03_Lecture(55页)烷烃的结构和立体化学.ppt

* File Name: AAAKPMH0 Figure: 03_16.jpg Title: Conformations of Cyclopropane Caption: Torsional strain in cyclopropane. All the carbon-carbon bonds are eclipsed, generating torsional strain that contributes to the total ring strain. Notes: The angle strain and the torsional strain in cyclopropane make this ring size extremely reactive. * File Name: AAAKPME0 Figure: 03_14.jpg Title: Ring Strain and Torsional Strain of Cyclobutane Caption: The ring strain of a planar cyclobutane results from two factors: Angle strain from the compressing of the bond angles to 90° rather than the tetrahedral angle of 109.5°, and torsional strain from eclipsing of the bonds. Notes: The angle compression for butane is 19.5°. Angle strain and torsional strain account for the high reactivity of 4-membered rings. * File Name: AAAKPMJ0 Figure: 03_18.jpg Title: Conformations of Cyclopentane Caption: The conformation of cyclopentane is slightly folded, like the shape of an envelope. This puckered conformation reduces the eclipsing of adjacent CH2 groups. Notes: To relieve ring strain, cyclopentane adopts the envelope conformation. * File Name: AAAKPMK0 Figure: 03_19.jpg Title: Conformations of Cyclohexane Caption: The chair conformation of cyclohexane has one methylene group puckered upward and another puckered downward. Viewed from the Newman projection, the chair conformation has no eclipsing of the carbon-carbon bonds. The bond angles are 109.5°. Notes: Cyclohexane can adopt four non-planar conformations: chair, boat, twist boat, and half-chair. The most stable conformation is the chair because it has all the C-H bonds staggered. * File Name: AAAKPML0 Figure: 03_20.jpg Title: Boat Conformation of Cyclohexane Caption: In the symmetrical boat conformation of cyclohexane, eclipsing of bonds results in torsional strain. In the actual molecule, the boat conformation is skewed to give the twist boat, a conformation with less eclipsing of bonds and less interference between the two