In Chapter 3, we will explore the factors that render compounds acidic or basic

Chapter 2, Problem 2.76

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In Chapter 3, we will explore the factors that render compounds acidic or basic. Tropolone (1) is a compound that is both fairly acidic and fairly basic (J. Org. Chem. 1997, 62, 32003207). It is acidic because it is capable of losing a proton (H+) to form a relatively stable anion (2), while it is basic because of its ability to receive a proton to form cation 3: H+ H+ @ ! O O 1 O O 2 O O 3 H H H (a) Draw all significant resonance structures of anion 2 and of cation 3 and explain why each of these ions is stabilized. (b) In compound 1, the bond lengths for the C!C bonds vary greatly and alternate in length (long, short, long, etc.). But in ions 2 and 3, the lengths of the bonds are similar. Explain. (c) The intramolecular hydrogen bonding interaction in 3 is significantly diminished in comparison to 1. Explain.