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ORGANIC CHEMISTRY

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Versione italiana
Academic year
2022/2023
Teacher
DANIELA PERRONE
Credits
6
Didactic period
Primo Semestre
SSD
CHIM/06

Training objectives

The main objective of the course is to give students a basic knowledge of organic chemistry through the study of the structure, properties, and reactions of simple molecules, in order to approach the study of more complex systems. Laboratory experiments have the goal to facilitate the discipline understanding and to suggest that organic chemistry is an indispensable tool for many other scientific disciplines.
The main gained knowledges will be:
-knowledge of nomenclature, structure, properties and general reactivity of the main classes of organic compounds
-knowledge of chirality and asymmetry of organic compounds
-knowledge the main classes of organic reaction
-knowledge of structures and properties of amino acids and carbohydrates.
The basic acquired abilities (that are the capacity of applying the acquired knowledge) will be:
-identification of molecular compounds on the base of their functional groups
-use of the nomenclature
-identification of the main classes of organic reaction
-prediction of reactivity according to the molecular structure.

Prerequisites

No formal propedeuticity is required, however, fundamentals of chemistry, physic and mathematic, are necessary

Course programme

The course includes 40 hours of lectures and 8 hours of laboratory exercises. The lectures include:
Introduction to organic chemistry: common features of all organic compounds. Carbon as a fundamental element of all living systems.
-General aspects of organic chemistry (3 h): Lewis structures, molecular geometry, bond angles, resonance, formal charge, polarity of organic compounds; hybridization of carbon bond orbital. Main functional groups.
-Acids and bases (2 h): Brønsted-Lowry acids and bases; strength of organic acids and bases; the pKa and the correlation between pH and pKa; relevant factors for the acid strength; Lewis acids and bases.
-Alkanes and cycloalkanes (2 h): general features, physical and chemical properties, and reactivity; structures of simple alkanes, and structural and conformational isomers; the IUPAC nomenclature.
-Alkenes and alkynes (3 h): general features, nomenclature, physical and chemical properties, and reactivity; cis-trans and E/Z isomers; the synthesis of some alkenes; electrophilic additions; carbocation formation and stability.
-Stereochemistry (2 h): chiral and achiral systems; enantiomers, racemic mixtures; optical activity of chiral compounds; the absolute configuration R, S; configurational diastereoisomers, meso compounds, cis-trans diastereoisomers; the influence of chirality in biological systems.
-Alkyl Halides (4 h): general features, nomenclature, physical and chemical properties, reactivity and synthesis of alkyl halides; nucleophilic substitution and elimination reactions.
-Benzene and aromatic compounds (3 h): general features, nomenclature, physical and chemical properties, aromatic and non-aromatic compounds, heterocyclic aromatic compounds, reactivity: the electrophilic aromatic substitution.
-Alcohols and ethers (2 h): general features, nomenclature, physical and chemical properties, reactivity and synthesis.
-Aldehydes and ketones (4 h): general features, nomenclature, physical and chemical properties, reactivity and synthesis; nucleophilic addition reactions; reduction and oxidation of carbonyl groups.
-Carboxylic acids and derivatives (4 h): general features, nomenclature, physical and chemical properties, reactivity; methods of preparation of most common derivatives
-Amines, Amino acids and proteins (4 h), amines: general features, nomenclature, physical and chemical properties, reactivity; methods of preparation. Amino acids and peptides: general features, structure and stereochemistry of proteinogenic amino acids; acid-base properties and isoelectric point; the peptide bond; primary and secondary structure of proteins.
-Carbohydrates (4 h): general features, nomenclature, and stereochemistry of monosaccharides; Fischer projections of linear monosaccharides; ring structures of monosaccharides; anomers, mutarotation. Reduction and oxidation of monosaccharides. The glycosidic linkage, common disaccharides and polysaccharides.
-Lipids and Nucleic Acids (3 ore), lipids: classification, triacylglycerols: structure and hydrogenation and saponification reaction; phospholipids. Nucleic Acids: general structure of DNA and RNA, purines and pyrimidines, nucleosides and nucleotides.

Laboratory experiments:
-Separation of proteinogenic amino acids by thin layer chromatography (TLC) (4 h)
-Benedict qualitative assays on carbohydrates (4 h)

Didactic methods

The course consists of lectures and tutorials in the organic chemistry laboratory. In particular, it provides a total of 48 hours teaching, including 40 hours of lectures and 8 hours of laboratory work. Classes are held weekly in the classroom and the exposure takes place by means of power-point slides. For the laboratory exercises, students are supposed to work in pairs. At the end of each practical experience, the student should provide professor with a written report. Practical experiences are not mandatory, but they are hyglhly recommended.

Learning assessment procedures

The aim of the examination is to test the level of achievement of learning objectives previously indicated. The exam consists of a written test based on 16 questions (multiple choice questions especially) on the main topics covered in the course. The assessment is expressed in thirtieths and and the test is passed with a minimum of 18 points.

Reference texts

-FONDAMENTI DI CHIMICA ORGANICA
L. G. Wade-PICCIN