Concept explainers
Interpretation:
Using Newman projection, the relative positions of the substituents on the bridgehead atoms of cis- and trans- decalin is to be depicted and the isomer which is more stable is to be determined and the reason for the same is to be explained..
Concept introduction:
Newman projected two types of spatial arrangements of molecules which are staggered and eclipsed Newman projections.
Staggered conformation: It is the arrangement of atoms or groups of atoms in a molecule resulting in a
Eclipsed conformation: It is the arrangement of atoms or groups of atoms in a molecule resulting in a
Want to see the full answer?
Check out a sample textbook solutionChapter 4 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
- Following is a structural formula for cortisol (hydrocortisone). Draw a stereo-representation of this molecule showing the conformations of the five- and six-membered rings.arrow_forwardDraw six isomeric cyclopentanes of molecular formula C7H14. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.arrow_forwardFor rotation about the C-a – C-b bond, using the following templates, draw the Newman Projection of the two staggered conformers that are different in energy. Fill each bond on Newman Projection with Hydrogen or Substituents. You may use Abbreviations such as Me for Methyl, Et for Ethyl, iPr for isopropyl. Circle the Newman projection of the most stable conformer.arrow_forward
- A structure with the formula C7H14O must be drawn that contains one stereocenter, an alcohol, and a disubstituted alkene including what the IUPAC name is for this compound. Dashes/wedges should be used to show which enantiomer is being drawn. In addition, what is the enantiomer drawing and IUPAC name of this compound, as well as the diastereomer of this compound and IUPAC name?arrow_forwardDraw structural formulas for the cis and trans isomers of hydrindane. Show each ring in its most stable conformation. Which of these isomers is more stable?arrow_forwardDraw all the possible conformations of trans- and cis-1,3-dimethylcyclobutane. Which of these conformations is the most stable conformation? Explain your answer. Discuss the type of strain(s) that affect the stability of these compounds.arrow_forward
- Draw a structural formula for cis-1-bromo-3-ethylcyclopentane. • Show stereochemistry only if given in the name. • In cases where there is more than one answer, just draw one.arrow_forwardThe energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).arrow_forwardWhich of the following is an incorrect statement: Isomers have the same molecular formula such as cyclohexane and 1-hexene. Conformational isomers are enantiomers or diastereomers, which can interconvert through rotations around bonds within molecules, which include anti and gauche butane. Stereoisomers have the same connectivity but different arrangement of their parts in space, which include enantiomers, diastereomer, and conformational isomers, which include cis and trans dichlorocyclobutane. O Structural or constitutional isomers are molecules of the same formula but different connectivity such as 1,1-dichlorocyclopropane and 1.2-dichlorocyclobutane.arrow_forward
- Write TRUE if the BOLD word/phrase makes the statement correct. Otherwise, write the correct WORD/PHRASE that will make the statement true. If there are two bold words/phrases in a number, write your answer for EACH of the bold words/phrases. 1. The anti-staggered conformation of butane, in which the methyl groups have a dihedral angle of less than 180°, has the highest energy. 2. The formation of 2-methylpropene as side product in the synthesis of tert-butyl chloride is a nucleophilic substitution reaction. 3. The generation of tertiary carbocation is the rate-determining step in tert-butyl chloride synthesis.arrow_forwardDefine conformational isomers. Draw or attach a photo then arrange the following conformers of butane in order of energy, lowest to highest: eclipsed, totally eclipsed, gauche, and anti.arrow_forwardOnly three stereoisomers are possible for 2,3-dibromo-2, 3-dichlorobutane. Draw them, indicating which pair are enantiomers (optical isomers). Why does the other isomer not have an enantiomer?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning