ORGANIC CHEMISTRY M - Z
Academic Year 2023/2024 - Teacher: COSIMO GIANLUCA FORTUNAExpected Learning Outcomes
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.
Course Structure
lectures, problem solving and lab experiments
Required Prerequisites
It is necessary to have already taken the exam of General and Inorganic Chemistry.
Attendance of Lessons
Strongly recommended although not mandatory to take the exam
Detailed Course Content
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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 El 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)
Textbook Information
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
Course Planning
Subjects | Text References | |
---|---|---|
1 | Il legame chimico nei composti del carbonio. Formule. Isomeria di struttura. Orbitali ibridi. | Capitoli introduttivi dei testi consigliati |
2 | Alcani: nomenclatura, sintesi e reazioni | Alcani |
3 | Stereochimica: enantiomeri e diastereomeri; nomenclatura R,S. Attività ottica | Stereochimica |
4 | Reazioni di sostituzione nucleofila: SN2 e SN1. Meccanismo, stereochimica, confronto. | Alogenuri Alchilici |
5 | Reazioni di sostituzione nucleofila: E2 e E1. Meccanismo, stereochimica, confronto tra SN2 ed E2 ed SN1 ed E1 | alogenuri Alchilici |
6 | Alcheni: Nomenclatura, sintesi e reazioni. Addizione elettrofile: Acidi alogenidrici, acqua, alogeni. Regola di Markovnikov. Ozonolisi. Ossidazione e riduzione | Alcheni |
7 | Alchini: Nomenclatura, sintesi e reazioni | Alchini |
8 | Dieni: classificazioni. Sintesi e reazioni di addizione 1,2 e 1,4. Controllo cinetico e termodinamico. Diels-Alder | Sistemi coniugati |
9 | Benzene: Aromaticità e risonanza. Reazioni di sostituzione elettrofila aromatica | Benzene |
10 | Meccanismo di Sostituzione nucleofila aromatica; Sistemi eterociclici (cenni); Benzeni sostituiti | Benzene |
11 | Alcooli e fenoli: Nomenclatura, concetto di ossidazione e riduzione*. Reazioni di preparazione. Reazioni con PBr3, SOCl2 | Alcooli |
12 | . Eteri ed Epossidi: Nomenclatura, preparazioni e reazioni con acqua e acidi alogenidrici | Eteri |
13 | Aldeidi e Chetoni: Nomenclatura; Sintesi; Reazioni di addizione nucleofila. Addizione di acido cianidrico, di acqua, di alcooli, dei reattivi di Grignard. Wittig | Composti carbonilici |
14 | Acidi carbossilici e derivati. Nomenclatura; Sintesi e reazioni di sostituzione nucleofila acilica. Esterificazione di Fisher. Saponificazione | Acidi carbossilici e derivati |
15 | Ioni enolato. Reazioni: Condensazione aldolica, condensazione di Claisen, Cannizzaro, sinetsi aceto-acetica, sintesi malonica | Enoli ed Enolati |
16 | Ammine: Nomenclatura, sintesi e reaioni. Sali di diazonio. Eliminazione di Hoffman e Cope | Ammine |
17 | . Carboidrati: classificazione, strutture furanosiche e piranosiche, anomeri, reazioni di ossidazioni | Carboidrati |
18 | . Amminoacidi e proteine: classificazione, legame peptidico, sintesi degli amminoacidi, struttura primaria delle proteine e determinazione, sintesi in fase solida | Amminoacidi e proteine |
19 | Lipidi | Lipidi |
Learning Assessment
Learning Assessment Procedures
Oral exam test. The exam involves the evaluation of the knowledge acquired through questions on the reaction mechanisms learned in class.
Examples of frequently asked questions and / or exercises
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;