lecture5 fall08 given - Lecture 5 Organic Chemistry I Prof....

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Organic Chemistry I 310/318M Pre-Health Professionals Unique numbers: 54410, 54435, 54440, 54445, and 54655 Prof. Jonathan L. Sessler Lecture 5 Notes: Monday recitations start PAI 4.28 right after class. Also, homework due at the start of class on Wednesday.
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Resonance - cont. Preference 1: Preference 1: filled valence shells – Structures in which all atoms have filled valence shells contribute more than those with one or more unfilled valence shells.
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Resonance Preference 2: Preference 2: maximum number of covalent bonds – Structures with a greater number of covalent bonds contribute more than those with fewer covalent bonds.
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Resonance Preference 3: Preference 3: least separation of unlike charge – Structures with separation of unlike charges contribute less than those with no charge separation.
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Resonance Preference 4: Preference 4: negative charge on the more electronegative atom. – Structures that carry a negative charge on the more electronegative atom contribute more than those with the negative charge on a less electronegative atom. CH 3 3 H 3 C 3 H 3 C C O C O H 3 C C O (b) Greater contribution (c) Should not be drawn (a) Lesser (1) (2)
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Practice Resonance Structures allyl cation isocyanate anion methyl isocyanate NC O O H 3 C O H 3 C O H 3 C Best Structure O
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Resonance of Neutral Compounds • Note that resonance structures contributors can also
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lecture5 fall08 given - Lecture 5 Organic Chemistry I Prof....

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