Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 15, Problem 15.79P
Interpretation Introduction
Interpretation: A stepwise mechanism for the conversion of A to
Concept introduction: The general steps followed by free-radical reaction are stated below:
1. First step is initiation that involves formation of radical.
2. Second step is propagation.
3. Third step is the termination that involves the formation of stable bond.
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Prostaglandins are a class of eicosanoids, fatty acid derivatives involved in a variety of important phenomena, including fever, inflammation, and pain. The first step in
prostaglandin synthesis involves the conversion of the 20-carbon fatty acid arachidonic acid to PGG2 by the enzyme prostaglandin endoperoxide synthase, or cyclooxy:
Ibuprofen is one of several inhibitors of cyclooxogenase used therapeutically.
Arachidonic acid
20₂
0.5
1.0
1.5
2.5
3.5
cyclooxrygenase
PGG₂
JOH
محمد
The following kinetic data were obtained for the enzyme cyclooxygenase in the absence of any inhibitor (1), and in the presence of ibuprofen (2) at a concentration of 48
[arachidonic acid] (uM)
(1) v(uM/min) (2) v(uM/min)
23.5
32.2
36.9
41.8
44.0
16.67
25.25
30.49
37.04
38.91
Ibuprofen
A. Plot the data in standard Michaelis-Menten form as well as in double-reciprocal form.
B. Determine Vmax and Km for the enzyme.
C. Based on this limited data set, what type of inhibition does ibuprofen likely exhibit?…
Draw the structures of A, B, C and D in each step.
NaH
A-
B
H₂SO4
C
150 °C
D
Prostaglandins are a class of cicosanoids, 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
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Problem 15.6 Using mechanism 15.1 as guide, write...Ch. 15 - Prob. 15.7PCh. 15 - Problem 15.8 Which bond in the each compound is...Ch. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Draw the products of each reaction.
a. b. c.
Ch. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Problem 15.20 Which compounds can be prepared in...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15.35 What is the major monobromination product...Ch. 15 - Prob. 15.36PCh. 15 - 15.37 What alkane is needed to make each alkyl...Ch. 15 - 15.38 Which alkyl halides can be prepared in good...Ch. 15 - Prob. 15.39PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.42PCh. 15 - 15.43 Draw the products formed when each alkene is...Ch. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - 15.45 Draw the organic products formed in each...Ch. 15 - Prob. 15.46PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - 15.48 Draw the products formed in each reaction...Ch. 15 - Prob. 15.49PCh. 15 - 15.50 Draw all the monochlorination products that...Ch. 15 - Prob. 15.51PCh. 15 - 15.52 (a) Draw the products (including...Ch. 15 - 15.53 Consider the following bromination: .
a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - 15.57 Devise a synthesis of each compound from...Ch. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - 15.60 Devise a synthesis of each compound using ...Ch. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.69PCh. 15 - Prob. 15.70PCh. 15 - 15.71 Draw a stepwise mechanism for the following...Ch. 15 - 15.72 As we will learn in Chapter 30, styrene...Ch. 15 - Prob. 15.73PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.75PCh. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.77PCh. 15 - Prob. 15.78PCh. 15 - Prob. 15.79P
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