Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 22, Problem 26P
Interpretation Introduction
Interpretation:
The structures of D –- psicose and D –- tagatose are to be shown.
Concept Introduction:
▸ Monosaccharides, fructose, sorbose, psicose and tagatose are ketohexoses. Monosaccharides allose and galactose are aldohexoses. All of them are reducing sugars.
▸ Compounds formed by the reaction of reducing sugars with excess of phenylhydrazine are called osazones. Osazones are products of oxidation and are produced by all of the reducing sugars.
▸ The Fischer projection is a way of representing
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Monosaccharide A is a diastereomer of d-lyxose. Treatment of A with nitric acid forms an optically inactive aldaric acid. A undergoes a Kiliani-Fischer synthesis to form B and C. B is oxidized by nitric acid to an optically active aldaric acid, and C is oxidized to an optically inactive aldaric acid. Wohl degradation of A forms D, which is oxidized by nitric acid to an optically inactive aldaric acid. Wohl degradation of D forms a d-aldotriose. Identify A, B, C, and D.
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.
Aldohexoses 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.
Chapter 22 Solutions
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...Ch. 22 - Prob. 1QCh. 22 - Prob. 2QCh. 22 - Give the structural formula of the monosaccharide...Ch. 22 - Prob. 4QCh. 22 - Prob. 5QCh. 22 - Prob. 6QCh. 22 - Prob. 7QCh. 22 - Prob. 8QCh. 22 - Select the reagent needed to perform the following...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two D-aldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A–C?arrow_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_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_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_forwardA 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?arrow_forwardThe anticoagulant heparin is a polysaccharide that contains alternating residues of -D- glucuronic acid-6- sulfate and N-sulfo-D-glucosamine-6sulfate connected by (1 B 4)- glycosidic linkages. Draw a part of heparin that shows one each of the two residues.arrow_forward
- Which D-aldopentoses are reduced to optically inactive alditols using NaBH,, CH;OH?arrow_forwardD-Aldopentose A is oxidized to an optically inactive aldaric acid. On Wohl degradation, A forms an aldotetrose B that is oxidized to an optically active aldaric acid. What are the structures of A and B?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_forward
- The following observations are obtained after a D-hexose was made to react with several reagents: (1) The reactions of a D-hexose with (a) to (d) below yields an aldaric acid (a) NH₂OH, (b) (CH3CO)₂O, NaOCOCH 3, and, (c) NaOCH3, and then, (d) HNO3, H₂O (2) HNO3 oxidation of the same D-hexose gives an aldaric acid. Predict the structures of the three (3) possible hexoses that can undergo the above reactions?arrow_forwardRaffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose doesnot reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinosegives d-glucose, d-fructose, and d-galactose. When raffinose is treated with invertase,the products are d-fructose and a reducing disaccharide called melibiose. Raffinose isunaffected by treatment with a b@galactosidase, but an a@galactosidase hydrolyzes itto d-galactose and sucrose. When raffinose is treated with dimethyl sulfate and basefollowed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetraO-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the completestructures of raffinose and melibiose, and give a systematic name for melibiose.arrow_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_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT