Organic Chemistry II and Laboratory M - Z

Module Module 1

The course aims to provide students with a more in-depth training in Organic Chemistry from the first basic course, particularly with regard to nomenclature, chemical properties and reactivity of multifunctional compounds; the main classes of organic compounds of biological significance: carbohydrates, amino acids and peptides, lipids; the major heterocyclic systems. Students will gain further knowledge on advanced organic synthesis reactions, learning to develop simple synthetic sequences of polyfunctional organic compounds and to apply the principles of modern synthetic strategies for disconnection approaches, formation of carbon-carbon bonds, deprotection protection of functional groups. 

Furthermore, in reference to the so-called Dublin Descriptors, this course helps to acquire the following skills:

D1 - Knowledge and understanding: The students will have to demonstrate their mastery of basic knowledge about the organic chemistry. In particular, the students must show their ability to rationalize property-structure correlations of organic molecules

D2 - Ability to apply knowledge: The students will have to show knowledge and understanding of organic reactions required to produce synthetic processes of relatively complex molecules.

D3 - Autonomy of judgment: The students will have to apply their knowledge, understanding and skills. Particularly, the students must show his ability to critical reasoning and their ability to identify the most appropriate chemical reactions aimed to the synthesis of organic molecules.

D4 - Communication skills: The students must be able to communicate clearly with a correct property of language and terminological rigor their conclusions.

D5- Learning skills: The students will have to develop learning skills that will enable them to continue studying in a self-directed or autonomous way.

The teaching will take place through the discussion of the various topics reported in the program and will include days dedicated to the clarification of doubts and the simulation of the oral exam.Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes with respect to previous statements, in line with the programme planned and outlined in the syllabus. Learning assessment may also be carried out on line, should the conditions require it. Exam schedule:

 Mercoledi 01/02/2023

Giovedi 23/02/2023

Mercoledi 05/04/2023 (sospensione didattica)

Martedi 27/06/2023

Mercoledi 19/07/2023

Giovedi 07/09/2023

Mercoledi 27/09/2023

Mercoledi 20/12/2023 (sospensione didattica)

The acquisition of the objectives relating to the following disciplines is required: General and Inorganic Chemistry, Organic Chemistry I

Strongly recommended although not mandatory to take the exam.

Enols, Enolates, enamines

Keto-enol  tautomerism –Enolization catalysed by acids and bases – Enols stability  - Acidity of a-hydrogens of carbonyl compounds  – Enolate ions –   Halogenation in a of carbonyl and carboxylic compounds –Haloform reaction –Alkylation of acarbons –  Alkylation and acylation  of acarbons by using enamines – The Aldol condensation: synthesis of  b-hydroxyaldehydes – Dehydratation of aldols  – Cross-condensation of aldols – The Claisen condensation: synthesis of  b-ketoesters – The Claisen ester condensation compared to the aldol condensation – Problems with acylation at carbon  –  Intramolecular  Claisen ester and aldol  condensations –Robinson annelation–   b-ketoacids  decarboxylation –Malonic synthesis –Acetoacetic synthesis

 

a,b- unsatured carbonyl compounds 

Electron Delocalization and Resonance - Conjugation effects  - Conjugate additions reactions  –  b-carbon alkylation  – Michael reaction – Conjugate addition  or direct addition to the carbonyl group - “hard” e “soft” nucleophiles -  Conjugate addition  of ammonia and amines– Conjugate addition  of alcohols and thiols – Reactions with organometallic reagents – The Effect of the  Cu(I) salts – Conjugate addition  of  enolates– Conjugate addition followed by cyclization  in the ring synthesis

 

Sulfur compounds

Thiols : structure, nomenclature, physical properties – Acidity - Preparation reactions – oxydation  reactions– Sulfides – Disulfides - Solfinic  and Solfonic acids

Aromatic heterocycles
Heteroaromaticity – Five- and six membered aromatic heterocyclic rings - Furan, pyrrole, thiophene, pyridine. Synthesis starting from 1,3 and 1,4-dicarbonylic compounds   –  Heteroaromatic rings with two o more heteroatoms- Benzo-fused heterocycles- Electrophilic Aromatic Substitution Reactions, Nucleophilic Aromatic Substitution Reactions, oxidations, reductions –Pyridine N-oxyde.

Carbohydrates

Classification of Carbohydrates - The D and L Notation - Configurations of Aldoses  and  Ketoses - Redox Reactions of Monosaccharides – Oxidation - Chain Elongation: the Kiliani–Fischer Synthesis -

Chain Shortening: the Wohl and Ruff Degradation- Cyclic Structure of Monosaccharides: Hemiacetal Formation - Acylation and Alkylation of Monosaccharides -Formation of Glycosides - The Anomeric Effect - Reducing and Nonreducing Sugars – Mutarotation – Disaccharides - Polysaccharides

Solar energy,  photosynthesis and the flow to Living Organisms- Some Eco Friendly  Products Derived from cellulose fermentation

Lipids

Fatty Acids- Fats and Oils – Waxes – Triglycerides – Saponification –Micelles - detergent properties- Soaps and detergents - Prostaglandins – Steroids – Terpenes – Phospholipids –Phospholipid bilayers assembly-  Liposomes - Cell membrane – Lecithins –Sphingolipids – Fat soluble vitamins

Required Texts 

1)  W.H.Brown, B.L.Iverson, E.V.Anslyn, C.S.Foote, CHIMICA ORGANICA, Edises
2) D. Sica, F. Zollo, CHIMICA DEI COMPOSTI ETEROCICLICI, Edises
3) P.Y.Bruice, CHIMICA ORGANICA, Edises
4) J. Claiden, N. Greeves, S. Warren, ORGANIC CHEMISTRY, Oxford University Press 2012

The final exam consists of an oral test. The oral exam consists in the discussion of the topics covered in the course and is aimed at verifying the knowledge and skills acquired by the student, his ability to connect the various topics covered with current problems and his ability to use an appropriate language in the expose the proposed topics. Verification of learning can also be carried out electronically, should the conditions require it.

Enols, enolates and enamines, Aldol condensation, Claisen condensation, Robinson ringing - Decarboxylation of ß-ketoacids - Malonic synthesis - Acetacetic synthesis, Carbonyl compounds alpha, beta unsaturated, Michael reaction, Aromatic heterocycle compounds: furan, pyrrole, thiophene and pyridine, Carbohydrates, Chain elongation: the Kiliani-Fischer synthesis - Chain shortening: Wohl's degradation.