Mothballs are composed of naphthalene, C10H8, a molecule of which consists of two six-member rings of carbon

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Mothballs are composed of naphthalene, C10H8, a molecule of which consists of two six-member rings of carbon fused along an edge, as shown in this incomplete Lewis structure:
Н Н C. Н. н .C. Н Н Н Н

(a) Write two complete Lewis structures for naphthalene.
(b) The observed C-C bond lengths in the molecule are intermediate between C-C single and C == C double bonds. Explain.
(c) Represent the resonance in naphthalene in a way analogous to that used to represent it in benzene.

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Chemistry The Central Science

ISBN: 978-0321696724

12th edition

Authors: Theodore Brown, Eugene LeMay, Bruce Bursten, Catherine Murphy, Patrick Woodward

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