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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5:58 minutes

Problem 43c

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the starting material and the desired product. The starting material is a secondary alcohol, and the desired product is a secondary alkyl bromide. This suggests that the reaction involves the conversion of an alcohol to an alkyl halide.

Step 2: Select an appropriate reagent for converting alcohols to alkyl halides. A common reagent for this transformation is phosphorus tribromide (PBr₃), which reacts with alcohols to produce alkyl bromides.

Step 3: Write the reaction mechanism. The alcohol reacts with PBr₃, where the hydroxyl group (-OH) is replaced by a bromine atom (Br). This occurs via nucleophilic substitution (SN2 mechanism) for secondary alcohols.

Step 4: Ensure reaction conditions are suitable. The reaction with PBr₃ typically occurs under mild conditions and does not require heating. It is important to use anhydrous conditions to prevent side reactions.

Step 5: Verify the stereochemistry of the product. Since the reaction proceeds via an SN2 mechanism, inversion of configuration at the carbon center may occur. Ensure the product matches the desired stereochemistry.

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Key Concepts

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

Radical Reactions

Radical reactions involve the formation and reaction of free radicals, which are highly reactive species with unpaired electrons. In organic synthesis, these reactions can be initiated by heat or light, leading to the substitution of atoms in a molecule. For example, in the synthesis of brominated compounds, a radical initiator can abstract a hydrogen atom from an alcohol, generating a radical that can then react with bromine.

Bromination of Alcohols

Bromination of alcohols typically involves converting the alcohol into a more reactive species, such as a bromide. This can be achieved through radical mechanisms where the hydroxyl group is replaced by a bromine atom. The process often requires the presence of a brominating agent, such as N-bromosuccinimide (NBS), which facilitates the substitution reaction under radical conditions.

Mechanism of Substitution Reactions

Substitution reactions can occur via different mechanisms, including radical, nucleophilic, and electrophilic pathways. In the context of radical bromination, the mechanism typically involves initiation, propagation, and termination steps. Understanding these steps is crucial for predicting the outcome of the reaction, including regioselectivity and stereochemistry, which are important for synthesizing the desired brominated compound.

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Textbook Question

Show how the following compounds could be prepared from 2-methylpropane:

b. 2-methyl-1-propene

Textbook Question

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.

Textbook Question

Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below. In each case, explain what unwanted reactions might produce undesirable impurities in the product.

Textbook Question

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)

Textbook Question

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

Textbook Question

Starting with cyclohexane, how could the following compounds be prepared?

Textbook Question

Starting with cyclohexane, how could the following compounds be prepared?

Textbook Question

Design a multistep synthesis to show how the following compounds can be prepared from the given starting material:

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

Key Concepts

Radical Reactions

Bromination of Alcohols

Mechanism of Substitution Reactions

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