https://auckland.h5p.

com/lti/launch

1a - Models of Enantiomers and Diastereomers

Paste an image of the molecule you prepared in activity 1a

(limonene)

1b - Models of Enantiomers and Diastereomers

Paste an image of the (R,R) isomer BEFORE performing the ‘equilibrium conformer’
calculation in the box below.

(R,R) - 2,3-difluorobutane

Is this consistent with what you would expect for the most stable conformer of this molecule?
Explain your reasoning.

- Yes. The (R,R) and (S,S) enantiomers have the same energy level whilst (R,S) and
(S,R) diastereomers have different energy levels due to their different spatial
arrangement of atoms.
Paste images of the four isomers of 2,3-difluorobutane into the boxes below.

(R,S) (S,R)

(R,R) (S,S)

Are these in line with what you would expect for the most stable conformers of each
molecule? Why/why not?

- No. Although it is in line with the (R,R) and (S,S) enantiomer, but not for the (R,S)
and (S,R) diastereomer because its calculations (both have an equilibrium conformer
of 49.29kJ/mol) are the same. I would have expected them to be different due to their
different spatial arrangements.

Did the pair(s) of enantiomers have the same energy? What about the pairs of
diastereomers? How might you explain this?

- Yes, the pairs of enantiomers have the same energy due to having their atoms
arranged in the same way.
- Although the (R,S)-2,3-difluorobutane have a minimised energy of 49.29kJ/mol and
(S,R)-2,3-difluorobutane have a minimised energy of 50.86kJ/mol, they both have an
equilibrium conformer energy 49.29kJ/mol. This may have been because the overall
 energy difference between the two diastereomers is quite small and as such may
have been considered energetically equivalent.

2b - Electrostatic Potential Maps

Paste the electrostatic potential maps for aspirin and your two analogues in the space below.

(Aspirin)

(Analogue 1)
(Analogue 2)

Are your electrostatic potential maps consistent with your predictions about the relative
polarities of the three molecules? Explain your reasoning.