EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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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 H3O+.
OH
HO
OH
OH
Ribose, C5H10O5
H
MeOH
H*
A & B
isomeric cyclic
acetals with
formula C6H₁2O5
1. NalO4
2. H₂O*
MeOH products
Assuming that ribose formed a six-membered ring cyclic hemiacetal, draw the structure of the sodium periodate digestion
products.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
4) Structure:
the appropriate box.
CHO
-OH
H-
HO- -H
HO -H
Write the requested cyclized form of the given carbohydrates in
B-pyranose
a-furanose
CH₂OH
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.
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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- 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 NaIO, then with H₂O*. HO OH OH OH Ribose, C5H10O5 H 9.81 ** MeOH H* A & B isomeric cyclic acetals with formula C6H12O5 Assuming that ribose formed a five-membered ring cyclic hemiacetal, draw the structure of the sodium periodate digestion products. ▼ • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. 1. NalO4, 2. H₂O* MeOH products 4 SIF Previous Nextarrow_forwardWhat is the product (from the image below) 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_forwardSugar 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 solutionarrow_forward
- 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.arrow_forwardHow would the reactant react with (CH2=CH)2CuLi ?arrow_forwardShow the structure of the furfural products/derivatives of the given compounds which were subjected to Molisch Test. compounds: starch, sucrose, and glucosearrow_forward
- What 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_forwardThe reagent periodate (IO,") oxidatively cleaves the carbon-carbon bonds between two adjacent carbons carrying hydroxyl groups. Explain how pe- riodate oxidation might be used to distinguish between methyl glycosides of glucose in the pyranose and furanose forms.arrow_forwardWrite the structure(s) for the organic product(s) of the carbohydrate reaction below. ball & stick v + labels HOCH2 Ag20 in aq. NH3 OH or Br2 in H20, pH 6 HO OH a-D-glucopyranose • Use the wedge/hash bond tools to indicate stereochemistry where it exists. If two diastereomers are formed, draw both. • If no reaction occurs, draw the organic starting material. Draw carboxylic acids in neutral (unionized) form. • Use “flat" representations of rings, not chairs, in your drawing. Do not draw your answer as a Haworth projection.arrow_forward
- The oil flave in wintergreen is an ester made from reaction of o-hydroxybenzoic acid (salicylic acid) with methanol in presence of H+ and heat. ALso, aspirin is made by salicylic acid with acetic acid in in presence of H+ and heat. Please provide the structure:arrow_forwardIn solution, glucose is mostly found in the cyclic hemiacetal state, which lacks an aldehyde group. How are mild oxidising agents able to oxidise glucose?arrow_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_forward
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