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An unknown ?-D-aldohexose has only one axial substituent.

Chapter 21, Problem 44P

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QUESTION:

Problem 44P

An unknown β-D-aldohexose has only one axial substituent. A Wohl degradation forms a compound which, when treated with sodium borohydride, forms an optically active alditol. This information allows you to arrive at two possible structures for the β-D-aldohexose.What experiment can you carry out to distinguish between the two possibilities?

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QUESTION:

Problem 44P

An unknown β-D-aldohexose has only one axial substituent. A Wohl degradation forms a compound which, when treated with sodium borohydride, forms an optically active alditol. This information allows you to arrive at two possible structures for the β-D-aldohexose.What experiment can you carry out to distinguish between the two possibilities?

ANSWER:

Solution 44P

From the given conditions we have the ?-D-aldohexose has only one axial substituent. This information gives three possibilities of the said aldohexose.

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