Solved: The organic molecules shown here are derivatives

Chapter , Problem 9.12

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The organic molecules shown here are derivatives of benzene in which six-membered rings are fused at the edges of the hexagons. Naphthalene Anthracene Tetracene Naphthalene Anthracene Tetracene (a) Determine the empirical formula of benzene and of these three compounds. (b) Suppose you are given a sample of one of the compounds. Could combustion analysis be used to determine unambiguously which of the three it is? (c) Naphthalene, the active ingredient in mothballs, is a white solid. Write a balanced equation for the combustion of naphthalene to CO21g2 and H2O1g2. (d) Using the Lewis structure for naphthalene and the average bond enthalpies in Table 8.4, estimate the heat of combustion of naphthalene in kJ>mol. (e) Would you expect naphthalene, anthracene, and tetracene to have multiple resonance structures? If so, draw the additional resonance structures for naphthalene. (f) Benzene, naphthalene, and anthracene are colorless, but tetracene is orange. What does this imply about the relative HOMOLUMO energy gaps in these molecules? See the Chemistry Put to Work box on orbitals and energy.