The course aims at providing the fundamental notions of safety to be adopted in an Organic Chemistry laboratory and at providing basic knowledge of the theoretical and practical aspects of the main Organic Chemistry laboratory techniques. 

The course aims at providing knowledge of the common purification techniques of organic compounds and the basic methodologies for their characterization by means of melting point and TLC. The concepts illustrated during the lectures will be applied during the laboratory sessions. At the end of the course the student will be able to carry out the synthesis and purification of simple organic compounds working in safe conditions and to prepare a report. 

With reference to the Dublin Descriptors, the expected learning outcomes are: 

D1 - Knowledge and understanding: students will acquire the rules to work in safety knowing the danger related to chemicals for the environment and human health; they will become familiar with the safety data sheet of chemicals used in the laboratory; they will have a thorough knowledge of the organic chemistry laboratory equipment and of the standard laboratory procedures for the preparation and purification of organic compounds. 

D2 - Ability to apply and understand: students will able to: manipulate organic compounds strictly comply with safety regulations; use the main equipment present in a basic organic chemistry laboratory; and report the experimental activities in a faithful and systematic way in the laboratory notebook. 

D3 - Independent judgment: students may be able to plan experiments similar to those performed during the course, independently. At the end of the course it is necessary to know how to use the collected data in a critical and correct way, correlating to the corresponding theoretical concepts. 

D4 - Communication skills: ability to communicate in written and oral form, through the use of an appropriate language the experimental data, including problems encountered and possible solutions. 

D5 - Learning Skills: Students may be able to apply a standard technique used in organic chemistry lab autonomously, showing the ability to deal with a problem through the application of acquired skills during the course. Finally, students will develop learning and in-depth skills to easily face subsequent organic chemistry laboratory courses. 

INFORMATION FOR STUDENTS WITH DISABILITIES AND/OR SLD: To ensure equal opportunities and in compliance with current laws, students concerned are invited to request a personal meeting in order to plan any necessary compensatory and/or dispensatory measures, based on the educational objectives and their specific needs.

The learning assessment procedure include an oral examination, integrated with module 1.

The examination will ascertain: (a) the acquisition of the basic concepts of the course and the ability to connect them to each other and to the experiments carried out in the laboratory; (b) the ability to clearly explain the concepts usingscientific language adequately, (c) the ability to use and quantitatively interpret experimental data by applying the concepts and methodologies acquired during the course.

The oral test will focus both on the discussion of a laboratory experience and on topics of the theoretical course. Duringthe exam, knowledge of the course topics will be assessed: level of correctness of the answers; correctness in thepresentation of the topics; profit in laboratory activity.

The student must produce a detailed report on each experiment. This will be delivered (also by email) within 7 days fromthe execution of the laboratory experience. At least 15 days before the exam date, the student have to communicate the participation to the exam in order to receive the reports.

The outcome of the learning assessment will also take into account the laboratory reports.

In the event that, for contingent reasons, it is necessary to activate distance learning, the examination will take placewith the provisions of the regulatory requirements that will be specifically approved by the University bodies.

Knowledge on the chemical properties of the main elements of the periodic table, types of chemical bonds, non-covalent interactions, equilibrium constant in chemical reactions, acid-base reactions, is mandatory.

The attedance is mandatory. The student must attend at least 70% of the total number of hours of the course (seesection 3.1of teaching regulation)

THEORY

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1.   The Organic Chemistry laboratory: rules to work in safe in the organic chemistry laboratory; labelling ofchemical compounds

2.   Laboratory glassware

3.   Characteristics of pure and mixed solvents

4.   Heating and cooling techniques

5.   Determination of physical constants: boiling point, melting point

6.   General techniques for purification of organic compounds: filtration; crystallization;

solvent extraction; distillation (at atmospheric-, reduced-, fractional-pressure and in steam current)

7.   Chromatography: adsorption chromatography: column and thin layer chromatography

8.   Synthesis of esters with different methods : Application of different reaction conditions to achieve the anti-inflammatory drug aspirin, and a fragrance employed in food, a

9.   Ester hydrolysis in basic conditions: soap preparation.

 

LABORATORY EXPERIENCES

 

1.   Purification of a mixture containing benzoic acid by crystallization

2.   Solvent extraction: liquid-liquid partition and separation of two organic molecules

3.   Hydrolysis of fatty acid esters: soap preparation.

4.   Extraction of pigments from spinach leaves and separation by column chromatography

5.   Synthesis and purification of aspirin

6.   Synthesis and purification of a fragrance employed in food

7.   Thin layer chromatography

• Joaquín Isac-García, José A. Dobado, Francisco G. Calvo-Flores, Henar Martínez-García. Experimental Organic Chemistry Laboratory Manual. Ed. Elsevier Scienc
  
• K. L. Williamson, K. M. Masters. Macroscale and Miscoscale Organic Experiments. Ed. K. Williamson, Houghton Mifflin
  

ADDITIONAL MATERIAL

The teaching material prepared by the teacher (slides, handouts), in addition to the recommended texts, will be available through the STUDIUM platform.

The learning assessment procedure includes an oral examination, integrated with module 1.

The examination will ascertain: 

(a) the acquisition of the basic concepts of the course and the ability to connect them to each other and to the experiments carried out in the laboratory; 

(b) the ability to clearly explain the concepts using scientific language adequately, 

(c) the ability to use and quantitatively interpret experimental data by applying the concepts and methodologies acquired during the course.

The oral test will focus on the discussion of laboratory experiences and how these techniques can be applied to other similas cases, to verify the level of knowledge on the standard laboratory procedures for the synthesis and purification of organic compounds; and on topics of the theoretical course. During the exam, knowledge of the course topics will be assessed: level of correctness of the answers; correctness in the presentation of the topics; profit in laboratory activity.

The student must produce a detailed report on each experiment. This will be delivered (also by email) within 7 days from the execution of the laboratory experience. At least 15 days before the exam date, the student have to communicate the participation to the exam in order to receive the reports.

The outcome of the learning assessment will also take into account the laboratory reports.

The final grade will be assigned based on the following criteria:

Grade 29–30 cum laude: The student has an in-depth knowledge of the purification techniques and synthesis strategies used in the laboratory; is able to integrate and critically analyze the questions presented, and to autonomously extend the topics studied to other cases; demonstrates excellent communication skills and command of language.

Grade 26–28: The student has a good knowledge of the purification techniques and synthesis strategies used in the laboratory; is able to describe a process, and to integrate and analyze the questions presented in a critical and coherent manner; presents the topics clearly, using appropriate language.

Grade 22–25: The student has a fair knowledge of the purification techniques and synthesis strategies used in the laboratory, and presents the topics in a reasonably clear manner with a fair command of language.

Grade 18–21: The student has minimal knowledge of the purification techniques and synthesis strategies used in the laboratory; has a modest ability to describe a purification process; presents the topics with sufficient clarity, although command of language is not well developed.

Failing grade: The student does not possess the minimum required knowledge of the main contents of the course. The ability to use specific terminology is very poor or absent, and the student is not able to independently apply the knowledge acquired.

In the event that, for contingent reasons, it is necessary to activate distance learning, the examination will take place with the provisions of the regulatory requirements that will be specifically approved by the University bodies.

The most frequent questions (not the only possible ones) concern:

•  Extraction with solvents: use of liquid-liquid partitioning for the separation of molecules with different chemical properties, description of the principle, glassware used, application examples.
• Characteristics of solvents: protic, aprotic, polar, apolar solvents.
• Chromatography: types of chromatography, theoretical principles of column chromatography.
• Characteristics of TLC chromatography.
• Synthesis of esters obtained in lab.
• Monitoring the progress of a reaction using the techniques studied.
• Separation of the product of a given reaction using the purification techniques studied.