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

Previous problemNext problem

Problem 79

Textbook Question

In Chapter 8, we learned about the chemistry of terpenes and the interesting reactions they can undergo. One such reaction is the acid-catalyzed conversion of nerol to terpineol. Suggest a mechanism for this transformation
.

Verified step by step guidance

Step 1: Recognize that this is an acid-catalyzed reaction. The first step in such reactions typically involves protonation. Protonate the hydroxyl group (-OH) of nerol using the acid catalyst (H⁺), forming a good leaving group (water).

Step 2: After protonation, the water molecule leaves, generating a carbocation intermediate. Identify the location of the carbocation on the nerol structure, ensuring it is consistent with the stability of the intermediate.

Step 3: Consider carbocation rearrangement. If a more stable carbocation can be formed (e.g., through hydride or alkyl shifts), this rearrangement will occur. Analyze the structure of nerol to determine if such a rearrangement is possible.

Step 4: Once the carbocation is stabilized, a nucleophilic attack by water occurs at the carbocation center. This step forms a new bond and introduces a hydroxyl group (-OH) at a different position.

Step 5: Deprotonate the newly added hydroxyl group to regenerate the acid catalyst and form the final product, terpineol. Verify the structure of terpineol to ensure it matches the expected product of the reaction.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

Key Concepts

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

Terpenes

Terpenes are a large and diverse class of organic compounds produced by various plants, particularly conifers. They are characterized by their strong odors and are often used in perfumes and flavorings. Terpenes are built from isoprene units and can undergo various chemical reactions, including rearrangements and functional group transformations, which are essential for understanding their reactivity.

Acid-Catalyzed Reactions

Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In the context of organic chemistry, acids can protonate functional groups, making them more reactive. This mechanism often leads to the formation of carbocations, which are key intermediates in many organic transformations, including the conversion of nerol to terpineol.

Reaction Mechanism

A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. It outlines the sequence of elementary steps, including bond breaking and formation, and the intermediates involved. Understanding the mechanism of the acid-catalyzed conversion of nerol to terpineol is crucial for predicting the outcome of the reaction and the stability of intermediates formed during the process.

Watch next

Master General properties of acid-catalyzed hydration. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Provide a mechanism for the following reactions occurring with rearrangement.

(a)

Textbook Question

Cyclooctene is one of the smaller rings that can form a trans alkene. Would you expect cis-cyclooctene or trans-cyclooctene to react more quickly in an acid-catalyzed hydration reaction?

Textbook Question

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

a. 1-methylcyclohexanol

Textbook Question

How can the following compounds be prepared from 3,3-dimethyl-1-butene?

b. 3,3-dimethyl-2-butanol

Textbook Question

The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.

(a) Propose a mechanism for the formation of an alcohol from an alkene.

Textbook Question

The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.

Textbook Question

Suggest a reagent to carry out each of the following conversions to an alcohol.

(b)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iii) H₂SO₄ , H₂O . If there is no reaction, write 'no reaction.'

(a)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

In Chapter 8, we learned about the chemistry of terpenes and the interesting reactions they can undergo. One such reaction is the acid-catalyzed conversion of nerol to terpineol. Suggest a mechanism for this transformation.

Key Concepts

Terpenes

Acid-Catalyzed Reactions

Reaction Mechanism

Watch next

In Chapter 8, we learned about the chemistry of terpenes and the interesting reactions they can undergo. One such reaction is the acid-catalyzed conversion of nerol to terpineol. Suggest a mechanism for this transformation
.