Learning objectives
To acquire knowledge and ability to understand matters of Organic Chemistry in advanced books. Ability to apply knowledge of Organic Chemistry with a professional approach, to design, to discuss and solve problems in the field of Organic Chemistry; to acquire maturity and the necessary skills to undertake studies of higher grade with a good degree of autonomy.
Knowledge of the structure and reactivity of organic molecules, with
particular attention to the biological substances. To acquire knowledge on
classification and nomenclature of the organic compounds by the identification of
their functional groups and , through these, on their reactivity. To learn the concepts
of isomerism, conformation and stereochemistry of organic molecules and of their
consequences in biological systems. To learn the principal concepts characterizing the reactivity of organic compounds in radicalic, electophilic and nucleophilic
reactions. To know the functional groups and properties of some important classes
of biological compounds, such as carbohydrates, triglycerides and amino acids.
To describe the biopolymers of fundamental importance in biological systems:
polisaccharides, peptides, nucleic acids, and their chemical features, their biological role and fundamentals about chemical synthesis of these molecules.
To acquire experience on the principal laboratory techniques for the purification and modification of organic compounds.
Prerequisites
Knowledge of the concepts of General and Inorganic Chemistry
Course unit content
Organic Chemistry
1-The covalent bond and the shape of molecules. Electronic structure-of atoms; bonds and intermolecular forces; composition, structure and formula of the organic molecules; structural isomers, resonance. Orbitals of the carbon atom in saturated and unsaturated compounds.
2-Alkanes. Structure, nomenclature, conformations. Reactivity: formation and stabilitiy of radicals in halogenation reactions.
3-Cycloalkanes. Ring strain, boat and chair conformations of cyclohexane and in substituted cyclohexanes.
4-Stereochemistry. Conformational and configurational isomers; chirality, optical activity, relaitve and absolute configurations; classification and separation of
stereoisomers; role of chirality in biological systems and in teechnological processes.
5-Alkenes. Cis/trans isomerism. Hydrogenation. Reactivity towards electrophiles.
Examples of polymerization. Dienes: classification. Conjugated dienes: chemical and electronic properties.
4-Alkynes. Structure and nomenclature.
5-Aromatic compunds. Definition of aromaticity. Hückel’s rules. Schematic
description of aromatic electrophilic substitution.
6-Haloalkanes. Structure and reactivity. General scheme for the nomenclature of functional groups. Substitution and elimination reactions, mono- and bimolecular.
Reaction mechanisms
7-Alcohols. Structure, nomenclature. Chemical properties: acidity, nucleophilicity.
Substitution and elimination reactions on alcohols . Structure and reactivity of ethers, epoxides, thiols and thioethers. Examples of natural products containing these functional groups.
8-Aldehydes and kentones . General structure; resonance formulae of the carbonyl group. Reactions of addition of nucleophilic species (reversible and irreversible).Oxidation and reduction. Keto-enol tautomerism. Alpha hydrogen acidity.
9-Carboxylic acids and their derivatives. Structure and nomenclature. Acidity of
carboxylic acids. Nucleophilic acyl substitution reaction. Order of reactivity.
Structure and reactivity of acyl chlorides, anhydrides, esters, amides. Structure of triglycerides. Basic hydrolysis.
Bioorganic Chemistry
1-Introduction to the chemistry of carbohydrates. Classification of carbohydrates.Monosaccharides and their properties. Glycosides. Mutarotation; disaccharides,
oligosaccharides and polysaccharides
2-Amines and amino acids. acid-base properties and reactivity.
3-Peptides and proteins. Chemical structure, physical properties and reactivity. Introduction to peptide synthesis. Protecting groups.
3-Nucleosides and nucleotides. Structure, physical properties and reactivity.
Introduction to DNA synthesis. Biological and biomedical use of nucleosides and nucleotides.
Practical part.
Tutorials: written exercises concerning fundamental concepts will be proposed, to help the students to practise with notations and tools of Organic Chemistry (structural formulae, resonance structures, conformation and stereochemical
aspects); through the discussion of cases of increasing diffculty. The discussion of exercises will help to clarify, with examples, the topics exposed in the frontal module.
Laboratory Practice.
Introduction to the laboratori safety probelms; risks connected with the use of chemicals and parameters describing hazards and risks.
Practical experiences:
1) Liquid-liquid exctraction of a compound using acid-base aquilibria . Melting point determination. Qualitative anaysis using thin layer chromatography (TLC).
2)Purification of alcohols using distillation. Quantitative analysis of purity by gaschromatography.
3)Synthesis of an ester and properties of carbohydrates.
The most common techniques for the separation and identification of organic compounds will be illustrated.
Full programme
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Bibliography
Theory
• P.Y. Bruice “Chimica Organica-2 Edizione” EdiSES (2nd-Edition 2011).
• J. McMurry “Chimica Organica” 8th Editione. Piccin (2013).
• B. Botta “Chimica Organica” EDI-ERMES (2011)
• W.H. Brown – C.S.Foote – B.L.Iverson E.V. Anslyn “Chimica Organica” V Edition EdiSES (2014)
• K. Peter, C. Vollhardt, N.E. Schore “Chimica Organica” 3 Edizione. Zanichelli (2005).
Copies of the lectures available at the course web site.
Laboratory Practice
W.H. Brown, B. L. Iverson, S. A. Iverson: “Guida alla soluzione dei problemi di
Chimica Organica” Edi Ses.
R.M. Roberts, J.C. Gilbert, S.F. Martin : " Chimica Organica Sperimentale"
Zanichelli Editore .
Copies of the lectures available at the course web site.
Teaching methods
Lectures, tutorials and laboratory practice. During the lectures the principles of organic chemistry nomenclature, physical and chemical properties and reactivity of the major classes of organic molecules and biological macromolecules will be addressed. In the tutorials exercises concerning the structure and reactivity of organic molecules and the related problems of understanding will be presented in an interactive manner and discussed with the students. The part of the practical training is preceded by an explanation in the classroom of the risks and protective measures to be used in the laboratory and by the detailed explanation of the procedures of each experience. The experiences consist of laboratory work in small groups (2-3 people) under the supervision of the teacher and experienced staff, followed by a re-elaboration by the student in a written report.
Assessment methods and criteria
The exam consists of a written test and an oral test upon delivery of lab reports
The knowledge required to pass the exam are:
Capacity
Demonstration of knowledge and understanding whilst supported by advanced textbooks of Organic Chemistry. Ability to apply knowledge of organic chemistry with a professional approach to design, sustain arguments and solve problems in the field of Organic Chemistry; acquire the maturity and knowledge necessary to undertake further studies with a high degree of autonomy
Skills
Demonstration of knowledge of the structure and reactivity of organic molecules, in particular of biological compounds. Knowledge in the classification and nomenclature of organic compounds through the identification of functional groups that characterize them and, through them, in the description of reactivity. Knowledge of the concepts of isomerism, conformation and stereochemistry of organic molecules and the consequences of these in biological systems. Knowledge about the major concepts that govern the reactivity of organic compounds in reactions of radical type, electrophilic or nucleophilic. Knowledge of the functional groups and the properties of some important classes of biological molecules such as carbohydrates, triglycerides and amino acids. The student should demonstrate that he understands and can re-elaborate the main laboratory techniques for purification and modification of organic compounds used during the practical sessions.
The written exam consists of 6 exercises of reactivity of organic compounds solve. It is passed with 4/6 questions are carried out correctly or, alternatively, if at least 60% of the total content expressed are correct and comprehensive.
The oral examination consists of the discussion of the laboratory notebook and a deepening of the theoretical part, in particular of parts not included in the written exam.
Other information
Contains a part of practical laboratory experiences
