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

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5:36 minutes

Problem 25b

Textbook Question

Show what happens when the product of part (a) is hydrolyzed using dilute acid.

Verified step by step guidance

Identify the product from part (a) and determine its functional groups. For example, if the product contains an ester group, hydrolysis will target this functional group.

Understand the mechanism of acid-catalyzed hydrolysis. In this reaction, the ester group reacts with water in the presence of a dilute acid (e.g., HCl or H2SO4) to form a carboxylic acid and an alcohol.

Write the general reaction for acid-catalyzed hydrolysis:

R O O R + H_{2} O \to R O H + R C O O H

, where R represents alkyl or aryl groups.

Propose the specific hydrolysis reaction for the product of part (a). Replace the generic R groups in the general reaction with the actual groups from the product of part (a).

Draw the structures of the resulting products (e.g., the carboxylic acid and alcohol) and ensure that the reaction is balanced. Verify that the hydrolysis mechanism is consistent with the functional groups present in the product of part (a).

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Key Concepts

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

Hydrolysis

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In organic chemistry, it often refers to the reaction of a compound with water or an aqueous solution, leading to the formation of new products. When hydrolyzing an organic compound, such as an ester or an amide, the reaction typically results in the formation of an alcohol and a carboxylic acid or an amine, respectively.

Dilute Acid

A dilute acid is an acid that has been mixed with a significant amount of water, reducing its concentration. In hydrolysis reactions, dilute acids, such as hydrochloric acid (HCl) or sulfuric acid (H2SO4), are often used as catalysts to facilitate the reaction. The presence of a dilute acid can help to protonate the reactants, making them more reactive and promoting the cleavage of bonds during hydrolysis.

Reaction Mechanism

A reaction mechanism is a step-by-step description of the process by which reactants are converted into products in a chemical reaction. Understanding the mechanism of hydrolysis is crucial, as it involves several stages, including protonation of the substrate, nucleophilic attack by water, and subsequent bond cleavage. This knowledge helps predict the products formed and the conditions required for the reaction to proceed efficiently.

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