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

28. Carbohydrates

Monosaccharides - Alkylation

Organic Chemistry

28. Carbohydrates

Monosaccharides - Alkylation

Previous problemNext problem

2:45 minutes

Problem 25a

Textbook Question

Show the product that results when fructose is treated with an excess of methyl iodide and silver oxide.

Verified step by step guidance

Identify the functional groups in fructose: Fructose is a monosaccharide with a ketone group (ketose) and multiple hydroxyl (-OH) groups. These hydroxyl groups are reactive and can undergo methylation.

Understand the role of methyl iodide (CH3I) and silver oxide (Ag2O): Methyl iodide is a methylating agent, and silver oxide acts as a base to facilitate the reaction. Together, they replace the hydrogen atoms of hydroxyl groups with methyl groups (-CH3).

Determine the reaction mechanism: Each hydroxyl group in fructose reacts with methyl iodide in the presence of silver oxide to form a methoxy group (-OCH3). This process is repeated for all hydroxyl groups, as the reaction is carried out with an excess of methyl iodide.

Account for the ketone group: The ketone group in fructose does not react with methyl iodide under these conditions, so it remains unchanged in the product.

Draw the final product: The final product is a fully methylated derivative of fructose, where all hydroxyl groups are converted to methoxy groups (-OCH3), and the ketone group remains intact. Represent this structure clearly, ensuring all substituents are shown.

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.

Fructose Structure and Reactivity

Fructose is a monosaccharide with a ketone functional group and multiple hydroxyl groups. Its structure allows it to undergo various chemical reactions, including alkylation. Understanding the specific sites of reactivity in fructose is crucial for predicting the products formed when it reacts with reagents like methyl iodide.

Alkylation Reaction

Alkylation is a chemical reaction where an alkyl group is transferred to a nucleophile. In this case, methyl iodide acts as the alkylating agent, providing a methyl group that can attach to the hydroxyl groups of fructose. Recognizing how alkylation modifies the structure of fructose is essential for determining the final product.

Role of Silver Oxide

Silver oxide serves as a base in this reaction, facilitating the deprotonation of the hydroxyl groups on fructose. This increases the nucleophilicity of the hydroxyl groups, making them more reactive towards methyl iodide. Understanding the role of silver oxide helps clarify how it influences the reaction mechanism and product formation.

Watch next

Master General Reaction with a bite sized video explanation from Johnny

Start learning