If there is no rotation of plane polarised light by a compound in a specific solvent, though thought to be chiral, it may mean that
- the compound is certainly meso
- there is no compound in the solvent
- the compound may be a racemic mixture
- the compound is certainly achiral.
Answer
(1) the compound is certainly meso
Solution
A compound containing chiral carbon atoms is expected to be optically active.
∵ In a meso compound the molecule has a plane of symmetry; the rotation caused by one half of the molecule is exactly cancelled by the other half (internal compensation).
⇒ The compound shows no rotation of plane polarised light even though it contains chiral centres, e.g. meso-tartaric acid.
As per NCERT, a racemic mixture also shows zero optical rotation, but it is an equimolar mixture of two enantiomers (external compensation), not a single compound.
∴ The single compound showing no rotation is a meso compound.
Answer: (1)