Chapter 7 Structure and Synthesis of Alkenes 有机化学英文版教学课件（美国达拉斯社区学院） 《Organic Chemistry 5th Edition (L.G. Wade JR.)》.pptVIP

Chapter 7Structure and Synthesis of Alkenes Functional Group Pi bond is the functional group. More reactive than sigma bond. Bond dissociation energies: C=C BDE 146 kcal/mol C-C BDE -83 kcal/mol Pi bond 63 kcal/mol  = Orbital Description Sigma bonds around C are sp2 hybridized. Angles are approximately 120 degrees. No nonbonding electrons. Molecule is planar around the double bond. Pi bond is formed by the sideways overlap of parallel p orbitals perpendicular to the plane of the molecule.  = Bond Lengths and Angles Hybrid orbitals have more s character. Pi overlap brings carbon atoms closer. Bond angle with pi orbitals increases. Angle C=C-H is 121.7? Angle H-C-H is 116. 6? = Pi Bond Sideways overlap of parallel p orbitals. No rotation is possible without breaking the pi bond (63 kcal/mole). Cis isomer cannot become trans without a chemical reaction occurring. Elements of Unsaturation A saturated hydrocarbon: CnH2n+2 Each pi bond (and each ring) decreases the number of H’s by two. Each of these is an element of unsaturation. To calculate: find number of H’s if it were saturated, subtract the actual number of H’s, then divide by 2.  = Propose a Structure: First calculate the number of elements of unsaturation. Remember: A double bond is one element of unsaturation. A ring is one element of unsaturation. A triple bond is two elements of unsaturation. = Heteroatoms Halogens take the place of hydrogens, so add their number to the number of H’s. Oxygen doesn’t change the C:H ratio, so ignore oxygen in the formula. Nitrogen is trivalent, so it acts like half a carbon. Structure for C6H7N? Since nitrogen counts as half a carbon, the number of H’s if saturated is 2(6.5) + 2 = 15. Number of missing H’s is 15 – 7 = 8. Elements of unsaturation is