28. Mechanism and Equilibrium of Carbonyl Reactions

Update: 2012-04-02

Description

This lecture aims at developing facility with devising plausible mechanisms for acid- and base-catalyzed reactions of carbonyl compounds, carboxylic acids, and their derivatives. When steric hindrance inhibits the A/D mechanism of Fischer esterification, an acid-catalyzed D/A mechanism can still occur. Substituent influence on the equilibrium constants for carbonyl hydration demonstrates four effects: bond strength, steric, electron withdrawal, and conjugation. Cyclic acetals play an important role in protecting the carbonyl groups of sugars, but acetals also can be used to protect alcohols, as can silyl ethers. Using amines instead of alcohols allows converting carbonyl compounds to imines via carbinolamines.

Complete course materials are available at the Open Yale Courses website: http://oyc.yale.edu

This course was recorded in Spring 2011.

Comments

In Channel

34. Acids and Acid Derivatives

2012-04-0250:28

27. Triphenylmethyl and an Introduction to Carbonyl Chemistry

2012-04-0200:02

6. Brønsted Acidity and the Generality of Nucleophilic Substitution

2012-04-0200:02

38. Review: Synthesis of Cortisone

2012-04-0200:03

37. Proving the Configuration of Glucose and Synthesizing Two Unnatural Products

2012-04-0200:03

36. [gr]α-Reactivity and Condensation Reactions

2012-04-0200:03

33. Green Chemistry. Acids and Acid Derivatives

2012-04-0200:02

35. Acyl Insertions and [gr]α-Reactivity

2012-04-0200:02

32. Measuring Bond Energies: Guest Lecture by Prof. G. Barney Ellison

2012-04-0200:02

30. Oxidation States and Mechanisms

2012-04-0200:02

31. Periodate Cleavage, Retrosynthesis, and Green Chemistry

2012-04-0200:02

29. Imines and Enamines. Oxidation and Reduction

2012-04-0200:03

28. Mechanism and Equilibrium of Carbonyl Reactions

2012-04-0200:02

26. Aromatic Substitution in Synthesis: Friedel-Crafts and Moses Gomberg

2012-04-0200:03

25. C-13 and 2D NMR. Electrophilic Aromatic Substitution

2012-04-0200:03

24. Higher-Order Effects, Dynamics, and the NMR Time Scale

2012-04-0200:03

23. Diamagnetic Anisotropy and Spin-Spin Splitting

2012-04-0200:02

22. Medical MRI and Chemical NMR

2012-04-0200:02

21. Functional Groups and Fingerprints in IR Spectroscopy. Precession of Magnetic Nuclei

2012-04-0200:03

20. Electronic and Vibrational Spectroscopy

2012-04-0200:02

00:00

28. Mechanism and Equilibrium of Carbonyl Reactions

#box-pro-ellipsis-176219966389383{-webkit-line-clamp:2;}28. Mechanism and Equilibrium of Carbonyl Reactions

28. Mechanism and Equilibrium of Carbonyl Reactions

J. Michael McBride

28. Mechanism and Equilibrium of Carbonyl Reactions