Predict the major organic product of the following reaction. <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch08_Q09_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains three reactants. The first reactant has the following structure: A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 3-carbon alkene chain depicted as a line structure using 2 zigzag lines. In the alkene chain, a double bond is present between C 2 and C 3. C 1 of the alkene chain is wedge bonded to C H 3 above in the form of a wedged line. The second reactants are H 2 O and H g (O A c) subscript 2 written over the reaction arrow. The third reactant is N a B H 4 written under 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

Alcohol Synthesis

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

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Multiple Choice

Predict the major organic product of the following reaction.

The figure illustrates the structures of two products labeled enantiomers. The first product has the following structure: A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 1 of the alkane chain is dash bonded to O H on the upper right and wedge bonded to C H 3 on the upper left in the form of a wedged line. The second product has the following structure: A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 1 of the alkane chain is wedge bonded to O H on the upper right and dash bonded to C H 3 on the upper left in the form of a dashed line.

The figure illustrates the structures of two products labeled diastereomers. The first product has the following structure: A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 1 of the alkane chain is wedge bonded to C H 3 above in the form of a wedged line. C 2 of the alkane chain is wedge bonded to O H below. The second product has the following structure: A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 1 of the alkane chain is wedge bonded to C H 3 above in the form of a wedged line. C 2 of the alkane chain is dash bonded to O H below.

The figure illustrates the structure of a molecule labeled only stereoisomer. A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 1 of the alkane chain is wedge bonded to C H 3 above in the form of a wedged line. C 3 of the alkane chain is single bonded to O H on the lower right.

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Verified step by step guidance

Identify the reaction type: The reaction involves the addition of water across a double bond using oxymercuration-demercuration, which is a method to hydrate alkenes.

Understand the mechanism: The first step involves the formation of a mercurinium ion intermediate by the reaction of the alkene with mercuric acetate (Hg(OAc)2) in the presence of water.

Determine regioselectivity: The water molecule attacks the more substituted carbon of the mercurinium ion, following Markovnikov's rule, leading to the formation of an organomercury alcohol intermediate.

Consider stereochemistry: The addition of water is anti to the mercurinium ion, leading to the formation of a racemic mixture of enantiomers if the starting alkene is not symmetrical.

Complete the reaction: The second step involves the reduction of the organomercury intermediate with sodium borohydride (NaBH4), replacing the mercury with a hydrogen atom, resulting in the formation of the alcohol product.