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

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 6b

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. d-Mannose is an aldohexose, meaning it is a six-carbon sugar with an aldehyde functional group at the first carbon. Its structure includes four chiral centers at carbons 2, 3, 4, and 5.

Draw the Fischer projection of d-mannose. In the Fischer projection, the aldehyde group (-CHO) is at the top, and the hydroxymethyl group (-CH2OH) is at the bottom. The hydroxyl groups (-OH) on carbons 2, 3, 4, and 5 are arranged as follows: -OH on the left at C2, -OH on the right at C3, -OH on the left at C4, and -OH on the right at C5.

Assign priorities to the substituents at each chiral center using the Cahn-Ingold-Prelog (CIP) priority rules. For each chiral center, assign priorities based on atomic number: the -OH group has the highest priority, followed by the -CH(OH) group, then the -CH2OH group, and finally the hydrogen atom.

Determine the configuration (R or S) for each chiral center. For each chiral center, orient the molecule so that the lowest-priority group (hydrogen) is pointing away from you. Trace the path from the highest-priority group to the second-highest and then to the third-highest. If the path is clockwise, the configuration is R; if counterclockwise, it is S.

Combine the systematic name of the sugar with the configurations of the chiral centers. The systematic name of d-mannose will include the prefix 'D-' (indicating the configuration at the highest-numbered chiral center, C5) and the configurations (R or S) of the other chiral centers in parentheses.

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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, naming substituents, and applying specific rules for functional groups and stereochemistry. Understanding this system is essential for accurately conveying the identity of a compound.

Stereochemistry and Chiral Centers

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. Chiral centers, or asymmetric centers, are carbon atoms bonded to four different groups, leading to non-superimposable mirror images known as enantiomers. Identifying the configuration of these centers as R (rectus) or S (sinister) is crucial for understanding the compound's properties.

D-Mannose and Its Configuration

D-Mannose is a naturally occurring sugar and an epimer of glucose, differing in the configuration around one specific carbon atom. It is important to recognize its structure and stereochemistry to determine its systematic name and the configuration of its chiral centers. The 'D' designation indicates the orientation of the hydroxyl group on the highest-numbered chiral carbon, which is vital for its classification.

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