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Correct answer: 16
- Identify the stereochemical features of an aldohexose
An aldohexose has the open-chain structure:
So, in the open-chain form, the stereogenic centers are at:
That means there are 4 chiral centers in the open-chain aldohexose.
- What does D-configuration fix?
For sugars, D/L is determined by the configuration at the last chiral carbon (here ).
So if the aldohexose is specified to be in its D-configuration, then the configuration at is fixed.
Thus, among the 4 original chiral centers:
- is fixed,
- can vary.
Hence the number of possible open-chain D-aldohexoses is:
- Conversion to pyranose form
In pyranose formation, the aldehyde group at reacts with the hydroxyl group at to form a cyclic hemiacetal.
This creates a new stereocenter at the anomeric carbon .
For each open-chain D-aldohexose, there are therefore 2 anomers:
So total stereoisomers in pyranose form:
- Final answer
Therefore, the total number of stereoisomers in the pyranose form of a D-aldohexose is:
- Comparison with stored correct answer
Stored correct answer =
My derived answer =
The stored answer appears to have counted only the D-aldohexoses in open-chain form and did not include the additional anomeric stereocenter formed in the pyranose ring.
Hence, I disagree with the stored answer.
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