Which of the following alkenes would form the given product upon treatment with elemental chlorine in water (Cl 2 , H 2 O)? <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch09_Q13_QT.jpg" alt="The figure illustrates the structure of a molecule. A 5-carbon alkane chain is depicted as a line structure using 4 zigzag lines. C 2 is single bonded to C H 3 above in the form of a line. C 3 is dash bonded to O H on the lower left and wedge bonded to C H 3 on the lower right in the form of a wedged line. C 4 is wedge bonded to C l above." />

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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

Halohydrin

Organic Chemistry

10. Addition Reactions

Halohydrin

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Multiple Choice

Which of the following alkenes would form the given product upon treatment with elemental chlorine in water (Cl₂, H₂O)?

The figure illustrates the structure of a molecule. A 5-carbon alkene chain is depicted as a line structure using 4 zigzag lines. A double bond is present between C 3 and C 4. C 2 is single bonded to C H 3 above in the form of a line. C 3 is single bonded to O H below.

The figure illustrates the structure of a molecule. A 4-carbon alkene chain is depicted as a line structure using 3 zigzag lines. A double bond is present between C 3 and C 4. C 2 is single bonded to C H 3 above in the form of a line. C 3 is single bonded to C H 3 below in the form of a line. C 4 is single bonded to C H 3 above in the form of a line.

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Verified step by step guidance

Identify the reaction type: The reaction involves the addition of Cl2 in water to an alkene, which typically results in a halohydrin formation.

Analyze the product structure: The product has a chlorine atom and a hydroxyl group on adjacent carbon atoms, indicating a halohydrin formation.

Determine the regioselectivity: In halohydrin formation, the hydroxyl group (OH) typically adds to the more substituted carbon of the alkene due to the formation of a more stable carbocation intermediate.

Consider the stereochemistry: The chlorine and hydroxyl groups are added in an anti fashion, meaning they will be on opposite sides of the former double bond.

Match the alkene: Compare the given alkenes to see which one, when reacted with Cl2 and H2O, would result in the observed product with the correct regioselectivity and stereochemistry.