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

Monosaccharide

Organic Chemistry

28. Carbohydrates

Monosaccharide

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6:08 minutes

Problem 24

Textbook Question

Draw the mechanism for the hydroxide ion–catalyzed cleavage of fructose-1,6-bisphosphate.

Verified step by step guidance

Identify the structure of fructose-1,6-bisphosphate. It is a six-carbon sugar with phosphate groups attached to the first and sixth carbons. The molecule contains a ketone functional group at the second carbon and hydroxyl groups on the remaining carbons.

Recognize that the reaction is catalyzed by hydroxide ions (OH⁻), which act as a nucleophile. Hydroxide ions will attack the electrophilic carbonyl carbon of the ketone group in fructose-1,6-bisphosphate.

Draw the nucleophilic attack of the hydroxide ion on the carbonyl carbon of the ketone group. This forms a tetrahedral intermediate, where the carbonyl oxygen becomes negatively charged.

Illustrate the breakdown of the tetrahedral intermediate. The negatively charged oxygen reforms the carbonyl group, leading to the cleavage of the C3-C4 bond. This results in the formation of two products: dihydroxyacetone phosphate (DHAP) and glyceraldehyde-3-phosphate (G3P).

Show the stabilization of the products. Both DHAP and G3P are stabilized by resonance and the presence of phosphate groups, which help to delocalize the negative charge. Ensure the final structures of the products are clearly drawn with proper stereochemistry and functional groups.

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Key Concepts

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

Enzyme Catalysis

Enzyme catalysis involves the acceleration of chemical reactions by enzymes, which are biological catalysts. In the context of fructose-1,6-bisphosphate cleavage, enzymes like aldolase facilitate the reaction by lowering the activation energy, allowing the reaction to proceed more efficiently. Understanding how enzymes interact with substrates is crucial for grasping the mechanism of this reaction.

Mechanism of Hydrolysis

The mechanism of hydrolysis refers to the chemical process where water is used to break down a compound. In the case of fructose-1,6-bisphosphate, hydroxide ions act as nucleophiles, attacking the carbonyl carbon of the phosphate group, leading to the cleavage of the molecule. Familiarity with nucleophilic attack and the role of water in hydrolysis is essential for understanding this reaction.

Phosphate Group Cleavage

Phosphate group cleavage is a critical reaction in biochemistry, where a phosphate group is removed from a molecule, often releasing energy. In the cleavage of fructose-1,6-bisphosphate, the breaking of the phosphate bond is a key step that leads to the formation of two three-carbon molecules. Recognizing the significance of phosphate groups in metabolic pathways is vital for comprehending the overall reaction.

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