18167 - Organic Chemistry Principles

Learning outcomes

At the end of the course the student acquires basic knowledge of the structure of matter and of the thermodynamic and kinetic principles that govern its transformation, as well as the fundamental skills for understanding the relationships between structure, properties and reactivity of organic molecules, with particular reference to the molecules of interest in the food. At the end of the course student is able to understand, at the molecular level, the chemical reactions that occur in the biosphere, as well as to predict the behavior of a molecule as a function of its structure.

Course contents

Prerequisites

What is taught in the General and Inorganic Chemistry course and in the preparatory courses.

Contents of the theoretical didactic unit. (36 hours)

1. Elements of general chemistry (electronic model of the atom, molecular orbital theory, hybridization); Alkanes: Nomenclature of linear alkanes, branched and cyclic). Alkenes and Alkynes: Nomenclature.

2. Stereochemistry. Definition and geometric considerations on isomers, divided into structural isomers and stereoisomers, the former divided into enantiomers and diastereoisomers. Nomenclature of chiral centers R-S. Cis-trans nomenclature. Chemical, physical, and interaction with polarized light of enantiomers and diastereoisomers. Meso compounds and racemic mixtures. The student must be able to determine the chirality of a chiral carbon of a molecule wrote according to Fisher rules.

3. Correlation between characteristics of organic molecules and their melting points and boiling. Elements of thermodynamics. Correlation between the characteristics of a molecule and its stability: the case of cyclic molecules.

4. IUPAC systematic nomenclature of alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, amines, thiols and thioethers. Carbonyl and carboxyl group. Correlation between the structure of a molecule and acid-base properties. The student must be aware of the role it plays the hybridization of the carbons of these substances on their acidity. The student must be aware of which substance gives rise to carbocations, carbanions and more stable and must be able to provide an interpretation of this experimental data.

5. Benzene and Aromaticity: description of the phenomenon of aromaticity - benzene derivatives - resonance in benzene derivatives - conjugative and inductive effects of the substituent groups - effect of the substituent on the acid-base properties of some aromatic molecules. Exercises about acidity or alkalinity of substances: conjugative and inductive effect exerted by the phenyl group and substituents that may be present on it.

6. Groups containing C = O: nomenclature and properties of carboxylic acids, aldehydes, ketones, carboxylic acids and esters, soaps and detergents, fats and oils. The student must know what are the structures which represent the limits of resonance to understand the reactivity of this functional group. Description of the addition reaction to the carbonyl carbon by a nucleophile.

7. Chemical reactions. Nucleophilic addition to the carbonyl carbon. Nucleophilic substitution at the carboxyl carbon. Acid and basic hydrolysis (saponification) of esters. Electrophilic addition to carbon unsaturated acid halide. Electrophilic substitution of the benzene ring. Bromination. Nitration. Sulfonation. Alkylation. Replacing the substituted ring. Activating, deactivating, ortho and meta-para orienting. Nucleophilic substitution at saturated carbon (sn1 sn2).

Contents of the laboratory and in-depth didactic unit (18 hours)

Laboratory - The student will be given explanations in the classroom on how it is useful to set up an experiment in the laboratory to highlight particular properties of a substance or sample of interest. The aspects on which attention will be focused will be the acid base properties of the substances, the inductive and conjugative effect of the functional groups. As an example of an activity that will be carried out in the laboratory, the student will use their smartphone as a spectrophotometer, to identify the dilution percentage of a colored liquid for food use. The student will be explained how to correctly set up a laboratory notebook and which are the aspects of a laboratory work that it is important to keep track of. The student will be asked to write laboratory reports. At the end of this didactic unit the student will have increased his / her ability to grasp the practical implications of the concepts learned in the first didactic unit.

Deepening - The students who follow the organic chemistry lessons are typically inhomogeneous for basic knowledge and aptitude for the study of scientific-technological disciplines. Some lesson hours of the second didactic unit have been expressly designed to help those who have found it more difficult to follow the lessons of the first didactic unit. These hours, in fact, will be dedicated to the students' requests for clarification on the topics covered in the first teaching unit. Requests may concern mere repetitions of what has already been explained, exercises aimed at a better understanding of the proposed topics or in-depth studies on any aspect of organic chemistry or of effective subjects of interest to students. The content of these lessons will therefore not be determined in any way by the teacher, but will be decided independently by the students.

Contents of the didactic data processing unit (6 hours)

The student will be helped to take the first steps in the way of collecting and processing (mathematics and graphics) of experimental data. As a pretext, the student will be described some of the indispensable tools for metabolomics. This is the systematic study of small-sized organic molecules, which represent the chemical footprints left by cellular processes. In the first part, the principles underlying proton nuclear magnetic resonance (1H-NMR) will be described, one of the analytical platforms that can be used for this purpose. In a second part it will be shown how to quantify organic molecules from 1H-NMR spectra. In a third, predominant part, students will be helped to take their first steps into the world of data processing, univariate and multivariate, in the open source R.

Readings/Bibliography

I strongly recommend that you equip yourself with Wade, "Fundamentals of organic chemistry", Piccin and to consider it the reference point as teaching material, to be read in its entirety, in the chapters covered in class, and to be consulted assiduously, together with your own (and not someone else's) notes taken in class.

The reason is that "Fundamentals of Organic Chemistry" textbooks are typically equivalent in terms of subject matter and level of coverage. However, some authors seem more sensitive to the difficulties of students in many science courses, and have adapted their texts accordingly.

Other very valid books, although set in a more classical way, are the following:

Solomons, "Fundamentals of organic chemistry", Zanichelli.

McMurray, "Fundamentals of organic chemistry", Zanichelli.

Teaching methods

The course is divided into three teaching units:

The first, theoretical, consists of frontal lessons accompanied by exercises to apply the concepts presented.

The second teaching unit includes laboratory activities aimed at deepening some aspects of the topics covered in class from an experimental point of view. The laboratory activities therefore aim at making students acquire the typical learning method of organic chemistry, i.e. the ability to translate a concrete problem into chemical language in order to determine its solution.

Some lesson hours of the second teaching unit will be dedicated to requests for clarification from students on the topics covered in the first teaching unit. Requests may concern mere repetitions of what has already been explained, exercises aimed at a better understanding of the topics proposed or in-depth studies on any aspect of organic chemistry or related subjects of interest to students. The content of these lessons will therefore not be determined in any way by the teacher, but will be decided independently by the students.

The third didactic unit will aim to describe, with the active involvement of students, IT tools useful for laboratory data processing at a professional level. The teacher will show what is necessary in the computer room, where the students will find dedicated freeware software pre-installed onto their computers.

Assessment methods

Durante la prova orale lo studente affronterà gli argomenti trattati a lezione, tutti disponibili nei testi consigliati, e anche le nozioni di Chimica Generale imprescindibili per la conoscenza della Chimica Organica. Lo studente sarà valutato sulla base dei seguenti criteri: (i) conoscenza, comprensione e approfondimento degli argomenti trattati; (ii) capacità critica ed espositiva; (iii) correttezza di linguaggio tecnico-scientifica. La prova orale potrà avere un punteggio massimo di 30 punti, eventualmente con lode. Lacune formative e/o linguaggio inappropriato – seppur in un contesto di conoscenze minimali del materiale d'esame - condurranno a un voto insufficiente.

Gli appelli vengono proposti nell’ambito delle apposite finestre definite nell’ambito del Corso di studi e gli studenti possono prenotarsi per la prova orale di esame esclusivamente utilizzando le modalità previste dal sistema online Alma Esami. Per eventuali informazioni sulle modalità di prenotazione, collegarsi all'applicativo "almaesami".

Teaching tools

The teacher does not use slides to support oral explanations, but writes on paper, which he shows to the entire classroom via video camera. This modality, which has received wide acclaim in the evaluation of teaching, favors learning by imitation, which in organic chemistry is at least as important as the notional one.

For further support, the teacher uses the textbook directly, so that he passes even better the concept that studying on it is fundamental. In fact, the teacher has chosen it carefully so that it fits in remarkably with the proposed course and addresses the issues as he deems necessary.

Office hours

See the website of Luca Laghi