Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 5, Problem 5.66P
Artemisinin and mefloquine are widely used antimalarial drugs. A ball-and-stick model of artemisinin appears on the cover of this text.
a. Locate the stereogenic centers in both drugs.
b. Label each stereogenic center in mefloquine as
c. What is the maximum number of stereoisomers possible for artemisinin?
d. How are the
e. Can two molecules of artemisinin intermolecularly hydrogen bond to each other?
f. What product is formed when mefloquine is treated with
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3. Refer to the data below to answer the following questions:
Isoelectric point
Amino Acid
Arginine
10.76
Glutamic Acid
3.22
Tryptophan
5.89
A. Define isoelectric point.
B. The most basic amino acid is
C. The most acidic amino acid is
sidizo zo
3. A gas mixture contains 50 mol% H2 and 50 mol% He.
1.00-L samples of this gas mixture are mixed with
variable volumes of O2 (at 0 °C and 1 atm). A spark is
introduced to allow the mixture to undergo complete
combustion. The final volume is measured at 0 °C and 1
atm. Which graph best depicts the final volume as a
function of the volume of added O2?
(A)
2.00
1.75
Final Volume, L
1.50
1.25
1.00
0.75
0.50
0.25
0.00
0.00
0.25
0.50
2.00
(B)
1.75
1.50
Final Volume, L
1.25
1.00
0.75
0.50-
0.25
0.00
0.75
1.00
0.00
0.25
Volume O₂ added, L
2
0.50
0.75
1.00
Volume O₂ added, L
2
2.00
2.00
(C)
(D)
1.75
1.75
1.50
1.50
Final Volume, L
1.25
1.00
0.75
0.50
Final Volume, L
1.25
1.00
0.75
0.50
0.25
0.25
0.00
0.00
0.00
0.25
0.50
0.75
1.00
0.00
0.25
Volume O₂ added, L
0.50
0.75
1.00
Volume O₂ added, L
2
Leucine is an essential amino acid with the systematic name 2-amino-3-methylpentanoic acid. It has pai
2.36 and pKa2 = 9.60.
H2N-C(R)H-COOH and R is -CH2-CH(CH3)2
A. Draw the condensed structure for leucine, and label all chirality centers with an asterisk.
B. How many possible stereoisomers of leucine are there?
C. Draw a Fischer projection of L-leucine and label the chirality center(s) as R or S.
D. What is the p/ of leucine?
E. Draw the structure of the predominant form of leucine at 10.00.
F.
Draw the structure of the predominant form of leucine at pH = 1.50.
G. Leucine is described as an essential amino acid. What does this mean?
H. Show the alkyl halide you would use to prepare leucine by the amidomalonate method.
=
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Draw the mirror image of each compound. Label each...Ch. 5 - Prob. 5.4PCh. 5 - Prob. 5.5PCh. 5 - Prob. 5.6PCh. 5 - The facts in section 5.4A can be used to locate...Ch. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Label each compound as R or S.Ch. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Which of the following cyclic molecules are meso...Ch. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - The amino acid (S)-alanine has the physical...Ch. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Prob. 5.34PCh. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Prob. 5.37PCh. 5 - Determine if each compound is identical to or an...Ch. 5 - Prob. 5.39PCh. 5 - Locate the stereogenic centers in each compound. A...Ch. 5 - Prob. 5.52PCh. 5 - Prob. 5.41PCh. 5 - Prob. 5.42PCh. 5 - Prob. 5.43PCh. 5 - Prob. 5.44PCh. 5 - Prob. 5.45PCh. 5 - Label each stereogenic center as R or S. a. c. e....Ch. 5 - Prob. 5.47PCh. 5 - Prob. 5.48PCh. 5 - Prob. 5.49PCh. 5 - Prob. 5.50PCh. 5 - Prob. 5.51PCh. 5 - Prob. 5.53PCh. 5 - Prob. 5.54PCh. 5 - Prob. 5.55PCh. 5 - Draw all possible stereoisomers for each...Ch. 5 - Prob. 5.57PCh. 5 - 5.59 Explain each statement by referring to...Ch. 5 - Prob. 5.59PCh. 5 - Prob. 5.60PCh. 5 - Prob. 5.61PCh. 5 - Prob. 5.62PCh. 5 - Prob. 5.63PCh. 5 - Prob. 5.64PCh. 5 - Prob. 5.65PCh. 5 -
5.67 Artemisinin and mefloquine are widely used...Ch. 5 - 5.68 Saquinavir (trade name Invirase) is a...Ch. 5 - Prob. 5.68PCh. 5 - Prob. 5.69PCh. 5 - Prob. 5.70PCh. 5 - Prob. 5.71PCh. 5 - Problem 5.73 An acid-base reaction of with a...
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