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Lecturers :

Renaud Nicolaÿ
  
Arthur Duprat
  

Teaching staff :
Véronique Bellosta
Domingo Gomez-pardo

Research center

Level : 1st year

Course Language : French

Term : core curriculum

Number of hours : 103

ECTS Credits : 7
CHO Organic chemistry
Teaching site :
Lectures: 22 h - Tutorials: 6 h - Preceptorship: 9 h - Laboratory sessions: 66 h

Objectives

The objective of the Organic Chemistry course is to provide all the students with the essential bases in this discipline. Once well assimilated, these bases will provide them with essential conceptual tools irrespective of their future specialisations (chemical or biological and even physical). The students should be capable of writing mechanisms for all the reactions studied.

Syllabus


  1. Background

    • Hybridization
    • Acidity and basicity in Organic Chemistry
    • Kinetic and thermodynamic control of reactions
    • Pearson theory

  2. Chirality and synthesis

    • Fischer projection
    • Relative configurations specifically applied to amino acids and sugars. D/L convention
    • Principle of enantioselective and diastereoselective reactions

  3. Aromatic compounds and their reactivity

    • Aromatic electrophilic substitution
    • Aromatic nucleophilic substitution
    • Coupling reactions
    • Reactivity of substituted benzenes
    • Reactivity of some aromatic heterocycles

  4. Study of functional groups

    • Aldehydes and ketones
    • Enols, enolates and enones
    • Carboxylic acids and their derivatives
    • Alkenes and alkynes

Preceptorships


  • Reviews of preparatory classes, nomenclature
  • Electronic effects, acids and bases, protective groups
  • Aldehydes and ketones, synthesis and reactivity
  • Diastereoselective additions on aldehydes and ketones
  • Enols, enolates and enones
  • Carboxylic acids and acid derivatives
  • Activation of carboxylic acids for preparation of esters and amides
  • Synthesis of a natural or of pharmaceutical interest product

Laboratory sessions


The objectives of this four and half week laboratory session are to teach (i) good laboratory practices (GLP) to get satisfactory yields in synthesized products and (ii) the necessary techniques to implement a reaction, follow its conversion with analytical tools, and check the structures of the obtained compounds. The students get also used to literature searches in computerized databases (Reaxys, Scifinder), simulation softwares to predict 1H and 13C NMR spectra (Chemdraw), and online consultation of scientific papers (Scifinder). The emphasis is in particular placed on learning how to be autonomous, follow the GLP in accordance with lab security rules, and write a laboratory notebook like a scientist. Finally students become aware of a more environmentally friendly chemistry (eco-compatible or green chemistry).
Twelve different experiments are conducted during the lab period in which new laboratory techniques like fractional distillation under vacuum, inert atmosphere handling, chromatographic column separation, multi-step synthesis or enzymatic/microwave synthesis become familiar to students. Each session starts with a brief presentation of the experiment of the day by a pair of students: the whole group (around 30 students) has the opportunity to discuss the mechanism of the reaction, to analyze the experimental conditions and to talk of the potential risks of the chemicals used. Classical analytical methods of synthetized compounds (melting and boiling points, optical rotation measurements and thin layer chromatography) are completed with spectroscopic analysis methods like 1H and 13C NMR, IR, GC-mass and supercritical chromatography (on chiral column, enantiomeric purity determination). During the last week, students use their deductive skills and their knowledge in organic chemistry to identify the structure of an unknown compound that is given to them with the matching spectra (1H, 13C, 1D et 2D NMR, mass and IR). It is also a good illustration for the 'Structure determination of organic compounds' module.

Here is a short list of some experiments done in the lab:

  • Knoevenagel reaction (with a Dean-Stark apparatus)
  • Biomimetic cyclization of citronellal (under argon)
  • Enantioselective reduction with baker's yeast
  • Multicomponent synthesis of an imidazole with microwave activation


Requirements : Chemistry level of preparatory classes or equivalent

Evaluation mechanism : Written exam with course questions and problems

Last Modification : Saturday 8 December 2018

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