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

Acid-Catalyzed Hydration

Organic Chemistry

10. Addition Reactions

Acid-Catalyzed Hydration

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6:09 minutes

Problem 36d,e,f

Textbook Question

d. Is the reaction of 1-butene with HBr regioselective?
e. Is it stereoselective?
f. Is it stereospecific?

Verified step by step guidance

Step 1: Analyze the reaction of 1-butene with HBr. This is an electrophilic addition reaction where the π-bond of 1-butene reacts with HBr. The H⁺ (proton) adds to one of the carbons in the double bond, and the Br⁻ (bromide ion) adds to the other carbon.

Step 2: Determine if the reaction is regioselective. Regioselectivity refers to the preference for the formation of one constitutional isomer over another. In this case, the reaction follows Markovnikov's rule, where the H⁺ adds to the carbon with more hydrogens (the terminal carbon), and the Br⁻ adds to the carbon with fewer hydrogens (the internal carbon). This makes the reaction regioselective.

Step 3: Evaluate if the reaction is stereoselective. Stereoselectivity refers to the preference for the formation of one stereoisomer over another. In this reaction, the addition of HBr does not show a preference for the formation of a specific stereoisomer because the intermediate carbocation is planar, allowing the Br⁻ to attack from either side. Thus, the reaction is not stereoselective.

Step 4: Assess if the reaction is stereospecific. Stereospecificity refers to a reaction where a specific stereoisomer of the reactant leads to a specific stereoisomer of the product. Since the reaction of 1-butene with HBr does not depend on the stereochemistry of the starting material and forms a racemic mixture (if applicable), it is not stereospecific.

Step 5: Summarize the findings. The reaction of 1-butene with HBr is regioselective due to Markovnikov's rule, but it is neither stereoselective nor stereospecific because the intermediate carbocation allows for non-specific attack by the bromide ion.

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Key Concepts

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

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the case of 1-butene reacting with HBr, the Markovnikov rule applies, indicating that the hydrogen atom from HBr will add to the carbon with the greater number of hydrogen substituents, leading to the formation of a more stable carbocation.

Stereoselectivity

Stereoselectivity describes a reaction's ability to preferentially form one stereoisomer over another when multiple stereoisomers are possible. In the reaction of 1-butene with HBr, the addition of HBr can lead to different stereoisomers, but the reaction does not favor one stereoisomer over the other, indicating that it is not stereoselective.

Stereospecificity

Stereospecificity is a property of a reaction where a specific stereoisomer of a reactant leads to the formation of a specific stereoisomer of the product. In the case of 1-butene and HBr, the reaction is not stereospecific because the addition of HBr does not result in a unique product based on the stereochemistry of the starting alkene, allowing for the formation of both stereoisomers.

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