The learning objective of the course is the understanding by the Students of the structural characteristics, nomenclature, chemical-physical properties and reactivity of the main classes of organic compounds through the study of the main reaction mechanisms. Indications are also given on the use of these organic derivatives as raw materials in industrial processes and on their role as pollutants.

Nucleophilic substitution at saturated carbon

Mechanism of first-order (SN1) and second-order (SN2) nucleophilic substitution, contrasts between SN1 and SN2, the leaving group in SN1 and SN2 reactions, the nucleophile in SN1 reactions, the nucleophile in SN2 reactions, nucleophiles and leaving groups compared , elimination and rearrangement reactions.

Elimination reactions

Substitution and elimination, how the nucleophile influences elimination versus substitution, E1 and E2 mechanisms. Substrate structure can enable E1, leaving group rule, Stereoselectivity in E1 reactions, periplanar transition state in E2, regioselectivity in E2, Stabilized Anions and alternative E1cB mechanism.

Review of spectroscopic methods

Spectroscopy and chemistry of the carbonyl group, IR spectroscopy of carboxylic acid derivatives, spectroscopic analysis of strained cyclic rings and alkynes, predicting the carbonyl stretching frequency, conformational analysis of cyclohexane via NMR spectroscopy, Couplings between heteronuclei, spectroscopic identification of products.

Electrophilic addition to alkenes

Addition of bromine, oxidation of alkenes to epoxides, regioselectivity to asymmetric alkenes, electrophilic addition to dienes, regioselective reactions of opening of asymmetric bromonium ions, stereospecific electrophilic additions, dihydroxylation, completely breaking the carbon-carbon double bond: scission with periodate and ozonolysis. Addition of water to the double bond.

Preparation and reactivity of enols and enolates.

Tautomerism: formation of enols by proton transfer, keto-enol equilibrium for aldehydes and ketones, experimental evidence of keto-enol equilibrium, acid and base catalyzed enolization, stable enols, consequences of enolization, reactions involving enols and enolates such as intermediates, stable equivalents of enolate anions, reactions of enols and enolates with oxygen: preparation of enol ethers and their reactions.

Electrophilic aromatic substitutions

Enols and phenols, electophilic substitution, activating/deactivating effects of the substituents present on the aromatic ring, orienting effects of the substituents present on the aromatic ring, reactions on polysubstituted aromatic compounds, peculiarities of electrophilic aromatic substitution reactions: advantages and disadvantages. Friedel Craft's reactions. Exploit the chemistry of the nitro group.

Conjugate additions and aromatic nucleophilic substitutions

Alkenes conjugated with carbonyl groups: electrophilic behavior of the alkene and carbonyl: conjugate additions and direct additions. Factors driving regioselectivity. conjugate substitution reactions, nucleophilic epoxidation, aromatic nucleophilic substitution, the addition-elimination mechanism: Nucleophilic substitution reactions via SN1: Diazonium salts. The mechanism via petrol.

Chemoselectivity and protecting groups

What is meant by selectivity, reducing agents, reduction of carbonyl groups, catalytic hydrogenation, removal of functional groups, reduction by dissolution of metals, selectivity in oxidation reactions, Competitive reactivity: which group reacts? Protective groups.

Regioselectivity

regioselectivity in aromatic electrophilic substitutions, electrophilic attack on alkenes, regioselectivity in radical reactions, nucleophilic attack on allyl compounds, electrophilic attack on conjugated dienes, conjugate additions, examples of regioselective reactions.

Alkylation of enolates

Different reactivities of carbonyl derivatives, Alkylation of nitriles and nitroalkanes, choice of electophile for alkylation, lithium enolates of carbonyl compounds and their alkylation, specific synthetic equivalents for the alkylation of aldehydes and ketones, alkylation of beta dicarbonyl compounds, regioselectivity of the alkylation of ketones, Michael acceptors.

Aldol condensation and Claisen condensation

The aldol reaction, equivalent nucleophiles of enols, control of aldol reactions of esters, aldehydes and ketones. intramolecular aldol reactions, carbon acylations, crossed ester condensations, synthesis of ketoesters by Claisen reaction, intramolecular crossed Claisen reactions.

Sulphur, silicon and phosphorus in organic chemistry.

Anions stabilized by sulfur, sulfonium salts, sulfonium ylides, comparison between silicon and carbon, nucleophilicity of allylic silanes, selective synthesis of alkenes. Selective synthesis of alkenes, alkene properties-geometry relationship, alkene equilibria, stereoselective synthesis of alkenes starting from alkynes, E alkenes via stereoselective reactions to alkynes. Julia olefination, Wittig reaction.

Retrosynthetic analysis

Disconnections attributable to known reactions, the synthons, multistep synthesis: control of chemoselectivity, functional group interconversion, C-C disconnections: starting materials, donor and acceptor synthons, functional groups with a 1.5 relationship, natural reactivity and umpolung.

Aromatic heterocycles: reactions

Heteroatomic aromatic compounds, pyridine, oxygen-containing six-membered aromaticin heterocycles, pentatomic heterocycles as substrates for electrophilic substitutions: furan, pyrrole and thiophene. Five- and six-membered rings with two nitrogen atoms. benzo-fused heterocycles, quinoline, and isoquinoline. Nitrogenous heterocycles containing sulfur and oxygen.

Aromatic heterocycles: synthesis

Synthesis of heterocycles: thermodynamic considerations, synthesis of pyrroles, thiophenes and furans from 1,4-dicarbonyl compounds. Hantzsch synthesis. Synthesis of pyrazoles and pyridazines from hydrazine and dicarbonyl compounds. Synthesis of pyrimidines and isoxazoles. Cycloadditions for the synthesis of tetrazoles and triazoles. Fischer synthesis of indoles. Synthesis of quinoline isoquinolines. the three main approaches for the synthesis of aromatic heterocycles.

• The student must demonstrate knowledge of organic reactions that characterize organic substances. Furthermore, they must demonstrate that they are able to design synthetic sequences that involve multiple reactions that allow the development of complex molecule formation processes.

• The student must demonstrate that they can apply their knowledge, understanding and problem-solving skills to topics related to the behavior of organic substances in a general context.

• The student must demonstrate that they can clearly communicate their conclusions, as well as the knowledge and rationale underlying them, to both specialist and non-specialist interlocutors using appropriate chemical language.

• The student must develop the ability to develop her scientific growth path in a critical and autonomous manner, being able to correctly use the study material provided by the teacher and the in-depth material that she herself can obtain. These skills, as far as possible, will be stimulated by the teacher by proposing in-depth studies and providing exercises to be solved at home during the course, which will then be explained and discussed during the lessons or hours of support activities.

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

Extracurricular exercises held by a different teacher. A formative assessment test (self-assessment) is planned, carried out at the end of the course and optional, consisting of a written paper composed of five open-ended questions.

Teaching

Lectures and exercises.

Innovative teaching methods

Problem-based learning. For learning based on problem solving.

Course books

Jonathan Clayden, Nick Greeves, Stuart Warren, Organic Chemistry

Assessment

The expected objectives are verified through two types of tests.
1. An optional partial assessment test focused on the first part of the program, carried out during the period of suspension of lessons at the end of the course, which consists of a written paper composed of five open-ended questions. The time available for the partial test is 90 minutes.
The partial assessment test (which has been awarded a score of at least 18/30) can be considered, at the choice of the student, contributing to passing the exam.
2. An oral interview.
At the discretion of the student who has passed the partial assessment test with a score of at least 18/30, the oral interview will focus on the second part of the program not covered by the partial test. The final grade will be determined by the arithmetic mean of the evaluations of the two tests, only if both are greater than or equal to 18/30.
The oral exam will instead focus on the entire program if the student decides not to take advantage of the partial evaluation test or if they have not passed or taken the partial evaluation test. The average duration of the oral exam is 40 minutes.
For both tests, the evaluation criteria are as follows:
- relevance and effectiveness of the answers in relation to the contents of the program;
- the level of articulation of the answer;
- adequacy of the disciplinary language used.
The final evaluation is expressed in thirtieths.

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.

Course books

Jonathan Clayden, Nick Greeves, Stuart Warren, Organic Chemistry

Assessment

The expected objectives are verified through an oral interview that will focus on the entire program. The average duration of the oral exam is 40 minutes.

The evaluation criteria are the following:

- relevance and effectiveness of the answers in relation to the contents of the program;

- the level of articulation of the answer;

- adequacy of the disciplinary language used.

The final evaluation is expressed in thirtieths.

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.