ETEXT+MASTERINGCHEMISTRY STANDALONE AC
7th Edition
ISBN: 9781269736947
Author: Bruice
Publisher: PEARSON
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Chapter 21, Problem 44P
Interpretation Introduction
Interpretation:
The two possible structures for the
Concept Introduction:
The Wohl-degradation is opposite of the Killiani-Fisher synthesis. It shortens an aldoses chain by one carbon. Hexoses are converted to pentoses and pentoses are converted to tetroses.
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d-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?
Which of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(
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 21 Solutions
ETEXT+MASTERINGCHEMISTRY STANDALONE AC
Ch. 21.1 - Prob. 1PCh. 21.2 - Prob. 2PCh. 21.2 - Prob. 3PCh. 21.3 - Prob. 4PCh. 21.3 - Prob. 5PCh. 21.3 - Prob. 6PCh. 21.4 - Prob. 7PCh. 21.4 - Prob. 8PCh. 21.5 - Prob. 9PCh. 21.5 - Prob. 10P
Ch. 21.5 - Prob. 11PCh. 21.6 - Prob. 12PCh. 21.6 - Prob. 13PCh. 21.6 - Prob. 14PCh. 21.7 - Prob. 15PCh. 21.8 - Prob. 16PCh. 21.9 - Prob. 18PCh. 21.10 - Prob. 20PCh. 21.10 - Prob. 21PCh. 21.10 - Prob. 22PCh. 21.11 - Prob. 24PCh. 21.11 - Prob. 25PCh. 21.15 - Prob. 27PCh. 21.16 - Prob. 28PCh. 21.17 - Prob. 29PCh. 21.18 - Refer to Figure 20.5 to answer the following...Ch. 21 - Prob. 31PCh. 21 - Prob. 32PCh. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - Prob. 35PCh. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Prob. 40PCh. 21 - Prob. 41PCh. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - Prob. 44PCh. 21 - The 1H NMR spectrum of D-glucose in D2O exhibits...Ch. 21 - Prob. 46PCh. 21 - Prob. 47PCh. 21 - Prob. 48PCh. 21 - Prob. 49PCh. 21 - Prob. 50PCh. 21 - Prob. 51PCh. 21 - Prob. 52PCh. 21 - Prob. 53PCh. 21 - Prob. 54PCh. 21 - Prob. 55PCh. 21 - A hexose is obtained when the residue of a shrub...Ch. 21 - Prob. 57PCh. 21 - Prob. 58PCh. 21 - Prob. 59PCh. 21 - Prob. 60PCh. 21 - Prob. 61PCh. 21 - Prob. 62PCh. 21 - Prob. 63PCh. 21 - Prob. 64PCh. 21 - Prob. 65PCh. 21 - Prob. 66P
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- A hexose was obtained after (+)-glyceraldehyde underwent three successive Kiliani–Fischer syntheses. Identify the hexose from the following experimental information: oxidation with nitric acid forms an optically active aldaric acid; a Wohl degradation followed by oxidation with nitric acid forms an optically inactive aldaric acid; and a second Wohl degradation forms erythrose.arrow_forwardA 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_forwardIf lactose is first hydrolyzed (by addition of sulfuric acid) into its constituent monosaccharide, and then subjected to complete methylation, what methylated products do you expect?arrow_forward
- 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_forwardd-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_forwardHow many d-aldoheptoses are possible? Draw the Fischer projection of one of them and its enantiomer.arrow_forward
- does structure E represent fructofuranose? explainarrow_forwardAldohexoses A and B are formed from aldopentose C via a Kiliani–Fischer synthesis. Nitric acid oxidizes A to an optically active aldaric acid, B to an optically inactive aldaric acid, and C to an optically active aldaric acid. Wohl degradation of C forms D, which is oxidized by nitric acid to an optically active aldaric acid. Wohl degradation of D forms (+)-glyceraldehyde. Identify A, B, C, and D.arrow_forwardDraw the structure of alpha-d-glucopyranose in straight chain cyclic, Haworth and cyclohexane-chair format. Draw the structures of two aldohexoses which are diastereomers but not epimersarrow_forward
- (a) Which of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(b) Which of the d-aldotetroses will give optically active aldaric acids on oxidation with HNO3 ?(c) Sugar X is known to be a d-aldohexose. On oxidation with HNO3, X gives an optically inactive aldaric acid. WhenX is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine thestructure of X.(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an opticallyactive aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form opticallyactive products?(e) Show what product results if the aldopentose formed from degradation of X is further degraded to an aldotetrose.Does HNO3 oxidize this aldotetrose to an optically active aldaric acid?arrow_forwardIdentify the sugar in each description. a. An aldopentose that is not d-arabinose forms d-arabinitol when it is reduced with NaBH4. b. A sugar that is not D-altrose forms d-altraric acid when it is oxidized with nitric acid. c. A ketose that, when reduced with NaBH4, forms d-altritol and d-allitol.arrow_forwardIllustrate the treatment of methyl α-D-glucopyranoside with aqueous acid forms a mixture of α- and β-D-glucose and methanol ?arrow_forward
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