Learning outcomes of the course unit
To introduce the student to the basic concepts of Organic Chemistry and to the properties and reactivity of the different classes of organic compounds.
Knowledge and understanding: aim of the course is to give to the student the fundamentals of Organic Chemistry and the essential instruments to understand the biochemistry phenomena and processes. The most important classes of organic compounds and of organic chemistry reactions for students in Biology will be especially discussed, highlighting the connections with the biological world. The thermodynamic and kinetic aspects of organic reactions will be also discussed together with the notational and stereochemical terms of organic compounds and reactions. The main classes of macromolecules of biological interest will be also presented and discussed in terms of structure and reactivity.
Applying knowledge and understanding: in parallel to theoretical explanations, the student will be guided through the resolution of organic chemistry problems also in order to train the student to apply and reinforce the concepts acquired.
Making judgements: The student will be possibly acquire a complete autonomy in the classification of organic compounds and an elementary ability to understand the properties and reactivity of organic and biological molecules.
Communication: at the end of the course, the student should be able to properly communicate using the typical terminology of organic chemistry and shouild also be able to discuss problems of stereochemistry and reactivity of the main classes of organic compounds.
Lifelong learning skills: although not the main objective of the course, the student will be trained to understand and interpret the reactivity of organic compounds through the observation of experimental results.
Prerequisites: the student should have already engaged the study of General and Inorganic Chemistry (especially concerning the basic concepts of atoms, bonds, equilibria and acid-base reactions) even though is not required to have passed the examination.
To successfully follow the course and pass the examination it is
possess most of the knowledge and concepts treated in the course of
Generale'. In particular, fundamental are the concepts related to the
structure of the atoms, to the chemical bond, to thermodynamics (with
regard to the chemical equilibria and to acid-base equilibria) and to the
kinetics. It is not compulsory to have passed the examination of Chimica Generale,
but it is
strongly recommended to be in possess of most of the concepts related
course before attending the lectures of Chimica Organica.
Course contents summary
The students will be first introduced to the basic theories of VSEPR and of
valence bond for the description of organic molecules. Some basic
chemical thermodynamics and kinetics will be also reminded with
attention to 1st and 2nd order reactions, to chemical catalysis and to
reactions. The concepts of nucleophile and electrophile will be compared
of Brønsted-Lowry and Lewis acid and base. The concepts of organic
stereochemistry will be described together with the stereochemical
and properties of the stereoisomers with particular attention to biological
A systematic survey of the structure, properties and reactivity of organic
divided by functional groups, will be undertaken. In particular this
include the following classes of organic compounds: Alkanes snd
Alkenes and Alkynes; Alkyl halides; Alcohols, Ethers and Thiols; Benzenes
Aromatic compounds; Amines; Ketones and Aldehydes; Carboxylic acids
In parallel to this theoretical part, a series of exercises will be presented
during separate tutoring lectures aiming at applying the concepts learnt
provide a constructivist approach to learning organic chemistry.
Introduction to Organic Chemistry; The C atom as central atom in organic
compounds; electronic and Lewis structures of atoms; Lewis bond model;
electronegativity; Lewis structures of molecules and ions; bond angles
and distances: shape of molecules according to the VSEPR theory; dipole
moment of bonds and molecules; resonance. Covalent bonds according
to the valence bond theory: hybridation of atomic orbitals. Introduction to
the functional group theory. Intermolecular forces (dipole-dipole
interactions, Hydrogen bonds, van der Waals forces); polarizability;
solubility and physical properties of organic compounds; properties of
solvents (apolar, dipolar aprotic and protic solvents); dielectric constants
Fundamentals of kinetics. First and second order reactions. Molecularity
of a reaction. Effect of the temperature on the rate of a reaction:
Thermodynamics and kinetics of organic reactions
Enthalpy and entropy of reaction. Kinetics of reactions: mechanism of a
reaction, rate determing steps, reaction intermediates, transition states
and activation energy; rate of a reaction and specific rate constant;
molecularity; Eyring equation. Chemical catalysis. Reactions under kinetic
or thermodynamic control. Competitive reactions. Hammond postulate.
Brønsted-Lowry acids and bases. Nucleophiles and electrophiles.
Structure analysis: properties and reactivity according to functional group
Alkanes. Nomenclature. Cycloalkanes. Nomenclature. Conformation of
alkanes. Conformation of cycloalkanes and substituted cycloalkanes.
Physical properties of alkanes and cycloalkanes. Sources of alkanes.
Reactivity of alkanes. Oxydation and combustion. Halogenation reaction.
Homolytic cleavage. Radical species. Hyperconjugation. Orientation in
halogenation reactions. Statistical and reactivity factors.
Reactivity/selectivity in organic reactions. Regiochemsitry in radical
Chirality. Chiral and achiral molecules. Definition of stereocenters.
Stereoisomers. R/S designation. Fischer projections. Enantiomers.
Molecules having more than one chiral center: diastereomers and meso mixtures and their resolution. Enantiomeric and diastereomeric excess.
Chirality in the biological world. Enantiomers in biology and drugs. Origin
of chiral homogeinity in nature.
Alkenes and alkynes. Structure and nomenclature. Geometric isomerism
(cis/trans and E/Z). Cycloalkenes. Terpenes. Alkenes reactions.
Electrophile addition to the double bonds and polymerization reactions.
Addition of halogenidric acids. Carbocation stability. Alkene hydration.
Chlorine and bromine addition to alkenes: the bromonium ion.
Stereoselective and stereospecific reactions. Glycols formation.
Reduction of alkenes: heats of hydrogenation and stability of alkenes.
Stereochemistry in the addition reactions to alkenes. Structure and
acidity of alkynes. Reactivity of alkynes. Addition of H2, X2, HX e H2O.
Isolated, conjugated and cumulated dienes. Heats of hydrogenation.
Polymerization of alkenes and dienes.
Halogenoalkanes: structure and nomenclature. Nucleophilic aliphatic
substitution. Nucleophiles and bases, electrophiles and acids. SN2 and
SN1 mechanisms: differences in the kinetics, in the mechanism and in
the stereochemistry of the products. Stereoselectivity and
stereospecificity of the reactions. Factors influencing the rates of SN2 and
SN1 reactions: structure of the nucleophile, of the RX, of the leaving
group and of the solvent. Examples of SN2 and SN1 reactions. Betaelimination
and dehydroalogenation reactions. Saitzev’s rule, E2 and E1
mechanisms. E2 vs E1. Stereochemistry of E2 reactions. Biosynthesis of
Alcohols, ethers and thiols: structure, nomenclature and physical
properties. Acidity of the alcohols according to the inductive effects of
substituents. Acidity of methanol, ethanol, iso-propanol and terz-butanol.
Reaction with active metals, c
· W. Brown, T. Poon: Introduzione alla Chimica Organica, 3^ Edizione,
To be consulted
· N. L. Allinger, M. P. Cava, D. C. De Jongh, C. R. Johnson, N. A. Lebel, C. L.
Stevens, Chimica Organica, 2^ Edizione, Zanichelli, Bologna.
· W. H. Brown, C. S. Foote: Chimica Organica, 2^ Edizione, EdiSES,
· J. McMurry, Chimica Organica, 1^ Edizione, Zanichelli, Bologna.
Oral lectures and practice on organic chemistry problems
Applying knowledge and understanding: Ability to analyse organic compounds and biomolecules in terms of functional groups and stereocenters. Ability to classify and to give a systematic name to the compounds belonging to the main classes of organic compounds. Ability to understand the mechanisms of the main organic chemistry reaction also via the use of curley arrows. To understand the connections between structure and properties/reactivity of organic molecules and of complex biological macromolecules such as peptide, carbohydrates, lipids and nucleic acids.
Exercises guided by the teacher in the class will start to make the student able to develop a judgement on the relationship between structure and reactivity.
Assessment methods and criteria
Written and oral exams. At the half and at the end of the semester, it is possible to attend two intermediate written tests related to the first and second part of the programme. Who will pass both the intermediate tests can directly access the oral examination.
Written and oral examinations will verifying the knowledge of the student through the discussion of organic chemistry problems with the aim to evaluate the ability to apply the competence acquired by the student on the structure and reactivity of organic and bio-organic compounds.
The exam is passed if the student is able to analyse the organic and bio-organic compounds in terms of functional groups and stereocenters present and if he is able to classify and assign the systematic IUPAC name to molecules belonging to the main classes of organic compounds.
The ability to describe the stereochemistry and the properties of stereoisomers will be also evaluated in details (up to further 3 points) toghether with the knowledge of the reactivity of the main classes of organic compounds (up to further 3 points).
It will be also evaluated the ability to correlate the molecular properties and reactivity of organic compounds with their molecular structures (structure-property relationship) and to describe the mechanism of the main organic reactions by using the curley arrows (up to further 3 points).
The ability to properly discuss the organic chemistry reaction in terms of kinetics and thermodynamics will allow to gain up to further 3 points.
Theoretical explanations (4 hours/week during 13 weeks) together with
activity (2 hours/week) consisting in exercises solved in classroom by the
and aimed at applying and reinforce the concepts learned.
The examination consists of a written and an oral proof.
At the half and at the end of the semester, it is possible to attend two
written proofs regarding the first and second part of the programme,
Who will pass both the intermediate proofs can directly access the oral