Find the structural formulas for salicylic acid, acetic anhydride, and aspirin. Use these structural formulas to construct a reaction equation describing the synthesis of aspirin.  (CH3CO)2O + HOC6H4COOH → CH3CO2C6H4CO2H + CH3COOH acetic anhydride   salicylic acid   acetylsalicylic acid   acetic acid

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter26: Lipids
Section: Chapter Questions
Problem 26.15P
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  1. Find the structural formulas for salicylic acid, acetic anhydride, and aspirin. Use these structural formulas to construct a reaction equation describing the synthesis of aspirin. 

    (CH3CO)2O

    +

    HOC6H4COOH

    CH3CO2C6H4CO2H

    +

    CH3COOH

    acetic anhydride

     

    salicylic acid

     

    acetylsalicylic acid

     

    acetic acid

Part I  Synthesis of Aspirin

Mass of salicylic acid used (g)

 2.029g

Volume of acetic anhydride used (mL)

 5ml

Mass of acetic anhydride used (vol. × 1.08 g/mL)

 5.4g

Mass of aspirin synthesized (g)

 3.256g

Part II  Melting Temperature Data

Melting temperature (°C)

 133°C

Part III  Salicylic Acid Standard Stock Solution

Initial mass of salicylic acid (g)

 0.210g

Moles of salicylic acid (mol)

 0.0147 mol

Initial molarity of salicylic acid (M)

 0.724 M

Part III  Beer’s Law Data for Salicylic Acid Standard Solutions

Trial

Concentration
(M)

Absorbance

Water (mL)

1

 10

 0.301

0

2

 7.5

0.219

2.5

3

 5.0

0.163 

5.0

4

 2.5

0.074 

7.5

 

Best-fit line equation for the salicylic acid standards

 

Test of the Purity of the Synthesized Aspirin

Initial mass of aliquot of product (g)

 0.210g

Absorbance of sample prepared from aliquot

 0.081

Moles of salicylic acid in sample (mol)

 138.121 g/mol

Mass of salicylic acid in sample (g)

 2.029g

Actual mass of aspirin in sample (g)

 3.256g

Percent aspirin in sample (%)

 62.31%

 

 

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