6.4: Exercise Questions
- Page ID
- 470377
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Part 1: Determining the absolute configuration of chiral centers in pharmaceuticals.
- Please assign priorities for the groups on the indicated chiral centers and then rotate the molecule such that the lowest priority group is facing back into the plane of the paper. For help please view the chemical structures of these molecules using the supporting files.
- Using Avogadro to assist, please assign the absolute configuration all the chiral centers in the molecule amoxicillin.
Part 2: Examining the Energy Differences Between Enantiomers and Diastereomers.
- Using the energy data provided in table 1, please determine the \(\Delta G\) values for the D and L enantiomers of threonine in kcal/mol. 1 Hartree (Eh) = 627.5 kcal/mol.\[\Delta G_{\text {Enantiomers }}=G_L - G_D \nonumber \]
- Using the energy data provided in table 1, please determine the \(\Delta G\) between L-Threonine and L-Allothreonine in kcal/mol. 1 Hartree (Eh) = 627.5 kcal/mol. Is this number what you would have expected when compared to the \(\Delta G\) value between the enantiomers of threonine? Explain. \[\Delta G_{\text {Diastereomers }}=G_{\text {LThreonine }} - G_{\text {LAllothreonine }} \nonumber \]
- Examine the ground state structures L/D-Threonine and L/D-Allothreonine in Avogadro. Propose a reason why the energy values are different between enantiomers of threonine and enantiomers of allothreonine.