Organic Chemistry II and Laboratory

The course aims to provide the student with an advanced training in Organic Chemistry, particular attention will be paid to the chemical properties and reactivity of multifunctional compounds, organic compounds of biological relevance (carbohydrates, amino acids and peptides, lipids), and heterocyclic systems. Students will also acquire knowledge on advanced organic synthesis reactions, learning to develop simple synthetic sequences of polyfunctional organic compounds and to apply the principles of modern synthetic strategies: disconnection approaches, carbon-carbon bond formation, protection/deprotection of functional groups.

The course, for the laboratory activities, aims to address the most common practices in the laboratory, particular attention will be paid to chromatographic techniques for isolating and purifying the products of synthesis and spectroscopic techniques for the characterization of organic structures. Among the main objectives there will be to recognize and correctly assemble laboratory glassware, depending on the experience to be carried out and the apparatus to be used. Finally, some basic knowledge will be imparted regarding the correct disposal of chemical products and waste accumulated during laboratory activity.

The specific objectives of the course are:

·        Know some important classes of organic compounds and their reactivity: enols and enolate anions, unsaturated alpha-beta carbonyl compounds, carbohydrates, amino acids and proteins, lipids, heterocyclic compounds, organometallic compounds.

·        Know the principles of advanced organic synthesis: pericyclic reactions, formation of new C-C bonds, protection/deprotection of functional groups.

·        Know how to plan the synthesis of organic compounds and assemble laboratory glassware for the appropriate apparatus;

·        Know how to isolate and structurally characterize an organic molecule using one or more instrumental techniques;

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

Focusing on 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.

Information for students with disabilities and/or DSA

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

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.

The acquisition of the objectives relating to the following disciplines is required: General and Inorganic Chemistry, Organic Chemistry I

Attendance at courses is mandatory (registration of attendance in the classroom and in the laboratory) 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. If this minimum number of hours is not reached for laboratoty activities, the student must pass a practical test before taking the ordinary exam.

If the lesson is given in a mixed or remote mode, the necessary changes with respect to what was previously stated may be introduced, in order to comply with the program envisaged and reported in the syllabus.

Carbonyl α-substitution reaction

Carbonyl condensation reactions

Reazioni di condensazione dei composti carbonilici

Carbohydrates

Amino acids, peptides and protein

Lipids

Organometallic compounds and cross-coupling reaction

Heterocyclic systems

Pericyclic reactions

Purification and characterization of organic compounds

·       General principles of absorption spectroscopy. IR spectroscopy: General principles and examples of applications to organic molecules. UV-Vis spectroscopy: General principles and examples of applications to organic molecules.

·       NMR spectroscopy, Fourier transform NMR, Screen effect, signal multiplicity, chemical shift, diamagnetic anisotropy, signal integration, coupling constants. 13C NMR spectroscopy.

·       High pressure liquid chromatography (HPLC). General principles.

·       Gas chromatography (GC): general principles. Chromatographic columns.

 

List of Experiments:

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

Synthesis of Dibenzalacetone: Claisen-Schmidt condensation.

Characterization of the products obtained by means of NMR spectroscopy.

P. Y. Bruice, Organic Chemistry - Global edition, Ed. Pearson

J. McMurry, Organic Chemistry, Ed. Brooks/Cole Pubco

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

R.M. Silverstein, F.X. Webster, Spectrometric identification of organic compounds, Ed. Wiley

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?