Organic Chemistry
A.Y. 2023/2024
Learning objectives
The aim of the course is to provide the necessary fundamentals for understanding the chemical structure of organic molecules and the most common reactions of organic compounds based on the description of the main characteristic organic classes, the study of their chemical-physical properties and their reactivity, accompanied by frequent references to environmental problems. During the course will be acquired the basic knowledge for understanding the topics of upcoming courses (in the 2nd and 3rd year) such as Environmental Chemistry, Biochemistry and Food Chemistry. The acquisition of the fundamental knowledge will be favored by classroom exercises. The course also includes a single-unit laboratory in which experiments will be carried out in order the student to acquire the ability for the correct execution of an organic chemistry experiment, including the basic safety rules regarding the handling and the disposal of organic substances. The laboratory experiments aim to instruct the basic knowledge of the fundamental purification techniques (crystallization, distillation and chromatography), the separation (extraction) and the reactivity of organic compounds.
Expected learning outcomes
At the end of the course the student will acquire the knowledge related to the structure and chemical-physical properties of the main classes of organic compounds. He will be able to utilize the concepts of polar covalent bonding, hybridization, sigma and pi-Greek bond, isomerism, and resonance for the identification of the arrangement of the molecules in space, for the recognition of the presented functional groups and for the assignment of the IUPAC name. He will be able to critically analyze organic molecules on the basis of their structure, to recognizing their acidity/basicity, nucleophilicity/electrophilicity and understanding their reactivity based on their structure and the environment in which they are found. Furthermore, the student will acquire the knowledge related to the mechanisms of the chemical reactions. This ability will be developed by exercises in the classroom thanks also to the discussion between students and the professor during the course. The students will have to acquire the ability to use a vocabulary and terminology related to Organic Chemistry in order to transmit and apply their knowledge. The laboratory experiments will allow the student to be able to perform standard laboratory procedures and use instruments for organic synthesis.
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
Responsible
Lesson period
Second semester
Course syllabus
Module 1: Chemical bonding and structure: Electronic configuration and hybridization of carbon atom. Ionic and covalent bonds; polarity. Intermolecular interactions. Structures and formulas of organic molecules. Functional groups in organic chemistry.
Alkanes. IUPAC nomenclature, conformational isomerism, Newman projections, Combustion and alogenation of alkanes. Cyclic alkanes. IUPAC nomenclature; ring strain. Substituted cycloexanes and conformational considerations. Cis and trans isomers.
The organic reactions. Main types of organic reactions: mechanisms and intermediates involved. Acid-base equilibria. Radical and ionic reactions.
Stereochemistry. Chiral molecules; optical activity; absolute configurations and R-S sequence rules; Fischer projections. Molecules with several stereocenters: diastereomers and meso compounds. Stereochemistry in chemical reactions; resolution of enantiomers.
Alkenes and alkynes: IUPAC nomenclature, structure and E/Z isomerism; relative stability. Synthesis and reactivity. Electrophilic addition.
Alkadienes: 1,2 and 1,4 Electrophilic addiction. Allylic system
Haloalkanes. IUPAC nomenclature. Nucleophilic substitution SN2 and SN1: mechanisms, stereochemistry. Elimination reactions: mechanisms E1 and E2.
Alcohols, Thiols, Ethers. IUPAC nomenclature. Alcohols as acids and bases. Reactivity. Oxidations. Oxidation of thiols. Synthesis and reactivity of ethers.
Organometallic compounds: Grignard reagents. Reaction with carbonyl compounds.
Aldehydes and ketones. IUPAC nomenclature, structure of carbonyl group. Keto-enol tautomerism. Reactions of nucleophilic additions: addition of water, alcohol, amines. Oxidations and reductions. Aldol condensation.
Carboxylic acids and derivatives. IUPAC nomenclature and acidity. Reactivity: nucleophilic acyl substitution. Esters, anhydrides, acid chlorides, amides, nitriles. Claisen and Dieckman condensation of esters.
Alkylamines. IUPAC nomenclature. Basicity and reactivity.
Benzene: structure, IUPAC nomenclature. Resonance energy. Huckel rule. Reactivity of benzene.
Phenol and aniline: nomenclature, Acidity and basicity. Reactivity. Reaction with nitrous acid.
Heteroaromatic compounds: nomenclature and reactivity in electrophilic substitution.
Phosphorus derivatives: Classification, hydrolysis and biologic rule.
Carbonic acid derivatives: Urea, carbammates.
Aminoacids. Structure and properties. Natural amino acids and their classification. Definition of peptide and protein.
Carbohydrates: nomenclature and reactivity.
Polymers: nomenclature; addiction and condensation polimers.
Module 2: Laboratory practies are preceded by the necessary theoretical explanations.
Learning the main techniques such as:
-purification: recrystallization and distillation;
-separation: solid / liquid and solid / solid extraction;
- chromatography on silica: TLC and gravimetric chromatographic column.
Practical examples of organic reactions will also be addressed: hydrolysis reaction, condensation, polycondensation.
Alkanes. IUPAC nomenclature, conformational isomerism, Newman projections, Combustion and alogenation of alkanes. Cyclic alkanes. IUPAC nomenclature; ring strain. Substituted cycloexanes and conformational considerations. Cis and trans isomers.
The organic reactions. Main types of organic reactions: mechanisms and intermediates involved. Acid-base equilibria. Radical and ionic reactions.
Stereochemistry. Chiral molecules; optical activity; absolute configurations and R-S sequence rules; Fischer projections. Molecules with several stereocenters: diastereomers and meso compounds. Stereochemistry in chemical reactions; resolution of enantiomers.
Alkenes and alkynes: IUPAC nomenclature, structure and E/Z isomerism; relative stability. Synthesis and reactivity. Electrophilic addition.
Alkadienes: 1,2 and 1,4 Electrophilic addiction. Allylic system
Haloalkanes. IUPAC nomenclature. Nucleophilic substitution SN2 and SN1: mechanisms, stereochemistry. Elimination reactions: mechanisms E1 and E2.
Alcohols, Thiols, Ethers. IUPAC nomenclature. Alcohols as acids and bases. Reactivity. Oxidations. Oxidation of thiols. Synthesis and reactivity of ethers.
Organometallic compounds: Grignard reagents. Reaction with carbonyl compounds.
Aldehydes and ketones. IUPAC nomenclature, structure of carbonyl group. Keto-enol tautomerism. Reactions of nucleophilic additions: addition of water, alcohol, amines. Oxidations and reductions. Aldol condensation.
Carboxylic acids and derivatives. IUPAC nomenclature and acidity. Reactivity: nucleophilic acyl substitution. Esters, anhydrides, acid chlorides, amides, nitriles. Claisen and Dieckman condensation of esters.
Alkylamines. IUPAC nomenclature. Basicity and reactivity.
Benzene: structure, IUPAC nomenclature. Resonance energy. Huckel rule. Reactivity of benzene.
Phenol and aniline: nomenclature, Acidity and basicity. Reactivity. Reaction with nitrous acid.
Heteroaromatic compounds: nomenclature and reactivity in electrophilic substitution.
Phosphorus derivatives: Classification, hydrolysis and biologic rule.
Carbonic acid derivatives: Urea, carbammates.
Aminoacids. Structure and properties. Natural amino acids and their classification. Definition of peptide and protein.
Carbohydrates: nomenclature and reactivity.
Polymers: nomenclature; addiction and condensation polimers.
Module 2: Laboratory practies are preceded by the necessary theoretical explanations.
Learning the main techniques such as:
-purification: recrystallization and distillation;
-separation: solid / liquid and solid / solid extraction;
- chromatography on silica: TLC and gravimetric chromatographic column.
Practical examples of organic reactions will also be addressed: hydrolysis reaction, condensation, polycondensation.
Prerequisites for admission
The student must have a good knowledge of general chemistry fundamentals, with particular attention to: atomic structure, nature of the chemical bond, principles of chemical equilibrium, acid and base.
Teaching methods
Theoretical lessons: 5 CFU
Classroom exercises: 1CFU
Laboratory: 2 CFU
Classroom exercises: 1CFU
Laboratory: 2 CFU
Teaching Resources
· Slides of the course on Ariel web (both for theoretical and lab. courses)
· Exercises conducted in the classroom and solutions on Ariel web
· W. H. Brown, T. Poon - Introduzione alla Chimica Organica - quinta ed., 2014 - Ed. Edises, Napoli
· J. G. Smith Fondamenti di Chimica Organica - quarta edizione - Ed. Mc Graw Hill
· J. McMurry Fondamenti di Chimica Organica - quarta edizione - Ed. Zanichelli
· D. Klein Fondamenti di Chimica Organica - Ed Pearson
· M. S. Erickson " Guida alla soluzione dei problemi" da "Introduzione alla Chimica Organica" quinta ed., 2006 - Ed. Edises, Napoli
· Chimica organica. Esercizi risolti di chimica organica. Con Contenuto digitale (
· H. Hart, L. Craine, D. Hart "Chimica Organica" sesta ed- Ed. Zanichelli, Bologna
· Slides available on the teacher's Ariel website
For insights:
· J. McMurry "Chimica Organica" nona ed., 2017, Ed. Piccin, Padova.
· K. P. C. Vollhardt, "Chimica Organica" quarta edizione, 2016 - Ed. Zanichelli,
For laboratory:
· D.L.Pavia, G.M.Lampman, G.S. Kriz "Il laboratorio di Chimica Organica" Ed. Sorbona
·M.D'Ischia "La Chimica Organica in laboratorio"- Ed Piccin - Bologna
· Exercises conducted in the classroom and solutions on Ariel web
· W. H. Brown, T. Poon - Introduzione alla Chimica Organica - quinta ed., 2014 - Ed. Edises, Napoli
· J. G. Smith Fondamenti di Chimica Organica - quarta edizione - Ed. Mc Graw Hill
· J. McMurry Fondamenti di Chimica Organica - quarta edizione - Ed. Zanichelli
· D. Klein Fondamenti di Chimica Organica - Ed Pearson
· M. S. Erickson " Guida alla soluzione dei problemi" da "Introduzione alla Chimica Organica" quinta ed., 2006 - Ed. Edises, Napoli
· Chimica organica. Esercizi risolti di chimica organica. Con Contenuto digitale (
· H. Hart, L. Craine, D. Hart "Chimica Organica" sesta ed- Ed. Zanichelli, Bologna
· Slides available on the teacher's Ariel website
For insights:
· J. McMurry "Chimica Organica" nona ed., 2017, Ed. Piccin, Padova.
· K. P. C. Vollhardt, "Chimica Organica" quarta edizione, 2016 - Ed. Zanichelli,
For laboratory:
· D.L.Pavia, G.M.Lampman, G.S. Kriz "Il laboratorio di Chimica Organica" Ed. Sorbona
·M.D'Ischia "La Chimica Organica in laboratorio"- Ed Piccin - Bologna
Assessment methods and Criteria
The exam consists of a written test lasting two hours, which aims to verify through the answer to 10 closed questions/exercises, the achievement of the following educational objectives: (i) knowledge of the fundamental concepts necessary for an understanding of the structure and the reactivity of organic molecules. (ii) ability to use the concepts acquired, to solve problems of reactivity and structure. Each correct exercise allows the acquisition of a score between zero and three points. Passing the written test, is achieved upon overall achievement of at least 18 points.
Passed the general chemistry propaedeutic exam,the student is admitted to the written exam only if he has previously delivered the Laboratory Report. The Laboratory Report toghether with the laboratory quality activity, will be included in the final evaluation (weighted average).
For first-year students, two written in-progress tests may be offered, the first one about halfway through the course and the second one at the end, both consisting of 10 questions on the program covered and lasting two hours. Passing the first test is essential for access to the second test.
Passing both written tests with a grade of 18/30 or higher exempts the student from taking the final exam. Details on the in itinere tests will be explained at the beginning of the course.
Passed the general chemistry propaedeutic exam,the student is admitted to the written exam only if he has previously delivered the Laboratory Report. The Laboratory Report toghether with the laboratory quality activity, will be included in the final evaluation (weighted average).
For first-year students, two written in-progress tests may be offered, the first one about halfway through the course and the second one at the end, both consisting of 10 questions on the program covered and lasting two hours. Passing the first test is essential for access to the second test.
Passing both written tests with a grade of 18/30 or higher exempts the student from taking the final exam. Details on the in itinere tests will be explained at the beginning of the course.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 8
Practicals: 16 hours
Single bench laboratory practical: 32 hours
Lessons: 40 hours
Single bench laboratory practical: 32 hours
Lessons: 40 hours
Professors:
Pellegrino Sara, Pini Elena Renata Elvira
Educational website(s)
Professor(s)
Reception:
By appointment
Via Golgi 19. Building 25010-Entrance C, IV floor