Organic Chemistry
A.Y. 2020/2021
Learning objectives
Aims of the course is to present all classes of organic compounds , describing their chemico-physical characteristics, the reactivity as well as some preparation method. Knowledge of carbohydrates, amino acids, and nucleotides will be increased.Particular attention is dedicated to stereochemistry, with the recognition of chiral molecules and assessments of their reactivity.
Expected learning outcomes
The main purpose of the course is to enable the student to recognize the class of belonging of every organic molecule and thus to predict its reactivity in the biological field as well. In addition, the course provides the minimum cognitive tools for predicting or explaining supramolecular interactions among organic molecules.
Lesson period: Second semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course cannot be attended as a single course. Please check our list of single courses to find the ones available for enrolment.
Course syllabus and organization
Single session
Lesson period
Second semester
Lectures and other face-to-face teaching activities will be delivered in blended mode, partly in person and partly online, preferably in synchronous mode with only specific contributes in asynchronous mode. Specifically, the "in presence" lessons will be planned from Wednesday to Friday, while during the remaining days of the week will be planned online lessons. In line with the Covid safety protocol approved by our University, the "in presence" lessons will be possible by rotation with seat reservations made by using the available app easy lesson.
All lectures will be recorded and made available to the students on dedicated platform (e.g. Ariel, TEAMS, etc.).
In case of new suspension of "in presence" lessons, all the face-to-face teaching activities students will be switched to synchronous distance learning. Each hour of the lesson will include 45min of formal teaching followed by 15min of discussion / interaction / question time.
Any notice regarding updates or changes of Covid-19 rules will be communicated by the Didactic Secretary
All lectures will be recorded and made available to the students on dedicated platform (e.g. Ariel, TEAMS, etc.).
In case of new suspension of "in presence" lessons, all the face-to-face teaching activities students will be switched to synchronous distance learning. Each hour of the lesson will include 45min of formal teaching followed by 15min of discussion / interaction / question time.
Any notice regarding updates or changes of Covid-19 rules will be communicated by the Didactic Secretary
Course syllabus
Introduction: Orbital hybridization, bond polarity, resonance forms, IUPAC nomenclature of the main classes of organic compounds.
Acid-Base reactions: chemical equilibrium, molecular structure and pH
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z. Nomenclature Cycloalkanes. Hydrocarbons from natural sources.
Stereochemistry: Symmetry and chirality. Stereogenic centers. Configuration at tetrahedral atoms.Cahn/Ingold and Prelog rules. Configuration at double bonds. Chirality and optical activity. Absolute configuration. Conformational isomers.
Nucleophilic substitution: SN2 and SN1reactions. Stability of carbocations. Reaction mechanisms
Elimination reactions: E1 and E2 mechanisms. Structure-reactivity features of E1 and E2 mechanisms. Competition between substitution and elimination.
Addition to double bonds: electrophilic addition of water, hydrogen halides, Hydrogenation.
Alcohols, thioalcohols, ethers, thioethers: Nomenclature. Physical properties, Acidity and basicity. The S-S bond.
Carbonyl group: Oxidation and Reduction in Organic Chemistry. Aldehydes and Ketones. Nucleophilic addition reactions to the carbonyl group. Keto-enolic tautomerism. Enolates. Aldol condensation.
Carboxylic Acids and derivatives: classification. Acidity. Physical properties. Acyl halides. Organic acid anhydride. Esters. Amides. Nitriles. Synthesis and reactivity.
Aromatic and heterocyclic compounds: benzene, benzene derivatives and main heterocyclic compounds. Resonance and electronic structure.
Electrophilic aromatic substitutio. Effects of substituent groups in the electrophilic aromatic substitution. Acidity of phenols.
Amines: Properties as bases. Reactivity as nucleophiles
Carbohydrates: Monosaccharides, disaccharides and polysaccharides. Aldoses and ketoses. D and L series. Mutarotation. Glycosides.
Aminoacids: Acidity and basicity.L and D series. Peptide bond. Peptide synthesis. Proteins.
Lipids: Saturated and unsaturated fatty acids. Triglycerides. Soaps
Nucleic acids: Nucleosides, nucleotides and nucleic acids
Organic Compounds of biological interest: Purines and pyrimidines.
Acid-Base reactions: chemical equilibrium, molecular structure and pH
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z. Nomenclature Cycloalkanes. Hydrocarbons from natural sources.
Stereochemistry: Symmetry and chirality. Stereogenic centers. Configuration at tetrahedral atoms.Cahn/Ingold and Prelog rules. Configuration at double bonds. Chirality and optical activity. Absolute configuration. Conformational isomers.
Nucleophilic substitution: SN2 and SN1reactions. Stability of carbocations. Reaction mechanisms
Elimination reactions: E1 and E2 mechanisms. Structure-reactivity features of E1 and E2 mechanisms. Competition between substitution and elimination.
Addition to double bonds: electrophilic addition of water, hydrogen halides, Hydrogenation.
Alcohols, thioalcohols, ethers, thioethers: Nomenclature. Physical properties, Acidity and basicity. The S-S bond.
Carbonyl group: Oxidation and Reduction in Organic Chemistry. Aldehydes and Ketones. Nucleophilic addition reactions to the carbonyl group. Keto-enolic tautomerism. Enolates. Aldol condensation.
Carboxylic Acids and derivatives: classification. Acidity. Physical properties. Acyl halides. Organic acid anhydride. Esters. Amides. Nitriles. Synthesis and reactivity.
Aromatic and heterocyclic compounds: benzene, benzene derivatives and main heterocyclic compounds. Resonance and electronic structure.
Electrophilic aromatic substitutio. Effects of substituent groups in the electrophilic aromatic substitution. Acidity of phenols.
Amines: Properties as bases. Reactivity as nucleophiles
Carbohydrates: Monosaccharides, disaccharides and polysaccharides. Aldoses and ketoses. D and L series. Mutarotation. Glycosides.
Aminoacids: Acidity and basicity.L and D series. Peptide bond. Peptide synthesis. Proteins.
Lipids: Saturated and unsaturated fatty acids. Triglycerides. Soaps
Nucleic acids: Nucleosides, nucleotides and nucleic acids
Organic Compounds of biological interest: Purines and pyrimidines.
Prerequisites for admission
No knowledge are required
Teaching methods
The course uses e-learning teaching material on the Ariel platform and consists of slides and films shown during the lessons. On the platform are also loaded exercises that will then be solved in the classroom. Class time is dedicated for 2/3 to the frontal lesson and 1/3 to the execution of exercises.
Teaching Resources
Brown, W.H.; Campbell, M. K.; Farrel, S. O. "Elementi di Chimica Organica" ed. Edises
Bruice P. Y. "Elementi di Chimica Organica" ed. Edises
Botta, B. "Chimica Organica Essenziale", edi-ermes
J. Gorzynski Smith "Fondamenti di Chimica Organica", Mc- Graw - Hill
McMurry, J. " Fondamenti di Chimica Organica" ed. Zanichelli.
Workbooks:
Felix S. Lee, Guida alla soluzione dei problemi da "Introduzione alla Chimica Organica" ed. Edises (4° ediz.)
Bruice P. Y. "Elementi di Chimica Organica" ed. Edises
Botta, B. "Chimica Organica Essenziale", edi-ermes
J. Gorzynski Smith "Fondamenti di Chimica Organica", Mc- Graw - Hill
McMurry, J. " Fondamenti di Chimica Organica" ed. Zanichelli.
Workbooks:
Felix S. Lee, Guida alla soluzione dei problemi da "Introduzione alla Chimica Organica" ed. Edises (4° ediz.)
Assessment methods and Criteria
The knowledge acquired by the students is verified through a written test. An oral test may be requested by the student if he wishes to modify the outcome of the written test. After completing about half of the program, a partial test is scheduled. aimed at ascertaining the actual degree of learning of the student and to lighten the final exam.
Exam test (written): the written test will be divided into two parts. The first part will include the topics required in the partial test. The second part will focus on the program carried out in the second half of the course. If the partial test proves insufficient or the student refuses the vote assigned he will have to complete the final final examination of the two parts.
Each partial test will require the execution of 5-6 exercises with a maximum score of 31 points which will allow the attribution of a mark out of thirty up to a maximum of 30 and praise. The final grade will be the average of the marks awarded in the two parts. The complete written test of the two parts therefore consists of 10/12 exercises. The student will have at least one and a half hours to perform each part (at least three and a half hours for the entire written test). Passing the exam involves reaching a score of at least 18/30 as the average of the two parts. The oral exam (at the request of the student): the oral exam may include the request for theoretical explanations underlying a certain phenomenon, discussed in class, or the solution of one or more exercises of similar type to those addressed in class.
Exam test (written): the written test will be divided into two parts. The first part will include the topics required in the partial test. The second part will focus on the program carried out in the second half of the course. If the partial test proves insufficient or the student refuses the vote assigned he will have to complete the final final examination of the two parts.
Each partial test will require the execution of 5-6 exercises with a maximum score of 31 points which will allow the attribution of a mark out of thirty up to a maximum of 30 and praise. The final grade will be the average of the marks awarded in the two parts. The complete written test of the two parts therefore consists of 10/12 exercises. The student will have at least one and a half hours to perform each part (at least three and a half hours for the entire written test). Passing the exam involves reaching a score of at least 18/30 as the average of the two parts. The oral exam (at the request of the student): the oral exam may include the request for theoretical explanations underlying a certain phenomenon, discussed in class, or the solution of one or more exercises of similar type to those addressed in class.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 8
Lessons: 64 hours
Professor:
Penso Michele