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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Organic Chemistry
- Given 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_forwardPredict the products formed when the following sugars react with excess acetic anhydrideand pyridine.(a) a-d-glucopyranosearrow_forward
- An 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_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_forwardDraw 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_forward
- 31. Which of the following statements about cholesterol is not correct? CH. HO Cholesterol 16 (a) Cholesterol is a steroid that contains a tetracyclic ring system. (b) Cholesterol is a steroid that contains 8 chiral carbons and can form 28 or 256 stereoisomers. (c) Each atom or group attached to a ring-junction carbon (i.e., carbons a-e) is in a trans or axial position. Because of this the tetracyclic ring system is mostly flat. (d) Cholesterol is used to synthesized vitamin D, bile acids, sex hormones, and adrenocorticoid hormones. (e) Cholesterol is not found in the cell membranes of animals.arrow_forwardGive the products of periodic acid oxidation of each of the following. How many moles of reagent will be consumed per mole of substrate in each case? (a) d-Arabinose (b) d-Ribose (c) Methyl β-d-glucopyranosidearrow_forwardRuff 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_forward