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STEREOCHEMISTRY

By German Fernandez, 24 February, 2024

Definition of Isomer
Isomers are molecules with the same molecular formula but different structures. They are classified into structural isomers and stereoisomers.

Structural Isomers
Structural isomers differ in the arrangement of atoms and are further classified into chain, position, and functional isomers.

Stereoisomers
Stereoisomers have identical bonds but differ in the spatial arrangement of groups. They are classified into cis-trans (geometric) isomers, enantiomers, and diastereomers.

Chiral or Asymmetric Center
A chiral or asymmetric center is an atom bonded to four different substituents. A molecule with a chiral center has a non-superimposable mirror image called an enantiomer.

Optical Activity
Enantiomers have almost identical physical properties except for optical activity. One enantiomer rotates polarized light to the right (dextrorotatory), while the other rotates it to the left (levorotatory).

The R and S enantiomers of Propranolol act very differently in the body. (R)-Propranolol is used as a contraceptive, while (S)-Propranolol is an antidepressant.

Stereochemistry in Reactions
Radical halogenation reactions on molecules that can form chiral centers produce mixtures of enantiomers in equal amounts or diastereomers in different proportions.

Separation of Enantiomers
Enantiomers have almost identical physical properties, differing in the rotation of polarized light, but having the same melting and boiling points and solubility. Therefore, traditional separation methods cannot be applied, and special techniques are needed. Separation via diastereomers involves transforming the enantiomer mixture into a diastereomer mixture by adding a chiral reagent; diastereomers are easily separable by physical methods.

(S)-Propranolol. Antihypertensive, β-blocker. Indicated for treating hypertension, cardiac arrhythmias, arrhythmia, and digitalis intoxication, and for preventing myocardial infarction

Learn More...

  • Isómeros Estructurales
  • Isómeros Geométricos
  • Enantiómeros
  • Diastereoisómeros
  • Enantiomers nomenclature
  • Racemic Mixture and Meso Form
  • Optical Activity
  • Proyección de Fischer
  • Notación R/S en Fischer
  • Estereoquímica de las Reacciones
  • Reacción Estereoespecífica y Estereoselectiva
  • Separación Enantiómeros
  • Problemas Resueltos de Estereoquímica (parte 1)
  • Problemas Resueltos de Estereoquímica (parte 2)

Book traversal links for ESTEREOQUÍMICA

  • Isómeros Estructurales

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