(R)-β-Butyrolactone (C₄H₆O₂) - R or S Configuration
Is (R)-β-Butyrolactone R or S?
(R)-β-Butyrolactone (C₄H₆O₂) has 1 chiral center. Ring ester with a chiral center in a 4-membered lactone ring. Tests that CIP rules are unchanged by ring context - the ring-O is still O at first level, and the CH₂ path reaches two oxygens via the carbonyl.. The configuration is R based on CIP priority rules.
| Formula | C₄H₆O₂ |
| Name | (R)-β-Butyrolactone |
| Number of Chiral Centers | 1 |
| Configuration(s) | R |
| Difficulty | Advanced |
Chiral Center Analysis
(R)-β-Butyrolactone (C₄H₆O₂) contains 1 chiral center. Ring ester with a chiral center in a 4-membered lactone ring. Tests that CIP rules are unchanged by ring context - the ring-O is still O at first level, and the CH₂ path reaches two oxygens via the carbonyl.. 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: -O- (ring) - Oxygen (Z=8) directly bonded - ring context doesn't change atomic number
- Priority 2: -CH₂C(=O)O- (ring) - C at 1st → {C, H, H} at 2nd → C leads to {O, O, O} (=O phantom + ring O) - beats methyl
- Priority 3: -CH₃ - C at 1st → {H, H, H} at 2nd - simple methyl, lowest among carbons
- Priority 4: H - Hydrogen (Z=1) - always lowest
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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