Ateneo - UPO

Module Organic Chemistry
The module provides the basic knowledge of organic chemistry: the concepts and language necessary for the study of organic chemistry as well as key elements on nomenclature, structure and reactivity of the most common classes of organic compounds.

Module laboratory
Students will be provided with basic knowledge on the techniques of purification, characterization and recognition of organic compounds, with particular attention to safety standards to be adopted in the laboratory.

1) William H. Brown, Brent L. Iverson, Eric V. Anslyn, Christopher S. Foote, Chimica organica – EdiSES
2) John McMurry –Chimica Organica – nona edizione, Piccin
3) Janice Gorzynski Smith, Antonella Capperucci, Stefano Menichetti, Fondamenti di Chimica Organica 4a ed - McGraw-Hill

Student solutions manual to accompany Introduction to organic chemistry
J. McMurry – Fundamentals of Organic Chemistry, 7th Edition

Module Organic Chemistry
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, streochemistry 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 present correctly, clearly and concisely, the mechanisms by which organic molecules react and know how to predict the products of a reaction.Making judgmentsThe student must be able to predict the properties and reactivity of a molecule on the basis of the structure of a compound and its similarity with the families of compounds studied.The student must also demonstrate the ability to link/compare the different topics covered during the course.Learning skillsThe student must be able to use the teaching material (slides and exercises provided by the teacher, textbooks) for a detailed, critical and reasoned study.

Module laboratory
The main purpose of the course is to provide students with the knowledge of the techniques and practical skills needed to recognize, separate and purify the main organic compounds; the knowledge of the techniques and the ability to perform tests for the functional groups present in an organic compound; the ability to work in groups and to issue a laboratory report. Communication skills and self judgement: familiarize the student with the drafting of the laboratory notebook and the writing of reports concerning the activities carried out in the laboratory and the interpretation of the results obtained during the experiments. Ability to learn and autonomy: the student must demonstrate how to draw correct conclusions about the basic reactivity and functional groups of an organic substance through experimental observation and autonomy in choosing the most appropriate experimental techniques.

Module Organic Chemistry
Knowledge of the subjects taught in the General Chemistry course.

Module laboratory
Attendance of General and Inorganic chemistry laboratory.

Module Organic Chemistry
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. The learning skills will be favored through the integration of textbooks with material provided by the teacher.

Module laboratory
The lab is divided into a section of theoretical classroom lessons followed by practical exercises. For each experience, the student is provided with an introductory part to the various experiments and questions that allow to underline what has been learned during the experiment.
During the course of experiences, the teacher and the tutor propose to the groups and collegially a comment and a discussion on the meaning of the operations carried out. The student should also individually prepare a lab sheet.

Module Organic Chemistry
There will also be teaching support that will carry out additional exercises with students. The teacher is available to the student for any clarification or explanation of the topics covered during the course.

Module laboratory
The learning control in progress will be carried out through the daily control of the laboratory notebook with descriptions and comments on the laboratory experiences and the answers to the questions found in the experience card.

Module Organic Chemistry
The exam consists of written exam with 10 exercises regarding the whole
program and subsequent oral discussion for those who have passed the
written exam. 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 pi-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 several
steps) and reaction mechanisms (the knowledge of a reaction mechanism
allows to predict the products). Both the written and oral exam allow 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 and on the
blackboard 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 (learning skills).
Excellence can be achieved by demonstrating a strong ability to linkcompare
different topics covered during the course (making judgements).
Module laboratory
The attendance in the laboratory is compulsory and the student must fill
in a laboratory notebook to develop the ability to correctly describe a
carried-out experience and collect data. The exam takes place with an
oral exam in conjunction with the oral discussion of the theoretical
module. The student is assessed on the basis of the verification of the
acquisition by the student of a sufficient understanding of the laboratory
experiences carried out, the results of the syntheses and the answers
given to questions of 1-H-NMR spectroscopy. The final evaluation will be
given by the weighted average of the two marks.

Module Organic Chemistry
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.
Module laboratory
The first part of the course concerns the most common techniques of
separation and purification of organic compounds (filtration, liquid-liquid
extraction, crystallization, column chromatography and thin layer
chromatography. In the second part, the techniques of NMR spectroscopy will be described, with brief mention to their theoretical bases and application to characterizze the molecular structure. This will be supported by an adequate number of
exercises on the interpretation of NMR. Then specific laboratory experiences are planned in order to train the student with the techniques outlined in the theoretical lessons.
An experiment on separation and isolation of organic compounds will be
performed; simple reactions such as benzaldehyde reduction, benzyl
alcohol oxidation, esterification of cinnamic acid and epoxidation of cinnamic acid acid. Claisen condensation reaction for the synthesis of
dibenzalacetone will be carried out. All reactions will be followed using the thin film chromatography technique. Purity will be determined by TLC and
identification by 1-H-NMR.

Module Organic Chemistry
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
nonmnemonic 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.
Module laboratory
Knowledge and understanding: knowledge of the principles of
chromatography and of the laboratory techniques such as extraction,
distillation, crystallization, solubilization of organic compounds;
knowledge of NMR spectroscopy;
acquisition of an appropriate scientific language. Applying knowledge and
understanding: ability to collect data in a suitable way and to fill in a
laboratory notebook; ability to apply the theory in the execution and
understanding of the laboratory experiments and to the explanation of
the results. Making judgements: ability to work in a group and analyze
critically the results of the practical experiences, understanding possible
errors and suggesting solutions; and to learn independently how to carry
out new organic chemistry experiments. Communication skills: ability to
report on the work done (and generally on chemical-scientific topics) in a
precise, concise and clear manner, both in written and oral form.Learning
skills: ability to use the teaching material for a critical and reasoned
study, also for a subsequent autonomous acquisition of superior
knowledge and for a continuous updating