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As mentioned in .58, some molecules are chiral even though
Chapter 5, Problem 5.6(choose chapter or problem)
As mentioned in 5.58, some molecules are chiral even though they lack a chirality center. For example, consider the following two compounds and explain the source of chirality in each case: (a) PPh2 PPh2 (S)-BINAP (b)
Questions & Answers
QUESTION:
As mentioned in 5.58, some molecules are chiral even though they lack a chirality center. For example, consider the following two compounds and explain the source of chirality in each case: (a) PPh2 PPh2 (S)-BINAP (b)
ANSWER:Step 1 of 2
(a) Although BINAP has no traditional chiral centers, the steric bulk of the aromatic systems cause them to skew out of plane.
Because the naphthyl regions are so large and the diphenylphosphino groups are also so large, BINAP cannot rotate around the single bond connecting the two regions, causing it to remain locked in one of the two skewed forms and giving the molecule chirality.
This type of compound that has chirality due to the inability to rotate around a single bond is known as an atropisomer.