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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12:24 minutes

Problem 6a

Textbook Question

What are the systematic names of the following compounds? Indicate the configuration (R or S) of each asymmetric center.
a. D-glucose

Verified step by step guidance

Step 1: Understand the structure of d-glucose. d-Glucose is an aldohexose, meaning it is a six-carbon sugar with an aldehyde group at the first carbon. The remaining carbons (C2 to C6) have hydroxyl (-OH) groups attached, and the configuration of these groups determines the stereochemistry of the molecule.

Step 2: Assign priorities to the substituents on each chiral center using the Cahn-Ingold-Prelog (CIP) priority rules. For each chiral carbon, rank the four groups attached to it based on atomic number and connectivity.

Step 3: Determine the spatial arrangement of the substituents around each chiral center. Orient the molecule so that the lowest-priority group is pointing away from you (into the plane of the paper or screen). Then, trace a path from the highest-priority group to the second-highest and then to the third-highest.

Step 4: Assign the configuration (R or S) for each chiral center. If the path traced in Step 3 is clockwise, the configuration is R. If it is counterclockwise, the configuration is S. Repeat this process for all chiral centers in d-glucose (C2, C3, C4, and C5).

Step 5: Combine the stereochemical designations with the systematic name. The systematic name of d-glucose includes the stereochemical configuration of each chiral center (e.g., (2R, 3S, 4R, 5S)-2,3,4,5,6-pentahydroxyhexanal). Ensure that the name reflects the correct 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.

Systematic Naming of Organic Compounds

Systematic naming, or IUPAC nomenclature, is a standardized method for naming chemical compounds based on their structure. It involves identifying the longest carbon chain, functional groups, and stereochemistry to create a unique name that conveys the compound's structure. For carbohydrates like d-glucose, the name reflects the specific arrangement of atoms and functional groups.

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 substituents, leading to non-superimposable mirror images called enantiomers. The configuration of these centers is designated as 'R' (rectus) or 'S' (sinister) based on the Cahn-Ingold-Prelog priority rules.

D- and L- Configuration in Sugars

The D- and L- notation in sugars refers to the configuration of the highest-numbered chiral center relative to the reference molecule, glyceraldehyde. D-glucose, for example, has the hydroxyl group on the highest-numbered chiral center on the right in a Fischer projection. This notation is crucial for distinguishing between different stereoisomers of sugars, which can have vastly different biological activities.

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