OVERVIEW

Nature and environment, as well as the uman body, are chemical labs. This course of chemistry helps students to understand what happens in Naure and environment at a molecular level

AIMS AND CONTENT

LEARNING OUTCOMES

This course illustrates the basic principles of Organic Chemistry, introducing students to chemical language and methodology and allowing them to understand the chemical content of the following courses.

AIMS AND LEARNING OUTCOMES

(i) Illustrating the importance of chemistry to understand what happens to matter, inside us and around us.

(ii) Showing that, by starting from the General Laws of Nature, we can understand molecular structure and then physical and chemical properties of organic compounds, though a unique reasoning developing from the first to the last lesson of the course

(iii) Visualizing, as far as possible in frontal lessons, both molecular structure by the use of molecular models, and chemical compounds by the study of physical properties and laboratory techniques.

TEACHING METHODS

Frontal lectures with slide projection and interaction with the students. Two written tests during the course.

"Students who have valid certification of physical or learning disabilities on file with the University and who wish to discuss possible accommodations or other circumstances regarding lectures, coursework and exams, should speak both with the instructor and with Professor Sara Ferrando (sara.ferrando@unige.it), the Department’s disability liaison.”

SYLLABUS/CONTENT

The importance of organic chemistry to understand nature and environment. Connections with the hystory of mankind. Organic chemistry today.

The General Laws of Nature. Molecular stability as determined by intramolecular attractive and repulsive forces.

From the Periodic Table to chemical bonds, valence, and the constitutional or structural formula. The three-dimensional structure of organic compounds and a simple rationale (VSEPR). Molecular models. Continuous and complete rotation around single bonds in open chains. Conformations. Rigid sub-structures around double bonds. Possible cis/trans (Z/E) configurations. Molecular symmetry planes. Chirality. Molecules with one asymmetric carbon. R/S configurations of an asymmetric carbon. Molecules with more asymmetric carbons. Fischer projections. Isomerism. Constitutional or structural isomerism. Configurational isomerism or stereoisomerism: enantiomers, diastereoisomers.

Aliphatic compounds. Functional Groups and homologue series of compounds. Tradictional and IUPAC nomenclature.

Polar covalent bonds. Intermolecular forces and physical properties. Molecular electric dipole moments, melting and boiling points, solubility in water and in organic solvents. Physical properties and isomerism. Main separation and purification techniques. Optical activity. Polarimeter.   

Probabilistic character of our knowledge of the electron position in an atom. Atomic orbitals. Molecular orbitals. The method of the hybrid atomic orbitals (sp3, sp2, sp). Sigma, pi, n, pi star and sigma star molecular orbitals. Colour. Colourless and coloured compounds for man eye. Reaction-rate measurements from Visible/UV spectra.  The resonance method: benzene, amides, carboxylic acids and carboxylate anions. Electron delocalization and resonance energy.

Alicyclic compounds. Impossible or restricted rotation around single bonds in a cycle. Cyclohexane: chair and boat conformations. Substituted cyclohexanes. Haworth projections.

Aromatic compounds. The so-called aromatic character and its rationale.

Heterocyclic compounds with or without aromatic character.

Chemical reactions. Calorimetry. When the entropy contribution to free-energy variations is really important. Diagram of the free energy of reagents vs. the reaction path. Free energy  of activation.  Possible contributions to the free energy of activation. The kinetic equation. Diagram of the free-energy of the reaction mixture vs the percentage of products. When chemical equilibrium is reached. The equilibrium constant, how it can be exploited and how it can be modified. How we can modify the free energy of activation. Homogeneous, heterogeneous and enzymatic catalysis. Two-step reactions and reaction intermediates. Main reactions: acid-base, redox, additions to C=C and C=O double bonds, aliphatic nucleophilic substitutions, acylic and aromatic substitutions.

Lipids and in particular fatty acids (palmitic, stearic, oleic, linoleic and linolenic acid) and triglycerides (fats and oils): the importance of the Z-configuration of double bonds in determining the liquid state of oils.

Main examples of alkaloids.

Aminoacids: nomenclature; zwitterion, cationic and anionic forms, isoelectric point. Proteogenic aminoacids: structure, steric series. The primary structure of proteins. The secondary struture: planar sub-units along the chain, beta-pleated-sheet and alpha-helix conformations and forces stabilizing them.The tertiary structure. Fibrous and globular proteins..The quaternary structure. Enzymes.

Carbohydrates. Main monosaccharides and their steric series. The intramolecular reaction, diastereoisomeric cyclic structures. Mutarotation. The so-called reducing sugars. Aldonic and aldaric acids, alditols. Glycosides. Disaccharides (cellobiose, maltose, lactose, sucrose). Polysaccharides (cellulose, starch, glycogen). A look at some ecological industrial processes to produce polymers, based on fermentation of polysaccharides from vegetables grown in the same area. 

RECOMMENDED READING/BIBLIOGRAPHY

Students can find in Aulaweb all that is necessary

Optional further reading:
- J. Gorzinski Smith, Chimica Organica, Ed. McGraw-Hill
- W. Brown, T. Poon, Introduzione alla chimica organica, 4° edizione, Edises

TEACHERS AND EXAM BOARD

LESSONS

Class schedule

ORGANIC CHEMISTRY

EXAMS

EXAM DESCRIPTION

The exam of the module of Organic Chemistry has to check that the student has acquired and (most important) understood the didactic material reported in Aulaweb with the possible exception of optional parts or further reading. The not-optional didactic material reported in Aulaweb documents what has been thoroughly discussed during the lessons.

The exam of this module consists of two written tests and an oral discussion. Each of the two written tests passed during the course can exempt from the corresponding exam written test. 

Students who have valid certification of physical or learning disabilities on file with the University and who wish to discuss possible accommodations or other circumstances regarding exams, should speak both with the instructor and with Professor Sara Ferrando (sara.ferrando@unige.it), the Department’s disability liaison.

ASSESSMENT METHODS

The general aim is to check that the candidate can discuss the studied subjects properly as he has not studied them by heart. For students examined for the first time the oral exam starts with a subject chosen by the candidate. The oral exam can include a discussion on the written tests. 

FURTHER INFORMATION

It is particularly useful to study after each lesson, attending all them, as the course is a unique reasoning developing from the first to the last lesson.

Missing one lesson can cause difficulty in understanding the following one.