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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3:23 minutes

Problem 35b

Textbook Question

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

Verified step by step guidance

Identify the structure of the alkene involved in the reaction. Alkenes are hydrocarbons with a carbon-carbon double bond, which is the site of reactivity in these reactions.

For the reaction with HBr alone, apply Markovnikov's rule. This 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, and the halogen will attach to the carbon with fewer hydrogen atoms. This results in the formation of the more stable carbocation intermediate.

Draw the intermediate carbocation formed after the initial addition of HBr to the alkene. Consider the stability of the carbocation, as tertiary carbocations are more stable than secondary, which are more stable than primary.

For the reaction with HBr and H₂O₂, apply anti-Markovnikov's rule. In the presence of peroxides, the addition of HBr to an alkene proceeds via a radical mechanism, where the bromine atom attaches to the carbon with more hydrogen atoms, opposite to Markovnikov's rule.

Draw the expected product for each reaction, considering the regioselectivity (Markovnikov vs. anti-Markovnikov) and the mechanism (ionic vs. radical) involved in each case.

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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 states that in the addition of HX (where X is a halogen) to an alkene, the hydrogen atom will attach to the carbon with more hydrogen atoms, and the halogen will attach to the carbon with fewer hydrogen atoms. This rule helps predict the major product in the absence of peroxides.

Anti-Markovnikov Addition

Anti-Markovnikov addition occurs when HBr is added to an alkene in the presence of peroxides (H₂O₂). The reaction proceeds via a radical mechanism, resulting in the bromine atom attaching to the less substituted carbon, opposite to Markovnikov's Rule, due to the influence of the radical initiator.

Radical Mechanism

A radical mechanism involves the formation of free radicals, which are highly reactive species with unpaired electrons. In the presence of peroxides, the addition of HBr to alkenes follows a radical pathway, leading to anti-Markovnikov products. Understanding this mechanism is crucial for predicting product formation in peroxide-mediated reactions.

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Related Practice

Textbook Question

Show how you would synthesize each compound using methylenecyclopentane as your starting material.

(b)

Textbook Question

Propose mechanisms consistent with the following reactions.

(a)

Textbook Question

Predict the major products of the following reactions, and propose mechanisms to support your predictions.

(b)

HINT: Remember to write out complete structures, including all bonds and charges, when writing a mechanism or determining the course of a reaction.

Textbook Question

Show how you would accomplish the following synthetic conversions.

(a) but−1−ene → 1−bromobutane

(b) but−1−ene → 2−bromobutane

Textbook Question

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

(c)

Textbook Question

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

(d)

Textbook Question

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

(a)

Textbook Question

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

(b)

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

Key Concepts

Markovnikov's Rule

Anti-Markovnikov Addition

Radical Mechanism

Watch next

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