Ch. 5 - ChiralityWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Solution: The 3 stereocenters in penicillin V, a broad spectrum antibiotic, are labeled “a,” “b,” and “c” in the structure shown below. In each part of this question, the four bonds to the stereocenter are reproduced in the same orientation as they are written in this structure. Assign priorites to each of the four groups attached to the stereocenter (1 = highest priority; 4 = lowest priority), and write the number associated with each group in the appropriate circle. Then, determine whether the absolute stereochemical configuration is (R) or (S). θ

Problem

The 3 stereocenters in penicillin V, a broad spectrum antibiotic, are labeled “a,” “b,” and “c” in the structure shown below. In each part of this question, the four bonds to the stereocenter are reproduced in the same orientation as they are written in this structure. Assign priorites to each of the four groups attached to the stereocenter (1 = highest priority; 4 = lowest priority), and write the number associated with each group in the appropriate circle. Then, determine whether the absolute stereochemical configuration is (R) or (S).

θ