Conformational analysis comes from the classical renaissance of physical organic chemistry in the 1950s and 60s. The following problem is taken from E. D. Hughes and J. Wilby J. Chem. Soc., 1960, 4094-4101, DOI: 10.1039/JR9600004094, the essence of which is that Hofmann elimination of a neomenthyl derivative (C below) was observed as anomalously faster than its menthyl analogue. Of course, what is anomalous in one decade is a standard student problem (and one Nobel prize) five decades later.
One can pose two questions about these systems:
Its a problem that simply requires a model to be built for its solution. And probably some hints. I give the students two:
So that I do not spoil your fun, I will not reveal (my) answers here, but in the next post. Try writing down answers to these two questions, and see if they agree with mine!
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