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

Halogenation

Organic Chemistry

10. Addition Reactions

Halogenation

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3:24 minutes

Problem 10a

Textbook Question

Predict the product of the following haloalkane syntheses.
(a)

Verified step by step guidance

Step 1: Analyze the given molecule, which is a cyclohexene derivative with a double bond. The reactions provided involve halogenation and hydrohalogenation, which target the double bond.

Step 2: For reaction (a) with Br₂, the double bond undergoes electrophilic addition. Bromine adds across the double bond, forming a vicinal dibromide. The stereochemistry of the product depends on anti-addition due to the bromonium ion intermediate.

Step 3: For reaction (b) with HBr, the double bond undergoes hydrohalogenation. According to Markovnikov's rule, the bromine atom will add to the more substituted carbon of the double bond, forming a bromoalkane.

Step 4: For reaction (c) with HBr and H₂O₂, the reaction follows anti-Markovnikov addition due to the presence of peroxides. Bromine adds to the less substituted carbon of the double bond, forming a bromoalkane.

Step 5: For reaction (d) with Cl₂, the double bond undergoes electrophilic addition similar to reaction (a). Chlorine adds across the double bond, forming a vicinal dichloride with anti-addition stereochemistry.

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Key Concepts

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

Electrophilic Addition Reactions

Electrophilic addition reactions are a fundamental type of reaction in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes or alkynes. In the context of haloalkanes, these reactions often lead to the formation of haloalkanes from alkenes by adding halogens or hydrogen halides across the double bond.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In the case of haloalkane syntheses, the regioselectivity can be influenced by the stability of the carbocation intermediate formed during the reaction, which determines the major product.

Mechanism of Halogenation

The mechanism of halogenation involves the addition of halogens (like Br2 or Cl2) to alkenes, resulting in the formation of vicinal dihalides. This process typically proceeds through a cyclic halonium ion intermediate, which is crucial for understanding the stereochemistry and regioselectivity of the products formed in the reaction.

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Related Practice

Textbook Question

Predict the product of the following addition reactions to dienes.

(c)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br₂ (ii) Cl₂.

(e)

Textbook Question

Provide an arrow-pushing mechanism that rationalizes the stereospecific formation of each dihalide in Assessment 9.6.

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br₂ (ii) Cl₂

(f)

Textbook Question

Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.

(c)

Textbook Question

In spite of being mechanistically similar to some of the reactions we saw in Chapter 8, rearrangement never occurred here in Chapter 9. Why doesn't rearrangement occur in the following bromination reaction despite the proximity of a more substituted carbon?

Textbook Question

In contrast to the addition of Br₂ the addition of HBr [Section 8.3] is not stereospecific. Why?

Textbook Question

Show how each of the following compounds can be synthesized from an alkene:

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