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Level 182

Conformations of Alkanes & Cycloalkanes


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torsional strain
Decreased stability of a molecule associated with eclipsed bonds
Steric strain
An increase in energy resulting when atoms are forced too close to one another
Van der Waal strain
When two substituents in a molecule approach each other with a distance less than the sum of their van der Waals radii
staggard/eclipsed
Most/least stable conformation of ethane
2.9 kcal/mol
Ea for ethane
gauche b/w two methyl groups
Most stable conformation of butane
gauche/anti/eclipsed
Rank the three conformations of butane from lowest to highest energy potential energy
240 pm
Van der Waal radius for two hydrogen atoms
Angle Strain
Energetically unfavorable due to bond angles being non-optimal
cyclopropane
bond angle is 60 but wnats 109.5 because of sp3 hybridization; unstable and flat
no, bent bonds
Are sp3 bonds present in cyclopropane? If not, what bonds are present?
Chair conformation
Most stable conformation of cyclohexane
half-chair conformation
Intermediate in the process of ring inversion with cyclohexane
strain
a measure of energy stored in a compound due to a structural distortion
conformation
any 3d arrangement of atoms that results from rotation about single bonds
Staggered Conformation
All bonds are distributed to be as far apart as possible
Eclipsed Conformation
All bonds are exactly lined up
conformational isomers
stereoisomers that can be converted into one another by rotation around a single bond
dihedral angle
60 degrees when staggered, 0 degrees when eclipsed
torsoinal strain
strain that arises when nonbonded atoms separated by three bonds forced from a staggered conformation to an eclipsed conformation
anti conformation
A conformation with a 180° dihedral angle between the largest groups. Usually the lowest-energy conformation.
Gauche conformatoin
conformation about single bond of alkane in which 2 groups on adjacent carbons lie 60 degrees
small ring strain
a strain associated with ring sizes below six arises from nonoptimal bond angles