Download PDF by El Sayed H. El Ashry and Ahmed A. Kassem: Account of microwave irradiation for accelerating organic

By El Sayed H. El Ashry and Ahmed A. Kassem

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17 The following molecular model is a representation of para-aminobenzoic acid (PABA), the active ingredient in many sunscreens. Indicate the positions of the multiple bonds, and draw a skeletal structure (gray ϭ C, red ϭ O, blue ϭ N, ivory ϭ H). para-Aminobenzoic acid (PABA) Summary Key Words antibonding MO, 21 bond angle, 13 bond length, 11 bond strength, 11 bonding MO, 21 condensed structure, 21 covalent bond, 8 electron-dot structure, 8 electron shell, 5 ground-state electron configuration, 6 isotope, 4 line-bond structure, 8 lone-pair electrons, 9 molecular orbital (MO) theory, 20 molecule, 8 node, 5 orbital, 4 organic chemistry, 2 pi (␲) bond, 15 sigma (␴) bond, 11 skeletal structure, 22 sp hybrid orbital, 17 sp2 hybrid orbital, 15 sp3 hybrid orbital, 12 valence bond theory, 10 valence shell, 8 The purpose of this chapter has been to get you up to speed—to review some ideas about atoms, bonds, and molecular geometry.

An atom consists of a positively charged nucleus surrounded by one or more negatively charged electrons. The electronic structure of an atom can be described by a quantum mechanical wave equation, in which electrons are considered to occupy orbitals around the nucleus. Different orbitals have different energy levels and different shapes. For example, s orbitals are spherical, and p orbitals are dumbbell-shaped. The ground-state electron configuration of an atom can be found by assigning electrons to the proper orbitals, beginning with the lowest-energy ones.

One part of the double bond results from ␴ (head-on) overlap of sp2 orbitals (green), and the other part results from ␲ (sideways) overlap of unhybridized p orbitals (red/blue). The ␲ bond has regions of electron density above and below a line drawn between nuclei. 16 chapter 1 structure and bonding As you might expect, the carbon–carbon double bond in ethylene is both shorter and stronger than the single bond in ethane because it has four electrons bonding the nuclei together rather than two. Ethylene has a C=C bond length of 134 pm and a strength of 728 kJ/mol (174 kcal/mol) versus a C–C length of 154 pm and a strength of 377 kJ/mol for ethane.

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Account of microwave irradiation for accelerating organic reactions by El Sayed H. El Ashry and Ahmed A. Kassem

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