EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
12th Edition
ISBN: 9781119233664
Author: Snyder
Publisher: VST
bartleby

Concept explainers

Question
Book Icon
Chapter 22, Problem 13PP
Interpretation Introduction

Interpretation:

The structure of L-(+)-threose and L-(+)-erythrose is to be represented and the aldotriose, which must be used for the preparation of the above-mentioned compounds in the Kiliani-Fischer synthesis, is to be determined.

Concept Introduction:

▸ The Kiliani-Fischer reaction is used for increasing the number of carbon atoms of an aldose molecule, as a result of the formation of the epimeric aldonic acid.

▸ It is an effective and economic process for the synthesis of monosaccharides by the process of hydrolysis of a cyanohydrin.

▸ Furthermore, it can also be used for the production of epimers of higher aldoses from a lower aldose, that is, a single aldose produces a mixture of two diastereomeric sugars called epimers.

Blurred answer
Students have asked these similar questions
An optically active D-aldopentose (A) produced an optically inactive alditol (B) upon treatment with H2/Pt. When the aldopentose (A) was subjected to a Ruff degradation, D-aldotetrose (C) was generated. The aldotetrose (C) gave an optically active aldaric acid (D) upon oxidation with HNO3. D-aldopentose (A) can be prepared from D-threose by a Killani Fischer synthesis. Propose structure of A through D.
b) Disaccharide E is a reducing sugar. It is hydrolyzed by an α-glycosidase enzyme, which means it contains an α- glycoside link. Treatment of E with Ag2O and excess MeDgives an octamethyl derivative F. Hydrolysis of F in dilute aqueous acid gives the pair of molecules shown below. Write the structures of E and F. (If the stereochemistry at a particular carbon is not determined by the above data, indicate this with a wavy line as shown below.) HO OMe OMe MeO MeO OH OMe Am OH OMe OMe
Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B alsoreacts with warm nitric acid to give an optically active aldaric acid, but A reacts to givean optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, whichgives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D isdegraded to (+)@glyceraldehyde. Deduce the structures of sugars A, B, C, and D, and useFigure 23-3 to determine the correct names of these sugars.
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning