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

Hydrohalogenation

Organic Chemistry

10. Addition Reactions

Hydrohalogenation

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1:19 minutes

Problem 11

Textbook Question

Specify the conditions that would allow the synthesis of the 1° and 3° bromoalkanes from the same starting alkene.

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Identify the starting alkene structure. Determine if it is symmetrical or asymmetrical, as this will influence the regioselectivity of the addition reactions.

For the synthesis of 1° bromoalkane, consider using hydroboration-oxidation followed by halogenation. Hydroboration-oxidation will convert the alkene into an alcohol, which can then be converted into a bromoalkane using PBr₃ or HBr.

For the synthesis of 3° bromoalkane, use Markovnikov addition of HBr to the alkene. This reaction proceeds via a carbocation intermediate, where the bromine will add to the more substituted carbon, resulting in a 3° bromoalkane.

Ensure that the reaction conditions for each synthesis are optimized. For hydroboration-oxidation, use BH₃ and THF followed by H₂O₂ and NaOH. For Markovnikov addition, use HBr in the presence of a peroxide to avoid anti-Markovnikov addition.

Consider stereochemistry and any potential rearrangements during the reactions. For example, carbocation rearrangements can occur during Markovnikov addition, potentially affecting the final product distribution.

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Key Concepts

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

Markovnikov's Rule

Markovnikov's Rule predicts the regiochemistry of electrophilic addition reactions to alkenes, stating that the hydrogen atom will attach to the less substituted carbon, while the halide will attach to the more substituted carbon. This rule is crucial for understanding how 3° bromoalkanes can be synthesized from alkenes.

Anti-Markovnikov Addition

Anti-Markovnikov addition occurs when the halide attaches to the less substituted carbon of the alkene, often facilitated by radical initiators like peroxides. This concept is essential for synthesizing 1° bromoalkanes, as it allows the bromine to add to the terminal carbon of the alkene.

Radical Mechanism

Radical mechanisms involve the formation of free radicals, which are highly reactive species with unpaired electrons. In the context of bromination, radicals can initiate anti-Markovnikov addition, enabling the formation of 1° bromoalkanes from alkenes under specific conditions, such as the presence of peroxides.

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Related Practice

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (i) HBr

(k)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions:(ii) HCl

(k)

Textbook Question

Imagine an electrophilic addition where the first step is exothermic. Which carbocation—2°, 3°, or neither—would you expect to form preferentially? Explain.

Textbook Question

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(a)

Textbook Question

The following haloalkanes can all be prepared starting from the same alkene. Give the alkene and the reagents needed for each.

Textbook Question

Predict the product and provide a mechanism for the reaction of 1-methylcyclohexene with HBr.

Textbook Question

Provide a mechanism for the following reactions occurring with rearrangement.

(b)

Textbook Question

Using an excess of HCl in the following reaction resulted in a product that was not simply the substitution of chlorine for the hydroxyl group. Predict the identity of the product obtained.

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