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Identify the sugar in each description.a. An aldopentose

Chapter 21, Problem 33P

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QUESTION:

Problem 33P

Identify the sugar in each description.

a. An aldopentose that is not D-arabinose forms D-arabinitol when it is reduced with NaBH4.

b. A sugar that is not D-altrose forms D-altraric acid when it is oxidized with nitric acid.

c. A ketose that, when reduced with NaBH4, forms D-altritol and D-allitol.

Questions & Answers

QUESTION:

Problem 33P

Identify the sugar in each description.

a. An aldopentose that is not D-arabinose forms D-arabinitol when it is reduced with NaBH4.

b. A sugar that is not D-altrose forms D-altraric acid when it is oxidized with nitric acid.

c. A ketose that, when reduced with NaBH4, forms D-altritol and D-allitol.

ANSWER:

Solution 33P

(a)

When D-arabinose is treated with NaBH4 followed by workup using dilute acid the aldehyde group is reduced into primary alcohol.

Now, another aldopentose which is not D-arabinose gives the same reduced product. Hence the probable structure of that compound could be that of opposite of arabinose i.e. the terminal CHO and CH2OH groups interchanged.

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