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
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
Section4.4: Conformations Of Cycloalkanes
Problem 10P
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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.
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