27868 - Laboratory of Organic Synthesis and Characterization (M-Z)

Learning outcomes

At the end of the course, the student will be able to synthesize and isolate organic material compounds by using the most common techniques of organic synthesis. The student will also be able to purify compounds by flash-chromatography and to identify the structure of simple organic molecules by the use of nuclear magnetic resonance spectroscopy (proton and carbon) and mass spectrometry.

Course contents

Safety information of organic reagents and solvents

Multistep synthesis of organic materials

• Use and properties of protective groups
• Organometals and inert gas techniques
• Flash-chromatograpy purifications
• Structural determination of organic products

Proton Nuclear Magentic Resonance spectroscopy

• Introduction to Nuclear Magnetic Resonance (NMR) spectroscopy techniques
• NMR instrumentations
• Energy absorption and chemical shifts
• Symmetry in determining the structure of organic molecules
• NMR signals integration
• Coupling constants

Carbon Nuclear Magentic Resonance spectroscopy

• Similarities and differences with proton NMR spectroscopy
• Energy absorption and chemical shifts

Introduction to mass spectrometry for simple organic compounds

 

Readings/Bibliography

Lecture notes will be available for download. No supplementary textbook will be needed. Interesting reference books are:

1. "Experimental Organic Chemistry", Royston M. Roberts, John C. Gilbert, Stephen F. Martin; Zanichelli
2. "A Complete Introduction to Modern NMR Spectroscopy", Roger S. Macomber, J. Wiley & sons

3. "Spectrometric Identification of Organic Compounds", Robert M. Silverstein, Francis X. Webster, David J. Kiemle

Teaching methods

• Oral lectures (3 CFU, 24 h) with multimedia support.
• Laboratory sessions (2 CFU, 32 h) to improve experimental skills in organic synthesis and characterization.
• Training in the interpretation of laboratory data (1 CFU, 12 h).

Slides will be available for download.

Assessment methods

The learning assessment implies a written exercise on the structural determination of an organic molecule through NMR spectroscopy and MS spectrometry and finally an oral examination. During the oral examination the student will be asked questions related to general laboratory techniques and to the mechanisms of the reactions performed in the practical sessions. The final vote is determined by the arithmetic mean of the results obtained in the two tests, where each one should be at least sufficient. The teacher may assign a maximum score of 3 points on the basis of the behavior during the practical laboratory sessions.

Grade 18-24: the student demonstrates partial knowledge of a limited number of course topics. Their understanding of organic synthesis and purification techniques is superficial, with difficulty in articulating fundamental concepts or linking theory to lab activities. Spectral interpretation (NMR, MS) is unclear or incomplete. Language use is adequate but not always precise.

Grade 25-29: the student has a good theoretical understanding of the course content, including laboratory-related topics. Students can clearly explain the principles of synthesis, purification, and spectroscopic analysis. They show autonomous ability to connect theory with experimental practice. They use accurate and appropriate terminology.

Grade 30-30L: the student demonstrates a comprehensive and well-structured understanding of the theoretical course topics, including modern synthesis, chromatography, and spectroscopy concepts. Students are able to argue critically and integrate theoretical knowledge with the applied aspects of the laboratory exercises. They show independent reflection, clear exposition, and precise, specialized language use.

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

Multimedia supported lectures. Lecture notes will be available for download.

Office hours:

See the website of Marco Lombardo

Office hours

See the website of Marco Lombardo