(R)-Serine (HOCH₂CH(NH₂)COOH) - R or S Configuration
Is (R)-Serine R or S?
(R)-Serine (HOCH₂CH(NH₂)COOH) has 1 chiral center. D-Serine, the mirror image of the common L-amino acid. Teaches comparing -COOH vs -CH₂OH - the carboxyl's double bond creates phantom atoms that give it higher priority.. The configuration is R based on CIP priority rules.
| Formula | HOCH₂CH(NH₂)COOH |
| Name | (R)-Serine |
| Number of Chiral Centers | 1 |
| Configuration(s) | R |
| Difficulty | Intermediate |
Chiral Center Analysis
(R)-Serine (HOCH₂CH(NH₂)COOH) contains 1 chiral center. D-Serine, the mirror image of the common L-amino acid. Teaches comparing -COOH vs -CH₂OH - the carboxyl's double bond creates phantom atoms that give it higher priority.. Each chiral center is analyzed below using CIP (Cahn-Ingold-Prelog) priority rules to determine R or S configuration.
CIP Priority Assignment
The four substituents on the chiral center are ranked by atomic number of the directly attached atom, with ties broken by exploring outward along each branch.
- Priority 1: -NH₂ - Nitrogen directly bonded (atomic number 7) - highest first-atom priority
- Priority 2: -COOH - Carboxyl: C bonded to O, O, O (=O counts twice as phantom) - three oxygens at second level
- Priority 3: -CH₂OH - Hydroxymethyl: C bonded to O, H, H - only one oxygen at second level vs three for COOH
- Priority 4: H - Hydrogen always lowest (atomic number 1)
R/S Configuration
With the lowest priority group (priority 4) oriented away from the viewer, the remaining three substituents trace a clockwise path from priority 1 to 2 to 3. This gives the R configuration.
Interactive stereochemistry explorer with guided walkthroughs and practice quizzes.
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