Solution: Which of the following compounds is a meso compound?

Problem

Which of the following compounds is a meso compound?

Solution

We’re being asked to identify the meso compound among the given structures.


Recall that meso compounds are superimposable mirror images despite having chiral centers. Meso compounds:

• have an internal line of symmetry achiral

• follow the 2n – 1 rule for total stereoisomers two stereoisomers are identical


A compound will be meso if it follows these criteria:

1. It has 2 or more chiral centers.

2. It is atomically symmetrical symmetrical in connectivity

3. An even number of chiral centers have opposite configuration (if one is R, the other should be S)


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