ORGANIC CHEMISTRY TEXT PACKAGED - 2 YE
10th Edition
ISBN: 9781260024241
Author: Carey
Publisher: MCG/CREATE
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 24, Problem 36P
Methyl glycosides of
methanol to unsaturated carbohydrates known as glycals.
Suggest a reasonable mechanism for this reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
What is the product/s when Asetone is allowed to react with KMno4, H2O, NaOH while being heated in the presence of HCl. is there any sereochemistry associated with this reaction
Illustrate the treatment of methyl α-D-glucopyranoside with aqueous acid forms a mixture of α- and β-D-glucose and methanol ?
Predict whether d-altrose exists preferentially as a pyranose or a furanose. (Hint: In the most stable arrangement for a five-membered ring, all theadjacent substituents are trans.)
Chapter 24 Solutions
ORGANIC CHEMISTRY TEXT PACKAGED - 2 YE
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
- Predict whether d-altrose exists preferentially as a pyranose or a furanose.arrow_forwardstructure of beta anomers of alpha D- mannopyranose and give their namesarrow_forwardShow the mechanism for the acid-catalyzed formation of 23c starting with the product obtained from its hydrolysis.arrow_forward
- Emil Fischer synthesized l-gulose, an unusual aldohexose that reduces to give d-glucitol.Suggest a structure for this l sugar, and show how l-gulose gives the same alditol asd-glucose. (Hint: d-Glucitol has ¬CH2OH groups at both ends. Either of these primaryalcohol groups might have come from reduction of an aldehyde.)arrow_forwardThe most stable conformation of most aldopyranoses is one in which the largest group, the CH2OH group, is equatorial. However, alpha-D-idopyranose exists primarily in a conformation with an axial CH2OH group. Write formulas for the two chair conformations of a-D-idopyranose (one with the CH2OH group axial and one with the CH2OH group equatorial) and provide an explanationarrow_forwardWhen the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of thehydrolysate is found to be tagatose. The following information is known about tagatose:(1) Molecular formula C6H12O6(2) Undergoes mutarotation.(3) Does not react with bromine water.(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives1,3,4,5-tetra-O-methyltagatose.(a) Draw a Fischer projection structure for the open-chain form of tagatose.(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatosearrow_forward
- When some sugars dissolve in water they spontaneously undergo changes in optical rotation called mutarrotation. The Mutarrotation of D-glucopyranose is catalyzed by acid and bases. 2-Hydroxypyridine is a more effective catalyst than phenol and pyridine for this reaction because: a.Both oxygen and N in 2-hydroxypyridine act as bases increasing the rapid interconversion of sugar b. The OH of 2-hydroxypyridine serves as the base while the current N as the acid. c. 2-hydroxypyridine acts both as a base to remove the proton from the hydroxyl group in the hemiacetal and as an acid to provide a proton to the oxygen in the hemiacetal. d.Phenol and pyridine are very expensive.arrow_forwardHyaluronic acid, a component of connective tissue, is the fluid that lubricates joints. It is a polymer of alternating N-acetyl-d-glucosamine and d-glucuronic acid subunits joined by β-1,3'-glycosidic linkages. Draw a short segment of hyaluronic acid.arrow_forwardThe formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.arrow_forward
- One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to glucose 6-phosphate. Propose a mechanism, using acid or base catalysis as needed.arrow_forwardwrite the product of the D-gulose reaction by: a. CH3I, Ag2O b. The product in (a), then H3O+ c. The product in (b), then C6H5CH2Cl, Ag2Oarrow_forwardAssume that for your Biochemistry practical, you were asked to synthesise D-Galactose. You went to chemical storage room to take some D-lyxose to use as the starting material. But there you found that labels had fallen off from the bottles containing D-lyxose and D-xylose. How could you determine which bottle contains D- lyxose?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License