EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Question
Chapter 24, Problem 24.28P
Interpretation Introduction
Interpretation:
The structure of aldehexose A which on reaction with nitric acid gives aldaric acid is to be identified
Concept introduction:
Aldoses are the carbohydrates in which an
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Check out a sample textbook solutionStudents have asked these similar questions
Draw the structures (using chair conformations of pyranoses) of the following disaccharides.(a) 4-O-(a-d-glucopyranosyl)-d-galactopyranose(
Lactose is a disaccharide in which a glycosidic linkage
connects the monosaccharides galactose and glucose.
OH
НО
OH
(a) Identify the glycosidic linkage and the acetal carbon
in lactose.
(b) What type of glycosidic linkage does lactose have
(i.e., is it 1,1'-, 1,2'-, etc., and is it a or B)?
(c) People who are lactose intolerant are deficient in
the enzyme lactase, and therefore cannot efficiently
break down the disaccharide into its monosaccharides. When lactose is treated with aqueous acid, however, this
hydrolysis can take place, though relatively slowly. Draw the complete, detailed mechanism and the products of the
acid-catalyzed hydrolysis of lactose.
Но
ОН
НО
ОН
ОН
Lactose
b) Compounds A and B have the following properties:
Compound A (C5H1005) is an optically active D-pentose that exists exclusively as an acyclic molecule. (Hint:
that sentence alone completely determines the structure of A! But we generously give you more information.)
• Compound A does not react with Br₂/H₂O.
• Reduction of A with NaBH4 gives only one product, B (C5H12O5), which is optically active.
Write acyclic Fischer projection structures of A and B.
Chapter 24 Solutions
EBK ORGANIC CHEMISTRY
Ch. 24 - Prob. 24.1PCh. 24 - Prob. 24.2PCh. 24 - Prob. 24.3PCh. 24 - Prob. 24.4PCh. 24 - Prob. 24.5PCh. 24 - Prob. 24.6PCh. 24 - Prob. 24.7PCh. 24 - Prob. 24.8PCh. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Prob. 24.15PCh. 24 - Prob. 24.16PCh. 24 - Prob. 24.17PCh. 24 - Prob. 24.18PCh. 24 - Prob. 24.19PCh. 24 - Prob. 24.20PCh. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Prob. 24.24PCh. 24 - Prob. 24.25PCh. 24 - Prob. 24.26PCh. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - Prob. 24.34APCh. 24 - Prob. 24.35APCh. 24 - Prob. 24.36APCh. 24 - Prob. 24.37APCh. 24 - Prob. 24.38APCh. 24 - Prob. 24.39APCh. 24 - Prob. 24.40APCh. 24 - Prob. 24.41APCh. 24 - Prob. 24.42APCh. 24 - Prob. 24.43APCh. 24 - Prob. 24.44APCh. 24 - Prob. 24.45APCh. 24 - Prob. 24.46APCh. 24 - Prob. 24.47APCh. 24 - Prob. 24.49APCh. 24 - Prob. 24.50APCh. 24 - Prob. 24.51APCh. 24 - Prob. 24.52APCh. 24 - Prob. 24.53APCh. 24 - Prob. 24.54APCh. 24 - Prob. 24.55APCh. 24 - Prob. 24.56APCh. 24 - Prob. 24.57APCh. 24 - Prob. 24.58APCh. 24 - Prob. 24.59APCh. 24 - Prob. 24.60APCh. 24 - Prob. 24.61APCh. 24 - Prob. 24.62AP
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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
- Compound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid F. What is the structure of compound F? • Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it. • Show stereochemistry in a meso compound. • Do not include lone pairs in your answer. They will not be considered in the grading.arrow_forwardGlycosaminoglycans (GAGs) are heteropolysaccharides composed of repeating disaccharide units. These units have some similar characteristics that allow them to be identified as GAGS. Which of the structures are examples of glycosaminoglycans? А. C. E. HO HO COO™ H Н ОН Н CH₂OH H H H OH OH Н CH₂OH Н OH H ОН o,so H H Н CH₂OH H H ОН H CH₂OSO H NH C=0 CH, H H Н NH c=0 CH3 H CH,OH OH Н ОН OH H B. D. Н НО H ОН H CH₂OH H ОН Н СОО ОН Н Н H H OSoz H Н OH б H CH₂OH ОН CH₂OSO H ОН H Н OSO, H Н NHSO,arrow_forwardArrange the following sugars according to their DECREASING reactivity with Benedict's reagent. [Fructose, maltose, glucose, sucrose, starch]arrow_forward
- Consider the following compound, which is used by insects and some fungi to store energy:arrow_forwardHow many chiral centers are in B-d-glucopyranose and a-D-galactopyranose? How many stereoisomers of these two aldohexoses can theoretically be drawn?arrow_forwardTrehalose and isomaltose are both dimers of glucose. However, they have considerablydifferent reactivities. Concisely explain why these differences are observed.arrow_forward
- Draw the structure of alpha-d-glucopyranose in straight chain cyclic, Haworth and cyclohexane-chair format. Draw the structures of two aldohexoses which are diastereomers but not epimersarrow_forwardProvide suitable responses for questions (a) –(j).| 6 CH2OH 4 ОН OH OH 2.arrow_forwardArrange the following sugars according to their DECREASING reactivity with Benedict’s reagent. [fructose, starch, maltose, sucrose, glucose]arrow_forward
- 1. Draw the two possible Haworth structures (both alpha and beta anomers) for the following monosaccharides and give their corresponding systematic names. [Show the stepwise process] (a) D-Ribosearrow_forwardXylulose has the following structural formula. To what carbohydrate class does xylulose belong based on the number of carbons and carbonyl functionality? A) aldotetrose B) aldopentose C) ketotetrose D) ketopentose E) ketohexosearrow_forwardPlease solve thisarrow_forward
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