Learning objectives
FIRST MODULE: Aim of the course is to acquire knowledge and understanding, concepts and
learning skills within the following domains:
1) Students should learn and understand the basic language of organic chemistry;
2) students should learn and understand the basic principles which connect the
structure of organic compounds with their physic-chemical properties;
3) students should learn and understand the key concepts of the basic organic
chemistry course in view of further in-depth study in the subsequent organic
chemistry course.
At the end of the course, students having followed all the theory and exercise
lessons are expected to be able to applying knowledge and understanding of the
above mentioned subject areas through the correct execution of problems and
exercises about:
1) recognizing, writing and naming the main organic molecule classes;
2) viewing simple organic molecules in three dimensions with an emphasis to their
stereochemical properties;
3) recognizing and analyzing the relationship between structure and properties
(reactivity) of basic organic molecules including alkanes, cycloalkanes, halogenoalkanes,
alkenes, alkynes, alcohols, polyols, ethers, epoxides, thiols;
4) proposing viable solutions as how to retro-synthesize, synthesize, transform, and
interconvert the above mentioned organic compounds.
Further aim of the course involves the acquisition of learning skills and
communication skills by employing appropriate language to both specialized and
non-specialized audience, in line with the above mentioned objectives.
SECOND MODULE:
Aim of the course is to acquire knowledge and understanding, concepts and
learning skills within the following domains:
1) students should learn, understand and deepen the basic principles which connect
the structure of organic compounds with their physico-chemical properties;
2) students should learn, understand and deepen the principles underlying organic
reactions allowing them to rationally interpret reaction mechanisms and to
understand similarities and differences among different reaction
pathways;
3) students should learn and understand close connections between organic
chemistry and neighboring disciplines such as biochemistry and medicinal
chemistry;
4) students should select information and notions in order to make judgments and
apply such information to solve ever emerging problems of organic chemistry, to
predict the outcome of known (and possibly unknown) organic transformations, to
propose ways to design and synthesize simple organic compounds;
5) students should acquire learning skills and communication skills by employing
appropriate language to both specialized and non-specialized audience, in line with
the above mentioned objectives.
At the end of the course, students having followed all the theory and exercise
lessons are expected to be able to applying knowledge and understanding of the
above mentioned subject areas through the correct execution of problems and
exercises about:
1) recognizing and analyzing the relationship between structure and properties
(reactivity) of organic molecules;
2) proposing viable solutions as how to retro-synthesize, synthesize, transform, and
interconvert the above mentioned organic compounds.
Prerequisites
FIRST MODULE: To fully appreciate the content of the course, it is necessary to acquire knowledge of
general and inorganic chemistry in a previous course. To access the final
examination, it is necessary to pass the “General and Inorganic Chemistry” exam.
SECOND MODULE:
To fully appreciate the content of the course, it is necessary to acquire knowledge of
general and inorganic chemistry and organic chemistry basics in previous courses.
To access the final examination, it is necessary to pass both the “General and
Inorganic Chemistry” exam and the Organic Chemistry Basics” exam.
Course unit content
FIRST MODULE: The introduction of the course is devoted to a general presentation of organic
chemistry as a scientific discipline, with a brief overview of its historical background
and an highlight of the significance and impact of organic chemistry on
contemporary science, culture, and life. Basic principles are then given emphasizing
the key connections between the structure of organic compounds and their physicochemical
properties, recalling some general concepts from the General Chemistry
course including thermodynamics principles, the kinetics and the structural theories.
The key concepts of isomerism are given (conformational and configurational
isomers) and an emphasis is placed to stereoisomerism. The second part of the
course comprises the systematic study of basic organic compounds including the
structure, nomenclature, natural occurrence, physical properties, reactivity, and
synthetic methods of alkanes, cycloalkanes, halogeno-alkanes, alkenes, alkynes,
alcohols, polyols, ethers, epoxides, thiols.
During the course, a series of exercises are proposed and solved at the blackboard,
with the purpose to applying the principles and concepts into a “real-world” context.
These exercises are open for free discussion between teacher and students and
they are considered an essential part of the course.
SECOND MODULE:
The first part of the course is devoted to recall and advance knowledge acquired in
the (Organic Chemistry Basics” course. The following subjects are then treated:
nucleophilic addition to carbon-oxygen double bond, acyl nucleophilic substitution,
brief description of the role of protecting groups in organic synthesis, brief survey of
qualitative identification of the main functional groups. The systematic study of the
following compound classes is then placed, comprising the structure, nomenclature,
natural occurrence, physical properties, reactivity, and synthesis of the following
compound classes: aldehydes, ketones, carboxylic acids, acyl halides, acid
anhydrides, esters, thioesters, lactones, amides, lactams, imides, nitriles, 1,3-
dicarbonyl compounds, alpha,beta-unsaturated compounds, aliphatic and aromatic
amines, nitro- and nitroso-derivatives.
The second part of the course allows students to acquire knowledge on carboncarbon
bond-forming reactions, synthesis of enols and enolates, imines and
enamines, alpha-alkylation and alpha-halogenation of enols and enolates, aldol
additions and condensations and variants thereof, Claisen condensations and
related reactions, Michael and Mannich addition reactions, examples of
transposition reactions.
The third part of the course allows students to acquire knowledge on the aromatic
domain including the concept of aromaticity and the systematic study of aromatic
compounds including the structure, nomenclature, natural occurrence, physical
properties, reactivity, and synthesis of the following compound classes: benzene,
substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines,
simple aromatic heterocycles, azo-compounds.
Full programme
FIRST MODULE: Origin and development of organic chemistry as a science. Functional groups of the
main organic compounds. The carbon atom as a focal element in organic chemistry.
Oxidation number assignment to a given atom within an organic molecule with a
special emphasis on the carbon atom. Relationship between the structure of an
organic compound and its physical and chemical behaviour. Hybridation (in aprticulr
of the carbon atom within organic molecules), molecular geometry,
electronegativity, polarity of organic compounds. Resonance in organic compounds.
Configurational and conformational isomerism. Conformational analysis of linear
and cyclic alkanes. Constitutional isomerism and stereoisomerism. Chirality,
enantiomers, diastereoisomers, meso compounds, geometric isomerism.
Thermodynamic and kinetic control of organic reactions. Reaction kinetics,
activation energy, catalysis. Reaction mechanisms. Radical and ionic reactions.
Nucleophilic and electrophilic species. Acidity and basicity in organic chemistry,
acid-base reactions. Oxidative-reductive reactions. Monomolecular and bimolecular
nucleophilic substitutions at saturated carbons. Monomolecular and bimolecular
beta-elimination reactions. Main solvents and their use in organic chemistry.
Organometallic reagents, Grignard reagents: generality and use. Electrophilic
addition reactions to alkenes and alkynes. Regioselective, stereospecific, and
stereoselective organic reactions.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties,
reactivity, and synthesis of the following compound classes: alkanes, cycloalkanes,
alkyl halides, alkenes, alkynes, alcohols, polyols, thiols, ethers, epoxides.
SECOND MODULE:
The first part of the course is devoted to recall and advance knowledge acquired in
the “Organic Chemistry Basics” course. The following subjects are then treated:
nucleophilic addition to carbon-oxygen double bond, acyl nucleophilic substitution,
brief description of the role of protecting groups in organic synthesis (carbonyl
compounds, phenols, aniline), brief survey of qualitative identification of the main
functional groups. The systematic study of the following compound classes is then
placed, comprising the structure, nomenclature, natural occurrence, physical
properties, reactivity, and synthesis of the following compound classes: aldehydes,
ketones, carboxylic acids, acyl halides, acid anhydrides, esters, thioesters, lactones,
amides, lactams, imides, nitriles, 1,3-dicarbonyl compounds, alpha,betaunsaturated
compounds, amines, nitro- and nitroso-derivatives.
The second part of the course allows students to acquire knowledge on carboncarbon
bond-forming reactions, synthesis of enols and enolates, imines and
enamines, alpha-alkylation and alpha-halogenation of enols and enolates, aldol
additions and condensations and variants thereof, Claisen condensations and
related reactions, Michael and Mannich addition
reactions, examples of transposition reactions.
The third part of the course allows students to acquire knowledge on the aromatic
domain including the concept of aromaticity and the systematic study of aromatic
compounds including the structure, nomenclature, natural occurrence, physical
properties, reactivity, and synthesis of the following compound classes: benzene,
substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines,
simple aromatic heterocycles, azo-compounds.
Bibliography
FIRST AND SECOND MODULE: Textbooks (one of the following to be chosen):
1. W.H. Brown, B. L. Iverson, E. V. Anslyn,C.S. Foote, “Chimica Organica”, V
Edizione, EdiSES, Napoli, 2014.
2. Autori vari, “Chimica Organica” (a cura di B. Botta), Edi.Ermes, Milano, 2016.
3. J. McMurry, “Chimica Organica”, VIII Edizione, Piccin, Padova, 2012.
4. M. Loudon, “Chimica Organica”, V Edizione, EdiSES, Napoli, 2010.
5. J. G. Smith, "Chimica Organica", McGraw-Hill, Milano, 2007.
6. G.H. Schmid, “Chimica Organica”, Casa Editrice Ambrosiana, Milano,
In considerazione del fatto che l’esame di Chimica Organica Propedeutica è
integrato con l’esame di Chimica Organica, la votazione unica finale è data dalla
media aritmetica delle votazioni dei singoli esami.
Programma esteso Origine e sviluppo della chimica organica come scienza. Generalità sui gruppi
funzionali dei principali composti organici. L’atomo di carbonio quale elemento
centrale in chimica organica. Assegnazione dello stato di ossidazione di un atomo
(in particolare l'atomo di carbonio) all'interno di una molecola organica. Relazione
tra la struttura di un composto organico di base e le sue proprietà chimico-fisiche e
di reattività. L’ibridazione (in particolare dell'atomo di carbonio), la geometria
molecolare, l’elettronegatività e la polarità delle molecole. Risonanza nei composti
organici. Isomeria configurazionale e conformazionale. Analisi conformazionale di
alcani lineari e cicloalcani. Isomeria costituzionale e stereoisomeria. Enantiomeri,
diastereoisomeri, composti meso, chiralità, isomeria geometrica. Controllo cinetico
e controllo termodinamico delle reazioni organiche. Velocità di reazione. Energia di
attivazione. Catalisi. Meccanismi di reazione. Reazioni radicaliche e reazioni
ioniche. Nucleofili ed elettrofili. I composti organici come acidi e basi, reazioni acidobase.
Reazioni di ossido-riduzione. Reazioni di sostituzione nucleofila alifatica
mono- e bimolecolari. Reazioni di beta-eliminazione mono- e bimolecolari.
Classificazione ed uso dei principali solventi utilizzati in chimica organica. Composti
organometallici, reattivi di Grignard: generalità ed uso. Reazioni di addizione
elettrofila al doppio e triplo legame carbonio-carbonio. Regioselettività,
stereospecificità e stereoselettività nelle reazioni organiche.
Parte alifatica. Struttura, nomenclatura, fonti naturali, proprietà fisiche, reattività,
metodi di sintesi di: alcani, cicloalcani, alogenoalcani, alcheni, alchini, alcoli, polioli,
tioli, eteri, epossidi.
1997.
Study guide and solution manual for exercises (at least one of the following to be
chosen):
1. M. V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo
Svolgimento di Esercizi di Chimica Organica”, seconda Edizione, Loghia Ed.,
Napoli, 2011.
2. B. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Brown, Foote,
Iverson – Chimica Organica”, 4° Ed., EdiSES, Napoli, 2014.
3. T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli
esercizi”, Seconda Edizione, Zanichelli, Bologna, 2010.
4. S. Cacchi, F. Nicotra, “Esercizi di Chimica Organica”, Casa Editrice Ambrosiana,
Milano, 1998.
Reference books:
1. J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford
Edition, 2001.
2. R. Norman, J.M. Coxon, “Principi di Sintesi Organica”, 2a Edizione Italiana,
Piccin Editore, Padova, 1997.
3. R.T. Morrison, R.N. Boyd, “Chimica Organica”, VI Edizione, Casa Editrice
Ambrosiana, 1997.
Additional teaching material for students:
Examples of organic chemistry exercises given in the previous examination
sessions
Teaching methods
FIRST MODULE: According to the above mentioned objectives and contents, the course is carried out
through frontal oral lessons and includes exercises at the blackboard dealing with
the design, synthesis, and transformation of simple organic molecules which could
be connected with the pharmaceutical and biological domains. These exercises are
open for free discussion between teacher and students and they are considered an
essential part of the course.
SECOND MODULE:
According to the above mentioned objectives and contents, the course is carried out
through frontal oral lessons and includes exercises at the blackboard dealing with
the design, synthesis, and transformation of simple organic molecules which could
be connected with the pharmaceutical and biological domains. These exercises are
open for free discussion between teacher and students and they are considered an
essential part of the course.
Assessment methods and criteria
FIRST MODULE: The final examination consists of a written exam. The written exam deals with the
execution of exercises on the synthesis and reactivity of organic compounds. This
test is aimed at verifying whether the student has developed the skill and ability of
1) using the language of organic chemistry, 2) recognizing the basic functional
groups, 3) recognizing the
relationship between structure and properties of basic organic compounds, 4)
predicting the behavior of a given organic chemistry transformation among those
comprised in the program, 5) selecting and deploying information from the theory
study in order to furnish solutions to a given practical organic chemistry problem.
The result of the written exam is marked in thirtieth. A minimum of eighteen thirtieth
is required as a threshold.
Since the “Organic Chemistry Basics” course is complemented by the subsequent
“Organic Chemistry” course, the final marking is given by the arithmetic mean of the
quotations of each part.
SECOND MODULE:
The final examination consists of a written exam followed by an oral colloquium. To
access the oral examination the student has to pass both the written exam of
Organic Chemistry Basics and Organic Chemistry). The written exam deals with the
execution of exercises on the synthesis and reactivity of organic compounds. This
test is aimed at verifying whether the student has developed the skill and ability of
1) recognizing the relationship between structure and properties of organic
compounds, 2) predicting the behavior of a given organic chemistry transformation
among those comprised in the program, 3) selecting and deploying information from
the theory study in order to furnish solutions to a given practical organic chemistry
problem. The result of the written exam is marked in thirtieth. A minimum of
eighteen thirtieth is required as a threshold. Having passed the written exam, a brief
colloquium is carried out aimed at verifying the communication skills and the correct
use of specialized language.
Since the “Organic Chemistry” course is the sequel of the “Organic Chemistry
Basics” course, the final marking is given by the arithmetic mean of the quotations
of each part.
Other information
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