Concept explainers
Interpretation:
The two chair conformations of
Concept introduction:
Cyclohexane exists in two chair conformations which interconvert through a chair flip. The hydrogen atoms in cyclohexane are either in axial or equatorial positions. During chair flip, the hydrogens that were in an axial position are in the equatorial position and vice versa. However, the two chair conformers of cyclohexane are indistinguishable as all atoms bonded to the ring carbons are small hydrogen atoms.
In substituted cyclohexane, the larger size of the substituent atom or group reduces the stability of one of the conformations. Bulky groups require more space than hydrogen atoms and, therefore, are more stable in the equatorial position. A substituent in axial position is close to the two hydrogen atoms in axial positions on the same side of the ring. There are no such hydrogens in close proximity to a substituent in an equatorial position. This makes the equatorial conformer more stable.
Want to see the full answer?
Check out a sample textbook solutionChapter 4 Solutions
ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
- Draw both chair conformations for both of the following cyclohexane derivatives and determine which chair conformer is lower energy and why.arrow_forwardProblem: Perform a conformational analysis 2-iodo-2-methylbutane, looking down the C2—C3 bond. Pay attention to the relative energies of the various conformations, but do not concern yourself with the actual energy values. Pleae draw newman projections.arrow_forwardDraw the Newman projection so that it corresponds to the molecule and conformation shown when viewed down the red bond in the direction of the arrow.arrow_forward
- The structure of a trisubstituted cyclohexane is shown, but no information is given about whether the groups are "up" or "down": that is, wedge and dash notation has not been used. Change the exo-cyclic bonds to represent the structure that will have the most stable chair conformation.arrow_forwarddrawn newman projection for most and least stable confirmation and look in direction of arrow. include strains that the least stable conformation has... Is the right side of the molecule an isopropyl?arrow_forwardDraw the Newman projection so that it corresponds to the molecule and conformation shown when viewed down the red bond in the direction of the red arrow. Your projection should be oriented as shown by the arrow marked up. So the CH2SH group on the front carbon should be above the H and H3C groups, no matter which template you usearrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning