Organic Chemistry I
1° Year of course - Second semester
Frequency Not mandatory
- 8 CFU
- 64 hours
- Italian
- Trieste
- Obbligatoria
- Standard teaching
- Oral Exam
- SSD CHIM/06
- Core subjects
D1. Knowledge and understanding.
Acquire fundamental concepts on structure and bonding in carbon compounds, on the mechanisms of organic reactions, on the reactivity of functional groups, on the synthesis of main classes of organic compounds, on stereochemical properties of organic molecules.
D2.Applying knowledge and understanding.
Predict the reactivity of organic molecules from the presence of functional groups. Propose a synthetic approach for simple (mono functional) organic compounds. Describe the stereochemical properties of organic molecules, in particular chirality.
D3. Making judgements. At the end of the course the student will be able to to critically analyze the relationships between structure and reactivity of simple organic molecules and, more in general, to assess the acquired knowledge in the broad framework of chemical knowledge and as a preparation to more advanced courses.
D4. Communication skills.
Describe the basic principles of organic chemistry using a tecnically correct language.
D5. Learning skills. At the end of the course the student will have acquired the fundamental principles of organic chemistry and the conceptual bases necessary for the learning of advanced organic chemistry and other subjects such as, for example, biological chemistry and pharmaceutical chemistry.
Good knowledge of general chemistry. A pass in the course "General Chemistry"
Structure and bonding of monofunctional organic molecules. Classes of organic compounds: nomenclature, physical properties, reactivity of functional groups, methods of synthesis. Chirality and
stereochemical properties of organic molecules.
"Organic Chemistry" Janice Gorzynsky Smith, Ed. McGraw-Hill
"Organic Chemistry" 8th ed. John McMurry. Brooks/Cole
"Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica" 2a edizione. M.V. D'Auria, O. Taglialatela Scafati, A. Zampella. Ed. Loghia.
Materials in the Moodle site of the course
1. Introduction. The carbon atom, Lewis structures, hybridization, single and multiple bonds. Geometry of simple molecules. Covalent bonds and electronegativity. Delocalization and resonance. Acids and bases. Reaction mechanisms. Carbocations, carbanions, radicals. Transition states and energy diagrams. Functional groups. Main classes of organic compounds. Physical Properties.
2. Alkanes. Structural isomers. Conformational isomers. Cycloalkanes and strain energy. Radical Substitution. Combustion and heats of combustion
3. Stereochemistry. Simmetry and chirality. Enantiomers and Diastereoisomers. C.I.P. Rules. Optical Activity. Diastereoisomers. Meso compounds.
4. Alkenes. Geometrical isomers. Synthesis via elimination reactions and hydrogenation of alkynes. Electrophilic addition. Markovnikov's Rule. Oxidation. Radical addition. Polymerization via polyaddition.
5. Alkynes. Synthesis via 1,2-eliminations. Electrophilic additions. Acidity of terminal alkynes and reactions of acetylides.
6. Conjugated Dienes. Delocalization and resonance. Conformation. Conjugate addition: kinetic and thermodynamic control. Diels -Alder Cycloadditions.
7. Benzene and aromatics. Resonance and aromaticity. Huckel rule. Polycyclic and heterocyclic compounds. Substituted benzenes. Substituents electronic effects and introduction to electrophilic aromatic substitution. Reactivity at the side chains of substituted benzenes.
8. Alkyl halides. Structure and properties. Synthesis from alkanes, alkenes and alcohols. Nucleophilic substitution. SN1 and SN2 mechanisms. Eliminations: E1 and E2 Mechanisms. Zaitsev’s rule. Organometallic Compounds.
9. Alcohols, Ethers, Epoxides. Synthesis of alcohols from alkenes, alkyl halides and carbonyl compounds. Conversion of alcohols to halides, alkenes and carbonyl compounds. Carbocations rearrangements. Acidity of alcohols and phenols. Williamson synthesis of ethers and addition of alcohols to alkenes. Substitution and elimination reactions. Synthesis, Structure and Reactivity of Epoxides. Thiols and sulfides.
10. Aldehydes and ketones. Structure and reactivity of carbonyl compounds, Keto-enol tautomerism. Synthesis from alcohols, carboxylic acids and alkenes. Nucleophilic addition to the carbonyl: cyanohydrins, acetals, imines and enamines. Wittig Reaction. Oxidation. alpha, beta-unsaturated carbonyl compounds.
11. Carboxylic acids and derivatives. Acidity and substituent effect. Synthesis from alcohols, aldehydes, alkyl halides. Conversion to amides, esters, anhydrides, acyl Chlorides. Nucleophilic acyl substitution. Functional group interconversion. Structure, synthesis and reactivity of nitriles.
Lessons and tutorials in the classroom. self-evaluation tests in the Moodle page of the course
Electronic support materials (slides of the lessons, software for the bi- and tri-dimensional representation of organic molecules, interactive exercises and self-evaluation tests) are available on Moodle (https://moodle2.units.it)
The examination comprises a written and an oral test. Students who pass the written test are admitted to the oral examination. Passing the written test is considered valid for the entire academic year. Two partial tests (intermediate/final) are offered during the course, to which only students who have passed the General Chemistry propaedeutic exam are admitted. Only students who have passed the first test are admitted to the second test. Students who pass both are admitted directly to the oral examination. The exercises in the written tests are of the same difficulty as those proposed in the classroom exercises.
The oral examination is conducted with open-ended questions and is aimed at ascertaining the student's knowledge of the topics covered during the course, his or her ability to connect different topics, expository ability and correctness of language.
Grades are in 30/30 with the pass threshold set at 18/30.
This course explores topics closely related to one or more goals of the United Nations 2030 Agenda for Sustainable Development (SDGs)