EBK ORGANIC CHEMISTRY
12th Edition
ISBN: 9781119233664
Author: Snyder
Publisher: VST
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Chapter 22, Problem 25P
Interpretation Introduction
Interpretation:
The aldose compounds that would yield phenylosazone similar to L-sorbose are to be identified.
Concept Introduction:
▸ Monosaccharide
▸ Compounds formed by the reaction of reducing sugars with excess of phenylhydrazine are called osazones. These are highly crystalline and colored compounds and are formed by the reducing sugar molecules.
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(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?
A D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?
Compound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is
converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid
F.
What is the structure of compound F?
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
You do not have to explicitly draw H atoms.
If a group is achiral, do not use wedged or hashed bonds on it.
• Show stereochemistry in a meso compound.
• Do not include lone pairs in your answer. They will not be considered in the grading.
Chapter 22 Solutions
EBK ORGANIC CHEMISTRY
Ch. 22 - Prob. 1PPCh. 22 - Prob. 2PPCh. 22 - Prob. 3PPCh. 22 - Prob. 4PPCh. 22 - Prob. 5PPCh. 22 - Prob. 6PPCh. 22 - Prob. 7PPCh. 22 - Prob. 8PPCh. 22 - Practice Problem 22.9 What products would you...Ch. 22 - Prob. 10PP
Ch. 22 - Prob. 11PPCh. 22 - Prob. 12PPCh. 22 - Prob. 13PPCh. 22 - Prob. 14PPCh. 22 - Prob. 15PPCh. 22 - Prob. 16PPCh. 22 - Prob. 17PPCh. 22 - Prob. 18PPCh. 22 - Prob. 19PPCh. 22 - Prob. 20PCh. 22 - Prob. 21PCh. 22 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Prob. 28PCh. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Prob. 37PCh. 22 - Prob. 38PCh. 22 - Arbutin, a compound that can be isolated from the...Ch. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - 22.44 The following reaction sequence represents...Ch. 22 - 22.45
The NMR data for the two anomers...Ch. 22 - Shikimic acid is a key biosynthetic intermediate...
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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?arrow_forwardDraw the Haworth structures for the following: - alpha-D-Gulopyranose - beta-D-Sorbofuranose - the two possivle isomers of alpha-D-altrose (furanose and pyranose forms)arrow_forwardThere are three (3) vials labeled A, B, and C known to contain the following monosaccharides. All three samples reduce Tollens and Fehling. By oxidation with dilute HNO3 an optically active aldaric acid is obtained for sample A and the remaining two give products without optical activity. When the three samples were subjected to an alkaline medium, it was observed that, after a certain time, samples A and C reached the same value of the specific rotation [α]. Select the RIGHT alternative: (a) Sample A is Galactose. (b) Sample B is Alosa. (c) Samples A and C are not related to each other by an epimerization process. (d) Sample C is Talose. (e) Samples B and C are epimers.arrow_forward
- Give me a clear handwritten answer with explanationarrow_forwardMonosaccharide A is a D-aldotetrose. Treatment of A with nitric acid gives an optically inactive aldaric acid (B). Killiani-Fischer chain extension of A gives two products (C & D). C on treatment with NABH4, gives an alditol (E) that is optically active. D gives an alditol (F) that is NOT optically active. Give Fischer projections for A, B, CD, E, and E.arrow_forwardWhich of the d-aldotetroses will give optically active aldaric acids on oxidation with HNO3 ?(arrow_forward
- Atorvastatin (Lipitor) is used to decrease patient serum cholesterol levels. It works by inhibiting an enzyme called HMG-CoA reductase. In one synthesis of atorvastatin that produces the desired single enantiomer of the final product, the following reagents are used. Draw the structure of synthetic intermediate A. to H3C- -CI NaCN A B HO, DMSO Pyridine Use the wedge/hash bond tools to indicate stereochemistry where it exists. Should you want to restart the exercise, the drop-down menu labeled on the sketcher. starting points can be used to redraw the starting molecule P aste ору H3C, „CH3 CHEH3 НО. CH3 Previous Next :Oarrow_forward21.80 Prednisolone is the synthetic glucocorticoid medicine most frequently prescribed to combat autoimmune diseases. Compare its structure to the natural glucocorticoid hormone cortisone. What are the similarities and differences in structure? НО. H₂C H₂C CH₂OH C=O -ОНarrow_forwardAn aldopentose "O", is oxidized with HNO3 to a diacid "P" which is optically active. The compound "O", is also degraded to an aldotetrose "Q" which undergoes another oxidation to an optically inactive diacid "R". Assuming that "O" has the configuration D-(4R); what are the structures of "O" to "R"?arrow_forward
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