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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1:58 minutes

Problem 39e

Textbook Question

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

Verified step by step guidance

Step 1: Recognize that the reaction involves HBr in the presence of peroxide. This indicates that the reaction will follow the anti-Markovnikov addition mechanism due to the radical pathway initiated by the peroxide.

Step 2: Analyze the structure of the alkene in each case. In the first image, the alkene is part of a cyclohexene ring with a methyl substituent. In the second image, the alkene is part of a cyclohexene ring with a vinyl group and a methyl substituent.

Step 3: Determine the site of radical formation. The anti-Markovnikov addition mechanism involves the bromine radical adding to the less substituted carbon of the double bond, forming the most stable radical intermediate.

Step 4: Predict the major product for each case. In the first image, the bromine will add to the less substituted carbon of the double bond, resulting in the formation of a bromocyclohexane derivative. In the second image, the bromine will add to the less substituted carbon of the double bond in the vinyl group, resulting in a bromocyclohexane derivative with a vinyl substituent.

Step 5: Compare the stability of the radical intermediates and steric effects to determine which alkyl halide will be obtained in the greatest yield. The product with the most stable radical intermediate and least steric hindrance will be favored.

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Key Concepts

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

Alkyl Halides

Alkyl halides are organic compounds derived from alkanes by replacing one or more hydrogen atoms with halogen atoms (such as fluorine, chlorine, bromine, or iodine). They are classified based on the type of carbon atom to which the halogen is attached: primary, secondary, or tertiary. The structure of the alkyl halide significantly influences its reactivity and the types of reactions it can undergo.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (like a halogen) by a nucleophile. The mechanism can follow either an SN1 or SN2 pathway, depending on the structure of the alkyl halide and the conditions of the reaction. Understanding these mechanisms is crucial for predicting which alkyl halide will be formed in greater yield, as they dictate the rate and outcome of the reaction.

Reaction Conditions and Yield

The yield of a reaction refers to the amount of product formed compared to the theoretical maximum. Factors such as steric hindrance, solvent effects, and temperature can influence the yield of alkyl halides in nucleophilic substitution reactions. Analyzing these conditions helps determine which alkyl halide will be produced in the greatest yield, as certain structures may favor more efficient pathways.

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Related Practice

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

Predict the product of the following alkene addition reactions.

(b)

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

Textbook Question

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

c. HBr + peroxide

d. HCl + peroxide

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