Why do enantiomers rotate polarized light?

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SUMMARY

Enantiomers, which are chiral molecules, exhibit the property of rotating polarized light in opposite directions; for example, the R enantiomer rotates light in the (+) direction while the S enantiomer rotates it in the (-) direction. The physical mechanism behind this optical rotation can be understood through the coupled oscillator model, where the spatial arrangement of chromophoric groups in a molecule influences the polarization of emitted light. As light interacts with these chiral molecules, the cumulative effect of scattering results in a consistent rotation of the polarization plane proportional to the distance traveled through the medium.

PREREQUISITES
  • Understanding of chirality in organic chemistry
  • Familiarity with optical isomer naming systems
  • Knowledge of chromophores and their properties
  • Basic principles of polarized light
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  • Study the coupled oscillator model in detail
  • Research the physical properties of chiral molecules
  • Explore the concept of optical rotation in different media
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EternusVia
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We are currently learning about enantiomers in organic chemistry class. So far, we've covered what makes an enantiomer, the concept of chirality, optical isomer naming systems, and the physical and chemical properties of enantiomers.

One of the physical properties listed is that enantiomers rotate polarized light. An enantiomer of type R might rotate polarized light in the (+) direction, while its counterpart (S) might rotate light in the (-) direction. The sources I've read don't explain the physical mechanism that produces this rotation.

My initial thought is that the light will bounce into and off of different enantiomers in different directions, presumably because of the spatial arrangement of the atoms. I'm hoping someone will be able to add more.

Thank you!
 
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EternusVia said:
My initial thought is that the light will bounce into and off of different enantiomers in different directions, presumably because of the spatial arrangement of the atoms. I'm hoping someone will be able to add more.

Yes, this is roughly correct. There are different models to understand optical rotation. One of the simplest is the coupled oscillator model. Consider a molecule with two chromophoric groups spaced by some distance d and rotated to each other by an angle phi. If the angle is not equal to 0 or 180 degrees, the molecule will in general be chiral.
Now if light is shone onto the molecule it may excite one of the two chromophores. If the two chromophores are coupled, the excitation may wander to the other chromophore and this chromophore may de-excitate emitting light again. But as the orientation of the chromophore is rotated with respect to the first one, the polarisation plane of the emitted light will be rotated, too. You can also convince yourself that a net effect will remain even if the molecules are oriented erratically.
The effect of consecutive scattering from different molecules is cumulative, so that the plane of polarization will rotate with a constant velocity with the distance the light travels in the medium.
 

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