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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

What two aldohexoses yield d-arabinose upon Wohl degradation?

Draw both pyranose anomers of each aldohexose using a three-dimensional representation with a chair pyranose. Label each anomers as αandβ.

(a.)

(b.)

Which aldoses are oxidized to optically inactive aldaric acids: (a) D-erythrose; (b) D-lyxose; (c) D-galactose?

Draw a Fischer projection of the monosaccharide from which each of the following glycosides was prepared.

Convert each compound to a Fischer projection and label each stereogenic center as R or S.

(a.)

(b.)

(c.)

(d.)

(e.)

(f.)
See all solutions

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