Rotation around C2-C3 in n-butane


So far, we have seen the rotation around the carbon-carbon axis of ethane and propane. In this exercise, we will be looking at the rotation around the C2-C3 axis of n-butane. Going from ethane to propane, nothing really unexpected happened; the energy profile looked quite the same, except for the slightly larger rotational barrier in propane.
For butane however, we get a really different energy profile:


Background


Whereas the energy profiles for rotation in ethane and propane were purely sinusoidal (i.e. only one maximum and one minimum energy, both repeated every 120°), the profile for butane contains local minima and maxima. Let's step through them, starting with the easy ones:

With this in mind, answer the question regarding the models below:

A B C D

Above are four models of 1,2-dichloroethane. Which of the lines below lists the conformations in order of decreasing energy?

  1. D - A - C - B
  2. D - C - B - A
  3. A - D - C - B
  4. A - C - B - D
  5. D - C - A - B
  6. B - A - C - D

At this point one should keep in mind that the animation shown above is only one particular degree of freedom for the molecule. Many more are possible, and the actual motion of the molecule butane will be a combination of these. To get an impression,
animate the structure on the left (on/off).

The next part is the quiz!



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