Asprin synthesis

Chemistry: An Atoms First Approach
2nd Edition
ISBN:9781305079243
Author:Steven S. Zumdahl, Susan A. Zumdahl
Publisher:Steven S. Zumdahl, Susan A. Zumdahl
Chapter13: Acids And Bases
Section: Chapter Questions
Problem 74E
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Asprin synthesis

1. The synthesis of Aspirin is shown below.
HO
HO
HO
+
H2SO4 cat.
CH3
60 °C
salicylic acid
acetic anhydride
acetyl salicylic acid
a. Account for the smell of vinegar when an old bottle of aspirin is opened. Write a
reaction scheme to support your answer.
b. Hydrochloric acid is about as strong a mineral acid as sulfuric acid. Why would HCl
not be a satisfactory catalyst in this reaction?
Transcribed Image Text:1. The synthesis of Aspirin is shown below. HO HO HO + H2SO4 cat. CH3 60 °C salicylic acid acetic anhydride acetyl salicylic acid a. Account for the smell of vinegar when an old bottle of aspirin is opened. Write a reaction scheme to support your answer. b. Hydrochloric acid is about as strong a mineral acid as sulfuric acid. Why would HCl not be a satisfactory catalyst in this reaction?
c. For the 'H NMR spectrum of acetyl salicylic acid shown below, assign each signal to
the proton to which it corresponds (the COOH proton does not appear on this
spectrum).
سالال ار
8.0
7.0
PPM (8)
HO
CH3
На
Hb
Hc
Luwwlwwwwluwlwlwlwuluululuwlwwluwlwuluulwluwlwluwlwwlwwlw
9.0
8.0
7.0
6.0
3.0
2.0
1.0
5.0
4.0
PPM (8)
Transcribed Image Text:c. For the 'H NMR spectrum of acetyl salicylic acid shown below, assign each signal to the proton to which it corresponds (the COOH proton does not appear on this spectrum). سالال ار 8.0 7.0 PPM (8) HO CH3 На Hb Hc Luwwlwwwwluwlwlwlwuluululuwlwwluwlwuluulwluwlwluwlwwlwwlw 9.0 8.0 7.0 6.0 3.0 2.0 1.0 5.0 4.0 PPM (8)
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