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

Alkyne Halogenation

Organic Chemistry

10. Addition Reactions

Alkyne Halogenation

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2:26 minutes

Problem 13b

Textbook Question

Drawing on what you know about the stereochemistry of alkene addition reactions,
b. predict the configuration of the product of the reaction.

Verified step by step guidance

Analyze the type of alkene addition reaction involved (e.g., hydrohalogenation, halogenation, hydration, etc.) and determine whether the reaction proceeds via a syn-addition, anti-addition, or a combination of both. This will help predict the stereochemical outcome.

Identify the reagents and reaction conditions provided in the problem. For example, if the reaction involves Br2 in an inert solvent like CCl4, it typically proceeds via anti-addition, forming a trans product.

Draw the starting alkene structure and consider its geometry (e.g., cis or trans configuration). This will influence the stereochemistry of the product.

Apply the stereochemical rules for the specific reaction mechanism. For example, in anti-addition, the two new substituents will add to opposite faces of the double bond, while in syn-addition, they will add to the same face.

Draw the product(s) of the reaction, ensuring that the stereochemistry is clearly indicated (e.g., using wedge and dash bonds to show 3D configuration). If the reaction produces enantiomers or diastereomers, include all possible stereoisomers.

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Key Concepts

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

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of alkene addition reactions, it is crucial to understand how the orientation of substituents around the double bond influences the configuration of the product, whether it be cis or trans.

Alkene Addition Reactions

Alkene addition reactions involve the addition of reagents across the carbon-carbon double bond of alkenes, resulting in the formation of saturated compounds. The mechanism of these reactions can lead to different stereochemical outcomes, depending on the nature of the reagents and the conditions under which the reaction occurs.

Regioselectivity and Stereoselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereoselectivity indicates the preference for one stereoisomer over another. In alkene addition reactions, understanding these concepts helps predict the configuration of the product, as certain pathways may favor the formation of specific stereoisomers based on the reaction conditions.

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Related Practice

Textbook Question

For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (viii) Cl₂ (1 equiv.). If you expect two products, show both.

(c)

Textbook Question

For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (ix) Br₂ (2 equiv.). If you expect two products, show both.

(c)

Textbook Question

Trans addition is heavily favored for the addition of Br₂ and Cl₂ to alkynes. With chlorination, however, more of the syn addition product is formed. Rationalize this fact in light of your answer to Assessments 10.50 and 10.51.

Textbook Question

Drawing on what you know about the stereochemistry of alkene addition reactions,

a. write the mechanism for the reaction of 2-butyne with one equivalent of Br₂.

Textbook Question

Show how hex-1-yne might be converted to

d. 1,1,2,2-tetrabromohexane.

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄

(b)

Textbook Question

Predict the products you would get when the following alkenes react under the following conditions: (i) H₂SO₄, H₂O and (ii) 1. Hg(OAc)₂, H₂O , 2. NaBH₄

(d)

Textbook Question

For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (ix) Br₂ (2 equiv.). If you expect two products, show both.

(f)

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Drawing on what you know about the stereochemistry of alkene addition reactions,b. predict the configuration of the product of the reaction.

Key Concepts

Stereochemistry

Alkene Addition Reactions

Regioselectivity and Stereoselectivity

Watch next

Drawing on what you know about the stereochemistry of alkene addition reactions,
b. predict the configuration of the product of the reaction.