The teaching aims to provide the student with a more in-depth training in Organic Chemistry than the first core courses. In particular, the course is aimed at providing students with the theoretical and logical tools to consider the relationships between the different spectroscopic methods used for structural identification of organic compounds and how they can be used in combination to assign structure to unknown compounds. Students will also gain knowledge of pericyclic reactions, rearrangement reactions, radical reactions, carbenes and nitrenes reactions, carbon-carbon bond formation, and the fundamentals of reactivity and asymmetric organic synthesis including first hints of organocatalysis, learning how to develop simple synthetic sequences of polyfunctional organic compounds and how to apply the principles of modern synthetic strategies: approaches by disconnection, carbon-carbon bond formation, organometallics, and protection and deprotection of functional groups. In addition, the main classes of biologically relevant organic compounds will be introduced: lipids, carbohydrates, amino acids and proteins, and nucleic acids.

1) Review of spectroscopic methods

Spectroscopy to distinguish and explain C=O group reactions - Spectroscopy to explain the reactivity and reaction products of a,b-unsaturated carbonyl compounds - Spectroscopy to explain the size of rings - Spectroscopy to assign the structure of unknown compounds - Some guidelines for solving unknown structures

2) Saturated heterocycles and stereoelectronic effects

Reactions of saturated heterocycles - Conformation of saturated heterocycles - Synthesizing heterocycles: ring closure reactions (Thorpe-Ingold effect - Baldwin's rules) - Ring size and NMR - Geminal coupling (2J) - Diastereotopic groups

3) Stereoselectivity

Stereochemical control in six-membered rings - Reactions of small rings - Stereochemical control in cyclohexene epoxides - Stereoselectivity in bicyclic compounds (bicyclic pontate, bicyclic fused, and spirocyclic) - Reactions with cyclic intermediates or cyclic transition states

4) Diastereoselectivity

Prochirality - The Felkin-Anh model - Stereoselective reactions of alkenes - Stereoselective aldol reactions

5) Pericylic reactions 1: cycloadditions

The Diels-Alder reaction - The “ene” Alder reaction - Photochemical [2 + 2] cycloadditions - Thermal [2 + 2] cycloadditions - 1,3-dipolar cycloadditions - Cycloaddition of alkenes with osmium tetroxide and with ozone

6) Pericylic reactions 2: sigmatropic and electrocyclic reactions

[3,3]-sigmatropic transposition (Claisen transposition, Cope transposition, Overman rearrangement) - [2,3]-sigmatropic transposition - [1,5]-sigmatropic hydrogen shifts - Electrocyclic reactions (Nazarov cyclization)

7) Participation, rearrangement and fragmentation reactions

The Payne rearrangement - The Wagner-Meerwein rearrangement - The pinacol rearrangement - The dienone-phenol rearrangement - The benzyl acid rearrangement - The Favorskii rearrangement - The Baeyer-Villiger reaction - The Beckmann rearrangement - Ring expansion via fragmentation - The Eschenmoser fragmentation

8) Radical reactions

How to form radicals - Stable radicals - Stability of radicals - Radical-radical reactions (Bouveault-Blanc reduction, pinacol reaction, McMurry reaction and acyloin reaction) - Chain radical reactions (chlorination and bromination of alkanes, allyl bromination) Reversal of selectivity: radical substitution of Br for H - Formation of carbon-carbon bonds with radicals

9) Synthesis and reactions of carbenes and nitrenes

Synthesis of methyl esters from carboxylic acids with diazomethane - Synthesis of carbenes from diazo compounds, from tosylhydrazones, from a-elimination and by cation deprotonation - Singlet and triplet carbenes - Reaction of carbenes: Insertion into p-bonds (cyclopropanation); insertion into s-bonds and rearrangements (Wolff rearrangement, Arndt-Eistert homologation, Corey-Fuchs homologation and Seyferth-Gilbert homologation) - Nitrenes - Reactions of nitrenes (Curtius rearrangement and Hofmann rearrangement) - Carbenoids (carbene bonded to a metal) and metathesis reactions - N-heterocyclic carbenes

10) Organometallic chemistry

Transition metal complexes - Bonding and reactions in transition metal complexes - Heck reaction - Cross-coupling of organometallic compounds and halides (Kumada reaction, Stille reaction, Negishi reaction and Suzuki reaction) - Sonogashira reaction - Buchwald-Hartwig amination - Wacker oxidation

11) Asymmetric synthesis

Resolution of a racemic mixture - Chiral auxiliaries - Chiral reagents - Asymmetric catalysis - Organocatalysis - Enzymes as catalysts

12) Biological Chemistry

Nucleic acids - Amino acids and proteins - Carbohydrates - Lipids - The mechanisms of biological chemistry - Natural products - Fatty acids and other polyketides derived from acetyl CoA -Terpenes

Passing the General and Inorganic Chemistry, Fundamentals of Organic Chemistry and Physical Chemistry, Physics with elements of math exams.

•     D1 - KNOWLEDGE AND UNDERSTANDING SKILLS.

Upon completion of this training activity, the student should demonstrate the ability to:

1) have a thorough understanding of the structure-property-reactivity relationships of the main families of polyfunctional organic compounds;

2) know the principles that guide organic reactions and allow the rational interpretation of reaction mechanisms;

3) know the physicochemical properties of polyfunctional organic molecules to familiarize themselves with compounds often used in the laboratory;

4) to know the centrality of organic chemistry at the interface with biochemistry and medicinal chemistry;

5) know the various spectroscopic investigation methods for structural identification of organic compounds.

These skills will be tested through a written test and oral questions.

•     D2 - ABILITY TO APPLY KNOWLEDGE AND UNDERSTANDING.

Upon completion of this training activity, the student should demonstrate the ability to:

1) describe reaction mechanisms in polyfunctional organic molecules;

2) classify organic transformations on the basis of the interactions between the different functional groups present in an organic molecule;

3) describe the design of organic transformations needed to prepare simple organic compounds;

4) describe the most functional recognition reactions of the major functional groups;

These skills will be assessed through a written test and oral questions.

•     D3 - AUTONOMY OF JUDGMENT:

Upon completion of this educational activity, the student should demonstrate the ability to:
1) acquire the basic principles of organic synthesis for the development of simple synthetic sequences of polyfunctional organic compounds;
2) ability to apply the acquired knowledge and understanding of reaction mechanisms to solve organic chemistry problems;
3) propose modern synthetic strategies for the synthesis of organic compounds; and
4) compare spectroscopic data in order to determine the structures of unknown organic compounds;
These skills will be tested by both written test and application-oriented oral questions.

• D4 - COMMUNICATION SKILLS.

Upon completion of the course, the student must demonstrate the ability to communicate clearly and in appropriate language the concepts learned during the course.
These skills will be tested through the oral test.

•     D5 - LEARNING SKILLS

Upon completion of this coursework, the student will be expected to demonstrate the ability to find and apply new information, relative to that provided during the coursework, necessary to design syntheses of new organic molecules.

The teaching material prepared by the lecturer in addition to recommended textbooks (such as for instance slides, lecture notes, exercises, bibliography) and communications from the lecturer specific to the course can be found inside the Moodle platform › blended.uniurb.it

Classroom exercises

Teaching

The course involves face-to-face lectures in which the lecturer explains the concepts and offers practical exercises to promote understanding.

Students may intervene in the lectures to request clarifications from the lecturer.

Attendance

There are no attendance requirements although attendance is strongly recommended.

Basic knowledge related to the disciplines of chemistry, physics and mathematics is required.

Course books

Organic Chemistry- Clayden, Greeves, Warren, Wothers - Second Edition, Ed. OXFORD

Assessment

The verification of learning that aims to ascertain the acquisition of the expected knowledge and skills is done through the final examination only, which consists of a written test and an oral test.

The written test consists of solving six exercises. The exercises will be written according to types similar to the exercises carried out in the classroom by the lecturer. The evaluation of the written test is given in thirtieths and will be considered passed with a minimum grade of 18/30. The duration of the written test is 2 hours.

The oral test is reserved for students who have passed the written test and achieved a minium grade of 18/30 and will focus on questions covered in the course syllabus.

The final grade, which takes into account the outcomes of the written test and the oral test, is given in thirtieths and reflects the candidate's overall evaluation.

Disability and Specific Learning Disorders (SLD)

Students who have registered their disability certification or SLD certification with the Inclusion and Right to Study Office can request to use conceptual maps (for keywords) during exams.

To this end, it is necessary to send the maps, two weeks before the exam date, to the course instructor, who will verify their compliance with the university guidelines and may request modifications.

Teaching

Teaching materials and specific teacher communications can be found, along with other supporting activities, within the Moodle platform ' blended.uniurb.it

Attendance

Non vi son obblighi di frequenza anche se è fortemente consigliata la presenza.

Sono richieste le conoscenze di base relative alle discipline di chimica, fisica e matematica.

Course books

Organic Chemistry- Clayden, Greeves, Warren, Wothers - Second Edition, Ed. OXFORD

Assessment

The verification of learning that aims to ascertain the acquisition of the expected knowledge and skills is done through the final examination only, which consists of a written test and an oral test.

The written test consists of solving eight exercises. The exercises will be written according to types similar to the exercises carried out in the classroom by the lecturer. The evaluation of the written test is given in thirtieths and will be considered passed with a minimum grade of 18/30. The duration of the written test is 2 hours.

The oral test is reserved for students who have passed the written test and achieved a a minium grade of 18/30 and will focus on questions covered in the course syllabus.

The final grade, which takes into account the outcomes of the written test and the oral test, is given in thirtieths and reflects the candidate's overall evaluation.

Disability and Specific Learning Disorders (SLD)

Students who have registered their disability certification or SLD certification with the Inclusion and Right to Study Office can request to use conceptual maps (for keywords) during exams.

To this end, it is necessary to send the maps, two weeks before the exam date, to the course instructor, who will verify their compliance with the university guidelines and may request modifications.

It is strongly reccommended to attend the class.