columbia大学有机化学课件 （十七）.pptVIP

5.5Physical Properties of Alkenes Dipole moments What is direction of dipole moment? Does a methyl group donate electrons to the double bond, or does it withdraw them? Dipole moments Chlorine is electronegative and attracts electrons. Dipole moments Dipole moment of 1-chloropropene is equal to the sum of the dipole moments of vinyl chloride and propene. Dipole moments Therefore, a methyl group donates electrons to the double bond. Alkyl groups stabilize sp2 hybridizedcarbon by releasing electrons 5.6Relative Stabilities of Alkenes Double bonds are classified according tothe number of carbons attached to them. Double bonds are classified according tothe number of carbons attached to them. Substituent Effects on Alkene Stability Electronic disubstituted alkenes are more stable than monosubstituted alkenes Steric trans alkenes are more stable than cis alkenes Figure 5.4 Heats of combustion of C4H8isomers. Substituent Effects on Alkene Stability Electronic alkyl groups stabilize double bonds more than H more highly substituted double bonds are morestable than less highly substituted ones. Problem 5.8 Give the structure or make a molecular model of the most stable C6H12 alkene. Problem 5.8 Give the structure or make a molecular model of the most stable C6H12 alkene. Substituent Effects on Alkene Stability Steric effects trans alkenes are more stable than cis alkenes cis alkenes are destabilized by van der Waalsstrain Figure 5.5 cis and trans-2-Butene Figure 5.5 cis and trans-2-Butene van der Waals Strain Steric effect causes a large difference in stabilitybetween cis and trans-(CH3)3CCH=CHC(CH3)3 cis is 44 kJ/mol less stable than trans 5.7Cycloalkenes Cycloalkenes Cyclopropene and cyclobutene have angle strain. Larger cycloalkenes, such as cyclopenteneand cyclohexene, can incorporate a double bond into the ring with little or no angle strain.  Stereoisomeric cycloalkenes cis-cyclooctene and trans-cycloocteneare stereoisomers cis-cycloocte