Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 25.3, Problem 7P
Interpretation Introduction
Interpretation:
Fischer projection of Arabinose are to be drawn.
Concept introduction:
Fischer Projections are typically used for depicting monosaccharides and amino acids. They are helpful with depicting monosaccharides, because they have so many stereocenters, and the different monosaccharides are all pretty similar, they are just different about the orientation of the stereocenters. The Fischer Projection allows us to quickly see the orientation of each monosaccharide.
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6 сH-он
(5
4
OH
1
2
ОН
3
OH
(c) Trace and identify the acetal in the above monosaccharide.
(d) Draw the hemiacetal that results from above acetal.
(e) Draw the open chain equivalent of the sugar in part (d).
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
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 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
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- Identify each amino shown below in Fischer projection. Indicate whether the D- or L-enantiomer is shown.arrow_forwardDraw the enantiomer and a diastereomer for the compound shown below, and label them as D and L sugarsarrow_forwardAssign r or s configuration to each chirality center of the following monosaccharide?arrow_forward
- ← Problem 23 of 37 Submit Draw the Fischer projection from the Haworth projection shown below. CH2OH H H OH H OH OH H OH Qarrow_forward2. How is each compound related to the simple sugar D-erythrose? Is it an enantiomer, diastereomer or identical? ОНС HO HOH C НО НОН С A с он E ОНС. CH₂OH OH CHO ОН CHO OH он OH D-erythrose CH₂OH ОНС НО HOH2C HO HOH C B D OH CH2OH ОН F CHO ОН CHO онarrow_forward7B Compound A shown below is given. OH A Complete the Fischer projection below to represent compound A CH₂CH3 CH₂CH₂CH3arrow_forward
- The 1H NMR spectrum of d-glucose in D2O exhibits two high-frequency doublets. What is responsible for these doublets?arrow_forwardE For the following Fischer projection: c-oH (a) Determine (R)/(S) configuration at each chiral center; (b) Show all stereoisomers, and based on your assignments from part (a), determine what would be (R) or (S) configuration at all chiral centers; (c) Show all enantiomeric and diastereomeric pairs.arrow_forwardAssign R, S designations to each stereogenic center in glucose.arrow_forward
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