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

Hydrohalogenation

Organic Chemistry

10. Addition Reactions

Hydrohalogenation

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1:47 minutes

Problem 49

Textbook Question

The following haloalkanes can all be prepared starting from the same alkene. Give the alkene and the reagents needed for each.

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Identify the haloalkanes given in the problem. Haloalkanes are organic compounds containing halogens (such as Cl, Br, I) attached to an alkane chain.

Determine the structure of the alkene that can serve as a precursor to these haloalkanes. Consider the position of the halogen in the haloalkanes to deduce the possible structure of the alkene.

Recall the addition reactions of alkenes with halogens or hydrogen halides. These reactions typically involve the electrophilic addition mechanism, where the alkene reacts with a halogen or hydrogen halide to form a haloalkane.

For each haloalkane, identify the specific reagent needed. For example, if the haloalkane is a chloroalkane, the reagent could be HCl or Cl₂. If it's a bromoalkane, the reagent could be HBr or Br₂.

Write the chemical equations for each reaction, showing the conversion of the alkene to the haloalkane using the identified reagents. Use MathML to represent the chemical structures and equations clearly.

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Key Concepts

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

Alkene Structure

Alkenes are hydrocarbons containing a carbon-carbon double bond, which is the site of reactivity in many organic reactions. Understanding the structure of alkenes, including the position and geometry of the double bond, is crucial for predicting the products of reactions involving alkenes.

Electrophilic Addition Reactions

Electrophilic addition is a key reaction mechanism for alkenes, where the double bond acts as a nucleophile and reacts with electrophiles. This mechanism is essential for converting alkenes into haloalkanes, as it involves the addition of halogens or hydrogen halides across the double bond.

Regioselectivity and Markovnikov's Rule

Regioselectivity refers to the preference for the formation of one constitutional isomer over another in a chemical reaction. Markovnikov's Rule predicts that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with more hydrogen substituents, while the halide will attach to the carbon with fewer hydrogen substituents, guiding the formation of specific haloalkanes.

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Related Practice

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions:(ii) HCl

(k)

Textbook Question

Imagine an electrophilic addition where the first step is exothermic. Which carbocation—2°, 3°, or neither—would you expect to form preferentially? Explain.

Textbook Question

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(a)

Textbook Question

Specify the conditions that would allow the synthesis of the 1° and 3° bromoalkanes from the same starting alkene.

Textbook Question

Predict the product and provide a mechanism for the reaction of 1-methylcyclohexene with HBr.

Textbook Question

Provide a mechanism for the following reactions occurring with rearrangement.

(b)

Textbook Question

Using an excess of HCl in the following reaction resulted in a product that was not simply the substitution of chlorine for the hydroxyl group. Predict the identity of the product obtained.

Textbook Question

Provide an arrow-pushing mechanism that rationalizes the formation of each alkyl halide in Assessment 8.19.

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