ORGANIC CHEMISTRY 1

Major objectives of this course are to enlighten the principles of Organic Chemistry, their applications in practical situations and their relevance to our lives, and in general in the world around us.

The course aims to provide students with a good training in Organic Chemistry 

The specific training objectives of the module are:

1)Knowing how to organize and assemble the laboratory glassware for the realization of a synthesis;

2)Knowing how to structurally characterize an organic molecule using one or more instrumental techniques;

3)Knowing how to interpret spectroscopic data to be able to trace the identity of an organic molecule

To acquire experience on the methodologies and techniques of organic synthesis through the preparation of some products and their structural determination. With reference to the Dublin Descriptors, this course aims to transfer the following transversal skills to the student:

Knowledge and understanding: Inductive and deductive reasoning skills;

Ability to rationalize and predict the reactivity of organic molecules; Ability to distinguish the different synthesis techniques;

Ability to distinguish the different laboratory instruments

Ability to apply knowledge:

Ability to design a synthetic path suitable for obtaining a precise organic molecule;

Ability to foresee the necessary instrumentation for the realization of the synthesis;

Ability to identify the optimal reaction conditions for a given reaction.

Autonomy of judgment: Critical reasoning skills;

Self-assessment of learning through interactions in the classroom with colleagues and with the teacher.

Communication skills: Ability to describe in oral and written form, with properties of language and terminological rigor, one of the topics covered, using both power point presentations and the blackboard

Information for students with disabilities and/or SLD

To guarantee equal opportunities and in compliance with the laws in force, interested students can request a personal interview in order to plan any compensatory measures, based on the educational objectives and specific needs.

lectures, problem solving and lab experiments

It is necessary to have already taken the exam of General and Inorganic Chemistry.

Strongly recommended although not mandatory to take the exam

1. 1. Introduction - Structure and Bonding in carbon compounds. Covalent Bonds. Single and multiple bonds. Hybridization. Polar and nonpolar molecules. Intermolecular interactions. Structure formulae and their representation Constitutional isomers. Three dimensional shape of organic compounds. Resonance. Functional groups and classification of organic compounds. Nomenclature. Molecular structure and physical properties.

   2. Introduction to organic reactions and mechanisms - Homolytic and heterolytic covalent bond cleavage. The use of curly arrows. Acids and Bases. Acid strength (Ka e pKa). Effects of structure on the strength of acids and bases. Acid-base reactions. Nucleophiles and electrophiles. Relationship between standard Gibbs energy and equilibrium constant. Rates of reactions and equilibrium constant. Energy profile diagram. Transition states and intermediates.

   3. Alkanes and Cycloalkanes – Structure and nomenclature. Sources. Physical properties. Conformational isomers. Pyrolysis. Combustion. Halogenation. Ring strain and axial/equatorial, cis/trans isomerism in cyclic compounds.

   4. Stereochemistry – Chirality. Stereoisomers: enantiomers, diastereoisomers. Asimmetric carbons and other stereogenic centres. Optical activity. Polarimeter. R-S configurations. Absolute configuration. Fischer projections. Resolution of racemic misture. The stereoisomers of tartaric acid. Chirality in Nature.

   5. Alkenes: Structure and Nomenclature. Cis-trans and (E)-(Z) nomenclature system. Reactivity. Reactions of electrophifilic addition (addition of H₂, X₂, HX, water). Markovnikov’s rule. Regioselettivity. Stereospecificity. Polymerization.

   6. Alkynes – Structure and Nomenclature. Reactivity. Addition of hydrogen, HX and water.

   7. Aromatic compounds - Structure and stability of benzene and its derivatives, aromaticity, Huckel’s rule, nomenclature of aromatic compounds. Electrophilic aromatic substitution . reactivity in substituted benzene rings, directing effect of substituents Nitration, halogenation sulfonation Friedel-Crafts alkylation and acylation. Aromatic heterocyclic (furan, thiophene, pyrrole, pyridine): structure and reactivity.

   8. Alkyl Halides - Nucleophilic Substitution. The SN₁ and SN₂ mechanisms. Stereochemistry of Nucleophilic Substitution. Elimination reactions. The E₂ and E_l mechanisms. Organochlorine pesticides (outlines).

   9. Alcohols, Phenols, ethers, thiols - Structure and nomenclature. Physical properties. Hydrogen bonding, Acidity and basicity. Review of synthesis. Reactivity (substitution reactions, oxidation, esterification). Cyclic ethers.

   10. Aldehydes and Ketons - Structure. Nomenclature. Physical properties. Review of synthesis. Reactivity: nucleophilic addition of organometallic reagents (Grignard reagents), HCN, alcohols (acetal, hemiacetal), amines (imine, enamine). Oxidation. Reduction. Acidity of a-hydrogens. Aldol condensation.

   11. Carboxylic acids and their derivatives - Structure. Nomenclature. Physical properties. Acidity. Review of synthesis. Reactivity: Nucleophilic acyl substitution. Esters. Anhydrides. Amides. Halogenures. Nitriles. Hydrolysis of esters. Saponification. Claisen condensation. Keto acids and keto esters. Hydroxyacids.

   12. Amines - Structure and basicity. Nomenclature. Physical properties. Stereochemistry. Reactivity: alkilation, amide formation, reaction with nitrous acid. Arendiazonium salts and their reactions. Diazo coupling.

   13. Carbohydrates – Structure. Nomenclature. Classification. Common names. Absolute configurations. Fischer projections. Cyclic structure and conformations of hexoses. Epimers, anomers. Mutarotation. Oxidation. Reduction. Disaccharides and polysaccharides: sucrose, maltose, lactose, cellulose, starch, glycogen. 

   14. Aminoacids and proteins – Natural and essential amino acids. Absolute configuration. Dipolar ions. Acid and basic properties. Important reactions. Peptide linkage. Hydrolysis. 1°, 2°, 3° and 4° structure of proteins.

   15. Lipids – Structure. Fats and oils. Free fatty acids. Triacyl glycerols. Terpenes. Steroids. Prostaglandins. Phospholipids and cell membrane. Wax.

   16. Nucleic acids (outlines)

1. T W Graham Solomons, Craig B Fryhle “Chimica organica”, Zanichelli

2. B. Botta “Chimica Organica, Edi-Ermes

3. W. H. Brown “Chimica Organica”, Edises

Oral exam test. The exam involves the evaluation of the knowledge acquired through questions on the reaction mechanisms learned in class.

Preparation of amines; 2 Claisen condensation; 3 Anomers; 4 Nucleophilic aromatic substitution 5 Fisher's esterification; 6 Nucleophilic substitutions; 7 Elimination of Hoffman and Cope; 8 Benzino; 9 Oxidation of aldehydes;