LABORATORY OF ORGANIC CHEMISTRY 3

The course fits perfectly in the course of master's studies in Chemistry and Sustainable technologies as it provides the student with information related to advanced concepts of selectivity, reactivity, reaction mechanism, synthesis procedure, isolation and characterization in advanced synthetic organic reactions of compounds (also chiral ones), all discussed under the 12 principles of green chemistry


STRUCTURE AND CONTENT OF THE COURSE COULD CHANGE AS A CONSEQUENCE OF COVID-19.

The purpose of this module 2 of the course of Organic Chemistry 3 is the experimental deepening of some themes and reactions selected by module 1, in the form of synthesis experiences that include the isolation and characterization of organic compounds in the laboratory.
The training objective is to give the student the tools that allow him to i) critically approach an experimental synthesis procedure of an organic compound, ii) analyze its safety aspects, iii) understand its chemical details related to the selectivity observed in the light of the reaction mechanism, iv) planning its execution in the laboratory as regards the required actions and times; v) analyze the result with respect to what is reported in the procedure, vi) confirm its molecular structure obtained through investigation techniques such as NMR, IR, mass spectrometry.
In fact, the module aims to guide the student from theory to practice, continuously stimulating him to analyze every single operation, reagent and experimental condition from a sustainability and congruence point of view with the 12 principles of green chemistry, in line with the educational objectives of the course of study.

The expected learning outcomes can be divided into the following specific aspects:
1. Knowledge and understanding
Knowledge of advanced synthesis reactions discussed in the course, knowledge of the various levels of selectivity in organic reactions, knowledge of basic stereochemistry concepts, knowledge of synthesis techniques even in controlled atmosphere, knowledge of product isolation and crystallization methods, knowledge of basic techniques of structural investigation IR, NMR and mass spectrometry

2. Ability to apply knowledge and understanding
Application of the knowledge in the execution of a series of experimental experiences of multistage synthesis of organic compounds, including chiral ones, and verification of the molecular structure by means of spectroscopic investigations

3. Ability to judge
Ability to analyze the various operations concerning experiences both from the point of view of safety and sustainability in light of the 12 principles of green chemistry

4. Communication skills
Ability to interact with the teacher during the lessons preceding the laboratory activities, ability to interact between students belonging to the same group and with the teacher during the experimental activity, ability to discuss during the oral exam

5. Learning skills
Ability to apply what has been learned during the first experimental activities to the following at all levels

In order to fully understand the course, the student should have acquired the training objectives as pre-requisites of the courses of Organic Chemistry 1 and 2 as it is required that the student is familiar with the reactivity of the functional groups and with the chemical-physical properties of organic substances

Particular importance is given to the aspects related to the selectivity of the reactions, as well as to the yield, the isolation processes, the mechanism of reactions always with an eye focused on expectations relating to safety and sustainability.
All laboratory activities will be preceded by lessons concerning: i) analytical techniques for structural determination (mass spectrometry, IR, NMR), ii) theoretical and mechanistic aspects of the reactions (review of all the concepts of selectivity and introduction to stereoisomerism), iii ) introduction to the laboratory, safety, materials and rules of conduct; iv) description of the experiences and expected results.

The laboratory activities, at compulsory frequency, will consist of 8 days (6 h) dedicated to the execution of a series of experiences among the following proposed (due to the interruption of the activities due to COVID-19, at the time of writing the syllabus it was not possible to fully test them previously):

Diastereoselective oxidation reaction of a natural chiral derivative through hydroboration-oxidation
Stereoselective reduction of a ketone by organocatalysis and determination of the enantiomeric excess
Synthesis of binaphthol and chemical resolution
Multistage synthesis of a cyclic compound through alcohol condensation, elimination, Michael addition, cyclization and decarboxylation reactions
Synthesis of cyclopropane derivatives containing stereocenters, also by phase transfer catalysis
Dearomatization reaction and cyclization of Diels Alder in water
Regioselectivity in the reaction of hetero-Diels Alder with two distinct dienophiles
Desymmetrization of an anhydride by means of a chiral organocatalyst to give corresponding monoester

The teaching material will be provided by the teacher during the lessons before the start of the experimental activities. Specific articles and videos available on the net will also be suggested.

M. D'Ischia, "La Chimica Organica in Laboratorio" (Tomo I e II) Piccin.
R. M. Roberts, J.C. Gilbert, S.M. Martin, Chimica Organica Sperimentale, Zanichelli.

Observation and discussion in the laboratory during the execution of the experiences. Evaluation of the reports related to the experimental activity and oral interview. Evaluation of the reports concerning the experimental activities with judgments A, B, C and D and E (A 30-28, B 27-25, C 24-22, D 21-18, E <18 to be rewritten and re-evaluated before the oral exam) . If the report has A grade, the oral grade is raised by one or 2 points, if B by 1 if C by 0 if D -1.

Slides of presentations, articles, documents and synthetic procedures provided by the teacher

The teacher is available to meet the students for further information on the course topics by email: alesca@unive.it
Accessibility, Disability and Inclusion
Accommodation and Support Services for students with disabilities or with specific learning disabilities:
Ca ’Foscari applies Italian law (Law 17/1999; Law 170/2010) for the support and accommodation services available to students with disabilities or specific learning disabilities. In the case of motor, visual, hearing or other disabilities (Law 17/1999) or a specific learning disorder (Law 170/2010) and support is needed (classroom assistance, technological aids for carrying out exams or individualized exams, accessible format material, notes recovery, specialist tutoring to support the study, interpreters or other), contact the Disability and DSA office disita@unive.it

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This subject deals with topics related to the macro-area "Circular economy, innovation, work" and contributes to the achievement of one or more goals of U. N. Agenda for Sustainable Development