ORGANIC CHEMISTRY-ACCESS
6th Edition
ISBN: 9781260475586
Author: SMITH
Publisher: MCG
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Chapter 26, Problem 63P
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.
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CH2OH
C=0
H-
OH
H-
-OH
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H-
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H-
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но
H-
Но
H-
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H-
H-
-H-
H20
H-
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O-
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-O-
H-
-OH
-O-
OH
ČHOH
CH,OH
ČH2OH
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(recovered
starting material)
D-glucose
Draw the steps and structures please.
5) Show the etherfication reaction of a-D glucopyranose.
α-D
glucopyranose
CH3 I
A920
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 26 Solutions
ORGANIC CHEMISTRY-ACCESS
Ch. 26.2 - Prob. 1PCh. 26.2 - Prob. 2PCh. 26.2 - Label each stereogenic center as R or S. a. b. c....Ch. 26.2 - Convert the ball-and-stick model to a Fischer...Ch. 26.2 - Prob. 5PCh. 26.2 - Prob. 6PCh. 26.3 - Prob. 7PCh. 26.3 - Prob. 8PCh. 26.4 - Prob. 9PCh. 26.4 - Prob. 10P
Ch. 26.6 - Prob. 11PCh. 26.6 - Prob. 12PCh. 26.6 - Prob. 13PCh. 26.6 - Prob. 14PCh. 26.6 - Prob. 15PCh. 26.7 - Prob. 16PCh. 26.7 - Draw a stepwise mechanism for the following...Ch. 26.7 - Prob. 18PCh. 26.8 - Prob. 19PCh. 26.9 - Prob. 20PCh. 26.9 - Prob. 21PCh. 26.9 - Draw the products formed when D-arabinose is...Ch. 26.9 - Prob. 23PCh. 26.10 - Prob. 24PCh. 26.10 - Prob. 25PCh. 26.10 - Prob. 26PCh. 26.10 - Prob. 27PCh. 26.11 - Prob. 28PCh. 26.11 - Prob. 29PCh. 26.12 - Prob. 30PCh. 26.12 - Prob. 31PCh. 26.13 - Prob. 32PCh. 26.13 - Prob. 33PCh. 26.13 - Problem-28.35
Draw the structures of the...Ch. 26.13 - Prob. 35PCh. 26 - 28.37 Convert each ball-and-stick model to a...Ch. 26 - Prob. 37PCh. 26 - Prob. 38PCh. 26 - 28.40 Convert each compound to a Fischer...Ch. 26 - Prob. 40PCh. 26 - Prob. 41PCh. 26 - 28.43 Draw a Haworth projection for each compound...Ch. 26 - Prob. 43PCh. 26 - 28.45 Draw both pyranose anomers of each...Ch. 26 - Prob. 45PCh. 26 - 28.50 Draw the products formed when D-altrose is...Ch. 26 - 28.58 Draw a stepwise mechanism for the following...Ch. 26 - Prob. 62PCh. 26 - Prob. 63PCh. 26 - Prob. 64PCh. 26 - Prob. 65PCh. 26 - Prob. 66PCh. 26 - Prob. 67PCh. 26 - Prob. 68PCh. 26 - Prob. 69PCh. 26 - Prob. 70P
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- Draw the organic products formed in the following reaction.arrow_forwardDraw the organic products formed in attached reaction, and indicate the stereochemistry of products that contain stereogenic centers.arrow_forwardAlthough 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_forward
- a. Which box contains a carbocyclic unsaturation? b. Which box contains an aryl structure? c. Which box contains carboxyl group? d. Which box contains a sulfide group? e. Which box contains an amide group?arrow_forwardMechanisms: Fischer Esterification Click on the basic site. „CH, H-O: H. CH비arrow_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
- Complete the following Fischer esterification reactionarrow_forwardDraw the two aldohexoses and one ketohexose that can be derived from the enol shownbelowarrow_forwardThe attached isomerization reaction, drawn using D-glucose as startingmaterial, occurs with all aldohexoses in the presence of base. Draw astepwise mechanism that illustrates how each compound is formed.arrow_forward
- A D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?arrow_forwardно CH₂OH Но НО anx CH₂OH НО OH CH3OH H* ӧ: H OH OH B-D-glucose Treatment of B-D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides. Draw curved arrow to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions HO H₂O CH₂OH Q-CH3 OCH3 + HO OH НО methyl B-D-glucoside CH₂OH -Ö: ний но НО CH₂OH НО он methyl a-D-glucoside OH OCH3 Н w-CH3 H2Oarrow_forwardDraw mechanism for fischer esterification using the reagents benzoic acid, methanol and sulfuric acid using the general mechanism attached as reference. HINT: You just need to replace the Rs in the general mechanism for the actual groups in your reagents.arrow_forward
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