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 the structural identification 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; types, characteristics, and mechanisms of the main chemical reactions applied to organic compounds; fundamentals of stereochemistry. The course is divided into 2 teaching units: 1) theoretical teaching unit; 2) laboratory teaching unit.

Contents of the theoretical teaching unit:

- Safety in the organic synthesis chemical laboratory.

- Design and setup of a reaction.

- Laboratory glassware and equipment.

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

- Organic compound identification techniques: thin-layer chromatography, polarimetry, and melting point.

- Organic molecule characterization techniques: infrared (IR) and NMR spectroscopy. For both techniques, theoretical foundations, spectral interpretation methods, and examples on small organic molecules will be provided. Exercises will include identifying the structure of a compound from spectra and predicting the spectra of a given compound.

- Preparatory exercises for the exam.

Contents of the laboratory teaching unit:

The laboratory activities consist of five experiments: 1) extraction of caffeine from tea; 2) two-step synthesis of aspirin; 3) synthesis of coumarin; 4) fractional distillation of whiskey components; 5) two-step synthesis of a dipeptide.

The practical implementation of these experiments aims to enable students to:

- experimentally apply the separation and purification techniques for organic compounds, from natural sources or synthetic processes, explained in class (liquid-liquid extraction, recrystallization, fractional distillation, vacuum distillation, vacuum filtration),

- experimentally apply the identification and characterization techniques for organic compounds explained in class (TLC chromatographic analysis, polarimetry, melting point, IR and NMR spectroscopy),

- personally synthesize some simple organic compounds using equipment suitable for room-temperature and heated synthesis.

Readings/Bibliography

The slides shown in class (which include useful web pages for further study and exercises), additional materials for interested students (not included in the exam syllabus), exercises (solved and unsolved) in preparation for the exam, videos of the laboratory experiments, and the procedures for the laboratory activities are available for download on Virtuale.

For further information and clarification, we recommend consulting the following texts (available in the library).

For practical laboratory activities:

- R. M. Roberts, J. C. Gilbert, S. F. Martin, Experimental Organic Chemistry, Zanichelli (Bologna)

- M. D'Ischia, Organic Chemistry in the Laboratory, Piccin (Padua)

For theoretical content and exam preparation:

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

- A. Randazzo, Practical Guide to the Interpretation of NMR Spectra, Loghia

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

Teaching methods

The course is divided into two teaching units:

1) Theoretical teaching unit, given by Professor Arianna Quintavalla with in-person classroom lectures, during which the topics listed in the Contents section are presented and discussed. These lectures are delivered with the aid of multimedia, and each topic is accompanied by exercises on the application of the concepts presented.

2) Laboratory teaching unit. The laboratory teaching unit aims to explore, from an experimental perspective, some of the most important methodologies for organic synthesis, purification, and characterization of organic compounds. The first part of this teaching unit is given in the classroom with lectures detailing the 5 laboratory experiments. The laboratory reactions will be designed with the students, discussing the procedures for their correct execution and evaluating the most appropriate techniques for the isolation and identification of the obatined organic compounds. These lectures (4 hours) are given by Professor Lucia Ferrazzano.

To ensure successful laboratory activities, students are divided into 2 groups, each carrying out their laboratory activities separately. The first afternoon (3 hours) of the laboratory (shared between both groups) is dedicated to a tour and presentation of the laboratory, including a description of the rules of conduct and best practices for working safely. Subsequently, each student completes the 5 experiments over the course of 7 afternoons (28 hours). The laboratory activities are conducted under the supervision of Professor Arianna Quintavalla or Professor Lucia Ferrazzano. Attendance at the classroom presentation of the experiments and the 8 laboratory afternoons is mandatory and verified by signature (one absence is permitted). Only students who attend, and therefore are familiar with the content of the experiments and the safety procedures, are allowed to attend the laboratory activities.

At the end of the laboratory activity (approximately within the next 4 weeks), students are required to write reports on their experiments in pairs (2 reports for each pair of students, drawn at the end of the lab activities), which must be submitted to the instructor. Failure to submit the reports will result in the student being denied attendance. Subsequently, the teachers correct and evaluate one report per pair of students. The evaluation results are communicated to the students before the exam so that they can use it to assess their learning and preparation.

The course participates in the University experimental teaching project. The innovative teaching section is divided into 3 parts:

- Video (can be held online): Students independently view videos describing the laboratory experiments. At the end, a meeting is held with the instructor and all students to discuss the key points, any unclear steps, the different protocols and methods presented in the videos, the reasons for certain choices, etc. Students are then given a timed online test (mostly multiple-choice) on the video contents, which allows the student to obtain up to 1.5 points to be added to those obtained in the final exam.

- Workgroups (can be held online): Students are divided into groups and compare the results obtained in the lab (described in the reports). At the end, everyone comes together to compare, under the guidance of the instructor, the data obtained in the lab by the various students, trying to formulate hypotheses and draw conclusions.

- Problem-solving (can be held online): Students, divided into groups, will be assigned a "synthetic problem" for which they will identify a solution. At the end of the allotted time, under the guidance of the instructor, the students compare and discuss the various proposed solutions.

As concerns the teaching methods of this course, all students must attend Modules 1 and 2 online [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], 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 the degree programme.

Assessment methods

The ORGANIC CHEMISTRY 2 course, along with the ORGANIC CHEMISTRY LABORATORY course, constitute the integrated ORGANIC CHEMISTRY 2 WITH LABORATORY course (IC).

Assessment is via a separate exam for each course, and the 2 exams can be taken in any order. Each exam is designed to assess the acquisition of the expected knowledge and skills. The final grade, which is recorded for the entire integrated course, is the arithmetic mean of the 2 exam grades. If the grade obtained in the Organic Chemistry 2 exam is higher than 30, it is deducted (x 0.89) to calculate the average with the grade obtained in the Laboratory Course exam.

For the ORGANIC CHEMISTRY LABORATORY course, the final exam consists of a written test (2 hours, without the use of notes, books, or electronic devices; calculators and periodic table allowed). The written exam consists of 5 open-ended questions designed to test the theoretical and practical knowledge acquired during the course. The questions focus on the following topics:

1) Chromatography (TLC) – 6 points,

2) Separation of compounds by liquid-liquid extraction – 5 points,

3) Polarimetry and stereochemistry – 7 points,

4) Spectroscopy (IR and NMR) – 7 points,

5) Question on a topic from the remaining part of the program (often including a question on laboratory activities) – 6 points.

The total score for the final written exam is 31, to which the following may be added:

- up to 1.5 points from the video quiz,

- 0.25 (satisfactory) to 1 (excellent) points from the reports evaluation. Students who receive an insufficient reports evaluation will not be eligible for any additional grade.

The final written exam is considered passed if the student achieves a total score of at least 18/30, and the grade obtained does not expire. To obtain 30 cum laude, a total grade of 32 must be achieved. The grade will be recorded informally by the instructor and will be recorded (as an average grade) only after the ORGANIC CHEMISTRY 2 exam has been passed.

The following exam dates are scheduled: January, February, April, June, July, September, and November (the latter at the instructor's discretion, to be evaluated annually).

Students who fail to attend the lab presentations and the 8 laboratory afternoons (1 absence permitted) or fail to submit their reports will not be allowed to take the exams. Students who fail to pass and have their grades recorded for the ORGANIC CHEMISTRY 1 course will not be allowed to take the exams for the integrated course.

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

Classroom lectures are presented using multimedia. Slides are made available to students before the lesson via the University system (Virtuale). The following will also be made available on Virtuale:

- videos of the laboratory experiments,

- additional material for interested students (not included in the exam syllabus),

- exercises (solved and unsolved) in preparation for the exam,

- procedures for the laboratory experiments,

- the report outline,

- spectroscopic data collected by students in the laboratory.

The innovative teaching sessions held online will be conducted on Zoom or Teams; the video quiz will be offered on Wooclap.

For laboratory experiments, students are required to purchase a personal lab coat. All other personal protective equipment, equipment, and raw materials required for the experiments are provided by the Course. Each student is required to sign a declaration regarding workplace health and safety, certifying that they have received the necessary training to work in the laboratory. Each student is provided with a paper copy of the detailed procedure, already explained in class and available on Virtuale, for the laboratory experiment to be performed that day. The procedure is briefly discussed before starting work, highlighting any critical aspects.

Office hours

See the website of Arianna Quintavalla

See the website of Lucia Ferrazzano