LABORATORY OF ORGANIC CHEMISTRY 2 - MOD.2

The Organic Chemistry II course is fundamental for the degree course in Chemistry and Sustainable Technologies and it is composed of two parts: one theoretical and one practical in the laboratory. The course leads students to understand the main reactions of organic chemistry, the reactivity of functional groups, to perform some reactions in the laboratory and to correctly use the terminology of this discipline.

For the contents of module 1 please see to the related syllabus. For the laboratory module 2, the specific training objective of the course is to provide practical knowledge of organic chemistry for (i) the preparation and execution of some basic reactions of organic chemistry; (ii) skills in isolation, purification, yield calculation and characterization of reaction products; (iii) the drafting of laboratory reports.
The practical course of Organic Chemistry II laboratory (module 2) completes and integrates some of the basic concepts of the practical course of Organic Chemistry I laboratory and provides students with basic experimental skills to plan and complete the operations of an organic synthesis sequence.

Having achieved the training objectives of the course of Organic Chemistry I and Laboratory. It is required that the student knows and is familiar with the structure and the properties of the main classes of organic substances, and that he/she knows how to operate in the laboratory in safety by usingthe basic techniques of the organic chemistry laboratory. It is therefore recommended that the student has passed the exam of Organic Chemistry I and Laboratory as well as the safety course.

The laboratory module 2 consists of 6 lectures and 8 laboratory sessions. In the classroom lessons the instructor illustrates the experiments, the list of experiences with the explanation and description of the procedures, the procedures for writing the laboratory reports and their weight towards the final exam grade. During the lectures the instructor also describes the main analytical techniques used in the laboratory to determine the purity and structure of the products: protonnuclear magnetic resonance, gas chromatography and mass spectrometry. During the sessions in the teaching laboratory, the students conduct the experiments indicated below. These laboratory experiences are carried out during several successive practical sessions.
- Experiment 1: Friedel-Crafts acylation
During this experiment the students learn to conduct all the operations of an aromatic electrophilic substitution reaction in the presence of aluminum trichloride as Lewis acid: reaction, hydrolysis, extraction, purification, characterization.
- Experiment 2: Modification of the Wittig reaction, Wadsworth-Emmons reaction.
During this experiment the students learn to conduct all the operations of a carbon-carbon double bond formation reaction by synthesizing a phosphonate salt and using an aldehyde: reaction, hydrolysis, extraction, purification, characterization.
- Experiment 3: Grignard reaction
During this experiment students learn to conduct all the operations for the preparation of alcohols from ketones through the synthesis and use of a Grignard reagent: reaction, hydrolysis, extraction, purification, characterization.
- Experiment 4: Synthesis of coumarin
During this experiment the students learn to conduct all the operations for the synthesis of coumarin starting from resorcinol and ethyl acetoacetate in the absence of solvent and using a recyclable solid acid catalyst: reaction, hydrolysis, extraction, purification, characterization.
- Experiment 5: Pinene hydroboration / oxidation
During this experiment students learn to conduct all operations for the synthesis of pinanol, through the use of the corresponding borane: reaction, hydrolysis, extraction, purification, characterization.

R. M. Roberts, J. C. Gilbert, S. F. Martin “Chimica organica sperimentale” 1999 Zanichelli Bologna.
In the instructor's moodle space, the handouts are made available to the students, and contain the experimental methods to be followed for each experiment.

For the laboratory module 2 it is mandatory for each group to write a scientific report for each laboratory experience. Each group receives an overall grade in thirtieths that is weighted (about 10%) with the oral examination of the lecture module 1.
It is mandatory to turn in the reports to the instructor by the deadline indicated during the lectures, approximately 20 days after the end of the course. Delays in delivery are penalized with deductions in the score (0.5 points for each day of delay up to a maximum of 5).
Each group must turn in 5 reports and each is assigned from 0 to 6 points for a maximum total of 30. These grades are available to the teacher of module 2 which weighs them in the total calculation of the vote about 10%.
The reports must be:
• clear
• concise,
• use appropriate terminology and scientific language,
• be written using the computer
• contain tidy reaction schemes and figures and clear characterization data to support the text.

The course consists of 6 2-hour lectures, followed by 8 laboratory sessions of 6 hours each. Students are grouped in two or three at the discretion of the teacher.
Attendance is mandatory, for this module a maximum of one (1) absence is allowed. In case of more absences, depending with the schedules and the availability of the teacher and the laboratory, make-up sessions can be arranged.

During the lessons in the laboratory it is mandatory to have a personal lab-coat and wear glasses and safety devices.

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