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Chapter 23: Q48P (page 1255)

Use fig. 23-3 (the D-family of aldoses) to name the following aldoses.

(a) The C2 epimer of D-xylose

(b) The C3 epimer of D-erythrose

(c) The C3 epimer of D-altros

(d) The enantiomer of D-talose

(e) The C-5 epimer of D-idose

Short Answer

Expert verified

(a) The C2 epimer of D-xylose:

(b) The C3 epimer of D-erythrose

(c) The C3 epimer of D-altros

(d) The enantiomer of D-talose:

(e) The C-5 epimer of D-idose:

Step by step solution

01

(a) The C2 epimer of D-xylose:  

C2 epimer of D-xylose is D-lyxose:

02

(b) The C3 epimer of D-erythrose:

C3 epimer of D-erythrose is L-Threose:

03

(c) The C3 epimer of D-altros:

C3 epimer of D-altros is D-mannose:

04

(d) The enantiomer of D-talose:

The enantiomer of D-talose is L-talose

05

(e) The C-5 epimer of D-idose:

The C-5 epimer of D-idose is L-glucose:

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Most popular questions from this chapter

Draw the Haworth projection for the cyclic structure of D-mannose by laying down the Fischer projection.

(a) Which of the D-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?

(b) Which of the D-aldotetroses will give optically active aldaric acids on oxidation withHNO3 ?

(c) Sugar X is known to be a D-aldohexose. On oxidation with HNO3 , X gives an optically inactive aldaric acid. When X is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine the structure of X.

(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an optically active aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form optically active products?

(e) Show what products results if the aldopentose formed from degradation of X is further degraded to an aldotetrose. DoesHNO3 oxidize this aldotetrose to an optically active aldaric acid?

. (a) An aliphatic aminoglycoside is relatively stable to base, but it is quickly hydrolyzed by dilute acid. Propose a mechanism for the acid-catalyzed hydrolysis.

(b) Ribonucleosides are not so easily hydrolyzed, requiring relatively strong acid. Using your mechanism for part (a), show why cytidine and adenosine (for example) are not so readily hydrolyzed. Explain why this stability is important for living organisms.

Show the products that result from hydrolysis of amygdalin in dilute acid. Can you suggest why amygdalin might be toxic to tumor (and possibly other) cells?

Treatment of either anomer of fructose with excess ethanol in the presence of a trace of HCI gives a mixture of the α and β anomers of ethyl-D-fructofuranoside. Draw the starting materials, reagents, and products for this reaction. Circle the aglycone in each product.
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