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Solutions to Additional Bonding Problems - Dartmouth …

1. Solutions to Additional Bonding Problems 1. For the following examples, the valence electron count is placed in parentheses after the empirical formula and only the resonance structures that satisfy the octet rule are given. H H. 4. H2C=NH C N. (12) : H. H H. H H C H. H C. C C C C. 5. C6H6. (30) C C C C. H. H C H H C. H H. H H. : : : 7. H2 CCO (16) C C O C C O: H. H. 7. HN3 (16). sp2 sp3 sp3. H sp H sp sp sp sp : : : : : : : : N N N N N N H N N N. : 2. H2 CNH -- Only 1 resonance structure: the formal charges on all the atoms = 0. C6H6 -- 2 possible resonance structures: the formal charges on all the atoms = 0. The actual structure is an equal mixture of the 2 resonance structures. 2. Since (a) involves no separation of formal charges, it makes a much larger contribution to the actual structure of HC(O)NH2 than does (b). Since structure (c) involves (i) separating larger formal charges of opposite sign and (ii) placing ike formal charges at a small separation corresponding to the N N bond length, it will make a much smaller contribution than either (a) or (b).

1 Solutions to Additional Bonding Problems 1. For the following examples, the valence electron count is placed in parentheses after the empirical formula and only the resonance structures that satisfy the octet rule are given.

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