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_forwardUnder acidic conditions (catalytic amount of acid) in anhydrous methanol, D-galactose can be converted to the methyl galactopyranoside X on the right side of the reaction arrow. Write a detailed mechanism for the reaction. OH H+ HO HO `Me MeOH HO 'OH HO "OH OH OH Xarrow_forwardCarbohydrates 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_forward
- 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-sugarsarrow_forwardFrom the choices given below select the L-aldopentose that yields an optically inactive alditol upon reduction with NaBH4. Select ALL monosaccharides that satisfy the requirement, excluding the structure referenced in the question. Note that only D structures are shown. To select an L structure click on the name. If no selection exists, then select the referenced structure. H H H CHO -OH -OH +OH CH₂OH D-Ribose L-Ribose HO- H H- CHO H OH -OH CH₂OH D-Arabinose L-Arabinose H HO H CHO OH -H -OH CH₂OH D-Xylose L-Xylose HO HO- H- CHO -H H -OH CH₂OH D-Lyxose L-Lyxosearrow_forwardThe enzyme that catalyzes the C-Cg bond cleavage reaction that converts serine to glycine removes the substituent (R) bonded to the a-carbon in the first step of the reaction. Starting with PLP bound to serine in an imine linkage, propose a mechanism for this reaction. (Hint: The first step involves removal of the proton from serine's OH group.)arrow_forward
- D-Tagatose is epimeric of D-Fructose at C4. What is the structure of α-D-Tagatofuranose?arrow_forwardThe structure given below is a tetrasaccharide. i) For each pair of sugars (I-II, Il-III, III-IV), identify the type of linkage (i.e., 1→4, 1→6, etc.) that connects them. You do not have to specify whether the linkage is alpha or beta. ii) Identify all sugars that are in a furanose form. ОН ОН I HO- OH ОН О II Но OH Но НО HO- II ОН ОН IVarrow_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_forward
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