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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3:29 minutes

Problem 53b

Textbook Question

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

Verified step by step guidance

Identify the target compound: The given compound is a vicinal dibromide, meaning two bromine atoms are attached to adjacent carbon atoms in the molecule.

Choose an appropriate alkene precursor: To synthesize a vicinal dibromide, the starting material should be an alkene with the same carbon skeleton as the target compound. In this case, the alkene would be 2-butene.

Select the reaction conditions: Vicinal dibromides are typically formed by the addition of bromine (Br₂) to an alkene in an inert solvent such as carbon tetrachloride (CCl₄). This reaction proceeds via an electrophilic addition mechanism.

Describe the mechanism: When bromine reacts with the alkene, the π-electrons of the double bond attack the bromine molecule, forming a bromonium ion intermediate. The second bromine atom then attacks the more substituted carbon of the bromonium ion, leading to the formation of the vicinal dibromide.

Verify regioselectivity and stereochemistry: The addition of bromine to the alkene is anti-addition, meaning the bromine atoms will add to opposite faces of the double bond. Ensure the stereochemistry matches the target compound.

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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. Their reactivity is primarily due to this double bond, which can undergo various reactions such as electrophilic addition, oxidation, and polymerization. Understanding the types of reactions that alkenes can participate in is crucial for synthesizing other compounds from them.

Synthesis Pathways

Synthesis pathways refer to the step-by-step methods used to convert one compound into another. In organic chemistry, this often involves a series of reactions, including functional group transformations and rearrangements. Identifying the appropriate synthesis pathway from an alkene to the target compound requires knowledge of reaction mechanisms and the properties of intermediates formed during the process.

Functional Group Transformations

Functional group transformations involve changing one functional group in a molecule to another, which is essential in organic synthesis. For example, alkenes can be converted into alcohols, halides, or carbonyl compounds through various reactions. Recognizing how to manipulate functional groups allows chemists to design effective synthetic routes to achieve desired products from alkenes.

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Related Practice

Textbook Question

Predict the product of the following haloalkane syntheses.

(a)

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

How does the first step in the reaction of propene with Br₂ differ from the first step in the reaction of propene with HBr?

Textbook Question

To understand why Br⁻ adds to a carbon of the bromonium ion rather than to the positively charged bromine, draw the product that would be obtained if Br⁻ did add to bromine.

Textbook Question

What is the product of the addition of I—Cl to 1-butene? (Hint: Chlorine is more electronegative than iodine [Table 1.3].)

Textbook Question

Using any alkene and any other reagents, how would you prepare the following compounds?

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