Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16, Problem 35P
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.
Draw the mechanism for the formation of b-lactose from α-d-galactose and β-d-glucose in dilute HCl.
An important technique for establishing relative configurations among isomeric aldoses and ketoses is to convert both terminal carbon atoms to the same functional group. This can be done either by selective oxidation or reduction. As a specific example, nitric acid oxidation of d-erythrose gives meso-tartaric acid . Similar oxidation of d-threose gives (2S,3S)-tartaric acid. Given this information and the fact that d-erythrose and d-threose are diastereomers, draw Fischer projections for d-erythrose and d-threose. Check your answers against Table 25.1.
Chapter 16 Solutions
Essential Organic Chemistry, Global Edition
Ch. 16.1 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.3 - Prob. 3PCh. 16.3 - Prob. 4PCh. 16.4 - Prob. 5PCh. 16.4 - Prob. 6PCh. 16.5 - Prob. 7PCh. 16.5 - Prob. 8PCh. 16.6 - Prob. 10PCh. 16.8 - Prob. 12P
Ch. 16.8 - Prob. 14PCh. 16.9 - Prob. 15PCh. 16.10 - Prob. 16PCh. 16.11 - Refer to Figure 16.4 to answer the following...Ch. 16 - Prob. 18PCh. 16 - Prob. 19PCh. 16 - Prob. 20PCh. 16 - Prob. 21PCh. 16 - Prob. 22PCh. 16 - Prob. 23PCh. 16 - Prob. 24PCh. 16 - Prob. 25PCh. 16 - Name the following compounds:Ch. 16 - Prob. 28PCh. 16 - Prob. 29PCh. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Prob. 33PCh. 16 - Prob. 34PCh. 16 - Prob. 35PCh. 16 - Prob. 36PCh. 16 - Prob. 37PCh. 16 - Draw the mechanism for the acid-catalyzed...Ch. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41P
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- Draw the mechanism for the formation of B-lactose from a-D-galactose and B-D-glucose in dilute HCI.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_forwardcan you please add an explanation.arrow_forward
- Carbohydrates a. 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.) H HIC OH CH₂OH D-Glyceraldehydearrow_forwardCompound 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_forwardGive Detailed explanation Solutionarrow_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_forwardIdentify the sugar in description. An aldopentose that is not d-arabinose forms d-arabinitol when it is reduced with NaBH4.arrow_forward(d) Use the diagram below to complete the cyclic alpha form of structure V (e) Circle the hemiacetal in cyclic alpha form of structure V. (f) Redraw the cyclic alpha form of structure V but replace the OH group on the anomericcarbon with a methoxy group. Is this modified monosaccharide a reducing sugar or anonreducing sugar?arrow_forward
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