Chapter 06 with notes - Chapter 6 Nucleophilic addition to...

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Chapter 6 Nucleophilic addition to the carbonyl group Instructor: Dr. Daniel Seidel Chem 315 The carbonyl group is arguably the most important group in organic chemistry. Examples of functional groups that contain carbonyl: The carbonyl group is highly polarized
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Review: The reaction of cyanide with acetone
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Review: Bonding in the carbonyl group Electronegativities, bond lengths, and bond strengths Representative bond energies, kJ mol –1 Representative bond lengths, Å Electronegativity C–O 351 C=O 720 C–O 1.43 C=O 1.21 C 2.5 O 3.5
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Addition to a carbonyl group: MO picture with HOMO-LUMO interactions
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Orbitals involved in the cyanide addition to aldehydes
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The cyanohydrin formation is reversible under basic conditions Reasons for the reversibility:
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The angle of nucleophilic attack on aldehydes and ketones The attack angle is known as the Bürgi–Dunitz trajectory (determined by crystallographic methods). The angle of attack is the result of a compromise between maximum orbital overlap of the HOMO with π
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