Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 20.3, Problem 20.4P
Interpretation Introduction
Interpretation:
The Haworth and chair conformations for methyl-a−D-mannopyranoside (methyl a-D-mannoside) should be drawn and the anomeric carbon and glycosidic bond should be labeled.
Concept introduction:
A common way of writing structural formula which represent the cyclic structure of monosaccharides is said to be the Haworth projection, which is best represented by chair conformations.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Be sure to answer all parts.
[1] classify the compound as a D or L monosaccharide; [2] draw the the enantiomer of the compound.
H.
но-
H.
-OH
но-
-H
ČH,OH
[1]
(select)
(select)
L
D
atching
an a 1,4 linkage
a ẞ-1,4 linkage
a nonreducing monosaccharide
a reducing sugar
a reducing disaccharide
a deoxy sugar
(A)
(c)
он
CH₂OH
(E)
1107
CHOH
CHOH
CH₂OH
CH₂OH
CHOH
CH₂OH
он
On
но-
OF
CHLOH
HO
Lot
HO OH
CH₂OH
HO
HOCH
OH
(F)
OH
(0)
a) Which of the following monosaccharides will react with Tollens' reagent? Circle all that
аpply.
СООН
CH2OH
CH2OH
OCH3
но-
H-
ОН
HO FH
OH
CH2OH
CH2OH
OH
II
III
IV
V
b) Decide whether the disaccharide shown below is a reducing or non-reducing sugar
CH2OH
но
Но-
ОН
CH2
но
Но
OH
OH
우 오
Chapter 20 Solutions
Introduction to General, Organic and Biochemistry
Ch. 20.1 - Prob. 20.1PCh. 20.2 - Prob. 20.2PCh. 20.2 - Prob. 20.3PCh. 20.3 - Prob. 20.4PCh. 20.4 - Prob. 20.5PCh. 20 - Prob. 20.6PCh. 20 - Prob. 20.7PCh. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Prob. 20.11PCh. 20 - Prob. 20.12PCh. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 20 - Prob. 20.16PCh. 20 - Prob. 20.17PCh. 20 - Prob. 20.18PCh. 20 - .19 What is an amino sugar? Name the three amino...Ch. 20 - Prob. 20.20PCh. 20 - Prob. 20.21PCh. 20 - Prob. 20.22PCh. 20 - Prob. 20.23PCh. 20 - Prob. 20.24PCh. 20 - Prob. 20.25PCh. 20 - Prob. 20.26PCh. 20 - Prob. 20.27PCh. 20 - Prob. 20.28PCh. 20 - Prob. 20.29PCh. 20 - Prob. 20.30PCh. 20 - Prob. 20.31PCh. 20 - Prob. 20.32PCh. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Prob. 20.35PCh. 20 - Prob. 20.36PCh. 20 - Prob. 20.37PCh. 20 - Prob. 20.38PCh. 20 - Prob. 20.39PCh. 20 - Prob. 20.40PCh. 20 - Prob. 20.41PCh. 20 - Prob. 20.42PCh. 20 - Prob. 20.43PCh. 20 - Prob. 20.44PCh. 20 - Prob. 20.45PCh. 20 - 6 Where is glycogen stored in the human body?Ch. 20 - Prob. 20.47PCh. 20 - 8 How is it possible that cows can digest grass...Ch. 20 - Prob. 20.49PCh. 20 - Prob. 20.50PCh. 20 - 1 Hyaluronic acid acts as a lubricant in the...Ch. 20 - 2 The anticlotting property of heparin is partly...Ch. 20 - Prob. 20.53PCh. 20 - Prob. 20.54PCh. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - Prob. 20.57PCh. 20 - Prob. 20.58PCh. 20 - Prob. 20.59PCh. 20 - Prob. 20.60PCh. 20 - Prob. 20.61PCh. 20 - 2 In making candy or sugar syrups, sucrose is...Ch. 20 - Prob. 20.63PCh. 20 - Prob. 20.64PCh. 20 - Prob. 20.65PCh. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 20 - Prob. 20.69PCh. 20 - 0 What are the structural differences between...Ch. 20 - Prob. 20.71PCh. 20 - Prob. 20.72PCh. 20 - Prob. 20.73PCh. 20 - Prob. 20.74PCh. 20 - Prob. 20.75PCh. 20 - Prob. 20.76PCh. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - Prob. 20.79PCh. 20 - Prob. 20.80PCh. 20 - Prob. 20.81PCh. 20 - Prob. 20.82PCh. 20 - Prob. 20.83PCh. 20 - Prob. 20.84PCh. 20 - Prob. 20.85PCh. 20 - Prob. 20.86PCh. 20 - Prob. 20.87PCh. 20 - Prob. 20.88PCh. 20 - Prob. 20.89P
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 Fischer projection of a monosaccharide is shown below: CH₂OH C=O H- H- HO- HO D▾ OH OH I Classify this manosaccharide (e.g., aldotriose) Submit Answer -H -H CH₂OH Does it have the D or L configuration? Retry Entire Group 9 more group attempts remainingarrow_forwardChoose the a-anomer of the following monosaccharide. CH2OH но -H он ČH2OH CH2OH CH2OH OH OH CH2OH он OH OH ČH2OH он ÓH он он он А В CH2OH CH2OH CH2OH -0 он CH2OH CH2OH OH Он OH OH ÓH он OH Он D E F CA OB OC OD CE OF Enter Your Answer:arrow_forward9 10 Visited M A Fischer projection of a monosaccharide is shown below: CHO H-OH HO- H- HO- H- OH CH₂OH Classify this monosaccharide (e.g., aldotriose) Does it have the D or L configuration? Submit Answer de - -H -OH -H 4+ Retry Entire Group Search 144 9 more group attempts remaining DI DDI D 31 9.arrow_forward
- 14) What type of glycosidic bond is shown here? Н OH A) a(1-4) B) a(1-6) C) B(1-4) D) B(1-6) CH₂OH H OH H I OH H H OH CH₂ H OH He od О I но-но- Н HOT1 OH OHarrow_forwarda) Draw the following pyranoside in its open chain form (using Fisher convention) оН ОН HO ÓH ÓH b) Is this a D or an L sugar? c) Draw its enantiomer.arrow_forwardUnderstanding monosaccharides (2-part problem) a) Draw both anomers of the 4C1 and 1C4 chairs of D-mannapyranose. Rank them from least stable to most stable, justifying your choice. b) Draw the acid-catalysed mechanism whereby D-fructose cyclizes to α-D-fructofuranosearrow_forward
- 1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.arrow_forward6 CH2OH 4 OH 2 ОН 3 OH (d) Draw the hemiacetal that results from above acetal. (e) Draw the open chain equivalent of the sugar in part (d). (f) Classify the monosaccharide below as a D-sugar or an L-sugar. H ОН O. ОН CH2OH ОН ОНarrow_forwardH OH The representation of a monosaccharide shown here is known as a(n) Go To Problem CH₂OH H OH OH A Fischer projection. B Haworth projection. OH C anomeric projection. H D aldose projection. E ketose projection.arrow_forward
- Draw the product of the mutarotation of the monosaccharide shown below. ОН CH₂OH ОН ОН H3O+ ОН of вarrow_forwardv Draw the Haworth projection of the disaccharide made by joining D-galactose and D-glucose with a B(1-4) glycosidic bond. If the disaccharide has more than one anomer, you can draw any of them. A 1 option Explanation Z No @ 2 W S Check X command Click and drag to start drawing a structure. ► #3 E D # $ 4 C R FL * be 10 % 5 V P T 80 G) 6 Y B & M 7 H U N * 8 00 © 2023 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center Accessibility 0₁ J X - Ö ( 9 M 3 K 4) ) O O < 1 n L 9. P O command + L S ? optionarrow_forward20) Designate either R or S to each of the following molecule. H3C H A) R B) S C) Undetermined D) No stereogenic-centerarrow_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 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