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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3:17 minutes

Problem 39f

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the reaction conditions. The presence of peroxide indicates that the reaction will follow the anti-Markovnikov addition mechanism due to the free radical pathway.

Step 2: Identify the structure of the alkene. The molecule contains a double bond between the CH=CH2 group and the cyclohexane ring. This is the reactive site for the addition of HBr.

Step 3: In the anti-Markovnikov mechanism, the bromine atom (Br) will add to the less substituted carbon of the double bond, while the hydrogen atom (H) will add to the more substituted carbon.

Step 4: Determine the less substituted carbon in the double bond. In this case, the terminal carbon of the CH=CH2 group is less substituted, while the internal carbon connected to the cyclohexane ring is more substituted.

Step 5: Predict the product. The bromine atom will attach to the terminal carbon of the CH=CH2 group, forming an alkyl halide with the bromine on the less substituted carbon. Ignore stereoisomers as instructed.

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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 containing a carbon atom bonded to a halogen atom (F, Cl, Br, I). They are formed through the substitution of hydrogen atoms in alkanes with halogen atoms. The reactivity and stability of alkyl halides depend on the structure of the carbon chain and the nature of the halogen, influencing their formation and yield in reactions.

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 rule helps predict the major product of the reaction, guiding the formation of more stable carbocations and thus influencing the yield of the resulting alkyl halide.

Radical Mechanism in Addition Reactions

In the presence of peroxides, the addition of HBr to alkenes can proceed via a radical mechanism, which differs from the typical ionic mechanism. This process leads to the formation of the less stable radical intermediate, resulting in the anti-Markovnikov product. Understanding this mechanism is crucial for predicting the major alkyl halide product and its yield in the reaction.

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Related Practice

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

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

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

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iii) HBr, H₂O₂

(b)

Textbook Question

Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. In Chapter 10, we begin developing multistep syntheses in this manner. For now, try to work backward a single step by suggesting an alkene and a reagent that would give products (a)–(i). [Your answers should not include alkenes that undergo rearrangement to give the desired products.]

(d)

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

Key Concepts

Alkyl Halides

Markovnikov's Rule

Radical Mechanism in Addition Reactions

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