Organic Chemistry II and Laboratory 2

Module MODULO 2

Il corso si propone di fornire allo studente le informazioni e gli strumenti per la comprensione della reattività chimica, con particolare riferimento alle reazioni organiche affrontate durante i turni di laboratorio. Il corso si propone di fornire le conoscenze di base di alcune delle principali tecniche spettroscopiche normalmente impiegate in chimica organica per la determinazione strutturale (NMR, IR; UV-Vis). Il corso di prefigge di fornire le conoscenze adeguate per l'applicazione delle procedure standard per purificare e caratterizzare le molecole organiche. Durante il corso, saranno ribadite informazioni indispensabili al corretto smaltimento dei prodotti chimici e dei rifiuti accumulati durante l’attività di laboratorio.

Alla fine del corso, lo studente sarà in grado di individuare la via più efficace tra quelle studiate per  la sintesi di una specifica molecola organica, e di definire le condizioni di reazione e la corretta vetreria di laboratorio da impiegare. Ricavare la struttura molecolare di una molecola sintetizzata, oppure di una molecola incognita sarà uno degli obbiettivi principali del corso. 

Regarding the Dublin Descriptors, this course aims to transfer the following transversal competences to the student:

Knowledge and understanding:
 Inductive and deductive reasoning skills;
 Ability to rationalize and predict the reactivity of organic molecules;
 Ability to distinguish the difference between laboratory instruments;
 Ability to predict the glassware necessary for a specific reaction.

Ability to apply knowledge:
 Ability to design a synthetic path suitable for obtaining a precise organic molecule;
 Ability to assembly the glassware for a specific reaction;
 Ability to identify the conditions for optimal reactions for a synthetic strategy.

Autonomy of judgment:
 Critical reasoning skills;
 Self-assessment of learning through interactions in the classroom with colleagues and with the teacher.

Communication skills:
 Ability to describe in oral and written form, with properties of language and terminological rigor, one of the topics covered, making use of both power point presentations and the blackboard.

The course consists of 6 ECTS credits, divided between theoretical lectures and laboratory practical sessions. The theoretical lectures provide the necessary background and are a prerequisite for the laboratory activities.

Compulsory, with the exceptions established by the teaching regulations of the CdS. It is necessary to exceed 70% of the scheduled hours to be able to take the exam. In the event that this minimum number of hours is not reached, the student must pass a practical test before taking the ordinary exam.

1. Introduction to the most common analytical techniques for molecular identification, including ¹H and ¹³C NMR, IR, and UV–Vis spectroscopy.

2. Theoretical principles concerning the safe and proper use of laboratory equipment for carrying out organic synthesis experiments.

3. Theoretical background and reaction mechanisms, together with the experimental procedures required for product isolation and purification.

4. Laboratory experiments involving the following organic reactions:

   • Electrophilic aromatic substitution: synthesis of p-nitroaniline (protecting group strategy).
   • Multistep synthesis: preparation of the local anesthetic benzocaine through nucleophilic acyl substitution.
   • Synthesis of dibenzalacetone via the aldol condensation reaction.
   • Synthesis of methyl salicylate, including purification by vacuum fractional distillation.

5. Isolation, purification, and characterization of the synthesized compounds using:

   • Melting point determination;
   • UV–Vis spectroscopy;
   • IR spectroscopy;
   • ¹H and ¹³C NMR spectroscopy.

Information for Students with Disabilities and/or Specific Learning Disorders (SLD)

In accordance with current legislation and to ensure equal opportunities, students with disabilities and/or specific learning disorders (SLD) are encouraged to request a confidential meeting with the course instructor. This will allow any appropriate reasonable accommodations and/or compensatory measures to be arranged, taking into account the learning objectives of the course and the student's individual needs.

1. D.L. Pavia, G.M. Lampman, G.S. Kritz, Introduction to Organic Laboratory, Saunder College Pubblishing.

2. R.M. Silverstein, F.X. Webster, Identificazione Spettroscopica di Composti Organici, Ambrosiana.

3. L.M. Harwood, C.J. Moody “Experimental organic chemistry” Ed. Wiley-Blackwell.

4. Teaching materials prepared by the instructor, including lecture slides and handouts, will be made available through the STUDIUM e-learning platform, in addition to the recommended textbooks.

The exam, integrated with module 1, is aimed at ascertaining the acquisition of the basic concepts of the course and the ability to connect them with each other and with the experiments carried out in the laboratory, the ability to clearly explain the concepts using properly using the language scientific, the ability to use and quantitatively interpret experimental data by applying the concepts and methodologies acquired during the course.

The oral exam will focus both on the discussion of a laboratory experience and on topics from the theoretical course.

For each laboratory experience, the student must submit a detailed report within 7 days of the exam date, which is also subject to evaluation during the exam.

Verification of learning can also be carried out electronically, should the conditions require it.

Assessment Criteria

The final grade will be assigned according to the following criteria:

• 29–30 cum laude: The student demonstrates an excellent and comprehensive understanding of the synthetic strategies employed in the laboratory and of the spectroscopic techniques used for structural characterization. They are able to critically analyze and integrate the concepts presented, independently apply the acquired knowledge to new situations, and communicate with clarity, precision, and appropriate scientific terminology.

• 26–28: The student demonstrates a good understanding of the synthetic strategies employed in the laboratory and of the spectroscopic techniques used for structural characterization. They are able to describe experimental procedures, critically analyze the topics covered, and present their knowledge clearly using appropriate scientific language.

• 22–25: The student demonstrates a satisfactory understanding of the synthetic strategies employed in the laboratory and of the spectroscopic techniques used for structural characterization. They are able to explain the main concepts with reasonable clarity and use scientific terminology with an acceptable degree of accuracy.

• 18–21: The student demonstrates the minimum level of knowledge required regarding the synthetic strategies employed in the laboratory and the spectroscopic techniques used for structural characterization. They have a limited ability to describe purification procedures and present the course contents with sufficient clarity, although their use of scientific terminology is only partially adequate.

• Fail: The student does not demonstrate the minimum knowledge of the fundamental course topics. They show little or no ability to use appropriate scientific terminology and are unable to apply the concepts independently.

Distance Learning

Should it become necessary, due to unforeseen circumstances, to deliver the course through distance learning, student assessment will be conducted in accordance with the regulations and provisions adopted by the University governing bodies.

column chromatographic separation

synthesis conditions

separation and purification of the desired compounds

spectroscopic characterization of organic compounds