ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
8th Edition
ISBN: 9780134595450
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Textbook Question
Chapter 4.15, Problem 54P
Chloramphenicol is a broad-spectrum antibiotic that is particularly useful against typhoid fever. What is the configuration of each of its asymmetric centers?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
How many carbon chirality centers does the molecule possess?
Which of the following compounds has one or more asymmetric centers?
Butaclamol is a potent antipsychotic that has been used clinically in the treatment of schizophrenia. How many asymmetric centers does it have?
Chapter 4 Solutions
ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
Ch. 4.1 - Prob. 2PCh. 4.1 - Prob. 3PCh. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Which of the roll owing compounds have a dipole...Ch. 4.2 - Draw and label the E and Z isomers for each of the...Ch. 4.2 - Assign relative priorities to each set of...Ch. 4.2 - Tamoxifen slows the growth of some breast tumors...Ch. 4.2 - Prob. 10PCh. 4.2 - Name each of the following:
Ch. 4.2 - Draw the Z isomer of an alkene that has a CH3 and...Ch. 4.3 - Prob. 13PCh. 4.4 - Prob. 14PCh. 4.5 - Prob. 16PCh. 4.6 - Prob. 17PCh. 4.7 - Prob. 18PCh. 4.8 - Prob. 20PCh. 4.8 - Prob. 22PCh. 4.8 - Prob. 23PCh. 4.8 - Prob. 24PCh. 4.8 - Draw a perspective formula for each or the...Ch. 4.8 - Prob. 27PCh. 4.9 - Prob. 28PCh. 4.9 - What is the configuration of the following...Ch. 4.9 - Prob. 32PCh. 4.10 - Prob. 33PCh. 4.10 - (S)-(+)-Monosodium glutamate (MSG) is a flavor...Ch. 4.11 - Prob. 35PCh. 4.11 - Prob. 36PCh. 4.12 - Prob. 38PCh. 4.12 - Prob. 39PCh. 4.12 - The stereoisomer of cholesterol found in nature is...Ch. 4.12 - Prob. 41PCh. 4.13 - 1-Bromo-2-methylcyclopentane has four pairs of...Ch. 4.13 - Prob. 43PCh. 4.13 - Draw all possible stereoisomers for each of the...Ch. 4.13 - Prob. 45PCh. 4.13 - Of all the possible cyclooctanes that have one...Ch. 4.13 - Prob. 47PCh. 4.13 - Prob. 48PCh. 4.14 - Which of the following compounds has a...Ch. 4.14 - Draw all the stereoisomers for each of the...Ch. 4.15 - Prob. 52PCh. 4.15 - Name the isomers you drew in Problem 52.Ch. 4.15 - Chloramphenicol is a broad-spectrum antibiotic...Ch. 4.15 - Draw a perspective formula for each of the...Ch. 4.15 - Name the following:Ch. 4.15 - Prob. 57PCh. 4.15 - Prob. 59PCh. 4.15 - Convert the perspective formula to a skeletal...Ch. 4.15 - Prob. 62PCh. 4.16 - Prob. 63PCh. 4.17 - Limonene exists as two different stereoisomers....Ch. 4 - a. Draw three constitutional isomers with...Ch. 4 - Prob. 65PCh. 4 - Prob. 66PCh. 4 - Which of the following has an asymmetric center?...Ch. 4 - Prob. 68PCh. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Prob. 71PCh. 4 - Assign relative priorities to each set of...Ch. 4 - Prob. 73PCh. 4 - Which of the following are optically active?Ch. 4 - Prob. 75PCh. 4 - Name the following:Ch. 4 - Which of the following has an achiral...Ch. 4 - Using skeletal structures, draw the stereoisomers...Ch. 4 - Prob. 79PCh. 4 - Citrate synthase, one of the enzymes in the series...Ch. 4 - Prob. 81PCh. 4 - Prob. 82PCh. 4 - Prob. 83PCh. 4 - Prob. 84PCh. 4 - Prob. 85PCh. 4 - Prob. 86PCh. 4 - Prob. 87PCh. 4 - Prob. 88PCh. 4 - Prob. 89PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 91PCh. 4 - Prob. 92PCh. 4 - Draw structures for the following: a....Ch. 4 - For each of the following structures, draw the...Ch. 4 - Prob. 95PCh. 4 - Prob. 96PCh. 4 - Prob. 97PCh. 4 - a. Using the wedge-and-dash notation, draw the...Ch. 4 - Prob. 99PCh. 4 - Prob. 100PCh. 4 - Prob. 101PCh. 4 - a. Draw the two chair conformers for each of the...Ch. 4 - Prob. 103PCh. 4 - Is the following compound optically active?Ch. 4 - Prob. 105P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Bystolic (shown below) is a pharmaceutical used to treat high blood pressure. How many asymmetric centers are present in this structure?arrow_forwardMevacor is used clinically to lower serum cholesterol levels. How many asymmetric centers does Mevacor have? Mevacor®CH3HO Oarrow_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_forward
- Tamiflu(shown below) is an antiviral medication used to treat influenza. How many asymmetric centers are present in the this structure?arrow_forwardAtorvastatin is sold under the trade name Lipitor and is used for lowering cholesterol. Annual global sales of this compound exceed $13 billion. Assign a configuration to each chiral center in atorvastatin: 12 32 33 18 36 39 42 13 11 OH OH 19 14 9 6 34 37 40 OH 41 15 3 20 35 38 H 1021 16 17 30 22 25 26 29 28 23 24 27 31 In the boxes below, first input the numbers corresponding to the chiral centers in numerical order as a comma separated list (e.g., "1,3,4"). Then input the configurations of the chiral centers in the same order and format (e.g., "R,S,S"). chiral center(s): Configuration(s):arrow_forwardHow many chirality centers does this molecule have?arrow_forward
- Indicate the stereochemical configuration for the tetrahedral center. OR H OH not a configuration center S Indicate the stereochemical configuration for the tetrahedral center. H₂N H S not a configuration center ORarrow_forward#23arrow_forwardANSWER THE FOLLOWING PROBLEM AND EXPLAIN YOUR ANSWER FOR BETTER UNDERSTANDINGarrow_forward
- Diastereomers are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other. OH OH НО Но ÕH ОН How many chiral centers are present in one of the structures above? 1 O 2 O0 Are the structures mirror images of each other (i.e., are ALL of the chiral centers exactly opposite)? no yes I can not tell. How are these two structures related to each other? Diastereomers Non-isomeric (different molecular formulas) O Constitutional (same MF but different connections) Enantiomers (non-superimposable mirror images)arrow_forwardMany biological relevant compounds such as steroid hormones have multiple stereocentres (chiral centers). How many stereocentres does the following compound contain? LO 5 6 7 8 9arrow_forward3. Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. Assign the absolute configurations of the two chirality centers as R or S. Ans: OH OH CO₂Harrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks ColeOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Group Theory - Learn like Expert with 3D animation | Introduction for Beginners | ONE Chemistry; Author: One Chemistry;https://www.youtube.com/watch?v=Lz2ih8fkgDs;License: Standard YouTube License, CC-BY