Predict the major, organic product for the following reaction. <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch13_Q05_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains two reactants. The first reactant has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. A double bond is present between C 5 and C 1. C 2 is wedge bonded to O H. C 5 is single bonded to C H 3 in the form of a line. The second reactant is P B r 3 written over the reaction arrow." />

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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

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions - SOCl2 and PBr3

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions - SOCl2 and PBr3

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Multiple Choice

Predict the major, organic product for the following reaction.

The figure illustrates the structure of a molecule labeled only stereoisomer. A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. A double bond is present between C 5 and C 1. C 2 is dash bonded to B r. C 5 is single bonded to C H 3 in the form of a line.

The figure illustrates the structures of two products labeled enantiomers. The first product has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. A double bond is present between C 1 and C 2. C 5 is wedge bonded to C H 3 on the lower left in the form of a wedged line and dash bonded to B r on the upper left. The second product has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. A double bond is present between C 1 and C 2. C 5 is dash bonded to C H 3 on the lower left in the form of a dashed line and wedge bonded to B r on the upper left.

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Verified step by step guidance

Identify the functional group in the starting material: The starting material is a cyclopentanol with a hydroxyl group (OH) attached to a cyclopentane ring.

Recognize the reagent: PBr3 is a reagent commonly used to convert alcohols into alkyl bromides through an SN2 mechanism.

Understand the mechanism: In the SN2 reaction, the hydroxyl group is replaced by a bromine atom. This reaction involves the inversion of configuration at the carbon center where the substitution occurs.

Consider stereochemistry: Since the reaction proceeds via an SN2 mechanism, the stereochemistry at the carbon center will be inverted. If the starting alcohol has a specific stereochemistry, the product will have the opposite configuration.

Predict the product: The major organic product will be a cyclopentyl bromide with the bromine atom replacing the hydroxyl group, and the stereochemistry will be inverted compared to the starting material.