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

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

Readings/Bibliography

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.
• V. Šunjić, V. Petrović Peroković, Organic Chemistry from retrosynthesis to asymmetric synthesis, Springer, 2016.

Oligonucleotides

• Gait, M.J. (ed.) Oligonucleotide Synthesis a Practical Approach (1984) IRL Press Oxford (UK).
• Blackburn G.M. e Gait, M.J. (eds.) Nucleic Acids in Chemistry and Biology II ed., (1996) or subsequent, Oxford University Press (UK).

 

Teaching methods

Lectures

Assessment methods

In the absence of restrictions imposed by the pandemic situation, 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 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.

Teaching tools

Presentations. Files of presentations will be made available for download.

Office hours

See the website of Stefano Masiero