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Chapter 28: Question 28.54 (page 1149)

What products are formed when each compound is subjected to a Kiliani–Fischer synthesis?

(a.)

(b.)

Short Answer

Expert verified

Answer

(a.)

(b.)

Step by step solution

01

Kiliani-Fischer synthesis

In the Kiliani-Fischer reaction, the monosaccharide is synthesized by the addition of new chiral carbon to the open-chain aldehyde. Kiliani-Fischer increases the length of the chain.

02

Kiliani-Fischer synthesis of reactant a

(a) When ribose is subjected to Kiliani-Fischer, we get the following structures.

Product formation from reactant a

03

Kiliani-Fischer synthesis of reactant b

(b) When glucose is subjected to Kiliani-Fischer, we get the following structures.

Product formation from reactant b

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Most popular questions from this chapter

Convert each cyclic monosaccharide into its acyclic form.

(a.)

(b.)

(c.)

(d.)

The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the αorβ anomers of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.

How would you convert d-glucose into each compound? More than one step is required.

(a.)

(b.)

(c.)

Draw the structure of each of the following compounds:

a. a polysaccharide formed by joining1→6-α D-glucosamine in glycosidic linkages

b. a disaccharide formed by joining D-mannose and D glucose in a -1→4-βglycosidic linkage using mannose’s anomeric carbon

c. an -N-glycoside formed from D-ribose and thymine

d. a ribonucleoside formed from D-ribose and thymine

What products are formed when each compound is treated with aqueous acid?

(a.)

(b.)

(c.)
See all solutions

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