Concept explainers
Interpretation:
The number of chiral centers in the open chain form of
Concept Introduction:
The carbon atom which is bonded to four different groups is known as stereogenic or chiral center.
Sodium borohydride
The structural representation of sugar molecule in cyclic form is known as Haworth projection. Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose.
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EBK ORGANIC CHEMISTRY
- An 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_forwardSketch the Fischer projection of each Stereoisomer(R and S) of the monosaccharide glyceraldehyde, , HOCH2CHOHCHO. Prioritize the four groups attached to the stereocenter with 1 being the highest priority and 4 being the lowest priority.arrow_forwardd-Xylose and d-lyxose are formed when d-threose undergoes a Kiliani–Fischer synthesis. d-Xylose is oxidized to an optically inactive aldaric acid,whereas d-lyxose forms an optically active aldaric acid. What are the structures of d-xylose and d-lyxose?arrow_forward
- The anticoagulant heparin is a polysaccharide that contains alternating residues of -D- glucuronic acid-6- sulfate and N-sulfo-D-glucosamine-6sulfate connected by (1 B 4)- glycosidic linkages. Draw a part of heparin that shows one each of the two residues.arrow_forwardIdentify the configuration of the stereogenic center (R or S)arrow_forwardThe C2-epimer of D-xylose is called (blank 1). The enediol rearrangementconverts an aldose into a (blank 2). The aldopentose embedded in RNA is(blank 3). An aldopentose would have (blank 4) possible stereoisomers,of whichBlankwould be D-sugars. An ketopentose would have (blank 4) possiblestereoisomers, of which (blank 5) would be D-sugarsarrow_forward
- Compound Z is an aldopentose. If Z is oxidized with nitric acid the product is optically active. If Z undergoes one Ruff degradation and the product of that degradation is reduced to the alditol using H2/Ni the resulting product is optically inactive. If compound Z undergoes two Ruff degradations, D-glyceraldehyde (shown below) is obtained. Draw the usual Fischer projection of Z (aldehyde at the top). (Hint: work backwards from D- glyceraldehyde.)arrow_forwardThe relative configurations of the stereoisomers of tartaric acid were established by the following syntheses:(1) d@(+)@glyceraldehyde T diastereomers A and B (separated)(2) Hydrolysis of A and B using aqueous Ba(OH)2 gave C and D, respectively.(3) HNO3 oxidation of C and D gave (-)@tartaric acid and meso-tartaric acid, respectively.(a) You know the absolute configuration of d-(+)-glyceraldehyde. Use Fischer projections to show the absolute configurations of products A, B, C, and D.(b) Show the absolute configurations of the three stereoisomers of tartaric acid: (+)-tartaric acid, (-)-tartaric acid, andmeso-tartaric acid.arrow_forwardDraw the Fischer projection of the product of the reduction reaction of D-Talose at C1C1. Drag the appropriate labels to their respective targets.arrow_forward
- A 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_forwardDraw Fischer projections for the product(s) formed by reaction of d-ribose with the following. In addition, state whether each product is optically active or inactive Q. NaBH4 in H2Oarrow_forwardShow the structures of the following and give their names: C-2 epimer of D-galactose Beta anomer of alpha D-mannopyranose Alpha anomer of beta-D-lyxofuranose Enantiomer of L-ribulose Diastereomer of D-xylulose C-3 epimer of D-tagatose Illustrate what is asked for: Molecular formula of D-erythrulose Fischer projection formula of L-sorbose Haworth formula of alpha-D-idopyranose Number of stereoisomers formed by D-sorbosearrow_forward