constriction of bronchial tubes. Cromolyn sodium is synthesized in the above series of steps. 1. Treatment of one mole of epichlorohydrin with two moles of 2,6-dihydroxyacetophenone in the presence of base gives I. 2. Treatment of I with two moles of diethyl oxalate in the presence of sodium ethoxide gives a diester II. 3. Saponification of the diester with aqueous NaOH gives cromolyn sodium. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions HO HO :A H-A H3C. :o: :0-H :o: :ö:

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter20: Carbohydrates
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hapter 21
[References)
^ constriction of bronchial tubes.
Cromolyn sodium is synthesized in the above series of steps.
1. Treatment of one mole of epichlorohydrin with two moles of 2,6-dihydroxyacetophenone in the presence of base gives I.
2. Treatment of I with two moles of diethyl oxalate in the presence of sodium ethoxide gives a diester II.
3. Saponification of the diester with aqueous NaOH gives cromolyn sodium.
Draw curved arrows to show the movement of electrons in this step of the reaction mechanism.
Arrow-pushing Instructions
HO
HO
H3C.
:A
H3C.
H-A
:0-H
:0:
:0:
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Transcribed Image Text:hapter 21 [References) ^ constriction of bronchial tubes. Cromolyn sodium is synthesized in the above series of steps. 1. Treatment of one mole of epichlorohydrin with two moles of 2,6-dihydroxyacetophenone in the presence of base gives I. 2. Treatment of I with two moles of diethyl oxalate in the presence of sodium ethoxide gives a diester II. 3. Saponification of the diester with aqueous NaOH gives cromolyn sodium. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions HO HO H3C. :A H3C. H-A :0-H :0: :0: Submit Answer Try Another Version 1 item attempt remaining 11:25 F 31% 4/20/20
HO
HO.
OH
base
CI
EIO-
C-OEt
epichlorohydrin
OH
NaOEt
2,6-dihydroxy-
acetophenone
*Na O2C.
.CO2 Na*
NaOH, H2O
II
OH
Cromolyn sodium
Cromolyn sodium, developed during the 1960s, has been used to prevent allergic reactions primarily affecting the lungs, as, for example, exercised-
induced emphysema. It is thought to block the release of histamine, which prevents the sequence of events leading to swelling, itching, and
constriction of bronchial tubes.
v Cromolyn sodium is synthesized in the above series of steps.
rch
31%
11:24 P
4/20/20-
Transcribed Image Text:HO HO. OH base CI EIO- C-OEt epichlorohydrin OH NaOEt 2,6-dihydroxy- acetophenone *Na O2C. .CO2 Na* NaOH, H2O II OH Cromolyn sodium Cromolyn sodium, developed during the 1960s, has been used to prevent allergic reactions primarily affecting the lungs, as, for example, exercised- induced emphysema. It is thought to block the release of histamine, which prevents the sequence of events leading to swelling, itching, and constriction of bronchial tubes. v Cromolyn sodium is synthesized in the above series of steps. rch 31% 11:24 P 4/20/20-
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