(R)-Naproxen (C₁₄H₁₄O₃) - R or S Configuration
Is (R)-Naproxen R or S?
(R)-Naproxen (C₁₄H₁₄O₃) has 1 chiral center. The inactive enantiomer of the anti-inflammatory drug (the active form is S). Same priority pattern as ibuprofen: COOH > naphthyl > methyl, but tests recognition of a fused bicyclic ring as a substituent.. The configuration is R based on CIP priority rules.
| Formula | C₁₄H₁₄O₃ |
| Name | (R)-Naproxen |
| Number of Chiral Centers | 1 |
| Configuration(s) | R |
| Difficulty | Advanced |
Chiral Center Analysis
(R)-Naproxen (C₁₄H₁₄O₃) contains 1 chiral center. The inactive enantiomer of the anti-inflammatory drug (the active form is S). Same priority pattern as ibuprofen: COOH > naphthyl > methyl, but tests recognition of a fused bicyclic ring as a substituent.. 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: -COOH - Carboxyl: C bonded to O, O, O (=O phantom) - oxygen at second level beats carbon
- Priority 2: -naphthyl - Naphthyl ring: C bonded to C, C at second level - aromatic ring carbons outrank methyl H's
- Priority 3: -CH₃ - Methyl: C bonded to H, H, H - lowest carbon substituent
- 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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