ORGANIC CHEMISTRY (LOOSELEAF)
6th Edition
ISBN: 9781260475630
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.
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
All are true or false
a)In solution, glucose is in the cyclic acetal form only.
b)The driving force for the Wittig reaction is the elimination of triphenylphosphine oxide
c)1H NMR spectroscopy, you can tell the difference between an aldehyde and a ketone because an aldehyde has a proton signal between 9–10 ppm.
d)When an aldehyde is reacted with excess ethanol with an acid as a catalyst it is called hemiacetal
e) You can't use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone because the ketone will be protonated and thus unreactive
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 (LOOSELEAF)
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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