ORGANIC CHEMISTRY 3

Aim of the course is to acquire the knowledge of the key concepts of the organic chemistry. In particular, the course is aimed:

- to introduce the fundamental knowledge for the study of the basic organic molecules in relation to its structure, reactivity, properties;

- to know the main classes of organic molecules;

- to the view of simple organic molecules in three dimensions with an emphasis to their stereochemical properties.

Furthermore, in reference to the so-called Dublin Descriptors, this course helps to acquire the following skills:

D1 - Knowledge and understanding: The students will have to demonstrate their mastery of basic knowledge about the organic chemistry. In particular, the students must show their ability to rationalize property-structure correlations of organic molecules

D2 - Ability to apply knowledge: The students will have to show knowledge and understanding of organic reactions required to produce synthetic processes of relatively complex molecules.

D3 - Autonomy of judgment: The students will have to apply their knowledge, understanding and skills. Particularly, the students must show his ability to critical reasoning and their ability to identify the most appropriate chemical reactions aimed to the synthesis of organic molecules.

D4 - Communication skills: The students must be able to communicate clearly with a correct property of language and terminological rigor their conclusions.

D5- Learning skills: The students will have to develop learning skills that will enable them to continue studying in a self-directed or autonomous way.

Classroom Lectures (56 hours – 8 CFU) and Exercises (12 hours – 1 CFU)

The students should have basic knowledge of General Chemistry (mandatory), Physics and, Mathematics

Attendance to the course is mandatory (at least 60% of the total number of hours of the course)

1. Introduction to Organic Chemistry - The chemical bond in carbon compounds. Hybrid orbitals. Models of the covalent bond. Single and multiple bonds. Polarity of bonds. Polar and non-polar molecules. Intermolecular interactions. Structural formulas. Three-dimensionality of molecules. Representation of structural formulas. Constitutional isomerism. Resonance. Classification and nomenclature of organic compounds based on structure and functional groups. Physical properties and molecular structure.

2. Introduction to organic reactions and mechanisms - Homolysis and heterolysis of covalent bonds. Use of curved arrows. Acids and bases. Strength of acids and bases (Ka and pKa). Structure-acidity relationship. Course of acid-base reactions. Nucleophiles and electrophiles. Free energy variations. Equilibria and reaction rates. Potential energy diagrams: transition states and reaction intermediates.

3. Alkanes and Cycloalkanes - Structure. Nomenclature. Sources. Physical properties. Conformational isomerism. Pyrolysis. Combustion. Halogenation. Ring tension and geometric isomerism of cycloalkanes.

4. Stereoisomerism - Chirality. Enantiomerism. Asymmetric carbon and other stereocenters. Optical activity. Polarimeter. Absolute configuration. The R-S convention. Fischer projections. Diastereoisomerism. Resolution of racemic mixtures. The stereoisomers of tartaric acid. Biological importance of chirality.

5. Alkenes - Structure. Nomenclature. Cis-trans and E-Z isomerism. Reaction mechanisms. Electrophilic addition reactions: hydrogenation; halogenation; hydrohalogenation; hydration and Markovnikov's rule. Regioselectivity. Stereospecificity. Polymerization.

6. Alkynes - Structure. Nomenclature. Chemical properties. Addition reactions: addition of hydrogen, halogen acids and water.

7. Alkyl halides - Nucleophilic substitutions. SN1 and SN2 mechanisms. Stereochemistry of nucleophilic substitutions. Effects of substrate, nucleophile and solvent structure. Elimination reactions. E2 and E1 mechanisms. Organic chloro-pesticides (notes).

8. Alcohols, phenols, ethers and sulfur compounds - Nomenclature. Hydrogen bond. Acidity and basicity. Preparation methods. Reactions. Thiols. Sulfides. Cyclic ethers.

9. Aromatic compounds - Benzene and derivatives - Structure. Nomenclature and properties of benzene and its derivatives. Resonance energy. Huckel's rule. Electrophilic substitution reactions: halogenation; nitration; sulfonation; Friedel-Crafts alkylation and acylation. Activating and deactivating substituents. Effect on reactivity and orientation. Aromatic heterocyclic compounds (furan, thiophene, pyrrole, pyridine): structures and reactivity.

10. Aldehydes and Ketones - Structure. Nomenclature. Methods of preparation. Nucleophilic addition reactions: addition of Grignard reagents, HCN, alcohols; formation of hemiacetals and acetals; addition of ammonia derivatives; formation of Schiff bases. Oxidation. Reduction. Acidity of hydrogens in the a position. Aldol condensation.

11. Carboxylic acids and derivatives - Structure. Nomenclature. Acidity constants. Methods of preparation. Nucleophilic acyl substitution reactions. Esters. Acid hydrolysis. Saponification. Acid halides. Anhydrides. Amides. Nitriles. Claisen condensation. Hydroxy acids and keto acids.

12.Reactions of the α-carbon to the C=O group. Enolate anions. Halogenation and polyhalogenation. Haloform reaction. Alkylation. Aldol condensation. Claisen and Dieckmann condensations. Decarboxylation of β-ketoacids, acetoacetic synthesis, malonic synthesis.

13. Amines - Structure. Nomenclature. Physical properties. Basicity. Methods of preparation. Reactions. Reactions of amines with nitrous acid. Reactions of diazonium salts. Diazocopulation.

14. Carbohydrates - Structure. Classification. Aldose and ketose series. Chirality. Optical activity. Fischer projections. Cyclic structures. Mutarotation. Oxidation and reduction reactions. Structures of the main disaccharides and polysaccharides: Sucrose. Maltose. Cellobiose. Lactose. Cellulose. Starch. Glycogen.

15. Amino acids and proteins - Natural and essential amino acids. Functions: acidic and basic properties; reactions of amino acids. Peptide bond. Primary, secondary, tertiary and quaternary structure of proteins.

16. Lipids - Fats and oils. Fatty acids and triacylglycerols. Terpenes and terpenoids. Steroids. Prostaglandins. Phospholipids and cell membranes. Waxes.

17. Nucleic acids (notes) 

1) William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric Anslyn -  Organic Chemistry - Cengage Learning

Textbook for exercises:

2) Thomas N. Sorrell - Solutions to Exercises, Organic Chemistry - Univ Science Books

The final exam consists of a written test containing problems that are proposed to the solution of the students (duration: 2 hours). The test must be passed with a mark equal or higher than 18/30. The written test will be followed by an oral test for the definition of the final mark. The oral examination focuses on the discussion of the written test and on other parts of the program that were not covered by the written test. The exam is aimed at verifying the knowledge and skills acquired by the student, his ability to connect the various topics covered during the lessons, and his ability to use appropriate language.

The final evaluation grade is in the 30/30 range.

Evaluation scale:

Unsuitable

Knowledge and understanding of the topic: Important deficiencies

Analysis and synthesis skills: irrelevant, too general

Scientific Language properties: completely inappropriate

18-20

Knowledge and understanding of the topic: basic and with many limitations

Analysis and synthesis skills: just sufficient

Scientific Language properties: just appropriate

21-23

Knowledge and understanding of the topic: slightly more than sufficient knowledge

Analysis and synthesis skills: fair analysis and synthesis skills; student argues logically but basic.

Scientific Language properties: basic

24-26

Knowledge and understanding of the topic: good knowledge

Analysis and synthesis skills: the student has good analysis and synthesis skills; the arguments are presented coherently

Scientific Language properties: The student uses the correct scientific language

27-29

Knowledge and understanding of the topic: more than good knowledge

Analysis and synthesis skills: The student has a notable analysis and synthesis skills

Scientific Language properties: The student has studied the topics in-depth and uses the scientific language properly

30-30 cum laude

Knowledge and understanding of the topic: excellent knowledge

Analysis and synthesis skills: The student has notable analysis and synthesis skills.

Scientific Language properties: The student has studied the topics in-depth, and shows a noticeable problem-solving capacity using the scientific language properly.