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Concept explainers
(a)
Interpretation:
The structure and name of the aldose and
Concept introduction:
The compounds which are composed of carbon, hydrogen, and oxygen possessing the general formula,
(b)
Interpretation:
The structure and name of the aldose and
Concept introduction:
The compounds which are composed of carbon, hydrogen, and oxygen possessing the general formula,
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Chapter 24 Solutions
EBK ORGANIC CHEMISTRY
- (a) Label all the O atoms that are part of a glycoside in rebaudioside A. Rebaudioside A, marketed under the trade name Truvia, is a sweet glycoside obtained from the stevia plant, which has been used for centuries in Paraguay to sweeten foods. (b) The alcohol or phenol formed from the hydrolysis of a glycoside is called an aglycon. What aglycon and monosaccharides are formed by the hydrolysis of rebaudioside A?arrow_forwardGiven the following structure of aldose, (a) how many chiral carbons are there? (b) is it a reducing sugar? and (c) is it an L or D sugar?arrow_forwardCompound 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_forward
- Predict the products formed when the following sugars react with excess acetic anhydrideand pyridine.(a) a-d-glucopyranosearrow_forwardAn optically active D-aldopentose (A) produced an optically inactive alditol (B) upon treatment with H2/Pt. When the aldopentose (A) was subjected to a Ruff degradation, D-aldotetrose (C) was generated. The aldotetrose (C) gave an optically active aldaric acid (D) upon oxidation with HNO3. D-aldopentose (A) can be prepared from D-threose by a Killani Fischer synthesis. Propose structure of A through D.arrow_forwardWhy is molecule "A" the major acetal formed when d-erythrose reacts with H2SO4 and acetone as opposed to molecule "B"?arrow_forward
- Ruff degradation of d-arabinose gives d-erythrose. The Kiliani–Fischer synthesis converts d-erythrose to a mixture of d-arabinose and d-ribose. Draw out these reactions, andgive the structure of d-ribosearrow_forwardA D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?arrow_forward(i) Acetylation of glucose with acetic anhydride gives glucose pentacetate. Write the structure of the pentacetate. (ii) Explain – Why glucose pentacetate does not react with hydroxylamine?arrow_forward
- 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-Ribose (b) D-Galactose (c) D- Fructosearrow_forward1. 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_forwardWhich aldoses are oxidized to optically inactive aldaric acids: (a) D-erythrose; (b) Dlyxose; (c) D-galactose?arrow_forward
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