ORGANIC CHEMISTRY W/OWL
9th Edition
ISBN: 9781305717527
Author: McMurry
Publisher: CENGAGE C
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Question
Chapter 25.7, Problem 24P
Interpretation Introduction
Interpretation:
The mechanism of aldol condensation is explained.
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Consider the reaction below to answer the following questions.
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H
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O
CH₂OH
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A. Which carbonyl compound functions as the electrophile in this reaction?
B. Draw the structure of the enolate ion that is generated during the course of this reaction.
C. This reaction is an example of:
a. a mixed Claisen condensation.
b.
C.
d.
a Dieckman condensation.
a Michael reaction.
a mixed aldol reaction.
HD
HD
Consider the reaction below to answer the following questions:
847
Acetoacetic ester can be prepared by the Claisen self-condensation reaction of ethyl acetate.
H₁C
0
H
0
IL
유
||
OCH2CH3
1. NaOEt, EtOH C
2. H₂O
H3C
CH₂
Cold not tobizmo. S
OCH2CH3
A. Write the complete stepwise mechanism for this reaction. Show all electron flow with arrows and
draw all intermediate structures.
B. Ethyl acetate can be prepared from ethanol as the only organic starting material. Show all reagents
and structures for all intermediates in this preparation.
C. Give the structures of the ester precursors for the following Claisen condensation product and
formulate the reaction.
ou
OEL
A.
What is the correct structure for a-D-glucopyranose?
CH₂OH
a
HO
HO-
OH
b
HO
HO-
OH
HOH₂C
OH
OH
OH
CH₂OH
HO
C.
HO
HO-
OH
OH
CH₂OH
OH
OH
B. Draw structures for the products you would expect to obtain from reaction of B-D-galactopyranose
with each of the following reagents. Be sure to include all relevant stereochemistry. [FOUR only]
A. CH, Ag₂O
B. warm dilute HNO3
C. (CH3CO)20, pryridine
D. NaBH in H₂O
E. CH₂OH, HCI
F. Br₂, H₂O
HO
CH₂OH
HO-
OH
OH
B-D-galactopyranose
Chapter 25 Solutions
ORGANIC CHEMISTRY W/OWL
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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