methyl-1-propene

Verified step by step guidance

Step 1: Begin with 2-methylpropane, which is an alkane. To convert it into 2-methyl-1-propene, you need to perform a dehydrogenation reaction to remove hydrogen atoms and form a double bond.

Step 2: Use a halogenation reaction to introduce a halogen atom (e.g., bromine or chlorine) into the molecule. This can be achieved by reacting 2-methylpropane with a halogen in the presence of UV light or heat, resulting in the formation of 2-methylpropyl halide.

Step 3: Perform an elimination reaction to remove the halogen atom and a hydrogen atom from adjacent carbon atoms. Use a strong base, such as potassium hydroxide (KOH) or sodium ethoxide (NaOEt), in an alcoholic solution to promote the formation of the double bond.

Step 4: The elimination reaction will result in the formation of 2-methyl-1-propene. Ensure that the reaction conditions favor the formation of the desired product by controlling temperature and solvent choice.

Step 5: Verify the structure of the product using spectroscopic techniques such as IR or NMR to confirm the presence of the double bond and the correct molecular structure of 2-methyl-1-propene.

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Key Concepts

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

Elimination Reactions

Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double bond. In the context of converting 2-methylpropane to 2-methyl-1-propene, a common method is dehydrohalogenation, where a hydrogen halide is eliminated from an alkyl halide. Understanding the mechanism and conditions for elimination reactions is crucial for synthesizing alkenes.

Rearrangement Reactions

Rearrangement reactions involve the structural reorganization of a molecule, often leading to more stable or reactive forms. In the case of 2-methylpropane, a carbocation intermediate may rearrange during the elimination process, affecting the final product. Recognizing how and when rearrangements occur is essential for predicting the outcome of organic reactions.

Alkene Stability and Reactivity

The stability and reactivity of alkenes are influenced by factors such as sterics and electronic effects. For example, 2-methyl-1-propene is a more stable product due to hyperconjugation and the presence of alkyl substituents. Understanding these principles helps in predicting the feasibility of reactions and the stability of intermediates formed during the synthesis process.

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The cationic polymerization of isobutylene (2-methylpropene) is shown in Section 8-16A. Isobutylene is often polymerized under free-radical conditions. Propose a mechanism for the free-radical polymerization of isobutylene.

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Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than six carbon atoms. You may use any additional reagents you need.

(a)

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Using the given starting material and any necessary organic or inorganic reagents, indicate how the desired compounds could be synthesized:

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