EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
3rd Edition
ISBN: 9780133858501
Author: Bruice
Publisher: PEARSON CO
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Question
Chapter 11, Problem 44P
Interpretation Introduction
Interpretation:
To predict the products obtained upon the hydrolysis of aspartame in an aqueous solution of hydrochloric acid.
Concept introduction:
Amides are generally very stable compounds however upon acid or base catalyzed hydrolysis the amide bond
The general mechanism for the acid hydrolysis of amides is given as,
Acid: Esters undergoes acid hydrolysis the which produces alcohols.
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Digitalis is a preparation made from the dried seeds and leaves of the purple foxglove,
Digitalis purpurea, a plant native to southern and central Europe and cultivated in the United
States. The preparation is a mixture of several active components, including digitalin. Digi-
talis is used in medicine to increase the force of myocardial contraction and as a conduction
depressant to decrease heart rate (the heart pumps more forcefully but less often).
HC
OH
H,C
H
CH3
H.
H.
(a) Describe this glycosidic bond
OCH, H
A (b) Draw an open-chain Fischer projection
of this monosaccharide
CH3
H.
(e) Describe this glycosidic bond
OCH, HA
H.
HO H)
H.
OH
НО
(d) Name this monosaccharide unit
H.
OH
Digitalin
Prostaglandins are a class of eicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues.
They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20-
carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a
cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins.
Rate of formation of PGG2 with 10 mg/ml
ibuprofen (mM/min)
Arachidonic
acid (mM)
Rate of formation
of PGG2 (mM/min)
0.190
12.3
0.228
13.9
0.342
17.5
0.570
1.33
22.2
28.8
7.71
8.88
11.9
16.3
24.0
The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing
here on the first two columns, determine the Vmax and Km of the enzyme.
Vmax
Km
=
mM/min
mM
Aspirin is the common name for the compound acetylsalicylic acid, widely used as a
fever reducer and as a pain killer. Salicylic acid, whose name comes from Salix, the
willow family of plants, was derived from willow bark extracts. In folk medicine, willow
bark teas were used as headache remedies and other tonics. Nowadays, salicylic acid
is administered in the form of aspirin which is less irritating to the stomach than salicylic
acid. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride.
A small amount of a strong acid is used as a catalyst which speeds up the reaction. In
this experiment, phosphoric acid will be used as the catalyst. The excess acetic acid
will be quenched with the addition of water. The aspirin product is not very soluble in
water so the aspirin product will precipitate when water is added. The synthesis
reaction of aspirin is shown below:
Actic anhydride
5 ml.
Acetic acid
Salicylic acid
28
Acetylsalicylie acid
Procedure
1)
Mix salicylic…
Chapter 11 Solutions
EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
Ch. 11.1 - The aromas of many flowers and fruits are due to...Ch. 11.1 - Name the following compounds:Ch. 11.1 - Prob. 3PCh. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.4 - a. What is the product of the reaction of acetyl...Ch. 11.4 - Prob. 7PCh. 11.5 - Using the pKa values listed in Table 11.1, predict...Ch. 11.6 - Starting with acetyl chloride, what neutral...Ch. 11.6 - Prob. 10P
Ch. 11.7 - Prob. 11PCh. 11.8 - Prob. 13PCh. 11.8 - Using the mechanism for the acidcatalyzed...Ch. 11.8 - Prob. 15PCh. 11.8 - Prob. 16PCh. 11.8 - Prob. 17PCh. 11.9 - Prob. 18PCh. 11.10 - Show how each of the following esters could be...Ch. 11.11 - Which of the following reactions would lead to the...Ch. 11.12 - Prob. 22PCh. 11.12 - Prob. 23PCh. 11.13 - Prob. 24PCh. 11.13 - Prob. 25PCh. 11.14 - Prob. 26PCh. 11.14 - Prob. 27PCh. 11.14 - Prob. 28PCh. 11.15 - Prob. 29PCh. 11.15 - How would you synthesize the following compounds...Ch. 11 - Write a structure for each of the following a. N,N...Ch. 11 - Prob. 32PCh. 11 - Which ester is more reactive, methyl acetate or...Ch. 11 - What products would be formed from the reaction of...Ch. 11 - What products would be obtained from the following...Ch. 11 - Prob. 36PCh. 11 - a. Which compound would you expect to have a...Ch. 11 - a. List the following esters in order of...Ch. 11 - D. N. Kursanov, a Russian chemist, proved that the...Ch. 11 - Prob. 40PCh. 11 - Using an alcohol for one method and an alkyl...Ch. 11 - Prob. 42PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Show how the following compounds could be prepared...Ch. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53P
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