B2145 - TECNICHE AVANZATE IN SINTESI ORGANICA

Learning outcomes

At the end of the course, the student will acquire in-depth knowledge in the use of advanced technologies in organic synthesis, such as: electrochemical synthesis/catalysis, electrochemical synthesis/catalysis combined with photocatalysis, mechanochemistry, and flow chemistry. The student will also gain experience in heterogeneous chemical catalysis with specific reference to anchoring methodologies of catalytic species on inert matrices. By the end of the course, the student will also possess detailed knowledge of current applications of the advanced techniques discussed in the productive sector.

Course contents

The student that plans to attend the course, in order to get maximum comprehension of the topics of the lessons must be confident with the programmes of the basic organic chemistry with particular concern to the synthesis and functionalization of the main organic functional groups (from alkanes to carboxylic derivates).

The text book “Organic Chemistry” by J. Clayden, N. Greeves, S. Warren is kindly suggested. Moreover, the student should already be practice with common lab glass-ware, with the setting of an organic reaction, monitoring of the process by means of TLC and classic work-up. Finally, the student is supposed to known how to get structural information on a title organic species via NMR-spectroscopy 1H and 13C (The latter part for what it does concern the laboratory section).

1. MechanoChemistry

1.1 Historical background
1.2 Basic principles
1.3 Ball milling apparatus and materials
1.4 Application in Organic Synthesis
1.5 Examples of large-scale productions

2. Electrosynthesis
2.1 Basic principles and historical background
2.2 Electrochemical cells for organic synthesis
2.3 Applications in organic synthesis

3. Visible-light promoted organic synthesis
3.1 Basic principles and historical background
3.2 Photochemical principles applied to organic synthesis
3.3 Photocatalysts
3.4 Examples of light mediated organic synthesis
3.5 Large scale applcations

4. Flow synthetic organic chemistry
4.1 Introduction
4.2 Why running a reaction in flow
4.3 Applications in organic synthesis
4.4 Phtochemistry in flow
4.5 Electrochemistry in Flow
4.6 Scale-up

5. CO₂ as C1-building block in organic synthesis
5.1 Greenhous effect, general consideration on the role of CO₂
5.2 CO₂: chemical properties
5.3 Chemical activation modes of CO₂
5.4. CO₂ in carboxylation processes
5.5 CO₂ in carbonylating processes.

6. Carbo-nanofomrs in organic synthesis
6.1 Zero, mono- and bidimensional ordered forms of carbon species
6.2 Fullerenes and their covalent modifications
6.3 Nanotubes and their covalent modifications
6.4 Graphene and graphene oxides: chemistry and application in organic synthesis
6.5. Use of carbon-based nanomaterials as inert supports

 

Teaching methods

Theoretical lessons (use of black-board, and projection of slides via ppt presentations).

Two-days laboratory training (8 h) based on syntheteic methodologies photo- and electro- promoted.

Assessment methods

The exam is oral and requires the prior submission of a short written report related to the laboratory activity.

Oral exam procedure: The oral exam, lasting approximately 30 minutes, includes a PowerPoint presentation (about 10 minutes) by the student on a topic/article of their choice, focused on one of the subjects covered in the course. This is followed by a Q&A session, with questions ranging from topics related to the presentation to others covered during the lectures. The student’s performance in the oral exam is graded on a scale of 26/26 points.

Assessment criteria for the laboratory and scientific report: At the end of the course, each student is assigned a literature article related to either a photocatalytic or electrosynthetic methodology that is closely connected to the reaction performed in the laboratory. At least 10 days before the oral exam, the student must submit a brief written report (about 4 pages) addressing the following key points: a short description of the transformation presented in the article, highlighting its synthetic or mechanistic significance, novelty, strengths, and any weaknesses. The report should also emphasize similarities and differences between the transformation in the article and the one carried out in the lab.

The student’s performance in the lab and the written report is evaluated on a scale of 7/7 points, divided as follows: 3 points are assigned at the end of the laboratory sessions based on the student’s conduct and performance, as evaluated by the course instructor. This evaluation will be communicated anonymously and collectively. 4 points are awarded based on the quality of the written scientific report.

The overall grade is the sum of the points obtained in the oral exam and the laboratory evaluation.

An overall grade of "not sufficient" (score < 18/30) indicates significant gaps in course content, failure to answer questions, or inadequate responses. The scores from the laboratory practice and the report are never insufficient by themselves.

An overall grade of "sufficient to fair" (18–24/30) indicates an acceptable level of preparation, but with noticeable gaps in knowledge or inadequately studied topics.

An overall grade of "good" (25–28/30) indicates that the student has a solid understanding of the course content and is able to make connections between different parts of the program. The student also successfully addressed the laboratory component and submitted a well-constructed report.

An overall grade of "excellent" (29–30/30 cum laude) indicates a thorough and in-depth preparation across the entire course program, with a clear and coherent understanding. The laboratory report is also of high quality and demonstrates extensive knowledge of the experimental techniques discussed during the practical sessions.

 

Students with learning disorders and\or temporary or permanent disabilities: please, contact the office responsible (https://site.unibo.it/studenti-con-disabilita-e-dsa/en/for-students ) as soon as possible so that they can propose acceptable adjustments. The request for adaptation must be submitted in advance (15 days before the exam date) to the lecturer, who will assess the appropriateness of the adjustments, taking into account the teaching objectives.

Teaching tools

Slides will be provided to the students. No comprehensive monographs dealing with all the topics of the course are available in the market.

Course organization: 28 hours theoretical teaching - 8 hours pratical courses.

Office hours

See the website of Marco Bandini