00148 - Organic Chemistry (M-Z)

Learning outcomes

The student will gain a good knowledge on the behaviour and application of the most important organic compounds, including biological molecules, such as peptides, carbohydrates, lipids and nucleic acids. The student will also learn the most important mechanisms of the organic reactions that will allow him to predict the reactivity of the functional groups.

Course contents

1.      The hybrid orbitals: sp3 hybridization, sp2 hybridization, sp hybridization. The chemical bond in organic compounds: ionic bond, covalent bond, polar covalent bond. Electronegativity. Bronsted acids and basis, Lewis acids and basis, nucleophiles and electrophiles, general definitions.

2.      The functional groups in organic chemistry: alkanes, alkenes and alkynes, arenes, alkyl halogenides, alcohols, phenols, ethers, amines, aldehydes, ketones, esters, anhydrides, amides, thioesters.

3.      Alkanes and cycloalkanes: nomenclature, structural isomers, radicalis. Alkanes reactions: methane alogenation.

4.       Stereochemistry: stereocenters, optical activity, CIP notational system. Fischer projection. Meso compounds, optical activity, racemic mixtures.

5.       Alkenes: structure, electrophilic addition, addition of water, of alogens, hydroboration. Carbocations. Markovnikov rule, addition stereochemistry. Oxidations and reductions of the alkenes.

6.       Alkynes: nomenclature, structure and reactivity. Alkylation of the acetylide ion: preparation of disubstituted alkynes.

7.       Nucleophiles and electrophiles: reaction SN1, SN2, E1 and E2. Mechanisms comparison. Grignard reagents: defintion and preparation.

8.       Aromatic hydrocarbons: nomenclature, aromaticity definition. Resonance: definition and examples. Aromatic electrophilic substitution. Reaction of aromatic compounds: bromination, clorination, solfonation, nitration and Friedel- Crafts reactions. Reactions of substituted aromatic rings: the regioselectivity. Pyridine reaction: the aromatic nucleophilic substitution.

9.       Alcohols: nomenclature, properties and reactions. Reactivity of ethers, epoxides and phenols.

10.     Carbonyl compounds: structure and reactivity of aldehydes and ketones. Aldol condensation.

11.     Carbohydrates: structure, classification and stereochemical representations. Monosaccharides: reaction. Disaccharides and polysaccharides. Deoxyribose and glucosamine.

12.     Carboxylic acids: nomenclature and reactivity.

13.     Carboxylic acids derivatives: esters, acyl chlorides, amides, anhydrides, thioesters. Acylic nucleophilic substitution: saponification, transesterification, synthesis of amides and acids.

14.     Amines: structure and basicity.

15.     Amino acids: structure, isoelectric point. Peptides: liquid phase synthesis and solid phase synthesis. The protecting groups and the use of DCC as coupling agent.

16.     Lipids: classification. Waxes, fatty acids, oils and soaps. Hydrolyzable lipids: acylglycerols, phospholipids, sphingomielins. Non hydrolyzable lipids: prostaglandins, isoprenes, steroids.

17.    Nucleic acids: definition of DNA and RNA. Chemical structure and stability of nucleic bases, nucleosides and nucleotides. Primary and secondary structures of DNA and RNA.

Readings/Bibliography

Janice Gorzynski Smith – Chimica Organica – McGraw-Hill

T. W. Graham Solomons, Craig B. Fryhle – Chimica Organica

John McMurry – Chimica Organica – Piccin

Brown & Foote – Chimica Organica – EdiSES

Janice Gorzynski Smith – Fondamenti di Chimica Organica – McGraw-Hill

Brown – Introduzione alla Chimica Organica – EdiSES

John McMurry – Chimica Organica - Un approccio biologico – Zanichelli

Teaching methods

The topics listed in the program will be fully covered, particularly the reaction mechanisms.

Assessment methods

The preparation is tested by a written and/or oral exam, whose aim is to verify both the knowledge of the subject.

Teaching tools

Overhead projector, PC

Office hours

See the website of Claudia Tomasini