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Chapter 23: Q24P (page 1226)

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

Short Answer

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An anomer is an epimer of a cyclic sugar which possess different configuration at the anomeric carbon. An epimer is one of a pair of stereoisomers which differs only at one stereocenter. For each set of anomers, there exists an alpha anomer and a beta anomer. Anomeric carbon is the hemiacetal or hemiketal carbon of that particular sugar. Fructose hasand-D-fructofuranose as anomers.

Step by step solution

01

Step-1.

An anomer is an epimer of a cyclic sugar which possess different configuration at the anomeric carbon. An epimer is one of a pair of stereoisomers which differs only at one stereocenter. For each set of anomers, there exists an alpha anomer and a beta anomer. Anomeric carbon is the hemiacetal or hemiketal carbon of that particular sugar. Fructose hasand-D-fructofuranose as anomers.

02

Step-2.

Treatment of either anomer of fructose with excess ethanol and trace of hydrochloric acid gives a mixture of and anomers of ethyl-D-fructofuranoside. Aglycone is the non-sugar part of the glycoside. Aglycone part is circled in both the products.

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Most popular questions from this chapter

Except for the Tollens test, basic aqueous conditions are generally avoided with sugars because they lead to fast isomerizations.

  1. Under basic conditions, the proton alpha to the aldehyde (or ketone) carbonyl group is reversibly removed, and the resulting enolate ion is no longer asymmetric. Reprotonation can occur on either face of the enolate, giving either the original structure or its epimer. Because a mixture of epimer results, this process is called epimerization. Propose a mechanism for the base-catalyzed equilibration of glucose to a mixture of glucose and its C2 epimer, mannose.
  2. Propose a mechanism for the isomerization of a ketose to an aldose, via the enediol intermediate, shown immediately above. Note that the enediol has twoprotons and removing one or the other gives two different enolate ions.

Question. (a) Figure 23-2 shows that the degradation of D-glucose gives D-arabinose, an aldopentose. Arabinose is most stable in its furanose form. Draw D-arabinofuranose.

(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Draw D-ribofuranose.

Draw and name the enantiomers of the sugars shown in Figure 23-2. Give the relative configuration (D or L) and the sign of the rotation in each case.

Draw the expected product of the reaction of the following sugars with excess methyl iodide and silver oxide.

  1. 伪-顿-蹿谤耻肠迟辞蹿耻谤补苍辞蝉别
  2. 尾-顿-驳补濒补肠迟辞辫测谤补苍辞蝉别

Draw the following sugar derivatives.

  1. ethyl-尾-D-glucopyranoside
  2. 2,3,4,6-tetra-O-ethyl-D-mannopyranose
  3. 1,3,6-tri-O-ethyl-D-fructofuranose
  4. Ethyl-2,3,4,6-tetra-O-methyl-尾-D-galactopyranoside
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