27868 - Laboratory of Organic Synthesis and Characterization (A-L)

Learning outcomes

Objective of the course is to develop basic skills in the synthesis of organic compounds by modern synthetic methods. The student will be able to analyze and purify substances by liquid chromatography. The student will develop basic skills in the identification of simple organic compounds through combined NMR, MS, IR.

Course contents

• Inert gas techniques, Schlenk line and syringe techniques.
• Grade and safety information of organic reagents, solvents and commercial details.
• Purification of organic compounds by chromatography: liquid chromatography (flash-chromatography), criteria for the choice of stationary phase and mobile phase.
• Introduction to mass spettrometry for simple organic compounds, electron impact (EI) and electronspray spectra (ESI).
• Applications of GC-MS and HPLC.
• Review of the fundamentals about Nuclear Magnetic Resonance (NMR).
• Advances NMR: generation of NMR signal and relaxation time.
• ¹H-NMR insights (symmetry in the determination of the structure of organic compounds, Karplus equation and coupling constants, spin systems and Pople enotation, coupling with heteronuclei).
• ¹³Carbon Nuclear Magnetic Resonance spectroscopy: similarities and differences with ¹H-NMR, chemical shifts and coupling with heteronuclei.
  
• Interpretation of spectroscopic data for the identification of simple organic compounds by NMR and MS spectra with exercises.

The course includes laboratory activities that will be conducted in U.E. 5 at the Navile campus. During these laboratory sessions, experiments involving the techniques discussed in class will be carried out. Additionally, the data collected in the laboratory will be subject to discussion during lectures. The purpose of the laboratory activities and exercises is to apply the theoretical concepts presented in class.

 

Readings/Bibliography

The materials provided by the teacher for the lessons, along with the lecture notes, are sufficient for preparing for the final exam.

All materials presented during lectures will be made available to students through Unibo's "virtuale" platform.

Interesting reference books are:

• La Chimica Organica in Laboratorio , M. D'Ischia, Ed. Piccin.

• Identificazione Spettrometrica di Composti Organici, Silverstein, edizione italiana a cura di Franca Zanardi. - 3. ed. condotta sulla 8. ed. americana; CEA, 2016 (consigliato).

• Advanced Practical Organic Chemistry, J. Leonard, B. Lygo, G. Procter. Ed Thompson.

Teaching methods

• Lectures (3 ECTS, 24 hours) in which the topics of the program are presented, examined in depth, and discussed.
• Laboratory session (2 ECTS, 32 hours) during which the student will individually conduct a multistage synthesis.
• Exercises (1 ECTS, 12 hours) for the interpretation of data obtained in the laboratory and for performing exercises on the interpretation of combined 1H-NMR, 13C-NMR, and MS spectra.

Attendance at laboratory sessions is mandatory and will be verified through an attendance signature. To fulfill the attendance requirement, students must attend at least 75% of the scheduled laboratory days.

Considering the types of activities and teaching methods adopted, participation in this educational activity requires all students to complete Modules 1 and 2 via e-learning and to attend Module 3, which covers specific training on safety and health in study environments. Information regarding dates and attendance procedures for Module 3 can be found in the dedicated section of the course website.

Assessment methods

To be eligible for the final examination, it is required to have passed the Organic Chemistry 2 exam and the Organic Chemistry laboratory course.

Attendance and active participation in lectures, as well as diligent completion of laboratory activities and assigned exercises, contribute significantly to a successful outcome in the final exam. Assessment of learning will be conducted through:

• A written test designed to evaluate the ability to solve a problem concerning the structural identification of an organic compound using NMR spectroscopy and mass spectrometry techniques. Provided materials include a 1H NMR spectrum, a 13C NMR spectrum, and an EI mass spectrum. The student must propose a molecular structure consistent with the given spectroscopic data, assigning signals to nuclei or fragmentations accordingly. The written test is considered passed if the proposed structure and signal assignments are compatible with the provided spectra and if a minimum score of 18 out of 30 is achieved. The duration of this test is 1 hour and 30 minutes; a calculator may be used (smartphones are not permitted).
• An oral examination (only if the written test is passed) will follow to assess knowledge. During the oral exam, four questions will be posed relating to: 1) laboratory techniques (inert atmosphere, solvent drying, flash chromatography); 2) mass spectrometry technique; 3) NMR technique; 4) laboratory experience.

The written examination remains valid for two consecutive sessions. Consequently, the oral examination may be taken during the session in which the written test was completed or the immediately following one. If the oral exam is not undertaken within this timeframe, retaking the written examination is required.

The final grade is expressed on a 30-point scale and is determined by calculating the arithmetic mean of the results obtained in both assessments, each of which must be individually sufficient. The teacher reserves the right to award up to 2 bonus points based on conduct demonstrated during laboratory practical exercises.

• An overall grade deemed "insufficient" (score below 18/30) signifies significant gaps in course content knowledge, failure to respond to questions, or inadequate answers.
• A grade ranging from "sufficient to fair" (18-24/30) reflects an acceptable level of preparation but indicates evident deficiencies in knowledge or insufficiently developed topics.
• A "good" overall grade (25-28/30) denotes that the student has a solid understanding of course material and can effectively establish connections among different parts of the syllabus.
• An "excellent" grade (29-30/30 cum laude) represents thorough and comprehensive mastery of the entire course program, with clear and coherent understanding.

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

The slides and videos shown during the lessons are available for download in the institutional deposit of the teaching materials of the University of Bologna.

Office hours

See the website of Andrea Gualandi