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
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Organic Chemistry
- 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_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw Newman projections for the conformations in which -CH3 and -Br are gauche (dihedral angles 60° and 300°).arrow_forwardDraw 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_forward
- The 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_forwardWrite 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_forward
- The skeletal line formula for a branched alkene is shown below. (i) What is the molecular formula of this compound? (ii) How many carbon atoms are in the longest chain, ignoring the double bond? (iii) What is the longest chain incorporating both carbons of the double bond? (iv) How many substituents are on this chain? (v) Give the IUPAC name for this compound. [6]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_forwardquestion no.4?arrow_forward
- draw and name two structures that match the description of a trans-dihalocyclopentanearrow_forwardDraw a skeletal (line-bond) structure of trans-1,3- dimethylcyclohexane. Use a dash or wedge bond to indicate the relative relationship of substituents , where applicable .arrow_forwardDraw and name the six isomeric cyclopentane of molecular formula C7H14. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning