1.Calcluate the theoretical yield of the coumerin prodcut from the reaction below. 2. Given an actual yield of 4.1 grams of coumarin. Calculate the percent yield of coumerin.

EBK A SMALL SCALE APPROACH TO ORGANIC L
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Chapter2: Crystallization
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1.Calcluate the theoretical yield of the coumerin prodcut from the reaction below.

2. Given an actual yield of 4.1 grams of coumarin. Calculate the percent yield of coumerin.

.CO2Et
.CO2E
(pКa 11)
ОН
НОАС
(pКa 5)
salicylaldehyde
ethyl malonate
EEOH
(pКa 8-9)
(РКa 13)
78°С, 2 h
Reagent table:
revised 03/09/2010ssh
reagent (source)
Mwt
mp °C bp OС
(Fp)
mmol (%)
mass
density
volume
salicylaldehyde
(Acros)
122.1
1-2
197
(76)
32.9 (99%) 4.02 g
1.16g/mL
3.5 mL
diethyl malonate
(Aldrich)
160.2
199
35.9 (99%) 5.75 g
1.06g/mL
5.5 mL
ethanol (100%)
(Pharmaco)
46.1
-117
78
0.79 g/mL 25 mL
piperidine
(Aldrich)
4.0 (99%)
0.34 g
85.2
-13
106
0.86 g/mL 0.40 mL
acetic acid
60.1
16
118
0.9
0.05 g
1.05 g/mL 0.05 mL
(Pharmaco)
glacial acetic acid
(99.7%)
7.18 g
ethyl 3-coumarin-
carboxylate
218.2
92-94
32.9
Transcribed Image Text:.CO2Et .CO2E (pКa 11) ОН НОАС (pКa 5) salicylaldehyde ethyl malonate EEOH (pКa 8-9) (РКa 13) 78°С, 2 h Reagent table: revised 03/09/2010ssh reagent (source) Mwt mp °C bp OС (Fp) mmol (%) mass density volume salicylaldehyde (Acros) 122.1 1-2 197 (76) 32.9 (99%) 4.02 g 1.16g/mL 3.5 mL diethyl malonate (Aldrich) 160.2 199 35.9 (99%) 5.75 g 1.06g/mL 5.5 mL ethanol (100%) (Pharmaco) 46.1 -117 78 0.79 g/mL 25 mL piperidine (Aldrich) 4.0 (99%) 0.34 g 85.2 -13 106 0.86 g/mL 0.40 mL acetic acid 60.1 16 118 0.9 0.05 g 1.05 g/mL 0.05 mL (Pharmaco) glacial acetic acid (99.7%) 7.18 g ethyl 3-coumarin- carboxylate 218.2 92-94 32.9
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