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This is represented as or chap 14 586 54 covalent

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Unformatted text preview: e unhybridized p orbitals overlap at the same time, resulting in π electrons that are delocalized over the entire surface of the molecule. This is represented as: or CHAP. 14 586 54. COVALENT BONDING: ORBITALS - EVEN-NUMBER PROBLEMS Benzoic acid (C7 H6 O2) has 7(4) + 6(1) + 2(6) = 46 valence electrons. The Lewis structure for benzoic acid is: O C H O C H H C C C The circle in the ring indicates the delocalized π bonding in the benzene ring. The two benzene resonance Lewis structures have three alternating double bonds in the ring (see Figure 14.48). C H C H H The six carbons in the ring and the carbon bonded to the ring are all sp2 hybridized. The five C−H sigma bonds are formed from overlap of the sp2 hybridized carbon atoms with hydrogen 1s atomic orbitals. The seven C−C σ bonds are formed from head to head overlap of sp2 hybrid orbitals from each carbon. The C−O single bond is formed from overlap of an sp2 hybrid orbital on carbon with an sp3 hybrid orbital from oxygen. The C−O σ bond in the double bond is formed from overlap of carbon sp2 hybrid orbital with an oxygen sp2 orbital. The π bond in the C−O double bond is formed from overlap of parallel p unhybridized atomic orbitals from C and O. The delocalized π bonding system in the ring is formed from overlap of all six unhybridized p atomic orbitals from the six carbon atoms. See Figure 14.50 for delocalized π bonding system in the benzene ring. Spectroscopy 56. νo = 1 2! k (14.003)(15.995) 1.66054 " 10 !27 kg amu " , µ= = 1 .2398 × 10−26 kg 14.003 + 15.995 amu ì νo = 1 1550. N m !1 1 kg m s !2 = 5.627 × 1013 s−1 " ! 26 2 ! 1.2398 " 10 kg N λ= c 2.9979 " 1010 cm s !1 = = 5.328 × 10−4 cm 13 !1 í 5.627 " 10 s Wave number = 1 1 = = 1877 cm−1 !4 ë 5.328 " 10 cm CHAP. 14 587 58. COVALENT BONDING: ORBITALS - EVEN-NUMBER PROBLEMS a. There are three sets of magnetically equivalent hydrogens (marked a , b, and c in the following structure). We are assuming that all the benzene ring hydrogens (marked c) are equivalent and do not exhibit spin-spin coupling...
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This note was uploaded on 01/26/2014 for the course CHEM 001 taught by Professor Giancoli during the Fall '12 term at UPenn.

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