Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 24, Problem 24.33P
Interpretation Introduction
Interpretation:
The product(s) obtained when cellulose is treated first exhaustively with dimethyl sulfate/
Concept introduction:
The hydrolysis of the disaccharides is done in the presence of an acid which acts as a catalyst. The hydrolysis of the disaccharide breaks the glycosidic linkage to give two monosaccharide units. Glycosidic linkage is linkage present between two monosaccharide units and this linkage gets hydrolyzed in the presence of an acidic solution.
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Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four-membered, five-membered, or six-membered ring. To determine which
ring is formed, ribose is treated with methanol in the presence of an acid catalyst. The products are then isolated and treated with NaIO4 then with H30*.
OH
Меон
1. NalO4
2. H30*
A & B
MEOH + products
HO
H.
H*
isomeric cyclic
acetals with
formula CgH1205
ÕH
ÕH
Ribose, C5H1005
Assuming that ribose formed a six-membered ring cyclic hemiacetal, draw the structure of compounds A and B.
Which of the following is NOT correctly paired?
- cellulose: beta-1,4-glycosidic linkage
- amylose: alpha-1,4-glycosidic linkage
- chitosan: alpha-1,4-glycosidic linkage
- cellubiose: beta-1,4-glycosidic linkage
H-
-OH
HO H
H OH
но-
Но
но-
--
H-
-OH
H-
-OH
но-
-OH
H-
-OH-
-OH
H OH
OH
он
OH
II
Two sugars differing in configuration at a single asymmetric carbon atom are known as
epimers.
D-mannose is a C-2 epimer of glucose (Structure I), while D-galactose is a C-4 epimer of
glucose. Structure || and III are
II: galactose, Ill: mannose
Il: mannose; II: galactose
Il and III are mannose
Il and III are galactose
OH
ÇOOH
HO H
H OH
H OH
COOH
HO H
но,
но,
II
What will be the result if Structure III is subjected to Benedict's test?
solution will change to red
solution will change to purple
silver mirror will form
no change in color
Sugar alcohols (alditols) are formed by chemically reducing aldoses or ketoses. Which one of the following sugars will give a negative Benedict's Test?
aldopentoses
alditols
2- Ketopentoses
an aldose undergoing mutarotation in solution
Chapter 24 Solutions
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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- Carbohydrates. Determination of the extent of branching in glycogen. The amount of branching (number of α 1⟶ 6 glycosidic bonds) in glycogen can be determined by the following procedure. A sample of glycogen is exhaustively methylated-treated with a methylating agent (methyl iodide) that replaces the hydrogen of every sugar hydroxyl with a methyl group, converting –OH to –OCH3. All the glycosidic bonds in the treated sample are then hydrolyzed in aqueous acid, and the amounts of α -D-2,3-di-O-methylglucopyranose and α -D-2,3,6-tri-O-methylglucopyranose formed are measured. 1- Draw the cyclic structure of α-D-glucopyranose, α-D-2,3-di-O-methylglucopyranose and α-D-2,3,6-tri-O-methylglucopyranose, including the numbering of carbon atoms. 2- Which of α-D-2,3-di-O-methylglucopyranose or α-D-2,3,6-tri-O-methylglucopyranose represents a glucose unit in glycogen which was originally carrying a α 1⟶ 6 glycosidic bond? Explain.arrow_forwardWhat is the product of the starting material D-glyceraldehyde which will (1) produce aldaric acid upon reacting with HNO3 + H2O, NaOCH2, NH2OH, and (CH3CO)2O + NaOCOCH3 (2) produce tartaric acid upon reacting with HNO3 + H2O, NaOCH3, NH2OH, and (CH3CO)2O + NaOCOCH3arrow_forwardGive the major organic product that is formed when the primary hydroxyl group of the following monosaccharide undergo nucleophilic substitution reaction with acetic anhydridearrow_forward
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- Part A What are glycosides, and how can they be formed? A glycoside is the acetal product that results from rerction of the hemiacetal -OH group of a carbohydrate with an aldehyd O A glycoside is the acetal product that results from reaction of the hemiacetal-OH group of a carbohydrate with an alcohol. A glycoside is the hemiacetal product that results from reaction of the acetal-OH group of a carbohydrate with an alcohol. Submit Previous Answers Request Answerarrow_forward2. Identify the carbon atoms of the carbohydrate rings at which the oxidation takes place by circling the carbon atoms in the structure that become an aldehyde or ketone group. Note: do this for the reducing sugars only! H -OH H HO Po-glucose он HO OCH, methyl e-D-glucoside но. HO OH OH a-D-fructone он HO HO HO, H HỌ HO- OH Suarose HO- HO maltosearrow_forwardDraw the products formed when β-D-galactose is treated with each reagent. a. Ag2O + CH3I b. NaH + C6H5CH2Cl c. The product in (b), then H3O+ d. Ac2O + pyridine e. C6H5COCl + pyridine f. The product in (c), then C6H5COCl + pyridinearrow_forward
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