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Concept explainers
Interpretation:
The relationship between the boxed atom and the circled atoms in the given structure has to be given.
Concept Introduction:
Cis, Trans Isomerism in Bicycloalkanes:
Depending on the orientation of two hydrogen atoms at the ring junction, whether the hydrogens are cis or trans to each other, two stereoisomers are possible for bicycloalkanes.
Example: Decalin:
Figure 1
Since both the ring in bicycloalkane is locked into one chair conformation, neither ring can invert to its alternative chair and thus the other substituent on ring which would be in equatorial position will remian equatorial and the substituent which would be in axial position will remain axial.
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Chapter 2 Solutions
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Which molecule would have their 2 chair conformations be of equal energies?arrow_forwardTamiflu(shown below) is an antiviral medication used to treat influenza. How many asymmetric centers are present in the this structure?arrow_forwardExplain the result of the specific rotation (-130\deg) shown by that compound (C13H1002) based on its molecular structure visualized in three dimensions.arrow_forward
- Butaclamol is a potent antipsychotic that has been used clinically in the treatment of schizophrenia. How many asymmetric centers does it have?arrow_forwardChloramphenicol is a broad-spectrum antibiotic that is particularly useful against typhoid fever. What is the configuration of each of its asymmetric centers?arrow_forwardTetracycline is called a broad-spectrum antibiotic because it is active against a wide variety of bacteria. How many asymmetric centers does tetracycline have?arrow_forward
- 5. For the molecules below assign the stereochemical configuration of the selected tetrahedral carbon chiral centers (R, S or N (not a chiral center)) and the alkene (E, Z or N (not a stereocenter)) that are indicated by the arrows (note that you do not have to assign the configuration of every chiral center in the molecule). If the atom in question is not a chiral center or is not a stereocenter circle N for neither. b) RSN RSN HO" RSN EZ N RSN НО. H₂N HO HO OH HO OH RSN RSN CH3 НИ H3 CH₂ RSN RSN RSN EZ N RSNarrow_forwardcis-1,2-Dimethylcyclohexane is optically inactive even though it has two chirality centers. Explain.arrow_forwardThe diaxial conformation of cis-1, 3-dimethylcyclohexane is approximately 23 kJ/mol (5.4 kcal/mol) less stable than the diequatorial conformation. Draw the two possible chair conformations, and suggest a reason for the large energy difference.arrow_forward
- myo-Inositol, one of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-inositol.arrow_forwardCompare the two possible chair conformations of this molecule. Given the AG for the two possible chair conformations, calculate the equilibrium constant for the interconversion between the two chair conformers at room temperature. CI H3C AG = 1.3 kcal/mol %3D AG = -RT In K %3D rearranges to K = e-AG/RT %3D R = 1.987 x 10-3 kcal/molK ||arrow_forwardWat are the four alcohols with the molecular formula C4H9OH. How many of these are chiral?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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