00152 - Organic Chemistry II

Learning outcomes

The aim of the course is to widen and deepen the knowledge of organic chemistry. The main C-C forming reactions will be presented and synthetic strategies will be discussed. The chemical properties of several classes of organic compounds, mostly of natural origin, will
be presented, together with synthetic approaches leading to them.
The student will acquire a deeper understanding of physical and chemical properties of organic compounds, which will allow an analytical approach to problem-solving and autonomous study in the field of organic chemistry.

Course contents

The course has Organic Chemistry 1 as a prerequisite. It may also be attended by students who have not yet passed the Organic Chemistry 1 exam, but knowledge of the topics covered in that course is essential.

• Heterocyclic aromatic compounds: pyrrole, furan, thiophene, pyridine and their derivatives: structure and reactivity.
• Nucleosides, nucleotides and nucleic acids.
• Free radicals and radical reactions.
• Stereochemistry: isomers classification, stereoisomers classifications, chirality: centre, axis, plane, helix, determination of enantiomeric excess and optical purity, basics of resolution techniques and asymmetric synthesis.
• Sugars: monosaccharides, disaccharides, polysaccharides: structure and reactivity.
• Aminoacids, peptides and proteins.
• Working out organic structures: C-C bond forming reactions, enolate chemistry, protecting groups, synthetic equivalents, retrosynthetic analysis.
• Exercises on retrosynthetic analysis and synthesis planning.
• Brief overview of the main synthetic approaches to the preparation of amino acids and peptides.

Readings/Bibliography

The list of texts below provides a starting point for further study of the various topics. The teaching material that will be used in class has been drawn from these texts.

This material, together with the notes taken during lectures, is normally sufficient to prepare for the exam.

Heterocyles

• Morrison, Boyd, Chimica organica, CEA, 1976 or subsequent.
• Hendrickson, Cram, Hammond, Chimica organica, Piccin 1973 or subsequent.
• D.T. Davies, Aromatic Heterocyclic Chemistry, Oxford University press, 1992.
• D. Sica, F. Zollo, Chimica dei composti eterociclici, Edises, 2001.

Stereochemistry

• B. Testa, Principles of organic stereochemisry, M. Dekker ed, 1979.
• E.L. Eliel, S.H. Wilen, Stereochemistry of organic compounds, Wiley ed., 1994.

Sugars

• Morrison, Boyd, Chimica organica, CEA, 1976 or subsequent.

Aminoacids and peptides

• W.H. Brown, Chimica organica, EdiSes, 1996 or subsequent.
• J. Jones, Amino acid and peptide synthesis, Oxford University Press, 1992.
• M. Bodanszki, Principles of peptide synthesis, 2nd ed. Springer, 1993.

Free radicals

• R.O.C. Norman, Chimica organica, Piccin, 1982 or subsequent.

Protecting groups

• Carey, Sundberg, Advanced organic chemistry, IV ed. or subsequent, Plenum Press.

Organic synthesis and C-C bond formation

• Carey, Sundberg, Advanced organic chemistry, IV ed. or subsequent, Plenum Press.
• March, Advanced organic chemistry, IV ed. or subsequent, Wiley.
• S. Warren, Organic Synthesis: The Disconnection Approach, Wiley, 1982 or subsequent.
• Willis, Willis, Organic synthesis, Oxford University Press, 1995.
• C. Trombini, The Construction of Molecular Architectures - Guidelines to Organic Synthesis Design, Bologna University Press, 2021, ISBN online 9788869237287

Teaching methods

Lectures and classroom exercises.

As per the regulations, attendance to the course is mandatory: attendance will be recorded through the "PRESENZE STUDENTI" application at the beginning of each lesson.

Assessment methods

In the absence of restrictions imposed by specific collective emergencies, the final examination, aiming at ascertaining the student's acquired skills, will consist of both a written and an oral test. The written test is the main one, where students will be presented with 3 questions, pertaining the course topics, which must be answered in 2 hours time (books, notes, digital supports etc. are not allowed). A maximum of 10 points will be given for each question. Students ranking above 17/30 will take the oral. The oral test (45 min ca.) is meant for a more precise evaluation of the candidate and it will have the written test as the starting point. Enrolment via AlmaEsami.

The examination will be held in person, except in the event of public health emergencies, flooding affecting the country, residence in areas classified as high-risk under the new regulations, and/or student vulnerability, as assessed by the University’s Disability and Specific Learning Disorders (DSA) Service. Each case will be evaluated individually and, where the relevant requirements are met, the examination may be conducted via Microsoft Teams.

Students with specific learning disorders (DSA) or temporary or permanent disabilities are advised to contact the relevant University Office well in advance (https://site.unibo.it/studenti-con-disabilita-e-dsa/it ). The Office will propose any appropriate accommodations to the students concerned. Such accommodations must, however, be submitted to the course instructor for approval at least 15 days in advance. The instructor will assess their suitability, also in relation to the learning objectives of the course.

The use of artificial intelligence is prohibited. Any use of AI constitutes a violation of academic integrity.

Teaching tools

Presentations. Files will be made available for download from the UniBO VIRTUALE platform.

Office hours

See the website of Stefano Masiero