Unit ORGANIC CHEMISTRY - PART 2
- Course
- Pharmacy
- Study-unit Code
- A003589
- Location
- PERUGIA
- Curriculum
- In all curricula
- Teacher
- Claudio Santi
- Teachers
-
- Claudio Santi
- Luca Sancineto (Codocenza)
- Ornelio Rosati
- Hours
- 26 ore - Claudio Santi
- 16 ore (Codocenza) - Luca Sancineto
- 12 ore - Ornelio Rosati
- CFU
- 6
- Course Regulation
- Coorte 2023
- Offered
- 2023/24
- Learning activities
- Base
- Area
- Discipline chimiche
- Academic discipline
- CHIM/06
- Type of study-unit
- Obbligatorio (Required)
- Type of learning activities
- Attività formativa monodisciplinare
- Language of instruction
- Italian
- Contents
- Structure of organic molecules, nomenclature, synthesis and reactivity of carboxyl derivtives, carbonyl derivatives, aromatic compounds, heterocycles, carbohydrates, amino acids and proteins
- Reference texts
- Peter C. Vollhardt, Neil E. Schore CHIMICA ORGANICA Zanichelli 4a ed
Brown, Iverson, Anslyn, Foote CHIMICA ORGANICA Edises, VI edizione - Educational objectives
- Knowledge of nomenclature and reactivity of gcarboxyl derivtives, carbonyl derivatives, aromatic compounds, heterocycles, amines, carbohydrates, amino acids and proteins, including stereochemical aspects. Being able to apply the acquired principles to the study of molecules of biochemical and pharmaceutical interest.
- Prerequisites
- The student should be familiar with the basic notions of general chemistry (inorganic and organic), in particular must have passed the exam of General Chemistry and Organic Chemistry I
- Teaching methods
- Frontal lectures where the professor will present all the topics of the course, introducing some exercises as example
- Other information
- Extra exercises will be provided during the course, at the end of the course and before the summer session. Before the other sections, the teacher and the integrative teaching staff will be available to provide students clarification and explanation.
- Learning verification modality
- The student will be graded through a written and oral test. The student will be asked to provide the correct nomenclature and configuration of organic molecules and to resolve exercises using notions he has learned on synthesis and reactivity. Changes in grading may be applied according to the COVID pandemic situation
- Extended program
- Benzene and aromaticity: Nomenclature of benzene derivatives - Structure and resonance energy of benzene: a first look at the aromaticity - Molecular p orbitals of benzene - Hückel's rule - Synthesis of benzene derivatives: electrophilic aromatic substitution - Halogenation of benzene: the need for a catalyst - Nitration and sulfonation of benzene - Friedel-Crafts alkylation - Limits of Friedel-Crafts alkylations - Friedel-Crafts acylation.
Control of regioselectivity of substituents: - Activating or deactivating effect of substituents on the benzene ring - Orienting electron-donor effects of alkyl groups - Orienting effects of substituents conjugated to the benzene-electrophilic ring on disubstituted benzenes
Aldehydes and ketones: The carbonyl group - Nomenclature of aldehydes and ketones - The structure of the carbonyl group - Preparation of aldehydes and ketones - Reactivity of the carbonyl group: addition mechanisms - The addition of water and the formation of hydrates - The addition of alcohols and the formation of hemiacetals and acetals - Acetals as protective groups - Nucleophilic addition of ammonia and its derivatives - Deoxygenation of the carbonyl group - Addition of hydrogen cyanide to give cyanohydrins - Additions of phosphorus ylides: the Wittig reaction Oxidation with peroxocarboxylic acids : Baeyer-Villiger oxidation - Oxidative assays for aldehydes
Enols, enolates and aldol condensation Aldehydes and ketones a, ß-unsaturated - Acidity of aldehydes and ketones: enolate ions - Keto-enol balances The halogenation of aldehydes and ketones - Alkylation of aldehydes and ketones - Attack of enolates to the carbonyl function : aldol condensation - Cross aldol condensation - Additions conjugated to aldehydes and ketones a, ß-unsaturated - Additions 1,2 and 1,4 of organometallic reagents - Conjugate addition of enolated ions: Michael's addition and Robinson's ringing
Carboxylic acids - The nomenclature of carboxylic acids - Structural and physical properties of carboxylic acids - Acid and basic character of carboxylic acids - Methods for the introduction of the carboxylic functional group - Substitution of carboxylic carbon: the mechanism of addition-elimination - Derivatives of carboxylic acids: acyl halides and anhydrides - Derivatives of carboxylic acids: esters, amides, halides, anhydrides, sinetheses and reactivity - Reduction of carboxylic acids with lithium aluminum hydride - Bromination in the position adjacent to the carboxylic group: the Hell-Volhard-Zelinsky reaction - Biological activity of carboxylic acids
Chemistry of benzene substituents Alkylbenzenes, phenols and benzenamines
Enolates of esters and Claisen condensation - Synthesis of ß-dicarbonyl compounds; equivalents of acyl-anions - Fatty Acids - Carbohydrates - Polyfunctional compounds in nature - Amino acids, peptides, proteins and nucleic acids - Obiettivi Agenda 2030 per lo sviluppo sostenibile
- Questo insegnamento concorre alla realizzazione degli obiettivi ONU dell'Agenda 2030 per lo Sviluppo Sostenibile