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Introductory Organic Chemistry - Lecture 16

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Lecture 16 - Recognizing Functional Groups

This lecture continues the discussion of the HOMO/LUMO view of chemical reactivity by focusing on ways of recognizing whether a particular HOMO should be unusually high in energy (basic), or a particular LUMO should be unusually low (acidic). The approach is illustrated with BH3, which is both acidic and basic and thus dimerizes by forming unusual "Y" bonds. The low LUMOs that make both HF and CH3F acidic are analyzed and compared underlining the distinction between MO nodes that derive from atomic orbitals nodes (AON) and those that are antibonding (ABN). Reaction of HF as an acid with OH- is shown to involve simultaneous bond-making and bond-breaking.

Prof. J. Michael McBride
CHEM 125: Freshman Organic Chemistry, Fall 2008
(Yale University: Open Yale)
Date accessed: 2009-11-11
License: Creative Commons BY-NC-SA

Lecture Material

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Supplementary lecture material is listed below.

1. Orbitals of HF an acid (substitution at H)
2. Orbitals of CH3F substitution at C (an acid)
3. Orbitals of O=CH2 the carbonyl group (an acid)



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