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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1:15 minutes

Problem 30a

Textbook Question

Predict the product of the following etherification reactions.
(a)

Verified step by step guidance

Identify the functional groups in the starting material. The molecule on the left is a sugar derivative with multiple hydroxyl (OH) groups and an ether linkage.

Recognize the reagents used in the reaction. Sodium hydride (NaH) is a strong base that will deprotonate the hydroxyl groups, forming alkoxide ions.

Consider the role of the alkyl bromide (Br) in excess. It will act as an alkylating agent, reacting with the alkoxide ions to form ethers through an SN2 mechanism.

Predict the sites of etherification. Each deprotonated hydroxyl group can react with the alkyl bromide, leading to the formation of ether linkages at each hydroxyl site.

Visualize the final product. The sugar derivative will have its hydroxyl groups replaced by ether linkages with the alkyl group from the alkyl bromide, resulting in a fully etherified sugar derivative.

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Key Concepts

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

Etherification

Etherification is a chemical reaction that forms an ether from an alcohol and a suitable reagent, typically an alkyl halide or an acid. In this process, the hydroxyl group (-OH) of the alcohol is replaced by an alkoxy group (-O-R), resulting in the formation of an ether. Understanding the mechanism of etherification, including nucleophilic substitution reactions, is crucial for predicting the products of these reactions.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, leading to the replacement of a leaving group. This mechanism can occur via two main pathways: SN1 (unimolecular) and SN2 (bimolecular), each with distinct kinetics and stereochemical outcomes. Recognizing the conditions that favor each pathway is essential for predicting the products of etherification reactions.

Reactivity of Alcohols

The reactivity of alcohols in etherification reactions is influenced by their structure and the presence of functional groups. Primary alcohols typically undergo SN2 reactions, while secondary and tertiary alcohols may favor SN1 mechanisms due to steric hindrance. Understanding the classification of alcohols and their reactivity patterns is vital for accurately predicting the products formed in etherification.