Organic Chem: Energy Barriers to Rotation

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SUMMARY

The discussion focuses on evaluating energy barriers to rotation in 1-chloropropane, specifically transitioning between anti and gauche conformations. The steric energy vs. dihedral angle graph reveals troughs for the anti and gauche conformations, with energy barriers represented by peaks in the graph. To calculate these barriers, one must identify the height of the peaks relative to the energy of the starting conformation. The highest energy peak corresponds to an eclipsing interaction between the methyl and chlorine groups, which is critical for understanding the rotational dynamics of the molecule.

PREREQUISITES
  • Understanding of steric energy and dihedral angles in organic molecules
  • Familiarity with Newman Projections for visualizing molecular conformations
  • Knowledge of conformational analysis in organic chemistry
  • Basic skills in interpreting graphs and energy profiles
NEXT STEPS
  • Study the concept of steric hindrance in organic molecules
  • Learn how to construct and interpret Newman Projections
  • Research energy profiles and potential energy surfaces in molecular conformations
  • Explore the effects of substituents on energy barriers in conformational analysis
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Chemistry students, organic chemists, and researchers focusing on conformational analysis and energy barriers in molecular rotation.

sam.
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I have a lab question that I'm stuck on.

For your assigned molecule evaluate the energy barrriers to the rotation:
from anti to gauche
from gauche to gauche
from gauche to anti

I have data/graph of steric energy vs. dihedral angle of 1-chloropropane, but I don't know how to use this information to calculate the energy barriers. Any help is appreciated!
 
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As the dihedral angle is varied from 0 to 2pi, the steric energy curve exhibits
a series of troughs separated by peaks. There should be a trough corresponding to the anti conformation and troughs at each of the gauche conformations. The energy barrier to go from one conformation to another is simply the height (relative to the energy of the conformation at which you are situated) of the peak that must be traversed to go from the first conformation to the second.
 
Sight your molecule along the C1-C2 axis. One carbon bears two hydrogens and a chlorine. The other carbon bears two hydrogens and a methyl group. Use a Newman Projection to help you visualize it. Hint: The highest peak will be from an eclipsing interaction between methyl and chlorine.
 
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