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

Anti Markovnikov Addition of Br

Organic Chemistry

11. Radical Reactions

Anti Markovnikov Addition of Br

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1:49 minutes

Problem 46b

Textbook Question

Predict the product of the following alkene addition reactions.
(b)

Verified step by step guidance

Identify the type of reaction: The presence of HBr and HOOH indicates a radical addition reaction, specifically anti-Markovnikov addition due to the presence of peroxide (HOOH).

Understand the mechanism: In anti-Markovnikov addition, the bromine atom will add to the less substituted carbon of the double bond, opposite to the Markovnikov rule.

Initiation step: Peroxides decompose to form radicals, which initiate the radical chain reaction. The peroxide radical abstracts a hydrogen from HBr, generating a bromine radical.

Propagation step: The bromine radical adds to the less substituted carbon of the alkene, forming a new radical at the more substituted carbon.

Termination step: The radical formed can react with another bromine radical or other radicals present to form the final product, completing the anti-Markovnikov addition.

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Key Concepts

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

Alkene Reactivity

Alkenes are unsaturated hydrocarbons characterized by at least one carbon-carbon double bond. This double bond is reactive and can undergo various addition reactions, where atoms or groups are added across the double bond. Understanding the nature of the alkene and the conditions of the reaction is crucial for predicting the products formed.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX (where X is a halogen) to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the regioselectivity of the reaction, guiding the formation of the more stable carbocation intermediate during the reaction process.

Stereochemistry of Addition Reactions

Addition reactions of alkenes can lead to different stereochemical outcomes, including syn and anti addition. The stereochemistry is important for determining the configuration of the product, especially in reactions involving chiral centers. Understanding how the addition mechanism affects stereochemistry is essential for predicting the final product's structure.

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Textbook Question

Predict the major products of the following alkene halogenation reactions. [D is the symbol for deuterium, an isotope of hydrogen.]

(a)

Textbook Question

Predict the major products of the following alkene halogenation reactions. [D is the symbol for deuterium, an isotope of hydrogen.]

(b)

Textbook Question

Provide the expected product for the reaction of each of the following alkenes with (i) HBr and (ii) HBr, H₂O₂.

(e)

Textbook Question

Which reagent system (HBr or HBr, H₂O₂) would you use to carry out the following transformations?

(c)

Textbook Question

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.

Textbook Question

Draw the structures of four six-carbon alkenes that form the same product, whether they react with HBr in the presence of a peroxide or with HBr in the absence of a peroxide.

Textbook Question

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.

Textbook Question

Draw the major product(s) of the reaction of 1-methylcyclohexene with the following reagents, disregarding stereoisomers:

3. HBr

4. HBr/peroxide

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