6. Brønsted Acidity and the Generality of Nucleophilic Substitution

Update: 2012-04-02

Description

The coincidentally substantial extent of ionic dissociation of water provides an example of Brønsted acidity, or nucleophilic substitution at hydrogen. Relative pKa values are insensitive enough to solvent that they provide insight on the role of energy-match, overlap, and resonance in ionic dissociation. The titration of alanine in water illustrates the experimental determination of pKa values and the phenomenon of buffering. The limited pKa scale in water can be extended dramatically by titration in other solvents, providing one of the best ways to measure many “effects” in organic chemistry. A wide range of important organic reactions discovered in the 19th century and many biochemical reactions can be understood under the rubric of nucleophilic substitution.

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

6. Brønsted Acidity and the Generality of Nucleophilic Substitution

#box-pro-ellipsis-176185207789877{-webkit-line-clamp:2;}6. Brønsted Acidity and the Generality of Nucleophilic Substitution

6. Brønsted Acidity and the Generality of Nucleophilic Substitution

J. Michael McBride

6. Brønsted Acidity and the Generality of Nucleophilic Substitution