Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 25.SE, Problem 33MP
D-Glicose reacts with acetone in the presence of acid to yield the nonreducing 1, 2: 5, 6-diisopropylidene-D-glucofuranose. Propose a mechanism.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
trehalose is a disacharide that can be obtained from fungi sea uchins and insects. acid hydrolysis of trehalose yields only D-glucose. trehalose is hydrolysed by a-glucosidase but not b-glucosidase.methylation of trhalose followed by hydrolysis yield two molar equivalents of 2-3-4-6 -tetra-O-methyl-D-glucopyranose. deduce the structure of the trehalose using the experimental data
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?
Prove that gentiobiose
forms osazone and can undergo mutarotation
can be hyrolyzed by Emulsin β-glycosidase
forms these hydrolysis products following permethylation: 2,3,4,6-tetra-O-methyl-D-glucose and 2,3,4-tri-O-methyl-D-glucose
Chapter 25 Solutions
Organic Chemistry
Ch. 25.1 - Prob. 1PCh. 25.2 - Prob. 2PCh. 25.2 - Prob. 3PCh. 25.2 - Prob. 4PCh. 25.2 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.4 - Prob. 8PCh. 25.4 - Prob. 9PCh. 25.4 - Prob. 10P
Ch. 25.5 - Prob. 11PCh. 25.5 - Prob. 12PCh. 25.5 - Prob. 13PCh. 25.5 - Prob. 14PCh. 25.5 - Prob. 15PCh. 25.6 - Prob. 16PCh. 25.6 - Prob. 17PCh. 25.6 - Prob. 18PCh. 25.6 - Prob. 19PCh. 25.6 - Prob. 20PCh. 25.6 - Prob. 21PCh. 25.6 - Prob. 22PCh. 25.6 - Prob. 23PCh. 25.7 - Prob. 24PCh. 25.8 - Show the product you would obtain from the...Ch. 25.SE - Prob. 26VCCh. 25.SE - Prob. 27VCCh. 25.SE - Prob. 28VCCh. 25.SE - Prob. 29VCCh. 25.SE - Prob. 30MPCh. 25.SE - Prob. 31MPCh. 25.SE - Glucosamine, one of the eight essential...Ch. 25.SE - D-Glicose reacts with acetone in the presence of...Ch. 25.SE - Prob. 34MPCh. 25.SE - Prob. 35MPCh. 25.SE - Prob. 36APCh. 25.SE - Prob. 37APCh. 25.SE - Prob. 38APCh. 25.SE - Prob. 39APCh. 25.SE - Prob. 40APCh. 25.SE - Assign R or S configuration to each chirality...Ch. 25.SE - Prob. 42APCh. 25.SE - Prob. 43APCh. 25.SE - Prob. 44APCh. 25.SE - Prob. 45APCh. 25.SE - Prob. 46APCh. 25.SE - Prob. 47APCh. 25.SE - Prob. 48APCh. 25.SE - Prob. 49APCh. 25.SE - Prob. 50APCh. 25.SE - Prob. 51APCh. 25.SE - Prob. 52APCh. 25.SE - Prob. 53APCh. 25.SE - Prob. 54APCh. 25.SE - Prob. 55APCh. 25.SE - Prob. 56APCh. 25.SE - Prob. 57APCh. 25.SE - Prob. 58APCh. 25.SE - Prob. 59APCh. 25.SE - Prob. 60APCh. 25.SE - Prob. 61APCh. 25.SE - Prob. 62APCh. 25.SE - Prob. 63APCh. 25.SE - D-Mannose reacts with acetone to give a...Ch. 25.SE - Prob. 65APCh. 25.SE - Prob. 66APCh. 25.SE - Prob. 67APCh. 25.SE - Prob. 68APCh. 25.SE - Prob. 69APCh. 25.SE - Prob. 70APCh. 25.SE - Prob. 71AP
Additional Science Textbook Solutions
Find more solutions based on key concepts
The active ingredient in Tylenol and a host of other over-the-counter pain relievers is acetaminophen (C8H9NO2)...
Chemistry: Atoms First
Characterize each of the following structures as aromatic, nonaromatic, or antiaromatic:
Answer: _____
Organic Chemistry As a Second Language: Second Semester Topics
Problem 11.1 Neopheliosyne B is a novel acetylenic fatty acid isolated from a New Caledonian marine sponge. (a)...
Organic Chemistry
The chapter sections to review are shown in parentheses at the end of each problem. A "chemical-free” shampoo i...
Basic Chemistry
The method to determine the volume of a powered solid, liquid and a rock needs to be determined. Concept introd...
Living By Chemistry: First Edition Textbook
Consider a sample of ideal gas initially in a volume V at temperature T and pressure P. Does the entropy of thi...
General Chemistry: Principles and Modern Applications (11th Edition)
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
- In dilute aqueous base, (R)-glyceraldehyde is converted into an equilibrium mixture of (R,S)-glyceraldehyde and dihydroxyacetone. Propose a mechanism for this isomerization.arrow_forwardOne 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_forwardA hexose is obtained when the residue of a shrub Sterculia setigeria undergoes acid-catalyzed hydrolysis. Identify the hexose from the following experimental information: it undergoes mutarotation; it does not react with Br2; and D-galactonic acid and D-talonic acid are formed when it reacts with Tollens’ reagent.arrow_forward
- A 2-ketohexose is reduced with NaBH4 in CH3OH to form a mixture of D-galactitol and Dtalitol. What is the structure of the 2-ketohexose?arrow_forwardKojibiose is a reducing sugar that forms D-glucose on hydrolysis with aqueous acid. Reaction of kojibiose with iodomethane and Ag20 yields an octamethyl derivative, which can be hydrolyzed with aqueous acid to give one equivalent of 2,3,4,6-tetra-O- methyl-D-glucopyranose and one equivalent of 3,4,6-tri-O-methyl-D-glucopyranose. If kojibiose is hydrolyzed by alpha-glucosidases but not beta-glucosidases, what is its structure?arrow_forwardPropose a mechanism for the formation of D-allose from D-glucose in a basic solution.arrow_forward
- Indicate the product obtained by reacting alpha-D-Gulopyranose with NaBH4 in CH3OH.arrow_forwardNaturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.arrow_forwardOne of the steps in the biosynthesis of uridine monophosphate is the reaction of aspartate with carbamoyl phosphate to give carbamoyl aspartate followed by cyclization to form dihydroorotate. Propose mechanisms for both steps.arrow_forward
- Fill in the missing structures and add curved arrows to show the mechanism of glycoside formation below. Step 1: Oxonium ion formation НО НО НО ОН НО- HO OH D-glucose Step 2: Alcohol addition OH + H-OH2 HO H-OR or H-OR НО НО OH HO oxonium ion :ÖH2 :ÖH2 НО HO НО + H2O НО ОН HO a B-D-glycoside OH НО OR OR an a-D-glycosidearrow_forwardPredict the products obtained when d-galactose reacts with each reagent. (c) CH3OH, H + (d) Ag(NH3) 2+ -OH(e) H2, Niarrow_forwardWhat products are formed when the following sugar reacts with catalytic H2SO4, H2O, and heat? Please show the mechanism for the reaction.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
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
DIGESTER-35 | VITAMINS AND THEIR RELATED COENZYMES| GPAT | NIPER | PHARMACIST| DI; Author: GPAT DISCUSSION CENTER;https://www.youtube.com/watch?v=CGrdNYmho0s;License: Standard YouTube License, CC-BY