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d) The equilibrium favors the reactants because the electron withdrawing effect of the F is stronger when it is closer to the basic O. O F + + e) The equilibrium favors the products. OH OH + Na OH CH₃CH-CO Na + HOH = f) The equilibrium favors the products. CH₃ CH₃ : + H₂O CH₃ 4.38 AICI₃ is the Lewis acid because AI has an empty p orbital, which can accept an electron pair. is the Lewis base because the has lone pairs of electrons to donate. 4.39 The basic electrons are on a nitrogen atom in both compounds. The unshared electron pair of the structure on the left is in a sp²-hybridized orbital, while in the structure on the right they are in a sp³-hybridized orbital. The sp² orbital is lower in energy than the sp³ orbital, so the structure on the left is a weaker base. Note that the compound on the left is stabilized by resonance, but the basic electrons are not involved in the resonance, so resonance has no effect on the basicity of the electrons. 4.40 The unshared electron pair on the nitrogen of this compound is in a p orbital which is conjugated with the p orbitals of the C=O group. These electrons are stabilized by resonance. If the nitrogen is protonated, this resonance stabilization is lost. The electron pairs on the oxygen atom are in atomic orbitals that are not involved in resonance. 60

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