Make an electron-flow-mechanism for this synthetic scheme. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shown. (D-GLUCOSE -> ASCORBIC ACID) MeМеAcetobacterОНOHОНOHОНsuboxydanspH 4-6, 30-35 °C3. Acetone,HOH2SO437 %о На. RaNiMeНОНОНо-OHquant.>90 %OHОНOHОНOHOHMeD-glucose (10)111213OHНОHO4.NaOCI, NICI, > 93 %5. Н20, H*, 82 %HOHstep 3+4 can be replacedby oxidation with Air &6. HCI, PhMe, AНоОНОН> 60 %HO.14OHAscorbic acid (15)PtO

Mechanism of synthesis of ascorbic acid from glucose is given below.

Make an electron-flow-mechanism for this synthetic scheme. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shown. (D-GLUCOSE -> ASCORBIC ACID)

Make an electron-flow-mechanism for this synthetic scheme. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shown. (D-GLUCOSE -> ASCORBIC ACID)

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

Chapter21: Lipids

Section: Chapter Questions

Problem 21.47P

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Question

Make an electron-flow-mechanism for this synthetic scheme. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shown. (D-GLUCOSE -> ASCORBIC ACID)

Me
Ме
Acetobacter
ОН
OH
ОН
OH
ОН
suboxydans
pH 4-6, 30-35 °C
3. Acetone,
HO
H2SO4
37 %
о На. RaNi
Me
НО
НО
Но
-OH
quant.
>90 %
OH
ОН
OH
ОН
OH
OH
Me
D-glucose (10)
11
12
13
OH
НО
HO
4.NaOCI, NICI, > 93 %
5. Н20, H*, 82 %
HOH
step 3+4 can be replaced
by oxidation with Air &
6. HCI, PhMe, A
Но
ОН
ОН
> 60 %
HO.
14
OH
Ascorbic acid (15)
PtO

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