Organic Chemistry
A.Y. 2023/2024
Learning objectives
The course aims to provide students with the basic knowledge of Organic Chemistry, useful for addressing any study path following the first interfaculty year. The laboratory exercises are intended to provide the student with the fundamental knowledge to carry out, effectively and safely, practical activities typical of an organic chemistry laboratory.
Expected learning outcomes
Knowledge and understanding
· know the graphic representation models of organic molecules and reaction mechanisms
· know the characteristics of the main functional groups, their nomenclature and reactivity
· know the characteristics of the main functional groups, their nomenclature and reactivity
· know the main reactions of organic molecules, recognize simple equipment in an organic chemistry lab, know the main techniques of preparation and purification of organic compounds
· know the safety regulations in force in a chemical laboratory
Ability to apply knowledge and understanding
· know how to correctly interpret the IUPAC name of the main classes of organic molecules
· recognize the main types of chemical reactions and know how to complete reaction schemes
· be able to conduct a laboratory experience using simple equipment, including data processing
Judgment capacity
· Ability to critically evaluate hypotheses concerning the interaction/transformation modalities of organic molecules relevant in the field of biotechnologies
· ability to assess the risk related to conducting a laboratory experiment
Communication skills
· communicate effectively, orally and in written form, correctly using terminology and graphic models typical of organic chemistry
· share an experimental laboratory space
Learning ability
· ability to understand a scientific text of organic chemistry and apply the information learned to the solution of a new problem
· ability to understand an experimental recipe and translate it into practical operations
· know the graphic representation models of organic molecules and reaction mechanisms
· know the characteristics of the main functional groups, their nomenclature and reactivity
· know the characteristics of the main functional groups, their nomenclature and reactivity
· know the main reactions of organic molecules, recognize simple equipment in an organic chemistry lab, know the main techniques of preparation and purification of organic compounds
· know the safety regulations in force in a chemical laboratory
Ability to apply knowledge and understanding
· know how to correctly interpret the IUPAC name of the main classes of organic molecules
· recognize the main types of chemical reactions and know how to complete reaction schemes
· be able to conduct a laboratory experience using simple equipment, including data processing
Judgment capacity
· Ability to critically evaluate hypotheses concerning the interaction/transformation modalities of organic molecules relevant in the field of biotechnologies
· ability to assess the risk related to conducting a laboratory experiment
Communication skills
· communicate effectively, orally and in written form, correctly using terminology and graphic models typical of organic chemistry
· share an experimental laboratory space
Learning ability
· ability to understand a scientific text of organic chemistry and apply the information learned to the solution of a new problem
· ability to understand an experimental recipe and translate it into practical operations
Lesson period: Second semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course can be attended as a single course.
Course syllabus and organization
Linea AK
Responsible
Lesson period
Second semester
Course syllabus
Theoretical lessons and classroom exercises
Introduction: Hybridization of atoms, bond types, bond polarity, resonance forms. IUPAC nomenclature of the main classes of compounds.
Acid-base reactions in organic chemistry, equilibrium position, molecular structure and acidity scales
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z nomenclature. Cycloalkanes.
Stereochemistry. Chirality and stereogenicity. Fischer projections. Enantiomerism and diastereoisomerism. Optical activity and polarimetry. Resolution of racemes. Cahn/Ingold/Prelog nomenclature. Conformational isomerism in linear and cyclic alkanes.
Nucleophilic substitution reactions. Haloalkanes. SN1 and SN2 reactions. Stability of carbocations. Factors affecting the reaction mechanism.
Elimination reactions. E1 and E2 reactions. Factors affecting the reaction mechanism. Competition between replacement and elimination.
Electrophilic addition reactions at the double bond. Halogenation, hydration, sum of hydrogen halides, catalytic hydrogenation.
Alcohols, thiols, ethers, thioethers. Classification. Physical properties. Acidity and basicity. The S-S bond.
Aromatic compounds. Benzene. Resonance and electronic structure of benzene. Influence of an aromatic ring on C, N and O atoms bonded to it. Acidity of phenols. Electrophilic aromatic substitution reactions: halogenation. Notes on heterocyclic compounds.
Amines. Basicity and acidity. Nucleophilic behavior and reactivity.
The carbonyl group. Concept of oxidation and reduction in organic chemistry. Aldehydes and ketones. Nucleophilic addition reactions. Keto-enol tautomerism. enolate ions. Aldol reaction
Carbohydrates. Nomenclature. Monosaccharides, disaccharides and polysaccharides. Aldoses and ketosis. D and L series. Hemiacetal structures. mutarotation. Glycosides.
Carboxylic acids and derivatives. Classification. Physical properties. Acyl halides. Anhydrides. Foreign. Amides. nitriles. Synthesis and reactivity. Addition/elimination reactions. Claisen condensation.
Amino acids. Acidity and basicity. D and L series. The peptide bond. Problems related to peptide synthesis and synthesis of a dipeptide. Protein.
Practical laboratory exercises
Introduction to the laboratory course. Basic safety rules in the laboratory. Purification techniques: distillation, crystallization.
Acid/base separation techniques. Separation of organic mixtures with aqueous solutions with variable pH.
Chromatographic separation techniques. Thin layer chromatography (TLC) and column.
Practical examples of organic reactions. Some simple reactions will be carried out to show the different phases of an organic synthesis process (i.e. stoichiometric calculations, dilutions, heating/cooling of the reaction environment, verification of the reaction progress, isolation of the product, purification, evaluation of the purity of the product obtained).
Introduction: Hybridization of atoms, bond types, bond polarity, resonance forms. IUPAC nomenclature of the main classes of compounds.
Acid-base reactions in organic chemistry, equilibrium position, molecular structure and acidity scales
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z nomenclature. Cycloalkanes.
Stereochemistry. Chirality and stereogenicity. Fischer projections. Enantiomerism and diastereoisomerism. Optical activity and polarimetry. Resolution of racemes. Cahn/Ingold/Prelog nomenclature. Conformational isomerism in linear and cyclic alkanes.
Nucleophilic substitution reactions. Haloalkanes. SN1 and SN2 reactions. Stability of carbocations. Factors affecting the reaction mechanism.
Elimination reactions. E1 and E2 reactions. Factors affecting the reaction mechanism. Competition between replacement and elimination.
Electrophilic addition reactions at the double bond. Halogenation, hydration, sum of hydrogen halides, catalytic hydrogenation.
Alcohols, thiols, ethers, thioethers. Classification. Physical properties. Acidity and basicity. The S-S bond.
Aromatic compounds. Benzene. Resonance and electronic structure of benzene. Influence of an aromatic ring on C, N and O atoms bonded to it. Acidity of phenols. Electrophilic aromatic substitution reactions: halogenation. Notes on heterocyclic compounds.
Amines. Basicity and acidity. Nucleophilic behavior and reactivity.
The carbonyl group. Concept of oxidation and reduction in organic chemistry. Aldehydes and ketones. Nucleophilic addition reactions. Keto-enol tautomerism. enolate ions. Aldol reaction
Carbohydrates. Nomenclature. Monosaccharides, disaccharides and polysaccharides. Aldoses and ketosis. D and L series. Hemiacetal structures. mutarotation. Glycosides.
Carboxylic acids and derivatives. Classification. Physical properties. Acyl halides. Anhydrides. Foreign. Amides. nitriles. Synthesis and reactivity. Addition/elimination reactions. Claisen condensation.
Amino acids. Acidity and basicity. D and L series. The peptide bond. Problems related to peptide synthesis and synthesis of a dipeptide. Protein.
Practical laboratory exercises
Introduction to the laboratory course. Basic safety rules in the laboratory. Purification techniques: distillation, crystallization.
Acid/base separation techniques. Separation of organic mixtures with aqueous solutions with variable pH.
Chromatographic separation techniques. Thin layer chromatography (TLC) and column.
Practical examples of organic reactions. Some simple reactions will be carried out to show the different phases of an organic synthesis process (i.e. stoichiometric calculations, dilutions, heating/cooling of the reaction environment, verification of the reaction progress, isolation of the product, purification, evaluation of the purity of the product obtained).
Prerequisites for admission
General and inorganic chemistry
Teaching methods
Theory 5 ECTS; Excercises 1 ECTS; Laboratory 2 ECTS
Teaching Resources
The teacher will publish the teaching material relating to each lesson on the ARIEL website.
Textbooks (teachers do not express particular preferences towards any of the following texts)
· Brown, W.H.; Poon, T. "Introduction to Organic Chemistry" ed. editions
· Bruice P. Y. "Elements of Organic Chemistry" ed. editions
· Botta, B. "Essential Organic Chemistry" ed. edi-ermes
· J. Gorzynski Smith "Fundamentals of Organic Chemistry" ed. McGraw-Hill
· McMurry, J. "Fundamentals of Organic Chemistry" ed. Zanichelli
Workbooks
· Felix S. Lee, Problem Solving Guide from "Introduction to Organic Chemistry" ed. Editions (4th ed.)
For each lesson, the teacher will prepare an exercise with the help of the Exam manager platform (EDISES publishing house). This exercise, which the student can carry out on his smartphone, is aimed at an immediate verification by the student of the contents of the lesson that has just ended. It will also prepare the student for the verification method using multiple choice questions. Mode also used in the exam.
Textbooks (teachers do not express particular preferences towards any of the following texts)
· Brown, W.H.; Poon, T. "Introduction to Organic Chemistry" ed. editions
· Bruice P. Y. "Elements of Organic Chemistry" ed. editions
· Botta, B. "Essential Organic Chemistry" ed. edi-ermes
· J. Gorzynski Smith "Fundamentals of Organic Chemistry" ed. McGraw-Hill
· McMurry, J. "Fundamentals of Organic Chemistry" ed. Zanichelli
Workbooks
· Felix S. Lee, Problem Solving Guide from "Introduction to Organic Chemistry" ed. Editions (4th ed.)
For each lesson, the teacher will prepare an exercise with the help of the Exam manager platform (EDISES publishing house). This exercise, which the student can carry out on his smartphone, is aimed at an immediate verification by the student of the contents of the lesson that has just ended. It will also prepare the student for the verification method using multiple choice questions. Mode also used in the exam.
Assessment methods and Criteria
The knowledge and skills acquired by students will be verified through a written test. After completing about half of the program, a partial test (prova in itinere) is scheduled to ascertain the student's actual level of learning. The ongoing test will consist of 15 multiple choice questions concerning the program carried out up to and including the functional group of alcohols. The time available to the student will be one hour.
The written test of the final exam will include the resolution of 15 multiple choice questions concerning the topics of the first part of the course (up to the functional group of alcohols included) plus 5 open questions concerning the second part of the course (from the carbonyl group to the end) . The student will have up to 2 hours available. The student must deserve a score of at least 18/30 to pass the exam.
The final result will also take into account the evaluation obtained by the student in the practical laboratory exercises which are mandatory. The student will be evaluated on the basis of the general behavior during the laboratory exercises and the completeness/correctness of the reports presented at the end of the exercises themselves.
The written test of the final exam will include the resolution of 15 multiple choice questions concerning the topics of the first part of the course (up to the functional group of alcohols included) plus 5 open questions concerning the second part of the course (from the carbonyl group to the end) . The student will have up to 2 hours available. The student must deserve a score of at least 18/30 to pass the exam.
The final result will also take into account the evaluation obtained by the student in the practical laboratory exercises which are mandatory. The student will be evaluated on the basis of the general behavior during the laboratory exercises and the completeness/correctness of the reports presented at the end of the exercises themselves.
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
Shifts:
Professor:
Gaggero Nicoletta Teresa
Turno 1
Professor:
Gaggero Nicoletta TeresaTurno 2
Professor:
Gori AlessandroTurno 3
Professor:
Brambilla ElisaLinea LZ
Responsible
Lesson period
Second semester
Course syllabus
Introduction: Atom hybridization, bond types, bond polarity, resonance forms. IUPAC Nomenclature of the main classes of compounds.
Acid-base reactions in organic chemistry, analysis of acid-base equilibria, relationship between molecular structure and acidity strength.
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z nomenclature. Cycloalkanes. Conformational isomerism in linear and cyclic alkanes.
Stereochemistry. Chirality and stereogenicity. Fischer projections. Enantiomers and diastereoisomers. Optical activity. Polarimetry. Resolution of racemic mixtures. Cahn/Ingold/Prelog nomenclature.
Nucleophilic Substitution reactions. Haloalkanes. SN1and SN2 reactions. Carbocation stability. Factors influencing the reaction mechanism.
Elimination reactions. E2 and E2 reactions. Factors influencing the reaction mechanisms. Competition between substitution and elimination.
Electrophilic Addition reactions to the double bond. Halogenation, hydration, halogen hydride addition, catalytic hydrogenation.
Alcohols, thiols, ethers, thioethers. Classification. Physical properties. Acidity and basicity. The S-S bond.
Aromatic and heterocyclic compounds. Benzene: resonance and electronic structure of the benzene ring. The influence of an aromatic ring to bonded C, N and O atoms. Acidity of phenols. Aromatic electrophilic substitution reactions (halogenation, nitration, sulfonation, Friedel-Craft alkylation and acylations). Heterocyclic compounds (only mention).
Amines. Basicity and acidity. Nucleophilic behaviour and reactivity.
The carbonyl group. Oxidation and reduction reactions in organic chemistry. Aldehydes and ketones. Nucleophilic additions. Keto-enolic tautomerism. Enolate ions. Aldolic reaction. Michael conjugate addition.
Carboxylic acids and their derivatives. Classification. Physical properties. Acyl halides. Anhydrides. Esters. Amides. Nitriles. Synthesis and reactivity: addition/elimination reactions. Claisen condensation.
Carbohydrates. Nomenclature. Monosaccharides, disaccharides e polysaccharides. Aldoses e ketoses. D- and L-series. Hemiacetalic structures. Mutarotation. Glycosides.
Amino acids. Acidity e basicity. D- and L-series. The peptide bond. Peptides and proteins, primary structure and its determination. Secondary structure: alfa-helices and beta-sheets. Tertiary and quaternary structures.
Lipids: triglycerides and fatty acids, soaps and detergents, phospholipids, steroids, prostaglandins, fat soluble vitamins. Structure and properties.
Nucleobases: purines and pyrimidines, Watson-Crick pairing, Hoogsteen's interactions and G-quadruplex.
Laboratory course
Introduction to the laboratory course. Basic safety rules in the laboratory. Purification techniques: distillation, crystallization.
Acid / base separation techniques. Separation of organic mixtures with aqueous solutions with variable pH.
Chromatographic separation techniques. Thin layer chromatography (TLC) and column chromatography.
Practical examples of organic reactions. Some simple reactions will be carried out to show the different phases of a process of organic synthesis (i.e. stoichiometric calculations, dilutions, heating/cooling of the reaction environment, verification of the progress of the reaction, isolation of the product, purification, evaluation of the purity of the product obtained).
Acid-base reactions in organic chemistry, analysis of acid-base equilibria, relationship between molecular structure and acidity strength.
Hydrocarbons: alkanes, alkenes and alkynes. Structure. E/Z nomenclature. Cycloalkanes. Conformational isomerism in linear and cyclic alkanes.
Stereochemistry. Chirality and stereogenicity. Fischer projections. Enantiomers and diastereoisomers. Optical activity. Polarimetry. Resolution of racemic mixtures. Cahn/Ingold/Prelog nomenclature.
Nucleophilic Substitution reactions. Haloalkanes. SN1and SN2 reactions. Carbocation stability. Factors influencing the reaction mechanism.
Elimination reactions. E2 and E2 reactions. Factors influencing the reaction mechanisms. Competition between substitution and elimination.
Electrophilic Addition reactions to the double bond. Halogenation, hydration, halogen hydride addition, catalytic hydrogenation.
Alcohols, thiols, ethers, thioethers. Classification. Physical properties. Acidity and basicity. The S-S bond.
Aromatic and heterocyclic compounds. Benzene: resonance and electronic structure of the benzene ring. The influence of an aromatic ring to bonded C, N and O atoms. Acidity of phenols. Aromatic electrophilic substitution reactions (halogenation, nitration, sulfonation, Friedel-Craft alkylation and acylations). Heterocyclic compounds (only mention).
Amines. Basicity and acidity. Nucleophilic behaviour and reactivity.
The carbonyl group. Oxidation and reduction reactions in organic chemistry. Aldehydes and ketones. Nucleophilic additions. Keto-enolic tautomerism. Enolate ions. Aldolic reaction. Michael conjugate addition.
Carboxylic acids and their derivatives. Classification. Physical properties. Acyl halides. Anhydrides. Esters. Amides. Nitriles. Synthesis and reactivity: addition/elimination reactions. Claisen condensation.
Carbohydrates. Nomenclature. Monosaccharides, disaccharides e polysaccharides. Aldoses e ketoses. D- and L-series. Hemiacetalic structures. Mutarotation. Glycosides.
Amino acids. Acidity e basicity. D- and L-series. The peptide bond. Peptides and proteins, primary structure and its determination. Secondary structure: alfa-helices and beta-sheets. Tertiary and quaternary structures.
Lipids: triglycerides and fatty acids, soaps and detergents, phospholipids, steroids, prostaglandins, fat soluble vitamins. Structure and properties.
Nucleobases: purines and pyrimidines, Watson-Crick pairing, Hoogsteen's interactions and G-quadruplex.
Laboratory course
Introduction to the laboratory course. Basic safety rules in the laboratory. Purification techniques: distillation, crystallization.
Acid / base separation techniques. Separation of organic mixtures with aqueous solutions with variable pH.
Chromatographic separation techniques. Thin layer chromatography (TLC) and column chromatography.
Practical examples of organic reactions. Some simple reactions will be carried out to show the different phases of a process of organic synthesis (i.e. stoichiometric calculations, dilutions, heating/cooling of the reaction environment, verification of the progress of the reaction, isolation of the product, purification, evaluation of the purity of the product obtained).
Prerequisites for admission
Have attended the General and Inorganic Chemistry and acquisition of the key competencies.
Mastering stoichiometry, different concentration units interconversion, acid-base equilibria.
Mastering stoichiometry, different concentration units interconversion, acid-base equilibria.
Teaching methods
The course is delivered by classroom lectures (5 CFU), classroom exercises (1 CFU), and laboratory (2 CFU).
Teaching Resources
Textbooks (The teacher does not express a specific preference over any of the following textbooks)
· J. Gorzynski Smith "Fondamenti di Chimica Organica" ed. Mc- Graw - Hill
· Brown, W.H.; Poon, T. "Introduzione alla Chimica Organica" ed. Edises
· Botta, B. "Chimica Organica Essenziale" ed. edi-ermes
· Bruice P. Y. "Elementi di Chimica Organica" ed. Edises
· McMurry, J. "Fondamenti di Chimica Organica" ed. Zanichelli
Problem-solving textbooks:
· Felix S. Lee, Guida alla soluzione dei problemi da "Introduzione alla Chimica Organica"
ed. Edises (4° ediz.)
· J. Gorzynski Smith "Fondamenti di Chimica Organica" ed. Mc- Graw - Hill
· Brown, W.H.; Poon, T. "Introduzione alla Chimica Organica" ed. Edises
· Botta, B. "Chimica Organica Essenziale" ed. edi-ermes
· Bruice P. Y. "Elementi di Chimica Organica" ed. Edises
· McMurry, J. "Fondamenti di Chimica Organica" ed. Zanichelli
Problem-solving textbooks:
· 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. After completing approximately half the program, a partial test will be scheduled to ascertain the student's actual learning level.
Written test: the written exam will be divided into two parts. The first part will include multiple-answer exercises (15 questions from 1 point each, no answer 0, wrong answer -0.25) on the program held in class up to the first partial test. The second part will focus on the program carried out in the second half of the course. It will consist of five open-ended exercises, one of which will be inherent to practical laboratory. Each open-ended exercise will be worth 3 points. The student will have at least one hour for each part (at least two hours for the whole written exam). Passing the exam requires the achievement of at least 8/15 in each of the two parts and the overall grade of 18/30.
The final mark will also take into account the evaluation obtained for practical laboratory exercises. The student will be evaluated based on her/his general behaviour during the laboratory exercises and on the completeness/correctness of the reports to be presented at the end of the exercises themselves.
Written test: the written exam will be divided into two parts. The first part will include multiple-answer exercises (15 questions from 1 point each, no answer 0, wrong answer -0.25) on the program held in class up to the first partial test. The second part will focus on the program carried out in the second half of the course. It will consist of five open-ended exercises, one of which will be inherent to practical laboratory. Each open-ended exercise will be worth 3 points. The student will have at least one hour for each part (at least two hours for the whole written exam). Passing the exam requires the achievement of at least 8/15 in each of the two parts and the overall grade of 18/30.
The final mark will also take into account the evaluation obtained for practical laboratory exercises. The student will be evaluated based on her/his general behaviour during the laboratory exercises and on the completeness/correctness of the reports to be presented at the end of the exercises themselves.
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
Educational website(s)
Professor(s)
Reception:
Only by appointment
Office at the chemistry department
Reception:
by appointment
Chemistry Department, via Golgi, 19, Building 5, 3rd floor, corpo (unit) B, Room 3058B