69081 - Organic Chemistry Lab

Learning outcomes

After completing this module, the student is able to perform a simple organic chemistry reaction on the basis of a known procedure in agreement with the safety standards. He/she knows how to perform standard separations and purifications (crystallization, distillation, liquid-liquid extraction), he/she knows how to perform identifications with the use of fundamental instrumental techniques (infrared spectroscopy, melting point, polarimetry, 1H-NMR).

Course contents

PRE-REQUIREMENTS: Characteristics and reactivity of functional groups in organic chemistry; typology, characteristics and mechanisms of the main chemical reactions applied to organic compounds; basic notions of stereochemistry.

COURSE CONTENTS:

- Safety in an organic synthesis lab.

- Reaction design and set up.

- Lab equipments.

- Separation and purification techniques : simple and fractional distillation, steam distillation, crystallization, filtration, liquid-liquid extraction.

- Experimental application of separation and purification techniques to the extraction of organic compounds from natural sources.

- Techniques for the identification of organic compounds: thin layer chromatography, polarimetry and melting point.

- Synthesis of some simple organic compounds.

- Identification of functional groups by infrared spectroscopy.

- 1H-NMR spectroscopy: theoretical overview, interpretation and prediction of the proton spectrum of simple organic compounds.

- Application of identification techniques to the characterization of the products obtained during the experimental work in the lab.

Readings/Bibliography

• R. M. Roberts, J. C. Gilbert, S. F. Martin, Chimica Organica Sperimentale, Zanichelli (Bologna)

• M. D'Ischia, La Chimica Organica in Laboratorio, Piccin (Padova)

• R. Silverstein, Spectrometric Identification of Organic Compounds, Wiley

• A. Randazzo, Guida Pratica alla Interpretazione di Spettri NMR, Loghia

• L. D. Field, S. Sternhell, J. R. Kalman, Organic Structures from Spectra, Wiley

Teaching methods

The course consists of lectures (during which all the topics reported in the contents section are presented and discussed) and in classroom exercises, during which the following activities are performed: a) the experimental reactions to be carried out by the students in the lab are presented and discussed, b) exercises for the exam preparation.

During the classroom exercises, the experimental reactions will be designed with the students, discussing the best methods for the correct execution and the most appropriate techniques for the isolation and identification of simple organic compounds.

The presence at the classroom exercises presenting the lab syntheses is compulsory, verified by signature. Only students who attended these lessons will be allowed to enter in the lab, since they know the work procedures and the safety rules.

The course also consists of the execution of experiments in the lab (8 afternoons for each student) during which the students will perform simple organic syntheses, assisted by the teacher (Prof. A. Quintavalla or Prof. L. Ferrazzano), tutors and by the technical staff of the Department. The attendance to the lab experience is compulsory and verified by signature (1 absence allowed). At the end of the lab activity (approximately in the following 3 weeks) the students in pairs will have to draw up the reports on the exercises performed (1 report for each experience), which will be delivered to the teacher.

The teacher will select a report for each pair of students that will be corrected and evaluated. The evaluation outcome will be communicated to the student before taking the exam and the judgment will be taken into account during the exam.

The course takes part in an experimentation of teaching innovation divided into 3 sessions:

- problem solving (online): students divided into groups will be assigned a "synthetic problem" for which a solution should be identified . At the end of the allotted time, with the guidance of the teacher, the gathered students will compare the various solutions.

- video (online): the students (in pairs with the colleague with whom the lab report will be drawn up) will independently view videos of the experiences to be performed in the laboratory. At the end, there will be a meeting with the teacher and all the students to discuss the salient parts, the unclear steps, etc.

- working groups (online): students will be divided into groups within which the results obtained in the laboratory (reports) will be compared. At the end, with the teacher's guide, all the students will compare the data obtained in the laboratory trying to make hypotheses and draw conclusions.

As concerns the teaching methods of this course unit, all students must attend Module 1, 2 [https://www.unibo.it/en/services-and-opportunities/health-and-assistance/health-and-safety/online-course-on-health-and-safety-in-study-and-internship-areas] online, while Module 3 on health and safety is to be attended in class. Information about Module 3 attendance schedule is available on the website of your degree programme.

Assessment methods

The course 69080 - ORGANIC CHEMISTRY 2 together with the course 69081 - LABORATORY OF ORGANIC CHEMISTRY give rise to the integrated course of ORGANIC CHEMISTRY 2 WITH LABORATORY (C.I.).

The assessment of learning takes place through a final exam for each course, which ensures the acquisition of the expected knowledge and skills. The final score that is recorded for the integrated course is the arithmetic average of the 2 scores obtained in the 2 exams.

For course 69081 - ORGANIC CHEMISTRY LABORATORY, the final exam consists of a written test (2 hours, without notes or books).

The written test consists of 5 or 6 questions: 1) chromatography, 2) separation of compounds via liquid-liquid extraction, 3) polarimetry + stereochemistry, 4) spectroscopy, 5) (and possible 6) question on a topic of the remaining part of the program. The sum of the scores obtainable reaches 32, corresponding to 30 with honors.

The written test is considered passed if a total score of at least 18/30 is achieved.

The obtained score will be informally recorded by the teacher and it will be officially recorded only after passing the exam of Organic Chemistry 2 course (as average rating). If the exam is passed, the grade obtained does not expire.

The following exam sessions are foreseen: January, February, April, June, July, September, December (the latter at the teacher discretion, to be evaluated year by year).

Teaching tools

The lessons are presented to students with the aid of multimedia supports. The slides are available for the students through the course web page of the Bologna University (Virtuale).

The online sessions (teaching innovation experimentation) will take place on Zoom or Teams, using EOL; videos of the experiences will also be provided.

Teacher notices and additional material are also published on the course web page and/or on the teacher web page.

During the lab experiments, the students are requested to provide for the personal lab coat. All other personal protective equipments, all the lab equipments and all the materials necessary for the execution of the experiences are provided by the teacher.

Each student is required to sign a declaration concerning safety and health at work, which certifies that the student has received the required training to work in the lab.

Each student is also provided of a copy of the experimental procedure (already explained in the classroom) of the activity to be performed in the lab. The procedure is briefly discussed, highlighting the critical issues, before starting to operate.

Office hours

See the website of Arianna Quintavalla

See the website of Lucia Ferrazzano