Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 4, Problem 69P
Chloramphenicol is a broad-spectrum antibiotic that is particularly useful against typhoid fever. What is the configuration of each of the asymmetric centers?
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Chapter 4 Solutions
Essential Organic Chemistry, Global Edition
Ch. 4.1 - Draw the cis and trans isomers for the following:...Ch. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Prob. 6PCh. 4.2 - Prob. 7PCh. 4.2 - Tamoxifen slows the growth of some breast tumors...Ch. 4.2 - Draw and label the E and Z isomers for each of the...Ch. 4.2 - Prob. 10PCh. 4.2 - Name each of the following:Ch. 4.2 - Draw the structure of (Z)-2,3-dimethyl-3-heptene.
Ch. 4.3 - Prob. 13PCh. 4.4 - Prob. 14PCh. 4.5 - Prob. 16PCh. 4.6 - Prob. 17PCh. 4.7 - Assign relative priorities to the groups or atoms...Ch. 4.7 - Name the following:Ch. 4.7 - Prob. 22PCh. 4.7 - Draw a perspective formula for each of the...Ch. 4.8 - Prob. 24PCh. 4.8 - Prob. 27PCh. 4.9 - Prob. 28PCh. 4.9 - Prob. 29PCh. 4.9 - Prob. 30PCh. 4.10 - Prob. 31PCh. 4.10 - Prob. 32PCh. 4.10 - Prob. 33PCh. 4.11 - Prob. 34PCh. 4.11 - a. Draw the stereoisomers of...Ch. 4.11 - Prob. 37PCh. 4.11 - Prob. 38PCh. 4.12 - Which of the following compounds has a...Ch. 4.12 - Draw all the stereoisomers for each of the...Ch. 4.12 - Limonene exists as two different stereoisomers....Ch. 4 - a. Draw three constitutional isomers with...Ch. 4 - Which of the following have an asymmetric center?...Ch. 4 - Prob. 45PCh. 4 - Prob. 46PCh. 4 - Of all the possible cyclooctanes that have one...Ch. 4 - Prob. 48PCh. 4 - Prob. 49PCh. 4 - Prob. 50PCh. 4 - Prob. 51PCh. 4 - Prob. 52PCh. 4 - Draw the stereoisomers of 2,4-dichlorohexane....Ch. 4 - Prob. 54PCh. 4 - Prob. 55PCh. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Prob. 59PCh. 4 - Prob. 60PCh. 4 - Prob. 61PCh. 4 - Prob. 62PCh. 4 - Draw structures for each of the following: a....Ch. 4 - Prob. 64PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 66PCh. 4 - Prob. 67PCh. 4 - Prob. 68PCh. 4 - Chloramphenicol is a broad-spectrum antibiotic...
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- Which of the following compounds has an asymmetric center? a. CH3CH2CHCH3-Cl b. CH3CH2CHCH3-CH3 c. CH3CH2C-CH3CH2CH2CH3 d. CH3CH2OH e. CH3CH2CH-BrCH2CH3 f. CH2=CHC-NH2HCH3arrow_forwardWhat is the configuration of the asymmetric centers in the following compounds?arrow_forwardWhich of the following compounds has one or more asymmetric centers?arrow_forward
- Chloramlhenicol, a powerful antibiotic in 1947 from the streptomyces venezuelae bacterium, is active against a broad spectrum of bacterial infections and is particularly valuable against typhoid fever. Assign R or S configurations to the chirality centers in chloramphenicolarrow_forwardCymbalta (shown below) is an antidepressant. How many asymmetric centers are present in this structure?arrow_forwardTamiflu(shown below) is an antiviral medication used to treat influenza. How many asymmetric centers are present in the this structure?arrow_forward
- High serum cholesterol levels often correlate with increased risk of heart attacks. The structure of cholesterol is shown below. Identify the chiral centers. How many chiral centers are there in cholesterol?arrow_forwardDetermine the absolute configuration of the asymmetric center in the following compound.arrow_forwardThe following bond-line structure represents one enantiomer of 2-amino-3-(3,4- dihydroxyphenyl)propanoic acid, used in the treatment of Parkinson’s disease. Assign the configuration of the chirality center in this compound. Show the chiral center, assign all priorities.arrow_forward
- Tetracycline is called a broad-spectrum antibiotic because it is active against a wide variety of bacteria. How many asymmetric centers does tetracycline have?arrow_forwardThe quantitative differences in biological activity between the two enantiomers of a compound are sometimes quite large. For example, the D isomer of the drug isoproterenol, used to treat mild asthma, is 50 to 80times more effective as a bronchodilator than the L isomer. Identify the chiral center in isoproterenol. Why do the two enantiomers have such radically different bioactivity?arrow_forward1. Determine whether the molecule is chiral or achiral 2. Oseltamivir phosphate (sold under the trade name Tamiflu®) is a prescription antiviral drug that is used in the treatment of both Influenza virus type A and Influenza virus type B. Identify all the stereocenters by labelling with an asterisk (*).arrow_forward
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