Concept explainers
(a)
Interpretation:
The product formed by the reaction of D-ribose with
Concept Introduction:
The reaction of
(a)
Explanation of Solution
The D-ribose is an aldopentose molecule. The carbonyl group present in D-ribose is
The D-ribitol is a meso compound and shows plane of symmetry. So, it is optically inactive.
(b)
Interpretation:
The product formed by the reaction of D-ribose with
Concept Introduction:
The reagent
(b)
Explanation of Solution
When the D-ribose molecule is made to react with
The D-ribitol is a meso compound and shows plane of symmetry. So, it is optically inactive.
(c)
Interpretation:
The product formed by the reaction of D-ribose with warm
Concept Introduction:
The reaction of warm
(c)
Explanation of Solution
The nitric acid (
The product formed is a meso compound and shows plane of symmetry. So, it is optically inactive.
(d)
Interpretation:
The product formed by the reaction of D-ribose with
Concept Introduction:
The reaction of
(d)
Explanation of Solution
When the D-ribose reacts with
The D-ribonic acid is a chiral molecule and is optically active.
(e)
Interpretation:
The product formed by the reaction of D-ribose with
Concept Introduction:
The reaction of
(e)
Explanation of Solution
The D-ribose molecule consumes
The products formed are achiral and are optically inactive.
(f)
Interpretation:
The product formed by the reaction of D-ribose with aniline (
(f)
Explanation of Solution
The D-galactose molecule reacts with aniline molecule and the aldehyde group of carbohydrate is reacted with the
The product formed is chiral and optically active.
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Chapter 25 Solutions
Organic Chemistry
- 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_forward(a) Figure 23-2 shows that the degradation of d-glucose gives d-arabinose, an aldopentose.Arabinose is most stable in its furanose form. Draw d-arabinofuranose.(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Drawd-ribofuranose.arrow_forwardMonosaccharide A is a diastereomer of d-lyxose. Treatment of A with nitric acid forms an optically inactive aldaric acid. A undergoes a Kiliani-Fischer synthesis to form B and C. B is oxidized by nitric acid to an optically active aldaric acid, and C is oxidized to an optically inactive aldaric acid. Wohl degradation of A forms D, which is oxidized by nitric acid to an optically inactive aldaric acid. Wohl degradation of D forms a d-aldotriose. Identify A, B, C, and D.arrow_forward
- Draw the structure of: (a) a polysaccharide formed by joining D-mannose units in 1->4-ß-glycosidic linkages; (b) a polysaccharide formed by joining D-glucose units in 1->6-a-glycosidic linkages. The polysaccharide in (b) is dextran, a component of dental plaque.arrow_forwardWhich D-aldopentoses are reduced to optically inactive alditols using NaBH4, CH3OH?arrow_forwardSub units G-J pleasearrow_forward
- Compound 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_forwardThere are three (3) vials labeled A, B, and C known to contain the following monosaccharides. All three samples reduce Tollens and Fehling. By oxidation with dilute HNO3 an optically active aldaric acid is obtained for sample A and the remaining two give products without optical activity. When the three samples were subjected to an alkaline medium, it was observed that, after a certain time, samples A and C reached the same value of the specific rotation [α]. Select the RIGHT alternative: (a) Sample A is Galactose. (b) Sample B is Alosa. (c) Samples A and C are not related to each other by an epimerization process. (d) Sample C is Talose. (e) Samples B and C are epimers.arrow_forwardAnswer the following questions. (I narrowed it down to only three subparts)arrow_forward
- Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a Daldotetrose that is oxidized to an optically active aldaric acid?arrow_forwardThe following observations are obtained after a D-hexose was made to react with several reagents: (1) The reactions of a D-hexose with (a) to (d) below yields an aldaric acid (a) NH₂OH, (b) (CH3CO)₂O, NaOCOCH 3, and, (c) NaOCH3, and then, (d) HNO3, H₂O (2) HNO3 oxidation of the same D-hexose gives an aldaric acid. Predict the structures of the three (3) possible hexoses that can undergo the above reactions?arrow_forwardAn unknown reducing disaccharide is found to be unaffected by invertase enzymes. Treatment with an a@galactosidasecleaves the disaccharide to give one molecule of d-fructose and one molecule of d-galactose. When the disaccharideis treated with excess iodomethane and silver oxide and then hydrolyzed in dilute acid, the products are2,3,4,6-tetra-O-methylgalactose and 1,3,4-tri-O-methylfructose. Propose a structure for this disaccharide, and give itscomplete systematic name.arrow_forward
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT