1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
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 Acids3h 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

21. Aldehydes and Ketones: Nucleophilic Addition

Naming Aldehydes

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Naming Aldehydes

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4:02 minutes

Problem 20-6bBruice - 8th Edition

Textbook Question

What are the systematic names of the following compounds? Indicate the configuration (R or S) of each asymmetric center.
b. d-mannose

Verified step by step guidance

Identify the structure of d-mannose, which is an aldohexose with the chemical formula C6H12O6.

Draw the Fischer projection of d-mannose, ensuring the aldehyde group is at the top and the hydroxyl groups are correctly positioned on the carbon chain.

Assign priorities to the substituents around each chiral center based on the Cahn-Ingold-Prelog priority rules.

Determine the configuration (R or S) for each chiral center by analyzing the direction of the priority sequence (clockwise or counterclockwise).

Combine the configurations with the IUPAC name of the sugar, ensuring to indicate the configuration of each chiral center in the name.

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Key Concepts

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

Systematic Naming of Organic Compounds

Systematic naming, or IUPAC nomenclature, is a standardized method for naming organic compounds based on their structure. It involves identifying the longest carbon chain, determining functional groups, and applying specific rules to create a unique name that conveys the compound's structure. Understanding this system is essential for accurately naming compounds like d-mannose.

Chirality and Asymmetric Centers

Chirality refers to the property of a molecule that makes it non-superimposable on its mirror image, often due to the presence of asymmetric centers, typically carbon atoms bonded to four different substituents. The configuration of these centers is designated as 'R' (rectus) or 'S' (sinister) based on the Cahn-Ingold-Prelog priority rules, which are crucial for determining the stereochemistry of compounds like d-mannose.

D-Mannose and Its Structure

D-mannose is a naturally occurring sugar and an epimer of glucose, specifically differing at one carbon atom. It is a six-carbon aldose with multiple asymmetric centers, making its stereochemistry important for its biological function. Recognizing its structure and how to derive its systematic name is vital for answering questions related to its configuration.