CH-233: Organic functions and reactions I

Summary

Le cours se focalisera sur les composés carbonyles: leur structures, réactivités, et leurs transformations; la réactivité des énols/énolates et leurs réactions fondamentales. L'importance de la compréhension des mécanismes réactionnels, de la chimio-, regio- and stéréo-sélectivité sera soulignée.

Official source

https://edu.epfl.ch/coursebook/en/organic-functions-and-reactions-i-CH-233

Moodle Page

http://go.epfl.ch/CH-233

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Lectures in this course (8)

Related concepts (160)

Related courses (16)

Related MOOCs (1)

Stereoselectivity

In chemistry, stereoselectivity is the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non-stereospecific creation of a new stereocenter or during a non-stereospecific transformation of a pre-existing one. The selectivity arises from differences in steric and electronic effects in the mechanistic pathways leading to the different products. Stereoselectivity can vary in degree but it can never be total since the activation energy difference between the two pathways is finite: both products are at least possible and merely differ in amount.

Thermodynamic versus kinetic reaction control

Thermodynamic reaction control or kinetic reaction control in a chemical reaction can decide the composition in a reaction product mixture when competing pathways lead to different products and the reaction conditions influence the selectivity or stereoselectivity. The distinction is relevant when product A forms faster than product B because the activation energy for product A is lower than that for product B, yet product B is more stable.

Baeyer–Villiger oxidation

The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899. In the first step of the reaction mechanism, the peroxyacid protonates the oxygen of the carbonyl group. This makes the carbonyl group more susceptible to be attacked by the peroxyacid.

Hydration reaction

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol. Several million tons of ethylene glycol are produced annually by the hydration of oxirane, a cyclic compound also known as ethylene oxide: C2H4O + H2O → HO–CH2CH2–OH Acid catalysts are typically used.

Organocerium chemistry

Organocerium chemistry is the science exploring the properties, structure, and reactivity of organocerium compounds, chemical compounds that contain one or more chemical bond between carbon and cerium. These compounds comprise a subset of the organolanthanides. In general, organocerium compounds are not isolable, and are rather studied in solution via their reactions with other species. There are notable exceptions, such as the Cp*3Ce(III) complex shown at right, but they are relatively rare.