Organic Chem 1- Chapter 4
cycloalkanes / alicyclic compounds are what?
Saturated cyclic hydrocarbons
What's the formula for alkenes?
CnH2n+2
Cycloalkanes have what traits?
Non polar
Non hydrogen bonding
Fairly Inert
Low in flexibility
Cycloalkanes with more carbon chains have what?
Rotational freedom
Stereoisomer
Atoms connected in the same order but differing in a three-dimensional orientation.
Stereochemistry
The three-dimensional aspects of structure and reactivity.
Cis (Z)
Function group on the same side of the plane
Trans (E)
Function group both on opposite sides of the plane
Angle strain
Strain due to the compression and expansion of the bond angle.
What are the 4 different bond angles
Propane- 60 degree
Butane- 90 degree
Pentane- 108
Hexane- 120
Which is more stained cyclohexane or cyclopropane
Cyclopropane
What's torsional strain?
Strain due to the eclipsing bonds between neighboring atoms
What's steric strain?
Strain due to repulsive interaction when atoms get to close to eachother.
Whose bonds can bend?
Cyclopropane
How is maximum bonding achieved in a unstrained alkene?
When two atoms have their overlapping orbitals pointing towards each other
What does cyclobutane have?
Cyclobutane has less angle strain than cyclopropane but has more torsional strain because of its larger number of ring hydrogens.
Cyclopentane has what?
Large torsional strain
What is a chair conformation?
A three dimensional shape of a hexane, with no strains
Twist boat conformation has what?
Both torsional and steric strain, higher in energy than the chair conformation- less stable
Substituent positions for the chair conformation are?
Axial- Parallel to the ring axis
Equatorial- are in the rough plane of the ring, around the ring equator.
What is the ring flip?
chair conformations interconvert and exchange axial and equatorial positions.
What is 1,3-diaxial interactions?
The energy difference between axial and equatorial conformations is due to steric strain
What's more stable? Gauche or anti Butane
Anti Butane
What is a polycyclic molecule?
when two or more cycloalkane rings are fused together along a common bond