General, Organic, and Biological Chemistry - 4th edition
4th Edition
ISBN: 9781259883989
Author: by Janice Smith
Publisher: McGraw-Hill Education
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Question
Chapter 15, Problem 57P
Interpretation Introduction
(a)
Interpretation:
The compound pairs should be classified as either enantiomers or diastereomers.
Concept Introduction:
Stereo isomers are molecules with same molecular formula, same molecular formula and different arrangement of atoms in space and they can be divided into two groups, enantiomers and diastereomers. Enantiomers are isomers which are mirror images of each other. Diastereomers are isomers which are not mirror images of each other.
Interpretation Introduction
(b)
Interpretation:
Constitutional isomer of molecule A should be drawn.
Concept Introduction:
In constitutional isomers molecular formula can be similar, but the
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4. 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
ОН
a) Which of the following monosaccharides will react with Tollens' reagent? Circle all that
apply.
СООН
CH2OH
CH2OH
OCH3
но-
H-
O:
OH
но
H-
но—н
OH
ČH2OH
ČH2OH
ÓH
II
III
IV
V
b) Which of the following carbohydrates is sucrose?
OH
OH
OH
но
OH
HO,
O.
OH
"OH
HO
OH
Он
HO
OH
II
I
HO,
HO.
Он
HO,
HO.
HO,
OH
Но
Он
но.
OH
HO,,
HO,
OH
HOl
HO
OH
но
он
III
Он
HO
IV
HO
но
9
A disaccharide consists of the molecules of D-glucose and D-glucosamine joined by a
(1a, 1b)-glucosidic bond.
a) Draw the structure of the disaccharide (Haworth projection) if you know that in D-
glucose the anomeric carbon has an a-configuration.
b) Give the name of the union you drew in question a.
c) Draw the structure of the product (cantilever conformation) resulting from the effect of
excess acetic anhydride and pyridine on the disaccharide.
Hint: D-glucosamine has the same structure as D-glucose, but C-2 has an amino group
instead of a hydroxyl.
Chapter 15 Solutions
General, Organic, and Biological Chemistry - 4th edition
Ch. 15.1 - Prob. 15.1PCh. 15.1 - Prob. 15.1PPCh. 15.1 - For trans-2-hexene: (a) draw a stereoisomer; (b)...Ch. 15.2 - Prob. 15.3PCh. 15.2 - Prob. 15.4PCh. 15.3 - Prob. 15.2PPCh. 15.3 - Prob. 15.5PCh. 15.3 - Prob. 15.6PCh. 15.3 - Prob. 15.3PPCh. 15.3 - Prob. 15.7P
Ch. 15.3 - Prob. 15.8PCh. 15.3 - Prob. 15.9PCh. 15.4 - Prob. 15.4PPCh. 15.4 - Prob. 15.10PCh. 15.4 - Prob. 15.11PCh. 15.4 - Prob. 15.12PCh. 15.5 - Prob. 15.13PCh. 15.6 - Prob. 15.5PPCh. 15.6 - Prob. 15.14PCh. 15.6 - Prob. 15.15PCh. 15.7 - Prob. 15.16PCh. 15.7 - Prob. 15.17PCh. 15.7 - Prob. 15.6PPCh. 15.7 - Prob. 15.18PCh. 15.8 - Prob. 15.7PPCh. 15.8 - Prob. 15.19PCh. 15.9 - Prob. 15.20PCh. 15 - Prob. 21PCh. 15 - Prob. 22PCh. 15 - Prob. 23PCh. 15 - Prob. 24PCh. 15 - Prob. 25PCh. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - Prob. 28PCh. 15 - Prob. 29PCh. 15 - Prob. 30PCh. 15 - Prob. 31PCh. 15 - Prob. 32PCh. 15 - Prob. 33PCh. 15 - Prob. 34PCh. 15 - Prob. 35PCh. 15 - Prob. 36PCh. 15 - How are the compounds in each pair related? Are...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - Prob. 47PCh. 15 - Prob. 48PCh. 15 - Prob. 49PCh. 15 - Prob. 50PCh. 15 - (a) Define the terms “optically active” and...Ch. 15 - Prob. 52PCh. 15 - Prob. 53PCh. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - Prob. 60PCh. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Prob. 67CPCh. 15 - Prob. 68CP
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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
- The oligosaccharide shown below is the repeating disaccharide found in dermatan sulfate, a biological glycosaminoglycan found throughout the body. a) Is ring A a D- or an L-sugar? How do you know based on the Haworth structure of ring A below? b) Is the ring Ba glucose derivative? How do you know based on the Haworth structure of ring B below? c) Describe the linkage between the monosaccharide moleties ring A to ring B. (See slides 9-10 of the Fischer Haworth PowerPoint presentation) 0,so CH,OH O OR coo NHCOCH, OH óso,arrow_forward(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 Barrow_forwardm) 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_forward
- OH ОН Which monosaccharide has a greater heat of combustion, B-D-glucopyranose or B-D-allopyranose? Explain. но НО Но OH OH OH OH OH B-D-Glucopyranose B-D-Allopyranosearrow_forwardA Fischer projection of a monosaccharide is shown below: CH₂OH C=O H НО HO -OH H H CH₂OH a. Classify this monosaccharide (e.g., aldotriose) b. Does it have the D or L configuration? c. Which carbon and oxygen become bonded in the furanose ring form of this monosaccharide (e.g., C206, where 06 means the oxygen on carbon 6, or "not formed")? d. Which carbon and oxygen become bonded in the pyranose ring form of this monosaccharide e.g., C206 or "not formed"?arrow_forward4 Draw a chair conformation for a β anomer of a disaccharide in which the two units of D-glucopyranose are joined by an α-1,6-glycosidic bond.arrow_forward
- A Fischer projection of a monosaccharide is shown below: H CH₂OH -OH H H HO C=O -OH -OH -H CH₂OH a. Classify this monosaccharide (e.g., aldotriose) b. Does it have the D or L configuration? c. Which carbon and oxygen become bonded in the furanose ring form of this monosaccharide (e.g., C206, where 06 means the oxygen on carbon 6, or "not formed")? d. Which carbon and oxygen become bonded in the pyranose ring form of this monosaccharide e.g., C206 or "not formed"?arrow_forward#6 B D F INSTRUCTIONS: Characterize the members of each of the following pairs of structures as enantiomers, diastereomers or neither enantiomers nor diastereomers.arrow_forward1. Which of the following is not true to the monosaccharide below? H. ОН но- -H- но ОН ĆH2OH O It is the Fischer Projection of D-glucose. It is an aldohexose having 4 chiral centers and 24 stereoisomers. It is has a D-glucose because OH- group bonded to the highest numbered chiral C is pointing to the right. It is a polyhydroxy ketone having 8 enantiomeric pair.arrow_forward
- 5. The Haworth projection of a simple sugar is given below. Note that the-OH group on the anomeric carbon can be either up or down. Using only this sugar, draw the Haworth projections of the following: a) an a-disaccharide with a B (1 3) glycosidic bond b) an a-disaccharide with an a (1→ 3) glycosidic bond c) a B-disaccharide with an a (1→4) glycosidic bond d) a B-disaccharide with an B (1 4) glycosidic bond CH2OH HO H H OH group can be either up or down OH H. OH Harrow_forwardThe enatiomer of D-sorbose: CH₂OH C: =0 H HO- H OH -H -OH CH₂OH D-sorbose Select one: Is an L-sugar that has opposite configuration around one carbon. Is an L-sugar that has opposite configuration around three carbons. Is a D-sugar that has opposite configuration around three carbons. Is a D-sugar that has opposite configuration around one carbon.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_forward
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