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4.32 The basic electron pair in each compound is the one on the nitrogen atom. Compound C is a weaker base than D because it has resonance stabilization of the basic electron pair. The nitro group of B provides even more resonance stabilization of the basic electrons. Compound A is the weakest base because the C=O is one of the best groups at stabilizing a pair of electrons on an adjacent atom by resonance. : NH₂ NH₂ NH₂ O CH₃CNH₂ V V V NO₂ A B C D O O O O 4.33 CH₃COH V V weakest acid strongest acid 4.34 a) The products are favored because butyllithium is a stronger base than LDA (see Table 4.4). b) The equilibrium favors the products because ammonia = 38) is a weaker acid than an alkyne = 25). c) The reactants are favored because an alcohol = 16), is a weaker acid than an alkyne = 25). 4.35 a) CH₃CH₃ is a weaker acid than CH₃CN, because the conjugate base of CH₃CN is stabilized by resonance, so the reactants are favored. H CH₃CH₂ + CH₂C=N: CH₃CH₂ ..- + H CH₂C=N: 57

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