draw the curly arrow mechanism for this experiment, include all details like electrons, curly arrows, by products etc

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter25: Biomolecules: Carbohydrates
Section25.SE: Something Extra
Problem 69AP
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draw the curly arrow mechanism for this experiment, include all details like electrons, curly arrows, by products etc 

3. Formation of trichloroacetimidate donor
2,2,3,3'4',6,6'-Hepta-O-acetyl-B-D-lactose trichloroacetimidate (3)
OAC
ACO
LOAc
Cl3CCN
Aco
LOAC
K₂CO3
AcO
DCM
OACACO-
OAc
NH
Compound
MW (g/mol) eq
n (mmol)
d (g/ml)
Sugar (crude)
636.55
1
4.71
Trichloroacetonitrile
144.39
8.5
1.44
Potassium carbonate
138.21
3
DCM
84.93
1.33
Apparatus: 50 round bottom flask, N₂ atmosphere
Reaction temperature: RT
Reaction time:
TLC: EtOAc/Tol 1:1 + 1% NET,
Reaction molarity: 0.2 M
The crude sugar is dissolved in dry DCM, trichloroacetonitrile and potassium carbonate are added.
Stirring at RT until starting material is consumed. After complete conversion, the solution is filtered,
concentrated in vacuo (water bath not warmer than 30 °C). Crude is used directly for next reaction.
C26H36018
636.5532
OH
AcO
OACACO-
m (g)
LOAC
OAC
C28H36C13NO 18
780.9403
V (ml)
CCI
Transcribed Image Text:3. Formation of trichloroacetimidate donor 2,2,3,3'4',6,6'-Hepta-O-acetyl-B-D-lactose trichloroacetimidate (3) OAC ACO LOAc Cl3CCN Aco LOAC K₂CO3 AcO DCM OACACO- OAc NH Compound MW (g/mol) eq n (mmol) d (g/ml) Sugar (crude) 636.55 1 4.71 Trichloroacetonitrile 144.39 8.5 1.44 Potassium carbonate 138.21 3 DCM 84.93 1.33 Apparatus: 50 round bottom flask, N₂ atmosphere Reaction temperature: RT Reaction time: TLC: EtOAc/Tol 1:1 + 1% NET, Reaction molarity: 0.2 M The crude sugar is dissolved in dry DCM, trichloroacetonitrile and potassium carbonate are added. Stirring at RT until starting material is consumed. After complete conversion, the solution is filtered, concentrated in vacuo (water bath not warmer than 30 °C). Crude is used directly for next reaction. C26H36018 636.5532 OH AcO OACACO- m (g) LOAC OAC C28H36C13NO 18 780.9403 V (ml) CCI
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