(a)Calculate theoretical yield of both williamson ether synthesis of phenacetine and amide synthesis of phenacetin. (b) calculate the percent yield of phenacetin obtained via williamson ether synthesis. (c) Calculate the percent yeild of phenacetin obtained via the amide synthesis.

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Data:

Density of p-phenetidine is 1.065g/mol

Williamson Ether Synthesis:

Mass of filter paper:   0.680 g

Mass of filter paper and product:  1.482 g

Melting Point:  134-136oC

Amide Synthesis:

Mass of filter paper:   0.686 g

Mass of filter paper and product: 1.589 g

Melting Point:  135-137oC

Mixed Melting Point (product of amide synthesis mixed with Williamson Ether synthesis product): 134-136oC

(a)Calculate theoretical yield of both williamson ether synthesis of phenacetine and amide synthesis of phenacetin.

(b) calculate the percent yield of phenacetin obtained via williamson ether synthesis.

(c) Calculate the percent yeild of phenacetin obtained via the amide synthesis.

b Js Reagents and Properties
bp
C)
molar mass
mp
C)
substance
quantity
(g/mol)
oi acetic anhydride
102.09
138-140
1.2 mL
activated carbon
deutero-chloroform"
0.4 g
1 mL
6 mL
120
61
ethanol, 95%
hydrochloric acid,
concentrated
1.0 mL
phenacetin'
p-phenetidine
potassium bromide
sodium acetate
179
134-136
1.38 g
100 mg
137.18
4
250
2.0 g
82.03
* for NMR
product
for IR
Transcribed Image Text:b Js Reagents and Properties bp C) molar mass mp C) substance quantity (g/mol) oi acetic anhydride 102.09 138-140 1.2 mL activated carbon deutero-chloroform" 0.4 g 1 mL 6 mL 120 61 ethanol, 95% hydrochloric acid, concentrated 1.0 mL phenacetin' p-phenetidine potassium bromide sodium acetate 179 134-136 1.38 g 100 mg 137.18 4 250 2.0 g 82.03 * for NMR product for IR
Reagents and Properties
bp
C)
molar mass
mp
(C)
substance
quantity
g/mol)
1,51g
1.64 g
1 mL
169-172
151.17
108.97
120
46.07
p-acetamidophenol
bromoethane
deutero-chloroform
ethanol, 100%
ethanol, 95%
phenacetin'
potassium bromide
25% sodium methoxide
in methanol
37--40
61
4 mL
78
6 mL
179
134-136
100 mg
2.5 mL
for NMR
product
for IR
Transcribed Image Text:Reagents and Properties bp C) molar mass mp (C) substance quantity g/mol) 1,51g 1.64 g 1 mL 169-172 151.17 108.97 120 46.07 p-acetamidophenol bromoethane deutero-chloroform ethanol, 100% ethanol, 95% phenacetin' potassium bromide 25% sodium methoxide in methanol 37--40 61 4 mL 78 6 mL 179 134-136 100 mg 2.5 mL for NMR product for IR
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