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

Useful notions of mathematics. Unit of measure commonly used. Such knowledge and skills are provided by the courses of Mathematics and Statistics (Mathematics with Elements of Statistics for students of VE). Matter and its main properties. Atoms and molecules. Size of atoms and molecules. Definition of atomic mass units. Atomic and molecular weights. Avogadro's number, mole concept. Nomenclature of inorganic compounds. Such knowledge and skills are provided by the courses of General Chemistry and Stoichiometry and Chemical Process.

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).

Upon completion of this course unit, students acquire the basic theoretical knowledge about the structure of matter and the thermodynamic and kinetic principles that govern its transformation. The student will also be able to predict, from the structure, properties and reactivity of the organic molecules. The student will finally be able to set up a chemical reaction from the theoretical point of view to the formation of some organic compounds of interest in the food field.

Contents of the laboratory didactic unit. (24 hours)

Laboratory (practical activities) - 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 what 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.

Laboratory (data processing) - 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 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 in the world of data processing, univariate and multivariate, in the open source R.

In-depth lesson - Students who follow organic chemistry lessons are typically uneven in terms of basic knowledge and aptitude for the study of scientific-technological disciplines. A few hours of lessons in the second teaching unit have been expressly designed to help those who have encountered more difficulties in following the lessons of the first teaching unit. These hours, in fact, will be dedicated to students' requests for clarification on the topics covered in the first teaching unit. The requests may concern mere repetitions of the foregoing, exercises aimed at better understanding the proposed topics or in-depth analysis on any aspect of organic chemistry or 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.

Detailed timetable

To have a better view of the hours dedicated to each topic, the student can refer to the teacher's official IOL page. 

Readings/Bibliography

1. McMurray, "Fondamenti di chimica organica", Zanichelli;

2. Solomons, "Fondamenti di chimica organica", Zanichelli.

3. Wade, "Fondamenti di chimica organica", Piccin.

Teaching methods

The course is divided into two teaching units:
The first, theoretical, consists of frontal lessons accompanied by exercises for the application of the notions presented.
The second teaching unit includes laboratory activities aimed at deepening from an experimental point of view some aspects of the topics covered in class. The laboratory activities therefore aim to make students acquire the typical method of learning organic chemistry, that is, the ability to translate a concrete problem into chemical language to determine its solution.
Some hours of lessons in the second teaching unit will be dedicated to requests for clarification by students on the topics covered in the first teaching unit. Requests may concern mere repetitions of the foregoing, exercises aimed at better understanding the proposed topics or in-depth analysis of 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.

Assessment methods

During the oral examination the student will address the topics covered in the lesson (available in the texts recommended for the study and in the teaching material presented) and will be evaluated on the basis of the following criteria: (i) knowledge, understanding and deepening of the topics covered; (ii) critical and exhibition capacity; (iii) correctness of technical-scientific language. The oral exam will have a maximum score of 30 points, possibly with honors. Training gaps and / or inappropriate language - albeit in a context of minimal knowledge of the exam material - will lead to an insufficient grade.

The examinations are proposed within the specific windows defined within the course of study and students can book for the oral exam exclusively using the methods provided by the online system Alma Esami. For any information on how to book, connect to the "almaesami" webpage.

Additional details valid until exhaustion of emergency COVID-19

The exam will be held orally through the teams platform. A basic system with audio and video will be required from the student so I can i) hear the voice of the student, ii) see the student, iii) see the sheet on which the studenti is writing the chemical formulas and reaction mechanisms, iv) briefly see what surrounds the student.

I will only question students enrolled in the exam on the AlmaEsami platform. A few days before the exam date, I will draw up a query order and communicate the approximate time of the exam through the email system in AlmaEsami. I take into account that many last-minute details will delay or accelerate my questioning rhythm. That's why I will also create a small website (of which I will give you the address) with which I will allow everyone to be updated in real time on the actual exam timetable. To interrogate a student, I will phone him via the teams platform. If it is not available or there are technical problems, I will call someone else and recover without problems when possible.

Teaching tools

Texts and other resources saved on IOL

Office hours

See the website of Luca Laghi