Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305864504
Author: Brent L. Iverson, Sheila Iverson
Publisher: Cengage Learning
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Question
Chapter 25, Problem 25.27P
Interpretation Introduction
Interpretation:
When the four aldopentoses are reduced by
Concept Introduction:
The reagent
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Cellobiose, a disaccharide obtained by the hydrolysis of cellulose, is composed of two glucose units joined together in a 1→4-β-glycoside bond. What is the structure of cellobiose?
Monosaccharides are cyclic hemiacetals that can react with alcohols to form acetals. The bond between the
anomeric carbon atom of the monosaccharide and the oxygen atom of the -OR group is called a glycosidic bond. The
name of the linkage contains the designation alpha (a) or beta (B) (from the anomeric carbon in the glycosidic bond)
and the carbon numbers for the carbons from the two sugars. For this example, the linkage is an a-1,4 glycosidic
bond.
Н
НО
HO
اب تاب است
H
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H
OH
-OH
Н
Н
OH
H
+
OH HO
a anomer
CH₂OH
H
Н
H
О
OH H2C
OH
Н
H
Classify the glycosidic linkage in the disaccharide.
Н
OH
Н
H
OH
OH
OH
-
HO
Н
H
HO
OH
OH
Н
CH₂OH
H
-OH
H
OH
он
H
H
-OH
Н
OH
an a glycosidic bond
Н
OH
+ H2O
о
о
о
о
В-1,6
a-1,6
a-1,1
B-1,5
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Amygdalin is a toxic component in the pits of bitter almonds, peaches, and apricots.
Q.) Name the two monosaccharide units in amygdalin and describe the glycosidic bond by which they are joined.
Chapter 25 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
Ch. 25.1 - Prob. 25.1PCh. 25.2 - Prob. 25.2PCh. 25.2 - Prob. 25.3PCh. 25.3 - Prob. 25.4PCh. 25.3 - Prob. 25.5PCh. 25.3 - Prob. AQCh. 25.3 - Prob. BQCh. 25.3 - Prob. CQCh. 25.3 - Prob. DQCh. 25.3 - How many stereoisomers would result from the...
Ch. 25.4 - Prob. 25.6PCh. 25 - Prob. 25.7PCh. 25 - Prob. 25.8PCh. 25 - Prob. 25.9PCh. 25 - Prob. 25.10PCh. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Prob. 25.22PCh. 25 - Prob. 25.23PCh. 25 - Prob. 25.24PCh. 25 - Prob. 25.25PCh. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Prob. 25.28PCh. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Prob. 25.31PCh. 25 - Prob. 25.32PCh. 25 - Prob. 25.33PCh. 25 - Prob. 25.34PCh. 25 - In making candy or sugar syrups, sucrose is boiled...Ch. 25 - Prob. 25.36PCh. 25 - Prob. 25.37PCh. 25 - Prob. 25.38PCh. 25 - Prob. 25.39PCh. 25 - Prob. 25.40PCh. 25 - Prob. 25.41PCh. 25 - Prob. 25.42PCh. 25 - Prob. 25.43PCh. 25 - Digitalis is a preparation made from the dried...Ch. 25 - Prob. 25.45PCh. 25 - Prob. 25.46PCh. 25 - Prob. 25.47PCh. 25 - Prob. 25.48PCh. 25 - Prob. 25.49PCh. 25 - Prob. 25.50P
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- (d) Draw the structure of the expected product when monosaccharide B undergo mutarotation upon dissolving in water in the presence of Tollens reagent (AGNO3, NHẠOH). он OH O. OH OH OH monosaccharide Barrow_forwardThere are four d-aldopentoses (Table 25.1). If each is reduced with NaBH4, which yield optically active alditols? Which yield optically inactive alditols?arrow_forwardIn glycoside formation, the hemiacetal functional group of a cyclic monosaccharide is converted to an acetal group by reaction with a(an)arrow_forward
- Which of the following saccharides has INCORRECT paired description/s? * D-mannose: Monosaccharide: Prevents UTI Cellobiose: Disaccharide: With 2 glucose units Heparin: Acidic polysaccharide: Blood coagulant N-acetyl-galactosamine: Amino sugar: Present in type-A blood Keratin sulfate: Structural Polysaccharide: Most heterogenous GAGSarrow_forwardDraw the structures (using chair conformations of pyranoses) of the following disaccharides. a-d-fructofuranosyl-b-d-mannopyranoside(arrow_forwardWhich D-aldopentoses are reduced to optically inactive alditols using NaBH4, CH3OH?arrow_forward
- Name the three most abundant hexoses in the biological world. Which arealdohexoses, and which are ketohexoses?arrow_forwardWhich statement about saccharides is correct? (A). Alpha anomers are more common than beta anoomers. (B). Two monosaccharides can form a disaccharide and oxygen. (C). Polysaccharides with alpha or beta glycosidic linkages have the different properties. (D). Disaccharides can be cyclic or acyclic.arrow_forwarda) Draw Haworth projections of both - and -anomers of D-fructose. Indicate which carbon is the anomeric carbon.b) Sucrose is a disaccharide made up of a molecule of D-fructose and D-glucose. Draw the structure of sucrose clearly indicating the linkage between the two monosaccharides and its biological significance.c) Tollen’s reagent is a very mild oxidizing agent which normally oxidize aldehydes but not ketones. However, both glucose and fructose give positive results with Tollen’s reagent and are classified as reducing sugars. Explain how fructose can also give positive results with Tollen’s reagent (illustrate using structures).arrow_forward
- Show the dehydration reaction of the following disaccharides and describe their functions, importance, sources and structures. a. Lactose b. Maltose C. sucrosearrow_forwardi need an answer pleaseeeearrow_forwardDetermine the identity of each monosaccharide (aldopentose, ketotriose etc) How does each monomer differ from glucose? How is each monomer similar?arrow_forward
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