LEARNING OUTCOMES

The course aims to deepen the various types of reaction in organic chemistry through the study of the kinetic and thermodynamic factors that influence them.

AIMS AND LEARNING OUTCOMES

Acquiring a good level of knowledge on:

- the main "construction" processes of a molecular structure, with particular attention to the formation of carbon-carbon bonds and to the synthesis of homo- and hetero-cyclic systems;

- the essential principles of retrosynthesis, a powerful method of approach to the construction of molecular structures, even of considerable complexity.

PREREQUISITES

For an optimal fruition of the course, the knowledge of the basic notions of General Chemistry and Organic Chemistry (Organic Chemistry I and II) is essential.

TEACHING METHODS

The course includes only frontal lessons, with the prevalent use of slides.

SYLLABUS/CONTENT

The chemistry of carbon nucleophiles, with particular regard to the chemistry of enolates and the related mechanistic and applicative aspects in organic synthesis.

The formation of carbon / carbon bonds, both single and double (olefination reactions) as fundamental processes for the construction of complex organic molecules.

The retrosynthetic approach, as an effective methodology in the design of synthetic protocols both in the field of basic organic chemistry and for the construction of structures of biological / pharmacological interest: an aspect of organic chemistry in which the carbon nucleophiles themselves are among the main actors.

General principles on the formation of cyclic systems, necessary for the correct application of the retrosynthetic approach: pericyclic reactions, Baldwin's rules.

Outline of the most common protection / deprotection techniques of functional groups.

Elements of stereochemistry and distinction between stereoselective and stereospecific reactions.

Basic principles on the main multicomponent reactions and their meaning in organic synthesis.

RECOMMENDED READING/BIBLIOGRAPHY

The slides of the lessons will be available in pdf format on Aulaweb.

For the review / deepening of basic organic chemistry topics, the latest editions of the same texts recommended for the courses of Organic Chemistry I and II can be used; in particular:

-- Brown, Foote, Iverson, Anslyn - Organic Chemistry - EdiSES

-- Bruice - Organic Chemistry - EdiSES

For the more specific topics of retrosynthesis addressed, we recommend reading the text:

-- Stuart Warren, Paul Wyatt - Organic synthesis - The Disconnection Approach, 2nd Edition - J. Wiley & Sons (2008).