Organic Chemistry
A.Y. 2023/2024
Learning objectives
The aim of this course is to provide the student with a basic knowledge of Organic Chemistry, obtained from the study of structure, properties and reaction of simple molecules. This knowledge will support the student in the following courses on more complicated systems.
Expected learning outcomes
Knowledge and understanding
·know nomenclature, structure, properties and general reactivity of the main classes of organic compounds
·know the stereochemistry
·know the main classes of organic reaction
·know structures and properties of amino acids, peptides, fatty acids and carbohydrates.
Ability to apply knowledge and understanding
·identification of molecular compounds on the base of their functional groups
·identification of the main classes of organic reaction
·use the nomenlcature
·graphically represent the main organic molecules
Judgment capacity
·capacity to understand and predict the chemical and physical properties and the reactivity of organic molecules in non-complex structures..
Communication skills
·extract and summarize the relevant information from a text concerning a chemical problem
·communicate effectively, both orally and in writing, using the correct terminology
Learning ability
·ability to understand a scientific text of organic chemistry and apply the information learned to the solution of a new problem.
·know nomenclature, structure, properties and general reactivity of the main classes of organic compounds
·know the stereochemistry
·know the main classes of organic reaction
·know structures and properties of amino acids, peptides, fatty acids and carbohydrates.
Ability to apply knowledge and understanding
·identification of molecular compounds on the base of their functional groups
·identification of the main classes of organic reaction
·use the nomenlcature
·graphically represent the main organic molecules
Judgment capacity
·capacity to understand and predict the chemical and physical properties and the reactivity of organic molecules in non-complex structures..
Communication skills
·extract and summarize the relevant information from a text concerning a chemical problem
·communicate effectively, both orally and in writing, using the correct terminology
Learning ability
·ability to understand a scientific text of organic chemistry and apply the information learned to the solution of a new problem.
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
Single session
Responsible
Lesson period
Second semester
Course syllabus
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. IUPAC nomenclature, structure and E/Z isomerism; relative stability. Synthesis and reactivity. Electrophilic addition. Alkynes. IUPAC nomenclature, acidity and reactivity.
Delocalized systems. Resonance theory. Allylic system and conjugated dienes. Benzene: structure, IUPAC nomenclature. Resonance energy. Huckel rule. Reactivity of benzene. Heteroaromatic compounds.
Haloalkanes. IUPAC nomenclature. Nucleophilic substitution SN2 and SN1: mechanisms, stereochemistry. Elimination reactions: mechanisms E1 and E2.
Alcohols, Phenols, Thiols, Ethers. IUPAC nomenclature. Alcohols as acids and bases. Reactivity. Oxidations. Acidity of phenols. Oxidation of thiols. Synthesis and reactivity of ethers.
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. Fatty acids and surface-active properties. Reactivity: nucleophilic acyl substitution. Esters, anhydrides, acid chlorides, amides, nitriles. Claisen and Dieckman condensation of esters.
Alkylamines. IUPAC nomenclature. Basicity and reactivity.
Aminoacids. Structure and properties. Natural amino acids and their classification. Definition of peptide and protein. Principles of peptide synthesis. Carbohydrates: nomenclature and reactivity.
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. IUPAC nomenclature, structure and E/Z isomerism; relative stability. Synthesis and reactivity. Electrophilic addition. Alkynes. IUPAC nomenclature, acidity and reactivity.
Delocalized systems. Resonance theory. Allylic system and conjugated dienes. Benzene: structure, IUPAC nomenclature. Resonance energy. Huckel rule. Reactivity of benzene. Heteroaromatic compounds.
Haloalkanes. IUPAC nomenclature. Nucleophilic substitution SN2 and SN1: mechanisms, stereochemistry. Elimination reactions: mechanisms E1 and E2.
Alcohols, Phenols, Thiols, Ethers. IUPAC nomenclature. Alcohols as acids and bases. Reactivity. Oxidations. Acidity of phenols. Oxidation of thiols. Synthesis and reactivity of ethers.
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. Fatty acids and surface-active properties. Reactivity: nucleophilic acyl substitution. Esters, anhydrides, acid chlorides, amides, nitriles. Claisen and Dieckman condensation of esters.
Alkylamines. IUPAC nomenclature. Basicity and reactivity.
Aminoacids. Structure and properties. Natural amino acids and their classification. Definition of peptide and protein. Principles of peptide synthesis. Carbohydrates: nomenclature and reactivity.
Prerequisites for admission
Knowledge of the laws and fundamental principles of general chemistry, such as: the atomic structure, the chemical bond, the chemical equilibrium and the concepts of acidity and basicity.
Teaching methods
Lectures and exercises
Teaching Resources
P. Y. Bruice - Elementi di Chimica Organica, EdiSES
W.H. Brown, E. Poon - Introduzione alla Chimica Organica EdiSES
McMurry - Fondamenti di Chimica Organica Zanichelli
Slides of the lectures
W.H. Brown, E. Poon - Introduzione alla Chimica Organica EdiSES
McMurry - Fondamenti di Chimica Organica Zanichelli
Slides of the lectures
Assessment methods and Criteria
Written test: 10 questions/exercises in two hours. Each exercise enables the acquisition of a score between zero and three points. The admission to the oral test is achieved with the obtainment of at least 18 points.
Oral test: after one or two weeks from the written exam and it is optional.
The following skills will be evaluated:
Knowledge and understanding ·know nomenclature, structure, properties and general reactivity of the main classes of organic compounds ·know the stereochemistry ·know the main classes of organic reaction ·know structures and properties of amino acids, peptides, fatty acids and carbohydrates. Ability to apply knowledge and understanding ·identification of molecular compounds on the base of their functional groups ·identification of the main classes of organic reaction ·use the nomenlcature ·graphically represent the main organic molecules Judgment capacity ·capacity to understand and predict the chemical and physical properties and the reactivity of organic molecules in non-complex structures.. Communication skills ·extract and summarize the relevant information from a text concerning a chemical problem ·communicate effectively, both orally and in writing, using the correct terminology Learning ability ·ability to understand a scientific text of organic chemistry and apply the information learned to the solution of a new problem.
Oral test: after one or two weeks from the written exam and it is optional.
The following skills will be evaluated:
Knowledge and understanding ·know nomenclature, structure, properties and general reactivity of the main classes of organic compounds ·know the stereochemistry ·know the main classes of organic reaction ·know structures and properties of amino acids, peptides, fatty acids and carbohydrates. Ability to apply knowledge and understanding ·identification of molecular compounds on the base of their functional groups ·identification of the main classes of organic reaction ·use the nomenlcature ·graphically represent the main organic molecules Judgment capacity ·capacity to understand and predict the chemical and physical properties and the reactivity of organic molecules in non-complex structures.. Communication skills ·extract and summarize the relevant information from a text concerning a chemical problem ·communicate effectively, both orally and in writing, using the correct terminology Learning ability ·ability to understand a scientific text of organic chemistry and apply the information learned to the solution of a new problem.
Educational website(s)
Professor(s)