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.
Want to see the full answer?
Check out a sample textbook solutionChapter 2 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- 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_forwardRank the compounds in order of increasing symmetry: (a) OF2, (b) CF4, (c) NF3.arrow_forwardChloramlhenicol, 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_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_forwardWat are the four alcohols with the molecular formula C4H9OH. How many of these are chiral?arrow_forward
- The chiral compound of the following is: 1- trans-1,3-dichlorocyclobutane II- trans-1,2-dichlorocyclobutane IV- cis-1,3-dichlorocyclobutane Il- cis-1,2-dichlorocyclobutane O II O II O IV O None of the abovearrow_forwardDraw the chair conformation for the lowest energy conformationarrow_forwardIs cis-1,2-dibromocyclohexane a meso compound? In its planar structure, it has a line of symmetry but it has two chiral carbons. However, in its chair conformation, it does not look like it has a line of symmetry but it has two chiral carbons.arrow_forward
- Compare 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_forwardassign 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.arrow_forwardassign 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.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 ColeOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning