Chemistry 2213A/B Lecture Notes - Lecture 4: Lone Pair, Electronegativity, Sulfur

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Factor 5: resonance: we can often draw multiple lewis structures that differ only in the positions of the electrons. Eg. the pka of acetic acid is about 4. 8, while that of methanol is about 15. 7. The acetate ion is resonance- stabilized, but the methoxide ion is not. Where all 6 carbon carbon ponds are the same. Make sure to draw the resonance arrow properly this is not the same as a double headed arrow: another example is the amide group. In this case, the two resonance structures differ in energy and are termed non-equivalent contributing structures. Rehybridize into sp2 since require orbital overlap for bonding. 2 resonance structures differ in energy called non equivalent contributing structures: group rehybridizes. Nitrogen because it is bond to the carbonyl group instead of binding as sp3 configuration (r = saturated no pi bond) it is instead in sp2 configuration to participate in resonance structures.

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