Learning objectives
Knowledge and understanding:
The course aims to teach students the scientific methodology that is the basis of organic chemistry and related disciplines; The course has the purpose of providing the basic concepts to understand, and also predict, the reactivity of the functional groups present in simple and complex organic molecules.The course also provides students with the basic language relating to the rationalization and interpretation of the main reaction mechanisms in correlation with the different mono and poly functional groups that are the subject of the course.
Applied knowledge and understanding :
The student will acquire the expertise to know the reactivity of functional groups present in organic molecules and to understand the reactivity of organic compounds according to the main reaction mechanisms.
Prerequisites
Having attended the course of Organic Chemistry 1
Course unit content
1: Heteroaromaticity - Aromaticity and Huckel rule for heteroaromatic systems; - 5 and 6 atom heterocycles, reactivity: orientation in the electrophilic aromatic substitution reactions; - Orientation in the electrophilic aromatic substitution of naphthalene ring. 2: Aldehydes and ketones – Reactivity: nucleophilic addition and protonation-addition reactions; - Reactions of hydration, formation of hemiacetals and acetals, formation of imines and enamines, Wittig reactions, reactions with carbon nucleophiles; - Nucleophilic Addition to conjugated α, β unsaturated systems, kinetic and thermodynamic control. Michael addition. Aldehydes and ketones as electrophiles in SEAR. 3: Carboxylic acids and derivatives - Acidity of carboxylic acids, influence of the substituents; - Discussion of nucleophilic acyl substitutions; - Derivatives of carboxylic acids, synthesis and reactivity; - Electrophilic rearrangements towards C, N and O electron deficient atoms; - Thioesters and symmetrical and mixed anhydrides. 4: Substitution reactions in alpha to the carbonyl group - keto-enol tautomerism, reactions of α substitution, halogenations; - Alkylation of enolates, malonic and acetacetic synthesis, direct alkylation; - Condensation reactions of carbonyl compounds, aldol condensation and dehydration, Koevenagel condensation, Claisen condensation, condensation of importance in biological components. 5: Amines - Basicity of amines - Synthesis and reactivity of amines - Quaternary ammonium salts. 6: Carbohydrates - Classification of carbohydrates, monosaccharides, disaccharides, polysaccharides – Five and six-atom cyclic structures - Stereochemistry, formulas of Fisher and Haworth, anomers and epimers; - Mutarotation, acetals and hemiacetals; - Glycosidic bond: formation and stereochemistry of this bond; - Cellulose, starch and glycogen. 7: Amino acids, peptides, proteins - Amino acids: structure and acidity, isoelectric points, the synthesis of amino acids – peptides: peptide bond, introduction to the synthesis of peptides; - Introduction to proteins. 8: Lipids - Lipids, waxes, fats and oils; - Triglycerides, phospholipids, sphingolipids, soaps; - Terpenes and steroids. 9: Nucleic Acids - Structure of nucleic acids, nucleosides and nucleotides; - Purine and pyrimidine bases.
Some synthesis of mono-and polyfunctional molecules will be discussed according to the retrosynthetic approach.
Full programme
1: Heteroaromaticity - Aromaticity and Huckel rule for heteroaromatic systems; - 5 and 6 atom heterocycles, reactivity: orientation in the electrophilic aromatic substitution reactions; - Orientation in the electrophilic aromatic substitution of naphthalene ring. 2: Aldehydes and ketones – Reactivity: nucleophilic addition and protonation-addition reactions; - Reactions of hydration, formation of hemiacetals and acetals, formation of imines and enamines, Wittig reactions, reactions with carbon nucleophiles; - Nucleophilic Addition to conjugated α, β unsaturated systems, kinetic and thermodynamic control. Michael addition. Aldehydes and ketones as electrophiles in SEAR. 3: Carboxylic acids and derivatives - Acidity of carboxylic acids, influence of the substituents; - Discussion of nucleophilic acyl substitutions; - Derivatives of carboxylic acids, synthesis and reactivity; - Electrophilic rearrangements towards C, N and O electron deficient atoms; - Thioesters and symmetrical and mixed anhydrides. 4: Substitution reactions in alpha to the carbonyl group - keto-enol tautomerism, reactions of α substitution, halogenations; - Alkylation of enolates, malonic and acetacetic synthesis, direct alkylation; - Condensation reactions of carbonyl compounds, aldol condensation and dehydration, Koevenagel condensation, Claisen condensation, condensation of importance in biological components. 5: Amines - Basicity of amines - Synthesis and reactivity of amines - Quaternary ammonium salts. 6: Carbohydrates - Classification of carbohydrates, monosaccharides, disaccharides, polysaccharides – Five and six-atom cyclic structures - Stereochemistry, formulas of Fisher and Haworth, anomers and epimers; - Mutarotation, acetals and hemiacetals; - Glycosidic bond: formation and stereochemistry of this bond; - Cellulose, starch and glycogen. 7: Amino acids, peptides, proteins - Amino acids: structure and acidity, isoelectric points, the synthesis of amino acids – peptides: peptide bond, introduction to the synthesis of peptides; - Introduction to proteins. 8: Lipids - Lipids, waxes, fats and oils; - Triglycerides, phospholipids, sphingolipids, soaps; - Terpenes and steroids. 9: Nucleic Acids - Structure of nucleic acids, nucleosides and nucleotides; - Purine and pyrimidine bases.
Some synthesis of mono-and polyfunctional molecules will be discussed according to the retrosynthetic approach.
Bibliography
- V. H. Brown, C. Foote: Chimica Organica, Casa Ed. Edises, Napoli
- Morrison-Boyd: Chimica Organica, Casa Ed. Ambrosiana, Milano.
- P. Volhardt, N. Schore: Chimica Organica, Casa Ed. Zanichelli, Bologna.
- J. McMurry: Chimica Organica, Casa Ed. Piccin, Padova
Teaching methods
Teaching materials available to students. The lectures are supplemented by tutoring activities in the classroom.
The teacher is available to students for explanations of the topics covered during the course, by appointment.
Assessment methods and criteria
The acquisition of a formally correct language will be checked, as well as the ability to express the content in a clear way and to connect the knowledge acquired in different parts of the course; it will be evaluated the ability to apply the fundamental concepts of organic chemistry in the rationalization and prediction of the reactivity of an organic compound (also complex).
In particular, the evaluation will be done through a written and oral exam, and will be based on the following parameters: a) knowledge and understanding of the methods and language of the discipline (6 points), b) understanding and ability to apply the knowledge acquired (15 points); c) independence of judgment in dealing with problems relating to the topics of the course (3 points); d) ability to express their knowledge and skills both in writing and verbally, using a chemical language appropriately (5 points).
The final evaluation is integrated with the course of the Laboratory of Organic Chemistry II.
Other information
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