Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 20, Problem 63P
Interpretation Introduction
Interpretation:
The mechanism that accounts for the incorporation of the deuterium atoms into
Concept Introduction:
Fructose exists as either a free sugar or in polysaccharide forms. The minor tautomers of fructose are
Tautomers are the isomers which makes the difference in the position of protons.
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When d-fructose is dissolved in D2O and the solution is made basic, the d-fructose recovered from the solution has an average of 1.7 deuterium atomsattached to the C-1 carbon per molecule. Show the mechanism that accounts for the incorporation of these deuterium atoms into d-fructose.
Show that Ruff degradation of d-mannose gives the same aldopentose (d-arabinose) asdoes d-glucose
The 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-sugars
Chapter 20 Solutions
Organic Chemistry (8th Edition)
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Prob. 4PCh. 20.3 - Prob. 5PCh. 20.3 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - Prob. 8PCh. 20.5 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.5 - Prob. 11PCh. 20.6 - Prob. 12PCh. 20.6 - Prob. 13PCh. 20.6 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.8 - Prob. 16PCh. 20.9 - Prob. 18PCh. 20.10 - Prob. 20PCh. 20.10 - Prob. 21PCh. 20.10 - Prob. 22PCh. 20.11 - Prob. 23PCh. 20.11 - Prob. 24PCh. 20.12 - Prob. 25PCh. 20.12 - Prob. 26PCh. 20.14 - Prob. 28PCh. 20.15 - Prob. 29PCh. 20.15 - Prob. 30PCh. 20.16 - Prob. 31PCh. 20.17 - Prob. 32PCh. 20.18 - Refer to Figure 20.5 to answer the following...Ch. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Prob. 43PCh. 20 - Prob. 44PCh. 20 - Prob. 45PCh. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - The 1H NMR spectrum of D-glucose in D2O exhibits...Ch. 20 - Prob. 50PCh. 20 - Prob. 51PCh. 20 - Prob. 52PCh. 20 - Prob. 53PCh. 20 - Prob. 54PCh. 20 - Prob. 55PCh. 20 - Prob. 56PCh. 20 - Prob. 57PCh. 20 - Prob. 58PCh. 20 - Prob. 59PCh. 20 - Prob. 60PCh. 20 - Prob. 61PCh. 20 - A hexose is obtained when the residue of a shrub...Ch. 20 - Prob. 63PCh. 20 - Prob. 64PCh. 20 - Prob. 65PCh. 20 - Prob. 66PCh. 20 - Prob. 67PCh. 20 - Prob. 68PCh. 20 - Prob. 69PCh. 20 - Prob. 70PCh. 20 - Prob. 71PCh. 20 - Prob. 72PCh. 20 - Prob. 73P
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- D-Glicose reacts with acetone in the presence of acid to yield the nonreducing 1, 2: 5, 6-diisopropylidene-D-glucofuranose. Propose a mechanism.arrow_forwardDraw the mechanism for the formation of b-lactose from α-d-galactose and β-d-glucose in dilute HCl.arrow_forwardD-Tagatose is epimeric of D-Fructose at C4. What is the structure of α-D-Tagatofuranose?arrow_forward
- d-Altrose is an aldohexose. Ruff degradation of d-altrose gives the same aldopentose asdoes degradation of d-allose, the C3 epimer of glucose. Give the structure of d-altrosearrow_forwardDraw the acid-catalysed mechanism whereby D-fructose cyclizes to α-D-fructofuranose.arrow_forwarddoes structure E represent fructofuranose? explainarrow_forward
- Illustrate (hand-drawn) the mechanism of intrahemiacetal or intrahemiketal formation in the following monosaccharides and identify/draw the possible products of these reactions. A. D-talose B. D-fructosearrow_forwardDeduce the structure of the disaccharide isomaltose from the following data.a. Hydrolysis yields D-glucose exclusively. b. Isomaltose is cleaved with α-glycosidase enzymes. c. Isomaltose is a reducing sugar. d. Methylation with excess CH3I, Ag2O and then hydrolysis with H3O+ forms two products:arrow_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
- Show the steps in converting Fischer to Haworth to: Convert D-Talose to its aIpha pyranose structure. Convert D-Tagatose to its beta furanose structure.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_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
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