ORGANIC CHEMISTRY LABORATORY AND INDUSTRIAL MOD.2

The teaching falls within the training activities characterizing the Master's degree program in Chemistry and Sustainable Technologies and allows the students to acquire the knowledge of important organic reactions of industrial interest. Module 2 deals with the laboratorial part of the course and the specific objective of the course is to enable students to apply some reactions of industrial interest for the synthesis of intermediates and products of industrial organic chemistry and to know and apply different methods of separation and characterization of the products obtained. Laboratory attendance is mandatory and the minimum attendance is 80% of experiences.

1. Knowledge and understanding
i) To Know the basic concepts of Organic Chemistry.
ii) To Know the basic concepts of catalysis.
2. Ability to apply knowledge and understanding
i) To Know how to use the concepts learned to carry out a chemical reaction.
ii) To Know how to identify the characteristics that allow to obtain the maximum efficiency of a reaction.
3. Ability to judge
i) To know how to evaluate the effectiveness of the synthetic routes applied for the preparation of a product.
ii) To compare and evaluate the advantages and disadvantages of two or more synthetic pathways of a process in terms of choice of catalysts, solvents and reaction conditions.
iii) To know how to evaluate any errors and / or causes that have led to unexpected results in the laboratory experiments.
4. Communication skills
i) To know how to communicate the knowledge learned and the result of their application using appropriate terminology, both in the oral and in written reports.
ii) To know how to interact with the teacher and with the classmates in a respectful and constructive way and show availability and collaboration during group laboratory experiments.
5. Learning skills
i) To be able to take notes and to evaluate which are the most important information.
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ii) To know how to interpret the experimental data obtained in the laboratory tests and to be able to express the experimental data in terms of formulas, reaction schemes and tables.

It is important to have achieved the training objectives of the Industrial Chemistry course and therefore to know what an industrial chemical process is. It is also necessary for the students to know the concepts of organic chemistry and to possess a basic knowledge of catalysis. It is therefore recommended that the students have passed the Chemistry and Technology of Catalysis exam and attended the courses of Industrial Chemistry II and of Catalytic Methodologies for Fine Chemicals.

In relation to the training objectives and expected learning outcomes, reported in the sections
relative, the contents of the course can be divided as follows:
- Introduction.
Description of the program, methods of examination and bibliography.
- Experience 1: Synthesis of a fragrance
Preparation of a non-commercial odorous substance, called Pseudolioral, by means of various steps: 1) 2-Ethylthiophene iodination reaction for the synthesis of 2-Iodo-5-ethylthiophene. Purification and characterization of the reaction product; 2) Preparation of the corresponding Grignard reagent starting from 2-Iodo-5-ethylthiophene; 3) Cross-coupling reaction between the Grignard reagent and allyl bromide catalyzed by PdCl2 (PPh3)2. Purification and characterization of the reaction product; 3) Preparation of the Pseudolioral by hydroformylation reaction of the cross-coupling product catalyzed by HRhCO (PPh3)3. Analysis and characterization of the reaction mixture.
- Experiences 2 and 3: Synthesis of 1- (5-ethylthiophen-2-yl) propan-1-one by two different synthetic pathways. 1) Synthesis of ketone 1- (5-ethylthiophen-2-yl) propan-1-one by reaction of 2-ethylthiophene with SnCl4 and propanoyl chloride in dichloromethane. Purification and characterization of the reaction product. 2) Synthesis of ketone 1- (5-ethylthiophen-2-yl) propan-1-one by reaction of 2-ethylthiophene with propionic anhydride in the presence of the heterogeneous catalyst Fe-Aquivion. Purification and characterization of the reaction product. Recovery and recycling of the Fe-Aquivion catalyst for a new synthesis of 1- (5-ethylthiophen-2-yl) propan-1-one and evaluation of the catalytic activity in the first and second use. Comparison between the two synthetic methods used for ketone synthesis.
- Experience 4: Reduction of 1- (5-Ethylthofen-2-yl) propan-1-one to the corresponding alcohol
Reduction reaction of 1- (5-ethylthiophen-2-yl) propan-1-one with NaBH4. Work-up of the reaction mixture and characterization of the product by GC and GC-MS.
- Experience 5: Oxidation reaction of an aldehyde to the corresponding carboxylic acid
Oxidation of cinnamaldehyde to cinnamic acid in the presence of sodium chlorite and hydrogen peroxide. Work-up of the reaction mixture and characterization of the obtained products.

Lecture notes

The students are admitted to the exam if they have performed at least 80% of the laboratory experiences. The verification of learning takes place through an oral test. The students must demonstrate to know the topics related to the program of the course by answering some questions in a clear and correct way by using an appropriate language. The oral exam lasts from 30 minutes to 45 minutes depending on the clarity and consistency of the answers to the questions asked and there are at least three questions concerning the laboratory activity.During the examination will be discussed and evaluated also the reports related to the laboratory experiments.

Teaching is organized in laboratory experiments that will be illustrated time by time before their realization. The topics presented during the lessons are illustrated in detail using power point slides projected on a screen. The teaching material shown in the classroom can be downloaded from the University's "moodle" platform.

Italian

The course can be defined as sustainable because it deals with reactions of industrial organic chemistry that for the most part take place in the presence of catalysts. It is known that the use of catalysts is one of the twelve principles of Green Chemistry, since the catalysts allow to carry out chemical reactions with a lower environmental impact and a lower energy expenditure and therefore with greater sustainability.

Accessibility, Disability and Inclusion
Accomodations and Support Services for students with disabilities or specific learning disorders:
Ca 'Foscari applies the Italian Law (Law 17/1999, Law 170/2010) for support services and accommodation available to students with disabilities or specific learning disorders. In case of motor, visual disability, hearing or other disabilities (Law 17/1999) or a specific learning disorder (Law 170/2010) and support is needed (assistance in the classroom, technological aids for exams) o individualized exams, material in accessible format, notes collection, specialized tutoring in support of the study, interpreters or other), contact the Disability office and DSA disabilita@unive.it.

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