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. (36 hours)

The student will be provided in the classroom with specific explanations on how to set up a lab experiment in order to highlight the particular properties of a substance or a sample of interest. The aspects on which focus the attention will be the acid base properties of the substances, the inductive effect of the functional groups and conjugative. As an example of activities that will be carried out in the laboratory, the student will separate 3 substances of different acidity through thin layer chromatography (TLC). The student will be able to assess the relative acidity of the substances examined in the light del'effetto inductive and conjugative of functional groups present in them. The student will be proposed some methods for recovering the substances themselves with a view to subsequent characterizations. The student will learn how to successfully set up a lab notebook and what are the aspects of a work in the laboratory is important to keep track of them. Students will be asked to write up a series of lab reports. Upon completion of this course unit, the student will have gained the necessary experience to understand the practical implications of the concepts learned in the first unit.

Detailed timetable

To have a better view of the hours dedicated to each topic, the student can refer to the teacher's official Unibo page, section "useful contents". 

Readings/Bibliography

1. McMurray, "Chimica Organica", Zanichelli;

2. Solomons, "Chimica Organica", Zanichelli.

Teaching methods

The course is divided into two teaching units: the first, theoretical, consists of lectures accompanied by exercises of application of the concepts presented. The theoretical presentation of each topic are followed by several lessons devoted to the solution of specific problems and exercises that emphasize the applied nature of the discipline and aim to instill in them the method, ie the ability to translate chemical language in a concrete problem to determine the solution. The second module includes laboratory activities aimed at deepening from a experimental point of view some aspects of the topics covered in class.

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 site: https://almaesami.unibo.it/almaesami/welcome.htm.

Teaching tools

Documents saved on AMS campus webpage which can be found by following the suitable links in the official Unibo web page of the tacher, section called "useful contents"

Office hours

See the website of Luca Laghi