Concept explainers
Interpretation:
The structure of the key intermediate when
Concept introduction:
Disaccharides are carbohydrates that yield two monosaccharide molecules on hydrolysis.
Disaccharides are glycosides in which the alkoxy group attached to the anomeric carbon atom is derived from a second sugar molecule.
Maltose is made up from hydrolysis of starch.
In maltose, two
The linkage in maltose is called
The change from one anomeric form to the equilibrium mixture is accompanied by a change in optical rotation is termed as mutarotation.
Diasaccharides undergo mutarotation when dissolved in water.
The mutarotation is a slow process in aqueous solutions but can be catalyzed by either acid or base.
A base abstracts an acidic proton in the given structure.
The flow of electrons in the mechanism is shown by the curved arrows.
The open chain form of the sugar is the key intermediate in the mutarotation of disaccharides.
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CAREY: ORGANIC CHEMISTRY
- Identify the organic functional group and reaction type for the following reaction. The reactant is a(n) - carboxylic acid hexose - Aldohexose - aldotetrose -deoxyhexose -carboxylic acid tetrose - ketohexose The product is a(n) - carboxylic acid tetrose - aldotetrose -alcohol hexose -aldohexose -carboxylic acid hexose - alcohol tetrose The reaction type is - hemiacetal formation -hydrolysis -oxidation( Benedict’s) -acetal formation -reduction( hydrogenation) - mutarotationarrow_forwardDraw the structure of the expected product when monosaccharide A undergo mutarotation upon dissolving in water in the presence of Tollens reagent (AgNO3, NH4OH).arrow_forwardA D-aldohexose A is formed from an aldopentose B by the Kiliani-Fischer synthesis. Reduction of A with NABH4 forms an optically inactive alditol. Oxidation of B forms an optically active aldaric acid. What are the structures of A and B?arrow_forward
- In 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_forwardC. Trehalose and maltose are both dimers of glucose. However, they have considereably different reactivities. Concisely explain why these differences are observed. HO НО НО HO Но HO OH Он HO OHOH Но trehalose maltose 1. Malthose is a reducing sugar while trehalose is not. 2. Trehalose is very resistant to acid hydrolysis while maltose can be acid-hydrolyzed with ease.arrow_forwardWhy can isomaltose be easily hydrolyzed through acid hydrolysis while trehalose cannot undergo acid hydrolysis?arrow_forward
- Carbonic anhydrase facilitates the dissolution of carbon dioxide gas into water by catalyzing its hydration. Is the catalyzed reaction efficient? By what criterion do you state that?arrow_forwardTrehalose and maltose are both dimers of glucose. However, they have considereably different reactivities. Concisely explain why these differences are observed. но но HO HO но "HO он но он OH O HO OHOH но trehalose maltose 1. Malthose is a reducing sugar while trehalose is not. 2. Trehalose is very resistant to acid hydrolysis while maltose can be acid-hydrolyzed with ease.arrow_forwardDraw the structures of the individual mutarotating a and b anomers of maltose.arrow_forward
- In glycoside formation, the hemiacetal functional group of a cyclic monosaccharide is converted to an acetal group by reaction with a(an)arrow_forwardExplain the group transfer reaction of glycosidic bond formation by describing the attacking nucleophile, the atom attacked, and the leaving group.arrow_forwardCellobiose, 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?arrow_forward
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