Learning objectives
At the end of the course the student is expected to be able to:
-to understand the scientific methodology that is the basis of organic chemistry and related disciplines
-to posses the basic concepts to understand, and also predict, the reactivity of the functional groups present in simple as well as complex organic molecules
-to know the basic language regarding 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.
-to posses the expertise to rationalize the reactivity of functional groups present in organic molecules and to preview the reactivity of organic compounds according to the main reaction mechanisms
-to apply the retrosynthetic approach to the preparation of simple organic compounds.
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, characteristics and reactivity: orientation in the electrophilic aromatic substitution reactions; Nucleofilic aromatic subtitution reactions- Orientation in the electrophilic aromatic substitution of naphthalene ring. 2: Aldehydes and ketones – Reactivity: nucleophilic addition and protonation-addition reactions; - Addition reactions of O-nucleophiles (hydration, formation of hemiacetals and acetals), N-nucleophiles (formation of imines, enamines and oximes), C-nucleophiles (synthesis of cyanidrins, alcohols and Wittig reaction); - 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. 4: Substitution reactions in alpha to the carbonyl group - keto-enol tautomerism, reactions of α substitution, halogenations; - Alkylation of enolates: malonic and acetacetic syntheses, direct alkylation; - Condensation reactions of carbonyl compounds, aldol condensation and mixed condensation, Koevenagel condensation. Ester autocondensation (Claisen condensation). Condensations in biological field 5: Amines - Basicity of amines - Synthesis and reactivity of amines – Hodmann elimination of quaternary ammonium salts. Reactivity of anilines. 6: Amino acids, peptides, proteins - Amino acids: structure and acidity, isoelectric point, titration curve, syntheses of amino acids – Peptides: peptide bond, synthetic strategy for dipeptide preparation, introduction to the solid phase synthesis of peptides; - Introduction to proteins. 7. : Carbohydrates - Classification of carbohydrates, monosaccharides, disaccharides, polysaccharides – Five and six-atom cyclic structures - Stereochemistry, Fisher’s and Haworth’s structures, anomers and epimers; - Relative configurations: treo/eritro , syn/anti- and meso compounds. Acetals and hemiacetals, mutarotation and reducing ability - Glycosidic bond: formation and stereochemistry of this bond;reactivity of the different hydroxy groups- Cellulose, starch and glycogen. 8: Lipids - Triglycerides (fats and oils), 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, characteristics and reactivity: orientation in the electrophilic aromatic substitution reactions; Nucleofilic aromatic subtitution reactions- Orientation in the electrophilic aromatic substitution of naphthalene ring. 2: Aldehydes and ketones – Reactivity: nucleophilic addition and protonation-addition reactions; - Addition reactions of O-nucleophiles (hydration, formation of hemiacetals and acetals), N-nucleophiles (formation of imines, enamines and oximes), C-nucleophiles (synthesis of cyanidrins, alcohols and Wittig reaction); - 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. 4: Substitution reactions in alpha to the carbonyl group - keto-enol tautomerism, reactions of α substitution, halogenations; - Alkylation of enolates: malonic and acetacetic syntheses, direct alkylation; - Condensation reactions of carbonyl compounds, aldol condensation and mixed condensation, Koevenagel condensation. Ester autocondensation (Claisen condensation). Condensations in biological field 5: Amines - Basicity of amines - Synthesis and reactivity of amines – Hodmann elimination of quaternary ammonium salts. Reactivity of anilines. 6: Amino acids, peptides, proteins - Amino acids: structure and acidity, isoelectric point, titration curve, syntheses of amino acids – Peptides: peptide bond, synthetic strategy for dipeptide preparation, introduction to the solid phase synthesis of peptides; - Introduction to proteins. 7. : Carbohydrates - Classification of carbohydrates, monosaccharides, disaccharides, polysaccharides – Five and six-atom cyclic structures - Stereochemistry, Fisher’s and Haworth’s structures, anomers and epimers; - Relative configurations: treo/eritro , syn/anti- and meso compounds. Acetals and hemiacetals, mutarotation and reducing ability - Glycosidic bond: formation and stereochemistry of this bond;reactivity of the different hydroxy groups- Cellulose, starch and glycogen. 8: Lipids - Triglycerides (fats and oils), 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
-W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. 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.
Teaching methods
Lesson and exercise discussion. The slides used during the lessons are available to the students in the web. The subscription to the online course is required to download the files containing the slides. 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
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Other information
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 of the reactivity of various compound classes studied during the course, it will be evaluated the ability to to apply the fundamental concepts of organic chemistry in the rationalization and prediction of the reactivity of organic compounds (also complexes).
In particular, assessment of the learning involves two moments, a written test and an oral exam.
1) The written test consists of discussion and resolution of some exercises. During the written test the student is required to
• be able to apply his/her knowledge of the reactivity of organic compounds belonging to the classes studied during the course
• be able to design the synthesis of an organic compound by applying the retrosynthetic approach.
The duration of the written test is 2:30 hours.
The assessment scale is 0-30 and the student is admitted to the oral test if the written test reaches 18.
The results of the written tests will be announced over the two weeks following the test using the ESSETRE platform.
2) The oral test consists of a critical discussion of any errors in the written test and other topics discussed during the course.
The oral test is evaluated on a scale of 0-30.
The final vote is the arithmetic mean of the votes of the two trials, and it shall be communicated immediately upon the end of the oral test.
Please note that online registration on the application is compulsory both in the case of the written test and in the case of the oral test
2030 agenda goals for sustainable development
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