27573 - Organic Chemistry 2

Learning outcomes

The student makes use of structure-reactivity correlations to anticipate the behaviour of organic polyfunctional molecules; knows mechanisitc bases of chemical reactivity; is in the position to propose a multistep synthesis of a simple organic molecule; knows the structure and properties of the most important classes of natural organic products.

Course contents

Aromaticity, properties and reactivity of homoaromatic compounds. Synthesis of polysubstituted benzene derivatives. Typical heteroaromatic compounds, their properties and reactivity: pyrrole, furan, thiophene and indole. Chemistry of enols and enolates. Fundamental concepts and procedures per the constructiuon of carbon-carbon bonds. Diels-Alder cycloaddition reactions. Sigmatropic rearrangements: 1,2 migrations to electron-poor centres, [3,3]-Claisen and related rearrangements. Organic stereochemistry: moleculòes with 2 or more stereocentres, meso structures. Compounds with chirality axes or planes. Aminoacids: structures, properties, preparation. Peptides: primary and secondary structure. Determination of the primary structure. Synthesis of peptides. Proteins: tertiary and quaternary structure, functions. Sugars: mono and polysaccharides. Glucose, mutarotation, ene-diol tautomerism, reactivity. Nucleosides and nucleotides: structural elements.Lipids: structure and elements of biogenesis of fatty acids and terpenes. Structure and reactivity of triacylglycerols, steroids. Surfactants.

Readings/Bibliography

These texts can be undifferently used:

Brown, Foote, Iverson, ORGANIC CHEMISTRY, Edises

Loudon, ORGANIC CHEMISTRY, Edises

Bruice, ORGANIC CHEMISTRY, Edises

Teaching methods

Lessons followed by exercitation in the classroom, aimed at verifying the understanding of concepts and stimulating problem solving skills, with the aid of projection of supplementary material.

Assessment methods

Final written examination followed by, if positive, the oral examination. The final mark is the average mark of the two exams.

It is also possible to do a partial written test at the end of the first semester and a second test at the end of the course, followed by the oral examination. The final mark is the average mark of the overall written and oral examination.

Teaching tools

Lessons with projection of notes, handouts and supplementary material available on-line

Office hours

See the website of Claudio Trombini