Learning objectives
To understand and acquire the basic knowledge of organic chemistry necessary for the understanding of biological phenomena of interest for biotechnologies.
Acquire knowledge and understanding skills characterized by the use of advanced organic chemistry textbooks. Ability to apply the knowledge of Organic Chemistry with a professional approach, to conceive, support arguments and solve problems in the field of Organic Chemistry; acquire the maturity and the knowledge necessary to undertake further studies with a good degree of autonomy.
Mastery of the structure of the organic compounds of their representation and of the formalisms of Organic Chemistry.
Knowledge of the main classes of organic molecules and of the main types of reactions of organic compounds, to understand the structural and functional properties of molecules of biological and biotechnological interest.
Knowledge of functional groups, in particular those constituting biomolecules.
Structure and reactivity of compounds of biological interest, carbohydrates, lipids, peptides and nucleic acids.
Acquisition of safety concepts and training in the chemical laboratory.
Basic techniques of the organic chemistry laboratory and of the purification, separation and characterization of organic compounds. Experience on the synthesis of organic molecules.
Prerequisites
Knowledge of the concepts of General and Inorganic Chemistry, with particular reference to: acidity, balancing of reactions, stoichiometry, concentrations.
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
A more detailed description of the Course can be found at the following llink:
http://prezi.com/1zw9ikojnwsc/?utm_campaign=share&utm_medium=copy&rc=ex0share
The program is the following, as reported above
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.
Bibliography
Theory
• P.Y. Bruice “Chimica Organica-3rd-Edition ” EdiSES (2017).
•W.H. Brown – C.S.Foote – B.L.Iverson E.V. Anslyn “Chimica Organica” V Edition EdiSES (2014).
•J. McMurry “Chimica Organica” 9th Edition. Piccin (2017).
• B. Botta “Chimica Organica” 2-Edition EDI-ERMES (2016)
• 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 .
Thhe slides used to support the lectures will be loaded weekly on the Elly SCVSA platform.
Registration for the online course is required to download the slides.
The slides are considered an integral part of the teaching material. We remind students not
attending to check the available teaching materials and the indications provided by the teacher through the Elly SCVSA platform.
On the same platform are available additional materials such as molecules in 3D, material safety data sheets for substances used in the Laboratory, and videos illustrating the laboratory experiences and techniques.
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) a written test; b) delivery of lab report; c) an oral test.
The knowledge required to pass the exam are the following.
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 exam consists of a deepening of the theoretical part, in particular of the parts not included in the written exam.
The assessment of the knowledge related to the laboratory part will be simultaneous with the oral theory exam and will weigh for about 3/30 of the final vote. The laboratory notebook (50% of the evaluation) and the knowledge of the topics covered in class and in the laboratory (50% of the evaluation) will be considered.
Other information
Contains a part of practical laboratory experiences
