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4.50 The NO₂ group stabilizes the conjugate base by resonance and increases acid strength. The compound on the right has less resonance stabilization because the p orbital on the nitrogen is not parallel to the p orbital on the ring because the oxygens of the NO₂ group bump into the CH₃ groups. Review of Mastery Goals After completing this chapter you should be able to: Write an acid-base reaction for any acid and base. (Problems 4.1, 4.2, 4.3, 4.4, 4.35, and 4.37) Recognize Lewis acids, Lewis bases, and the reactions between them. (Problems 4.5, 4.25, 4.26, and 4.38) Recognize acid or base strengths from Kₐ or pKₐ values and use these to predict the position of an acid-base equilibrium. (Problems 4.6, 4.7, 4.8, 4.9, 4.10, 4.21, 4.34, 4.35, 4.36, 4.37, and 4.41) Predict and explain the effect of the structure of the compound, such as the atom bonded to the hydrogen, the presence of an electron donating or withdrawing group, hydrogen bonding, the hybridization of the atom attached to the hydrogen, or resonance on the strength of an acid or base. (Problems 4.13, 4.14, 4.16, 4.18, 4.29, 4.30, 4.35, 4.39, 4.40, 4.41, 4.42, and 4.43) Using the same reasoning, arrange a series of compounds in order of increasing or decreasing acid or base strength. (Problems 4.19, 4.20, 4.31, 4.32, 4.33) Identify the most acidic proton in a compound. (Problems 4.15, 4.17, 4.24, 4.36, 4.42, and 4.43) 64

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