Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 28, Problem 28.62P
Interpretation Introduction
Interpretation: The stepwise mechanism for the isomerization of D-glucose to form the given compounds is to be drawn.
Concept introduction: Carbohydrates are naturally occurring organic compounds. The monosaccharide glucose is called an Aldohexose as it contains six carbon atoms as well as an
Glucose and mannose are
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The following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of
base. Draw a stepwise mechanism that illustrates how each compound is formed.
сно
сно
сно
CH2OH
C=0
H-
OH
H-
-OH
но-
H-
но
H-
"OH
но
H-
Но
H-
но
H-
H-
-H-
H20
H-
HO-
O-
H-
-O-
H-
-OH
-O-
OH
ČHOH
CH,OH
ČH2OH
ČH2OH
(recovered
starting material)
D-glucose
Draw the organic products formed in each reaction.
The following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of base. Draw a stepwise mechanism that illustrates how each compound is formed.
Chapter 28 Solutions
Organic Chemistry-Package(Custom)
Ch. 28 - Prob. 28.1PCh. 28 - Prob. 28.2PCh. 28 - Label each stereogenic center as R or S. a. b. c....Ch. 28 - Convert the ball-and-stick model to a Fischer...Ch. 28 - Prob. 28.5PCh. 28 - Prob. 28.6PCh. 28 - Prob. 28.7PCh. 28 - Prob. 28.8PCh. 28 - Prob. 28.9PCh. 28 - Prob. 28.10P
Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.18PCh. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.23PCh. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29PCh. 28 - Prob. 28.30PCh. 28 - Prob. 28.31PCh. 28 - Prob. 28.32PCh. 28 - Prob. 28.33PCh. 28 - Prob. 28.34PCh. 28 - Problem-28.35
Draw the structures of the...Ch. 28 - Prob. 28.36PCh. 28 - 28.37 Convert each ball-and-stick model to a...Ch. 28 - Prob. 28.38PCh. 28 - Prob. 28.39PCh. 28 - Convert each compound to a Fischer projection and...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - Prob. 28.43PCh. 28 - Prob. 28.44PCh. 28 - Prob. 28.45PCh. 28 - Draw both pyranose anomers of each aldohexose...Ch. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - Prob. 28.50PCh. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - What products are formed when each compound is...Ch. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - Prob. 28.58PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.60PCh. 28 - Prob. 28.61PCh. 28 - Prob. 28.62PCh. 28 - Prob. 28.63PCh. 28 - Prob. 28.64PCh. 28 - Prob. 28.65PCh. 28 - Prob. 28.66PCh. 28 - Prob. 28.67PCh. 28 - Prob. 28.68PCh. 28 - Prob. 28.69PCh. 28 - Prob. 28.70PCh. 28 - Prob. 28.71PCh. 28 - Prob. 28.72PCh. 28 - Prob. 28.73PCh. 28 - Prob. 28.74PCh. 28 - Prob. 28.75PCh. 28 - Prob. 28.76PCh. 28 - Prob. 28.77PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.79P
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- Although reaction occurs in sugars also. H, OH H H-C-OH Oxidizing agent OH OH Н-С-ОН Н-С-ОН C=0 R OH R R R Aldose Aldonic acid anion Ketose Enediol Copyright © 2007 Pearson Prentice Hall, Inc. Draw the reaction above substituting D-fructose instead of the generalized ketose structure shown above (you need to draw all 4 structures). Slan and upload your drawing.arrow_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 B anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.arrow_forwardDraw a mechanism for the conversion of glucose from its aldehyde form to its hemiacetal form and then to its methyl glycoside (acetal) form under acidic conditions. Show all bond breaking and bond forming steps; show all intermediates.arrow_forward
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