Saint-Louis University - Bruxelles
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INGE1240 - Chemistry II



Credits : 0

Lecturer :
Teaching assistant :
Mode of delivery :
Face-to-face , second term, 30 hours of theory and 15 hours of exercises.

Language of instruction :
The course is given in French. Supporting documents may however come from English or Dutch sources.

Learning outcomes :
By the end of the course, the student should:
- be able to understand organic chemistry formalism;
- be able to develop with precision and logic, simple reactions of organic chemistry with applications to polymer chemistry;
- have understood our great dependency on organic chemistry in everyday life;
- be willing to inform himself through different conflicting sources and study them with a discerning mind in order to build a personal opinion for himself concerning ethical problems that are prevalent in our society and related to chemistry;
- have understood that the development axes of chemistry are closely dependent on circumstances relating to politics (wars...) and economy (raw materials, patents...), and on the character and charisma of researchers and industrials;
- be able to discern the practical problems that researchers are faced with, through a personal experience acquired in the laboratory;
- understand that the same product may be useful or harmful depending on how it is used.

Prerequisites :
For the Bachelor : Business Engineering :


Co-requisites :
None

Course contents :
In this part of the course, we will define, describe with precision and name organic molecules considering:
- bonds between atoms;
- geometry of molecules and their conformation;
- functional groups;
- isomers.

A. Birth of synthetic organic chemistry (10%)
a) Background
We will see how a young science has radically changed our way of life. (1rst molecule synthesized in 1828).
We will show how the first factories of organic products made synthetic dyes and how these products changed many aspects of the economic life of that time. We will also study how the pharmaceutical industry stems directly from the dye industry and we will show the economic power of the industry of organic products based on the list of global chemical companies and their current economic weight.

b) Petroleum Chemistry and Introduction to biofuels
As the development of organic chemistry is related to petroleum production, we will study petroleum chemistry (history, boring and exploitation, refining) with its corollary: gasoline production and a direct application: the internal combustion engine. We will then develop the synthesis of biofuels: bioethanol and biodiesel.

Note: At the beginning of each following chapter, we will present the nomenclature and structure of the studied compounds.

B. Alkyl halides (20%)
- Synthesis of Alkyl halides
We enter straight into organic chemistry when we functionalise alkanes originating directly from petroleum, natural gas or coal. We start with functionalisation of Alkyl halides because halides may be transformed into various other functions.
- Importance of Alkyl halides
We begin with the controversy between ecologists and scientists concerning chlorinated compounds, illustrating the topic with conflicting articles. Then we will study the importance of these compounds used as such in everyday life and we will present the issues of chemical warfare, fertilisers, pesticides (DDT), herbicides, CFC's.
- Characteristics and reactions of Alkyl halides
The reactions of Alkyl halides have been the subject of in-depth studies; which is why they were chosen as standard reagents to present different aspects of synthetic organic chemistry.
This allows notably:
- to show the differences and similarities between inorganic and organic halides, between inorganic and organic reactions;
- to highlight the importance of polarity on reactivity;
- to study reactions from a thermodynamic, kinetic and stereochemical point of view;
- to see the influence of solvents;
- to introduce the concepts of optical activity and debate the importance of optically pure compounds in the pharmaceutical industry and in agro chemistry;

C. Alcohols, phenols and amines (15%)
- Alcohols and phenols
We will study the properties and reactivity of these compounds starting from the writing of the function. We will consider successively their behaviour as acids, bases, nucleophiles and substrates. This allows us to introduce the notion of hydrogen bonds and to highlight the relation between microscopic structure and macroscopic behaviour.
We will illustrate this chapter with the industrial synthesis of alcohols that can be found in the "top 50" of organic compounds produced on a large scale in the world, which allows us to highlight the vital economic importance of polymers (plastic, rubber, adhesives, resins…) of which these alcohols are precursors.

- Amines
After having studied the properties and reactivity of amines, we will illustrate this paragraph by mentioning some natural amines, amino acids, proteins and alkaloids.

D. Aromatic hydrocarbons (10%)
After a theoretical introduction to conjugation and aromaticity, we will study the characteristic reactions of the benzene ring with emphasis on its mechanisms. We will finish this chapter with the synthesis of two interesting types of compounds used in everyday life:
- Bakelite;
- azo dyes.
The students will synthesise Bakelite and one of its substitutes in the didactic laboratory as well as an azo dye, methyl-orange (titration indicator).

E. Alkenes (25%)
This class of compounds is extremely important from an industrial point of view because alkenes are precursors of polymers. After having observed the properties of a C=C double bond, we will present different access routes to this type of compounds, which enables to bring together some reactions studied previously.
While we will study the reactivity of alkenes, the focus will be put on the synthesis of polymers (PS, PE, PVC, Teflon, PP, polybutadiene, rubber...). We will also present their physical properties, their formation, their use and recycling which brings us to the issue of waste. Some other reactions that lead to fine chemicals (drugs, additives…) are then suggested. The focus will be put on the reaction mechanism. This section is illustrated by the synthesis of iso-octane. Octane is well known by motorists.

F. Carboxylic acids and some derivatives: acid chlorides, anhydrides, esters and acids (20%)
- Carboxylic acids
The synthesis of carboxylic acids involves notions acquired previously. The reactivity of these compounds is considered from two axes:
- reactivity as acids;
- reactivity as addition-elimination substrate on C=O.
Transformation of acid functions into other functions is illustrated through:
- the synthesis of PET (synthesis of esters);
- the industrial synthesis of nylon 6,6 (synthesis of amides).

- Acid chlorides, anhydrides, esters and amides
After having studied the parallelism between these functions and their method of production, we will illustrate their reactivity through the synthesis of well-known products, which are in some cases, carried out by the students in the laboratory.
- Acid chlorides: nylon 6,6 (synthesis in the didactic laboratory);
- anhydrides: aspirin, (synthesis and purification in the didactic laboratory), glycerophthalic resin;
- esters: glycerine and soaps (production of soap in the didactic laboratory);
- amides: proteins.

(1) This program is often shortened because it is adapted according to the students' responsiveness. Every year, a new interesting development in chemical news brings the focus on one or another subject of the content, or brings us to include some additional information.
(2) The time spent on each chapter is mentioned in % next to the titles.

Planned learning activities and teaching methods :
The lecture is accompanied by theoretical and practical exercise sessions that cover different aspects of organic chemistry:
- synthesis (aspirin, polymers, dye);
- purification (crystallization, distillation, decantation, chromatography);
- identification (chromatography).
Each chapter of the syllabus is completed by documents. The reading of these documents is generally not assessed. They aim to increase the students' general knowledge in the field of chemistry and to develop their inquisitive and discerning mind.
The course begins with the film “La chimie au quotidien”, which, better than words, shows the importance in life of chemistry and what it produces. The course is illustrated by slides and the students may handle many samples and molecular models, which will enable them to visualize accurately the geometry of molecules.

Assessment methods and criteria :
The students are assessed through a three-hour written examination. This examination includes:
- questions on theory;
- new exercises similar to those done in class;
- an open question requiring personal reflection. The laboratory sessions are completed by a corrected report that is handed out to the students. The students will be given personal advice relating to the correction of their exercises.

Recommended or required reading :
- AFTALION F., Histoire de la chimie, Paris, Masson, 1988
- ARNAUD, Chimie organique générale, Paris, Masson, 1981
- ARNAUD, C. ,Chimie organique 3e édition, Mémo-guides, Paris, Masson, 1995
- CAILLET D., DEVALANCE J-P., ETCHEBERRIGARAY F., ETCHEBERRIGARAY J. TermS, Faire le point, Paris, Hachette Education, 1998
- COLONNA P., La Chimie Verte, Londres Paris New York, Editions TEC & DOC Lavoisier 2006
- CRAM et HAMMOND, Chimie organique, Québec, Les Presses de l'Université Laval, 1963
- DURUPTY A., DURUPTY O., GIACINO M., JAUBERT A., Chimie Term S, Collection Durupty, Paris, Hachette Education, 1999
- GREEN M. M., WITTCOFF H. A. , Organic Chemistry Principles and Industrial Practice, Weinheim, Willey-VCH, 2003
- HART et CONIA, Introduction à la chimie organique, Paris, Inter Editions, 1987
- JOHNSON A. W. Invitation à la Chimie Organique, Paris, Bruxelles, De Boek Université, 2003
- MARTEL B, Aide-mémoire de chimie organique industrielle, Paris, Dunod, 1996
- McMURRY J., Chimie organique. Les grands principes, Paris, Dunod, 2000
- ROBERTS J. D. et CASERIO M. C., Basic Principles of Organic Chemistry, New-York, W. A. Benjamin, Inc. 1964.
- SCOTT G., Polymers and the environment, Cambridge, The Royal Society of Chemistry, 1999
- TOON E. R., ELLIS G. L., DOYLE L., IVANCO J., PERCIVAL S., Foundations of Chemistry, Toronto, Holt, Rinehart and Wiston of Canada, 1989
- VOLLHARDT K. P. C., SCHORE N. E., Traité de chimie organique, Paris, Bruxelles, De Boek Université, 1999
- WEISSERMEL K., ARPE H.-J. Industrial Organic Chemistry "Important Raw Materials and Intermediates",Weinheim, New York, Verlag Chemie, 1978.

Other information :
Supports: Film “la chimie au quotidien”, blackboard + chalk, slides, molecular models, samples.