The general values for steric and torsional strain are provided. Use these values to calculate the barrier to rotation for 2-methylpentane looking down the C2-C3 bond. Assume that methyl/ethyl steric interactions are the same as methyl/methyl. H. H H CH₂ CH₂ HH H H H HH H H H H₂C CH₂ CH₂ H H CH3/CH3 gauche 3.8 kJ/mol steric strain H/H eclipsed bond 4 kJ/mol torsional strain CH₂/H eclipsed bond 5.6 kJ/mol torsional strain CH3/CH3 eclipsed 11 kJ/mol torsional & steric strain

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter2: Alkanes And Cycloalkanes
Section: Chapter Questions
Problem 2.45P: Gibbs free energy differences between axial-substituted and equatorial-substituted chair...
icon
Related questions
icon
Concept explainers
Question
100%
The general values for steric and torsional strain are provided. Use
these values to calculate the barrier to rotation for 2-methylpentane
looking down the C2-C3 bond. Assume that methyl/ethyl steric
interactions are the same as methyl/methyl.
H
H
H
CH3
CH3
14 18 jä
H CH3
H₂C CH3
CH3/CH3 gauche
3.8 kJ/mol steric strain
H/H eclipsed bond
4 kJ/mol torsional strain
CH₂/H eclipsed bond
5.6 kJ/mol torsional strain
CH3/CH3 eclipsed
11 kJ/mol torsional & steric strain
h
1
4
7
+/-
2
5
8
kJ/mol
3
6
9
0
X
C
x 100
Transcribed Image Text:The general values for steric and torsional strain are provided. Use these values to calculate the barrier to rotation for 2-methylpentane looking down the C2-C3 bond. Assume that methyl/ethyl steric interactions are the same as methyl/methyl. H H H CH3 CH3 14 18 jä H CH3 H₂C CH3 CH3/CH3 gauche 3.8 kJ/mol steric strain H/H eclipsed bond 4 kJ/mol torsional strain CH₂/H eclipsed bond 5.6 kJ/mol torsional strain CH3/CH3 eclipsed 11 kJ/mol torsional & steric strain h 1 4 7 +/- 2 5 8 kJ/mol 3 6 9 0 X C x 100
Your submission:
7.6 kJ/mol
Feedback:
To calculate the barrier to rotation, subtract the
energy of most stable (lowest energy)
staggered conformation from the least stable
(highest energy) eclipsed conformation.
Transcribed Image Text:Your submission: 7.6 kJ/mol Feedback: To calculate the barrier to rotation, subtract the energy of most stable (lowest energy) staggered conformation from the least stable (highest energy) eclipsed conformation.
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Carbohydrates
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning