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Chapter 28: Question 28.11 (page 1106)

Question: Referring to Figure 28.5, which d-ketohexoses have the S configuration at C3?

Fig. 28.5

Short Answer

Expert verified

Answer

All the d-ketohexoses have the R configuration.

Step by step solution

01

d-Ketohexoses

Any monosaccharide that has six carbon atoms with a ketone functional group with three chiral centers that rotate is known as a d-ketohexose. Examples of d-ketohexoses include fructose, psicose, sorbose, and tagatose

02

Identifying configuration

Among the given d-ketohexoses, the C3 carbon atom is a chiral center. The Fischer projections are converted to the wedge and dash structures as follows.

From the wedge-dash structures, all the d-ketohexoses have the R configuration.

Wedge-dash structures of the given ketohexoses

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Most popular questions from this chapter

Question: Draw two possible epimers of D-erythrose. Name each of these compounds using Figure 28.4.

Draw the尾 anomer of a monosaccharide epimeric with D-glucose at C2 using a Haworth projection.

Draw a stepwise mechanism for the following reaction.

A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani-Fischer synthesis, A is converted to two D-aldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A-C?

Consider the following six compounds (A-F).


How are the two compounds in each pair related? Choose from enantiomers, epimers, diastereomers but not epimers, constitutional isomers, and identical compounds.

A and B

A and C

B and C

A and D

E and F
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