Ateneo - UPO

The course features the teaching of organic chemistry in its fundamentals. It is divided into three parts, the former being a structural section (functional groups, stereochemistry, etc), the second being a survey of the elementary reactivity in organic chemistry (nucleofilic substitutions, b-eliminations, electrofilic additions, reactions of carbonilic compounds) and the third part is dedicated to biomolecules

W. H. Brown, T. Poon - Introduction to Organic Chemistry, 5th Edition
McMurry – Fundamentals of organic chemistry – Zanichelli.
B. Botta (and others), "Basic Organic Chemistry"; edi-ermes
Student solutions manual to accompany Introduction to organic
chemistry
J. McMurry – Fundamentals of Organic Chemistry, 7th Edition
The slides used in the lessons are available for students on DiR learning
platform.

Knowledge and understanding.
The course aims to provide the basics of the chemistry of carbon
compounds through the knowledge of the structure and reactivity of the
main functional groups, the mechanisms of the most important reactions
and the fundamental principles of organic stereochemistry.
Ability to apply knowledge and understanding.
The student will be able to apply the theoretical concepts assimilated to
solve exercises of nomenclature, stereochemistry and reactivity of organic
molecules.
Communication skills.
The student must have acquired and will have to know how to use an
appropriate chemical vocabulary in relation to the topics covered in the
course. It should also be able to predict the products of a reaction
correctly, clearly and concisely.

Basic knowledge of general chemistry is strongly recommended.

The course is based on classroom lectures, powerpoint presentations and
guided exercises. The slides used during the lessons will be provided to
the students through the D.I.R. platform.
In addition to the lectures, exercises will be held in the classroom by the
teacher also with the involvement of students to learn more in detail
about the topics covered in class. The concepts covered by the course
will be discussed collegially in the classroom and applied directly in the
exercises to stimulate students' critical sense and independence of
judgment. Communication skills will be stimulated using appropriate
terminology.

Learning control: Every 3-4 lessons, one hour (half-lesson) is dedicated to
the review of the latest subjects. This is realized by means of examples
and exercises, which the students are requested to perform, and whose
results are thoroughly discussed with the teacher (or the assistant
trainer).
The teacher is available to the student for any clarification or explanation
of the topics covered during the course.
Students with physical disabilities, Learning Disabilities or Special Education Needs can request specific services and tools via the Staff Sviluppo e Coordinamento Carriere e Servizi alle Studentesse e agli Studenti, consulting the University webpage: https://www.uniupo.it/en/services/servicesstudents-physical-or-learning-disabilities.
Students with disabilities, learning disabilities or special education needs, once they have contacted the University Staff, can refer to the tutor in charge of the course to define the examination modalities, concerning academic aspects.

The exam consists of written exam with 10 exercises regarding the whole
program. Each exercise has the same weight in the final score (from 0 to
3 points per exercise). In particular, there will be 5 exercises on
nomenclature (correctly write the structure of a molecule from the name
IUPAC and vice versa), isomerism and resonance (assign the
configurations of stereocentres and the arrangement of electrons within
a molecule able to give resonance) and 5 exercises on reactivity (predict
the products of a reaction), synthesis (identifying a synthetic pathway
also of 2-3 steps) and reaction mechanisms (the knowledge of a reaction
mechanism allows to predict the products).
The written exam allows to evaluate the student's theoretical knowledge,
his ability to write formulas and reaction mechanisms and the ability to
predict the products of a reaction starting from certain reagents as well
as explaining the evolution and the stereochemistry of a reaction based
on its mechanism.
The passing grade is achieved by demonstrating that the student has
understood the subject and is able to use the basic concepts of the topics
covered during the course through the exercises. The ability to correctly
write formulas and reaction mechanisms in the written exam is also
essential in order to pass the exam. Other parameters of judgment are:
the ability to organize and clearly expose the answer and the acquisition
of the appropriate terminology. Excellence can be achieved by correctly
performing all the exercises in the written exam.

Covalent bond, shape of the molecules. Ibridation and bond angles.
Alkanes and cycloalkanes Constitutional Isomers. IUPAC nomenclature.
Functional groups. Conformational isomers. Geometric isomers in cycloalkanes and alkenes. The E/Z system. Chirality. Stereoisomerism.
The R,S system. Enantiomers separation. Resonance and electronic delocalization.
Carbocations and carbanions. Inductive and mesomeric effects.
Nucleophiles and electrophiles. Radicals and radicalic reactions. Bronsted and Lewis Acid and bases. Molecular structure and acidity. Alkanes and alkenes reactivity. Reaction mechanisms and energetic profiles.
Electrophilic addition reactions. Oxidation and reduction of alkenes.
Alkynes. Electrophilic addition of alogens and water. Hydrogenation.
Alogenoalkanes. Nucleophilic substitution reactions SN1 e SN2. Analysis
of the factors influencing the reaction rates. Elimination reactions E1 and E2. Competition between substitution and elimination reactions. Alcohols, eters and thiols. Reactivity of alcohols and ethers. Epoxides. Acid or base catalysed epoxide ring opening. Aromatic compounds. Benzene and
aromaticity. Electrophilic aromatic substitution. Phenols. Oxidation in
benzylic position. Aldehydes and ketones. Carbonyl group structure and reactivity. Nucleophilic addition of carbanions, alcohols and amines.
Reaction mechanisms. Oxidation and reduction. Keto-enol tautomerism.
Carboxylic acids and their derivatives. Reduction. Esterification.
Conversion to acyl chlorides. Reaction with amines. Hydrolysis of functional derivatives. Amines and other azo-compounds. Structure and basicity. Preparation and reactivity. Carbohydrates. Monosaccharides.
Cyclic structure of monosaccharides and their reactions. Disaccharides and polysaccharides. Lipids. Triglycerids. Soaps and detergents. Steroids. Phospholipids. Amino acids, peptides and proteins. Acid-base properties
of amino acids. Primary, secondary and tertiary structure of peptides and
proteins. Nucleotides and nucleic acids.

Knowledge and understanding
Knowledge of the chemical and electronic structure of organic molecules
and their implications for their reactivity.
Knowledge of the meaning of isomerism in all its declinations.
Knowledge of the main reactivity of each functional group.
Knowledge of the main reaction mechanisms.
Knowledge of the meaning of aromaticity.
Applying knowledge and understanding:
Ability to recognize functional groups in order to give the proposed molecules the correct nomenclature according to IUPAC rules.
Obtain the molecular structure from the IUPAC name and vice versa.
Recognize the stereochemistry of a molecule.
Ability to explain the course and the stereochemistry of a reaction on the
basis of its mechanism.
Acquisition of knowledge and skills on the properties of the major classes
of organic compounds and their chemical behavior.
Making judgements
Ability to evaluate from the structure of a compound and its similarity with the families of compounds studied which predictions can be made about its molecular properties.
Ability to interpret and rationalize organic reactions in terms of reaction mechanism and to address the study of the subject through critical and non-mnemonic learning.
Communication skills
Ability to rationalize a set of data on a family of organic compounds and connect them to the core principles of the discipline.
Ability to connect and compare different topics covered during the course.
Ability to clearly organize the answer by acquiring the appropriate terminology.
Learning skills
Ability to use teaching material for a critical and rational study.