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

Epoxide Reactions

Organic Chemistry

10. Addition Reactions

Epoxide Reactions

Previous problemNext problem

8:48 minutes

Problem 47f

Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

f. peroxyacetic acid in acidic water

Verified step by step guidance

Step 1: Analyze the structure of limonene. Limonene is a cyclic terpene with two double bonds: one in the six-membered ring and one in the exocyclic position. These double bonds are reactive sites for electrophilic addition reactions.

Step 2: Understand the reagent peroxyacetic acid in acidic water. Peroxyacetic acid is an oxidizing agent that facilitates the formation of epoxides from alkenes through an electrophilic addition mechanism.

Step 3: Predict the reaction mechanism. Each double bond in limonene will react with peroxyacetic acid to form an epoxide. The reaction involves the attack of the alkene's π-electrons on the electrophilic oxygen of the peroxyacetic acid, forming a three-membered cyclic ether (epoxide).

Step 4: Consider the stereochemistry. The reaction can produce stereoisomers depending on the approach of the peroxyacetic acid to the double bonds. Both double bonds in limonene will be converted into epoxides, and the stereochemistry of the products should be carefully considered.

Step 5: Draw the expected products. The final products will have two epoxide groups: one on the six-membered ring and one on the exocyclic double bond. Ensure the correct placement of the epoxide groups and consider stereochemical outcomes.

Verified video answer for a similar problem:

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

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Limonene Structure and Properties

Limonene is a cyclic monoterpene with a distinctive structure characterized by a six-membered ring and a double bond. It is known for its citrus aroma and is commonly found in the peels of citrus fruits. Understanding its structure is crucial for predicting its reactivity with various reagents.

Reactivity of Alkenes

Limonene contains a double bond, making it an alkene, which is reactive towards electrophiles. In the presence of reagents like peroxyacetic acid, alkenes can undergo reactions such as epoxidation or oxidation, leading to the formation of various products. Recognizing these reaction pathways is essential for predicting the outcomes of the reaction.

Peroxyacetic Acid as an Oxidizing Agent

Peroxyacetic acid is a strong oxidizing agent that can react with alkenes to form epoxides or other oxidized products. In acidic conditions, it can facilitate the formation of reactive intermediates that further react with water or other nucleophiles. Understanding its role in organic reactions helps in predicting the products formed when it reacts with limonene.

Watch next

Master Acid-Catalyzed Epoxide Ring-Opening with a bite sized video explanation from Johnny

Start learning