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Organic Chemistry 312
Organic Chemistry 312 Excerpt

Organic Chemistry 312


Detailed topics of this course include: Alcohols, Ethers, Sulfides, and Epoxides, Spectroscopy techniques, Organometallic Compounds, Carbonyl compounds, Chemistry of Amines, Enolates and Enamines, Conjugated Systems and Aromaticity.

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[...] You need to master the fundamental concepts and reactions covered in part one of organic chemistry in order to follow and do well in CH 312. All students are encouraged to review the course work presented in CH 311.


Lecture Notes 32

Reactions of Alcohols Continued

Pinacol Rearrangement

Pinacol rearrangement is the term used to describe the dehydration of a glycol (1,2 diol). The mechanism involves many steps but the same principles involved in alcohol dehydration are involved. These principles are:

  1. Hydroxyl group activation by H+.
  2. Formation of a carbocation by loss of H2O.
  3. Rearrangement occurs.

See if you can follow:

What is “strange” about this rearrangement?

The carbocation is stabilized by the lone pairs on the oxygen, making it a little more stable than an ordinary 2o carbocation.

About the Author

Glenn W.D. Phillips, Ph.D.

Assistant Professor (Oakwood since 2006)
Oakwood University Chemistry Department

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