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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2:14 minutes

Problem 31d

Textbook Question

What is the expected product for the reaction of each of the following alkenes with (i) HBr and (ii) HCl?
(d)

Verified step by step guidance

Identify the structure of the alkene in part (d). Alkenes are hydrocarbons with a carbon-carbon double bond, which is the site of reactivity in addition reactions.

Understand the mechanism of electrophilic addition of HX (where X is a halogen, such as Br or Cl) to alkenes. The reaction proceeds via the formation of a carbocation intermediate.

For the reaction with HBr, the alkene will react with HBr to form a carbocation. The hydrogen from HBr will add to the less substituted carbon of the double bond, following Markovnikov's rule, which states that the more stable carbocation is formed.

Once the carbocation is formed, the bromide ion (Br-) will attack the positively charged carbon, resulting in the formation of the alkyl bromide product.

Repeat the process for the reaction with HCl. The mechanism is similar, where the chloride ion (Cl-) will attack the carbocation formed after the addition of HCl, resulting in the formation of the alkyl chloride product.

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Key Concepts

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

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, while the halogen will attach to the carbon with fewer hydrogen atoms. This rule helps predict the major product in electrophilic addition reactions.

Electrophilic Addition Reaction

Electrophilic addition is a reaction where an electrophile reacts with an alkene, resulting in the addition of atoms across the double bond. The alkene's π electrons attack the electrophile, forming a carbocation intermediate, which is then attacked by a nucleophile, leading to the final product.

Carbocation Stability

Carbocation stability is crucial in determining the major product of an electrophilic addition reaction. Tertiary carbocations are more stable than secondary, which are more stable than primary. The stability is influenced by hyperconjugation and the inductive effect, guiding the formation of the most stable intermediate during the reaction.

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Related Practice

Textbook Question

Predict the major products of the following reactions, and propose mechanisms to support your predictions.

a. pent-1-ene + HCl

Textbook Question

What is the major product of each of the following reactions, assuming that one equivalent of each reagent is used in each reaction?

Textbook Question

Predict the product(s) of each of the following reactions. If you expect a racemic mixture, draw both enantiomers.

(c)

Textbook Question

Suggest an alkene that, upon reaction with the appropriate hydrohalic acid, will produce only the alkyl halide shown. [Ignore stereochemistry.]

(b)

Textbook Question

Would you expect but-2-ene or 2-methylbut-2-ene to react more quickly with HBr?

Textbook Question

If you react carvone with a single equivalent of HBr, only one product is produced, even though carvone has two carbon–carbon double bonds. Explain this observation.

Textbook Question

The reaction of (E)-3-chlorohex-3-ene with HCl results in the selective formation of 3,3-dichlorohexane instead of 3,4-dichlorohexane. Explain this result.

Textbook Question

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

(b)

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