Chapter 3: 47P (page 190)
Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two isomers is more stable. Explain your reasoning.
Short Answer
Trans isomer of is more stable than cis isomer of .
/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none}
Learning Materials
Features
Discover
Chapter 3: 47P (page 190)
Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two isomers is more stable. Explain your reasoning.
Trans isomer of is more stable than cis isomer of .
All the tools & learning materials you need for study success - in one app.
Get started for free
(a) Draw both chair conformations of cis - 1,4 -dimethylcyclohexane and determine which conformer is more stable.
(b) Repeat for the trans isomer.
(c) Predict which isomer (cis or trans) is more stable.
Each of the following descriptions applies to more than one alkane. In each case draw and name two structures that match the description.
(a)
(b)
(c)
(d)
(e)
(f)
Use your models to do a chair-chair interconversion on each ring of the conformation of shown in Figure 3-27. Draw the conformation that results.
Question: Conformational studies on ethane-1,2-diol (HOCH2 -CH2OHhave shown the most stable conformation about the central C-Cbond to be the gauche conformation, which is 9.6 KJ/mol (2.3 kcal/mol)more stable than the anti-conformation. Draw Newman projections of these conformers, and explain this curious result.
Question: Draw a graph, similar to Figure 3-9, of the torsional strain of as it rotates about the bond between and . Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.
What do you think about this solution?
We value your feedback to improve our textbook solutions.