Naproxen is a commercially available anti-inflammatory sold under the name Aleve.
(a) Assign the absolute configuration as R or S.

검증된 단계별 안내

Identify the chiral center in the Naproxen molecule. A chiral center is a carbon atom bonded to four different groups.

Assign priorities to the four groups attached to the chiral center based on the Cahn-Ingold-Prelog (CIP) priority rules. These rules prioritize groups based on the atomic number of the atoms directly attached to the chiral center. If two atoms are the same, move outward along the chain until a difference is found.

Orient the molecule so that the group with the lowest priority (priority 4) is pointing away from you (into the plane of the paper or screen).

Determine the order of the remaining three groups (priority 1, 2, and 3) as you look at the molecule. Trace a path from priority 1 to 2 to 3. If the path is clockwise, the configuration is R (rectus). If the path is counterclockwise, the configuration is S (sinister).

Verify your assignment by double-checking the priority order and the orientation of the lowest-priority group to ensure the configuration is correctly assigned as either R or S.

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주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. Molecules that possess chirality typically have a carbon atom bonded to four different substituents, leading to two distinct configurations known as enantiomers. Understanding chirality is essential for determining the absolute configuration of compounds like Naproxen.

Cahn-Ingold-Prelog Priority Rules

The Cahn-Ingold-Prelog (CIP) priority rules are a set of guidelines used to assign priorities to the substituents attached to a chiral center. According to these rules, substituents are ranked based on atomic number, with higher atomic numbers receiving higher priority. This ranking is crucial for determining whether the configuration around a chiral center is R (rectus) or S (sinister).

R and S Configuration

The R and S configuration system is used to describe the absolute configuration of chiral centers in molecules. If the highest priority substituent is positioned clockwise when viewed from a specific perspective, the configuration is designated as R. Conversely, if the highest priority substituent is counterclockwise, it is designated as S. This system is vital for accurately describing the stereochemistry of compounds like Naproxen.

Naproxen is a commercially available anti-inflammatory sold under the name Aleve.(a) Assign the absolute configuration as R or S.