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Ch.9 - Molecular Geometry and Bonding Theories

Chapter 9, Problem 9e

The molecule shown below is called furan. It is represented in typical shorthand way for organic molecules, with hydrogen atoms not shown, and each of the 4 vertices representing a carbon atom.

(e) The C¬C¬C bond angles in furan are much smaller than those in benzene. The likely reason is which of the following: (i) The hybridization of the carbon atoms in furan is different from that in benzene, (ii) Furan does not have another resonance structure equivalent to the one above, or (iii) The atoms in a five-membered ring are forced to adopt smaller angles than in a six-membered ring.

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