EBK ORGANIC CHEMISTRY
10th Edition
ISBN: 9781259636875
Author: Carey
Publisher: MCGRAW HILL BOOK COMPANY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 24, Problem 28P
Interpretation Introduction
Interpretation:
The
Concept introduction:
Reduction of monosaccharides with sodium borohydride reduces the
Oxidation of monosaccharides with bromine oxidizes the aldehyde group to carboxylic acid.
Oxidation of monosaccharides with nitric acid oxidizes the aldehyde group as well as the terminal
Carbohydrates undergo enolization in the open-chain form. The aldehyde oxygen is protonated by the hydrogen from C2, converting it to hydroxyl group and forming a double bond between C1 and C2.
Carbohydrates that differ in configuration only at C2 give the same enediol.
A molecule with more than one chirality center can be optically inactive if it has a plane of symmetry of a center of symmetry.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
(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?
Which of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(
An unknown β-d-aldohexose has only one axial substituent. A Wohl degradation forms a compound which, when treated with sodium borohydride, forms an optically active alditol. This information allows you to arrive at two possible structures for the β-d-aldohexose. What experiment can you carry out to distinguish between the two possibilities?
Chapter 24 Solutions
EBK ORGANIC CHEMISTRY
Ch. 24.2 - Prob. 1PCh. 24.3 - Problem 24.2 Which aldotetrose in the structure...Ch. 24.4 - Prob. 3PCh. 24.4 - Prob. 4PCh. 24.6 - Prob. 5PCh. 24.6 - Prob. 6PCh. 24.7 - Prob. 7PCh. 24.8 - Prob. 8PCh. 24.8 - Prob. 9PCh. 24.9 - Prob. 10P
Ch. 24.10 - Prob. 11PCh. 24.10 - Prob. 12PCh. 24.11 - Prob. 13PCh. 24.12 - Prob. 14PCh. 24.14 - Prob. 15PCh. 24.14 - Prob. 16PCh. 24.14 - Prob. 17PCh. 24.14 - Using Mechanism 24.2 as a guide, write a stepwise...Ch. 24.15 - Prob. 19PCh. 24.17 - Prob. 20PCh. 24.17 - Prob. 21PCh. 24.18 - Prob. 22PCh. 24.18 - Prob. 23PCh. 24.18 - Prob. 24PCh. 24.20 - Prob. 25PCh. 24 - Prob. 26PCh. 24 - Prob. 27PCh. 24 - Prob. 28PCh. 24 - Prob. 29PCh. 24 - Prob. 30PCh. 24 - Prob. 31PCh. 24 - Prob. 32PCh. 24 - Prob. 33PCh. 24 - Prob. 34PCh. 24 - Prob. 35PCh. 24 - Methyl glycosides of 2-deoxy sugars have been...Ch. 24 - Prob. 37PCh. 24 - Prob. 38PCh. 24 - Prob. 39PCh. 24 - Prob. 40PCh. 24 - Treatment of d-mannose with methanol in the...Ch. 24 - Prob. 42PCh. 24 - Prob. 43PCh. 24 - Prob. 44PCh. 24 - Prob. 45DSPCh. 24 - Prob. 46DSPCh. 24 - Prob. 47DSPCh. 24 - Prob. 48DSPCh. 24 - Prob. 49DSP
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 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_forwardd-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_forwardWhat aldoses are formed when the following aldoses are subjected to the Kiliani–Fischer synthesis: (a) d-threose; (b) dribose; (c) D-galactose?arrow_forward
- Illustrate the treatment of methyl α-D-glucopyranoside with aqueous acid forms a mixture of α- and β-D-glucose and methanol ?arrow_forwardWhich aldoses are oxidized to optically inactive aldaric acids: (a) D-erythrose; (b) D-lyxose; (c) D-galactose?arrow_forwardDraw the expected product of the reaction of the following sugars with excess methyliodide and silver oxide.(a) a-d-fructofuranose (b) b-d-galactopyranosearrow_forward
- An aldose A, is reduced by sodium borohydride to an optically inactive alditol B. The Ruff degredation of A forms C. Oxidation of C by nitric acid generates the optically inactive diacid D. The ruff degreation of C forms D-glyceraldehyde. draw the structures for compounds A through D and discuss a mechanism for the reduction step using sodium borohydridearrow_forwardDeduce the structure of trehalose using 2,3,4,6-tetra-O-methyl-D-glucopyranosearrow_forwardDraw the product that is expected when the β-pyranose form of compound A is treated with excess ethyl iodide in the presence of silver oxide. The following information can be used to determine the identity of compound A: The molecular formula of compound A is C6H12O6. Compound A is reducing sugar. When compound A is subjected to a Wohl degradation two times sequentially, Derythrose is obtained. Compound A is epimeric with D-glucose at C3. The configuration at C2 is R.EXPLAIN IN DETAIL.arrow_forward
- Is bupropion chiral? If so, how many of the possible stereoisomers are formed in this synthesis?arrow_forwardShow the product that results when fructose is treated with an excess of methyl iodideand silver oxide.(b) Show what happens when the product of part (a) is hydrolyzed using dilute acid.(c) What do the results of parts (a) and (b) imply about the hemiacetal structure of fructose?arrow_forwardTreatment with sodium borohydride converts aldose A to an optically inactive alditol. Wohl degradation of A forms B, whose alditol is optically inactive. Wohl degradation of B forms d-glyceraldehyde. Identify A and B.arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
