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Chapter 5

Q. 5.5

Distinguishing Chiral Compounds from Meso Compounds

Does cis-1,2-dimethylcyclobutane have any chirality centers? Is it chiral?

S t r a t e g y
To see whether a chirality center is present, look for a carbon atom bonded to four different groups. To see whether the molecule is chiral, look for the presence or absence of a symmetry plane. Not all molecules with chirality centers are chiral overall—meso compounds are an exception.


Verified Solution

A look at the structure of cis-1,2-dimethylcyclobutane shows that both methyl- bearing ring carbons (C1 and C2) are chirality centers. Overall, though, the compound is achiral because there is a symmetry plane bisecting the ring between C1 and C2. Thus, cis-1,2-dimethylcyclobutane is a meso compound.

Does cis-1,2-dimethylcyclobutane have any chirality centers? Is it chiral?