ORGANIC CHEMISTRY LABORATORY AND 3 -MOD.2

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

The aim of this module 2 of the Organic Chemistry 3 course is the in-depth study of some advanced organic chemistry topics that complement module 1. In particular, much attention will be paid to the reaction mechanisms and methods for their study and validation. Further insights will be related to metal-mediated reactions with examples of industrial applications in the field of pharmaceutical synthesis and multicomponent reactions that allow complex molecular structures to be obtained starting from three or more reagents simultaneously. A part of the theoretical lessons will be preparatory to the experimental activities that will be carried out in the relevant educational laboratory module
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

1) Advanced concepts of selectivity in organic reactions. Stereoisomerism and chirality. Synthesis of enantioenriched or enantiopure products
2) Introduction to the laboratory, safety, materials and rules of conduct
3) Description of the experiences and expected results
4) Analytical techniques for structural determination (mass spectrometry, IR, NMR)
5) Thermodynamics and kinetics of reactions: application to advanced synthetic reactions
6) Investigation of the mechanism of a reaction
7) Analysis of possible intermediates and transition states
8) Reaction mechanism analysis techniques: isotope labeling, cross-substitution reactions, Hammett free energy correlations, kinetic and thermodynamic isotope effect
9) Examples of validations of advanced reaction mechanisms in organic chemistry
10) Concepts of catalysis: specific acid and basic catalysis, general acid and basic catalysis, catalysis by pre-organization of the substrate
11) Examples of enzymatic catalysis and artificial supramolecular enzymes
12) Metal catalysis in organic synthesis
13) Reactions of oxidation, reduction and formation of C-C and C-heteroatom bonds mediated by metal complexes
14) Examples of applications of stereoselective reactions mediated by metal complex catalysts
15) Multicomponent reactions: historical examples and applications for screening of molecular structures

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.

Jonathan Clayden, Nick Greeves e Stuart Warren "Chimica organica" Piccin. Excellent book with a modern writing style, full of useful examples.
Jonathan Clayden e Stuart Warren "Eserciziario di Chimica Organica" Piccin. Excercise book.
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.

Written and oral exam together with module 1. For details, visit the syllabus for module 1 of the course. The two modules together give rise to a single final vote.

written and oral

The exam of module 2 is integrated with module 1 and consists of two parts.
Written exam on the content of the program consisting of 4 exercises (8 points each) to assess basic preparation. The written exam assigns a merit class: A (30-27), B (26-23), C (22-18), D (17-15). It is necessary to obtain at least class D to access the oral exam.
Second oral part: presentation and discussion of an article from the scientific literature, identified by the student through the use of bibliographic search engines, on a topic of advanced organic synthesis in which some of the reagents are eco-sustainable and renewable.
What is evaluated: (1) the ability to identify a scientific article consistent with the purpose of the course, (2) the ability to deepen and explain the topic under consideration, (3) the use of appropriate and precise scientific language, (4) critical ability, (5) the demonstration of being able to write reactions and mechanisms with correct and clear scientific symbology. The oral exam lasts between 20 and 30 minutes.
The final score of the exam is calculated by adding the grade from the written test (75% of the score), the evaluation of the oral test (25%), integrated (positively or negatively) by the grade obtained in the laboratory reports (A=+2, B=+1, C=0, D=-1, E=-2 points). For the laude, one must obtain an A grade in the written test, perform excellently in the oral test, and at least a B grade in the laboratory.

Slides of presentations, articles, documents and synthetic procedures provided by the teacher.
In order to monitor student learning and make them aware of the level achieved and any aspects that require further study, a series of anonymous self-assessment tests will be administered on an ongoing basis (Socrative) which will subsequently be discussed in the class.
Activities will also be carried out in which students will work in groups, for example problem solving, bibliographic research, flipped classroom.

Italian

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

This subject deals with topics related to the macro-area "Climate change and energy" and contributes to the achievement of one or more goals of U. N. Agenda for Sustainable Development