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Correct answer: 3
- Understand the substrate
The given compound is
This is a cyanohydrin-containing ketone. The structure can be viewed as:
- The carbonyl carbon of the ketone is planar and can react with .
- The adjacent carbon is already a stereogenic center because it is attached to:
Since the compound is given as , the reactant is a racemic mixture of two enantiomers.
- What happens on addition of HCN?
HCN adds to the ketone carbonyl:
Now the former carbonyl carbon also becomes a stereogenic center because it gets:
- the adjacent substituted carbon
So in the product there are two stereocenters.
- Maximum possible stereoisomers
With 2 stereocenters, the maximum number is:
These would normally be:
- Check for meso possibility
The product has the general form:
Both stereocenters have the same set of substituents. Therefore, the and forms are actually the same meso form due to an internal plane of symmetry.
Hence, total distinct stereoisomers are:
- one meso form
- one pair of enantiomers
So total number of stereoisomers:
- Effect of starting with a racemate
Since the starting material is , both enantiomers are present and reaction at the planar carbonyl carbon gives all possible product stereoisomers. Distinct products remain the same count: 3.
- Final answer
The derived answer matches the stored correct answer.
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