Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 20, Problem 49P
The 1H NMR spectrum of D-glucose in D2O exhibits two high-frequency doublets. What is responsible for these doublets?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The 1H NMR spectrum of d-glucose in D2O exhibits two high-frequency doublets. What is responsible for these doublets?
(d) Draw the structure of the expected product when monosaccharide B undergo
mutarotation upon dissolving in water in the presence of Tollens reagent (AGNO3,
NHẠOH).
он
OH
O.
OH
OH
OH
monosaccharide B
Two sugars differing in configuration at a single
asymmetric carbon atom are known as
epimers.
D-mannose is a C-2 epimer of glucose
(Structure I), while D-galactose is a C-4 epimer
of glucose. Structure Il and IIl are
H-
-OH
но-
-H
H OH
HO H
но-
H
HO H
H
-OH
H-
-OH
HO OH
H -OH
H-
-OH
H OH
HO.
HO,
OH
II
II
Which of the following represents an
aldopentose?
OH
H O
HO O
HO H
но н
HO H
но-
HO H
HO H
HO-
H OH
H OH
H OH
H OH
OH
HO
Он
of
но"
HO O
OH
он
III
IV
These are chemical messengers that are
secreted by endocrine glands and carried
through the bloodstream to target tissues.
prostaglandin
deoxysugar
glycoside
hormones
Which of the following is NOT correctly paired?
cellulose: beta-1,4-glycosidic linkage
amylose: alpha-1,4-glycosidic linkage
chitosan: alpha-1,4-glycosidic linkage
cellubiose: beta-1,4-glycosidic linkage
Chapter 20 Solutions
Organic Chemistry (8th Edition)
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Prob. 4PCh. 20.3 - Prob. 5PCh. 20.3 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - Prob. 8PCh. 20.5 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.5 - Prob. 11PCh. 20.6 - Prob. 12PCh. 20.6 - Prob. 13PCh. 20.6 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.8 - Prob. 16PCh. 20.9 - Prob. 18PCh. 20.10 - Prob. 20PCh. 20.10 - Prob. 21PCh. 20.10 - Prob. 22PCh. 20.11 - Prob. 23PCh. 20.11 - Prob. 24PCh. 20.12 - Prob. 25PCh. 20.12 - Prob. 26PCh. 20.14 - Prob. 28PCh. 20.15 - Prob. 29PCh. 20.15 - Prob. 30PCh. 20.16 - Prob. 31PCh. 20.17 - Prob. 32PCh. 20.18 - Refer to Figure 20.5 to answer the following...Ch. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Prob. 43PCh. 20 - Prob. 44PCh. 20 - Prob. 45PCh. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - The 1H NMR spectrum of D-glucose in D2O exhibits...Ch. 20 - Prob. 50PCh. 20 - Prob. 51PCh. 20 - Prob. 52PCh. 20 - Prob. 53PCh. 20 - Prob. 54PCh. 20 - Prob. 55PCh. 20 - Prob. 56PCh. 20 - Prob. 57PCh. 20 - Prob. 58PCh. 20 - Prob. 59PCh. 20 - Prob. 60PCh. 20 - Prob. 61PCh. 20 - A hexose is obtained when the residue of a shrub...Ch. 20 - Prob. 63PCh. 20 - Prob. 64PCh. 20 - Prob. 65PCh. 20 - Prob. 66PCh. 20 - Prob. 67PCh. 20 - Prob. 68PCh. 20 - Prob. 69PCh. 20 - Prob. 70PCh. 20 - Prob. 71PCh. 20 - Prob. 72PCh. 20 - Prob. 73P
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) Label compounds A, B, and C as D- or L-sugars. (b) How are compounds A and B related? A and C? B and C? Choose from enantiomers, diastereomers, or constitutional isomers.arrow_forwardMonosaccharides can be drawn in a variety of ways, and in truth, often a mixture of cyclic compounds is present in a solution. Identify each monosaccharide, including its proper D,L designation, drawn in a less-than-typical fashion.arrow_forwardReactions (chemical equation) of test samples with 2,4-DNPH: Cyclohexanone Acetone Benzaldehyde Glucose Fructosearrow_forward
- Draw the isomers for each aldotetrose and ketopentose in the figure below and designate each isomer as a D or L sugar and designate also the R and S in every chiral centers. Label the enantiomers and diastereomers respectively. CH,OH C=0 Н—С—ОН Н-С—ОН Н—С—ОН H-C-OH ČH,OH ČH,OHarrow_forward(A) Is the trisaccharide a reducing sugar? (B) Identify the type of glycosidic linkage of the colored bond.arrow_forward4. Identify the component monosaccharides of each of the following compounds and describe the type of glycosidic linkage in each. Но он Но OH HO он Но- Но- (a) OH (c) CH,OHO. (b) CH2OHO Lon OH HO H ČHOH H OH ÓH ОНarrow_forward
- (d) Use the diagram below to complete the cyclic alpha form of structure V (e) Circle the hemiacetal in cyclic alpha form of structure V. (f) Redraw the cyclic alpha form of structure V but replace the OH group on the anomericcarbon with a methoxy group. Is this modified monosaccharide a reducing sugar or anonreducing sugar?arrow_forwardOne pathway for the metabolism of D-glucose 6-phosphate is its enzyme-catalyzed conversion to D-fructose 6-phosphate. Show that this transformation can be accom- plished as two enzyme-catalyzed keto-enol tautomerisms. СНО CH,OH C=0 enzyme catalysis Но Но H OH H H. O- H- -HO- ČH,OPO, ČH,OPO, D-Glucose 6-phosphate D-Fructose 6-phosphatearrow_forwardClassify the structures as being either an enantiomer, diastereomer or diastereomer/epimer of D-glucose. Structure A: CH H- -OH Structure B: но- H- H- OH Structure C: H- он H- -H D-Glucose: OH || CH CH CH он H- он но -H H- он но он но но- H- но H- OH OH но -- H- -H H -Ç-H Structure A: OH Structure B: OH Structure C: OHarrow_forward
- m) Which pyranose ring (A, B, C, or D) in the tetrasaccharide below is derived from D-altrose? The Fischer projections for the four aldohexoses that make up this tetrasaccharide are shown below. B C D HOH CHO CHO CHO CHO HO+H HTOH Fонно н HOH HOH H-OH H-OH H-+-OH H-TOHHOH HOH H+OH HOHнтон нон CHOH CHOH CHOH CHOH De D-glue Dalose Datrone i NH Į HOH STEP 1 OH, HO- answer 1. Just add arrows and charges for steps 1, 2, and 3 in formation of this enamine з no arrows needed here OH н Н ЮН -OH STEP 3 :ÖH н H STEP 2 на это про за почarrow_forwardThe most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the a or ß anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.arrow_forwardBarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher: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
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY