Organic Chemistry II and Laboratory M - Z

Module Module 2

The course aims to provide information on basic topics in experimental organic chemistry, with particular attention to the most common practices in the laboratory. The module aims to provide the student with the tools for understanding both chemical reactivity and strategies for isolating and characterizing organic molecules. Define the molecular structure of a synthesized molecule, or of an unknown molecule will be one of the main objectives of the course. Furthermore, one of the main objectives will be to recognize and correctly assemble the laboratory glassware, according to the experience to be carried out. Some basic knowledge will also be imparted on the proper disposal of chemicals and waste accumulated during laboratory activities.

The specific training objectives of the module are:

·         How to organize and assemble the laboratory glassware for the realization of a synthesis;

·         How to characterize an organic molecule using one or more instrumental techniques;

·         How to interpret spectroscopic data in order to trace the identity of an organic molecule

·         Acquire experience on the methodologies and techniques of organic synthesis through the preparation of some products and their structural characterization.

With reference to the Dublin Descriptors, this course aims to transfer the following transversal skills 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 different experimental techniques;

·         Ability to distinguish the different laboratory instruments

Ability to apply knowledge:

·         Ability to design a synthetic pathway suitable for obtaining a precise organic molecule;

·         Ability to define the instrumentation required for the realization of the synthesis;

·         Ability to identify the optimal reaction conditions for a given reaction.

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 proper technical language and terminology, one of the topics covered, using both power point presentations and the blackboard.

Lectures and laboratory exercises.
If the teaching is taught in mixed or remote mode, the necessary variations may be introduced with respect to what was previously stated, in order to respect the program foreseen and reported in the Syllabus.

Basic concepts of General and Organic Chemistry

Introduction to common characterization techniques such as: ¹H - and ¹³C-NMR, IR and UV-Vis.

 List of Experiments:

    Electrophilic aromatic substitution: p-nitroaniline synthesis (protecting groups).

    Multistep synthesis: preparation of a local anesthetic (benzocaine): nucleophilic acyl substitution.

    Synthesis of Dibenzalacetone: Claisen-Schmidt condensation.

Isolation, purification and characterization of the products obtained in the single experiments by means of: melting point, UV-Vis, IR, ¹H- and ¹³C-NMR.

Information for students with disabilities and/or SLD.

To guarantee equal opportunities and in compliance with the laws in force, interested students can request a personal interview in order to plan any compensatory measures, based on the educational objectives and specific needs.

The exam includes an oral test on all the contents of the course, including laboratory experiences.

All topics covered are considered essential for passing the exam.

For laboratory experiences, the student must submit detailed reports within 15 days of the exam date, which will also be evaluated during the exam.

Comment on the mechanism of reaction X
How are carbohydrates classified?
What is the difference between triglycerides and phospholipids?
What is the isoleelectric point? Describe the acid-base properties of amino acid X
Describe the reactivity of imines
Describe the reactivity of Heterocyclic compounds
What is a Cross-coupling reaction?
What is the symmetry of the molecular orbitals of butadiene?
Describe and comment on the procedure of experience
What is PPE? How are they classified? How can I find information on the chemical products to be used?
Why is it important to control T during organic reactions? What systems can we use?
How can I monitor the progress of an organic reaction?
What does the frequency of a particular stretching motion depend on? Which approximation is used? What does the intensity and width of an IR signal depend on?
What regions can we identify in an IR spectrum? What are the characteristic bands of the OH, NH and CH groups?
What can influence the stretching of the C=O group?
Which region of the electromagnetic spectrum does NMR setroscopy use? What transitions does the interaction of NMR radiation with matter generate?
What is the Larmor frequency? How can I obtain the absorption conditions?
What are the 3 parameters to consider when analyzing an NMR spectrum?
What does the chemical shift of different groups depend on? Why is it measured in ppm and not Hz? Why is TMS (or similar compounds) used as a reference?
What is spin-spin coupling? How is the multiplicity of a signal determined? What are two equivalent protons? Why can I have equivalence?
Comment on the 1H-NMR spectrum of compound
What are the differences between 1H and 13C NMR spectroscopy?
What type of solvents do we use for NMR analysis?
Which region of the electromagnetic spectrum does UV-vis setroscopy use? What transitions does the interaction of UV-vis radiation with matter generate?
What are transmittance and absorbance? What does A depend on? What energy levels are involved in UV-vis spectra? Why do we observe bands?
How does increased conjugation affect the UV-vos spectrum? Give an example
What are the characteristic bands of aromatic systems? How are they affected by substituents?
What is the difference between chromophore and auxochrome groups?