Organic Chemistry A
A.Y. 2026/2027
Learning objectives
Aims of the course are: to improve the knowledge on the structure of organic molecules and of reaction mechanisms; to provide concepts about reactions of great interest in organic synthesis, that are not discussed in basic organic chemistry courses; to improve experimental lab's techniques and practical skills
Expected learning outcomes
The student will acquire skills complementary to those already attained in the field of stereochemistry, in advanced organic synthesis and specific reactions mechanisms and pericyclic reactions. From the laboratory training he will gain expertise in the execution and work up of sophisticated organic reactions performed under inert atmosphere and with stereochemical aspects.
Lesson period: First semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course can be attended as a single course.
Course syllabus and organization
Single session
Responsible
Lesson period
First semester
Course syllabus
Pericyclic reactions (24 hours)
Electrocyclic reactions, sigmatropic rearrangements, cycloadditions, and group transfer reactions. Molecular orbitals of alkenes and conjugated polyenes: frontier molecular orbital (FMO) theory. Conrotatory and disrotatory reaction modes and their stereochemical consequences. The Nazarov cyclization as a representative electrocyclic reaction. Cope and Claisen rearrangements (including selected variants) as examples of sigmatropic rearrangements. Suprafacial and antarafacial processes. Hydrogen and alkyl shifts as examples of sigmatropic rearrangements. Oxy-Cope, anionic oxy-Cope, and aza-Cope rearrangements. [4+2] and [2+2] cycloadditions. Endo and exo selectivity. Inverse electron-demand cycloadditions. Lewis acid-catalyzed cycloadditions.
Stereochemistry (8 hours)
Methods for the preparation of enantiomerically pure compounds. Determination of enantiomeric excess. Methods for assigning absolute configuration. Molecular symmetry. Chirality arising from stereogenic elements other than carbon. Additional sources of chirality, including allenes, biaryls (atropisomerism), planar chirality, and helical molecules.
Regio- and stereochemistry (8 hours)
Formation of heterocyclic compounds. The Thorpe-Ingold effect. Baldwin's rules for ring closure. Exo/endo and tet/trig cyclizations. Stereochemical control in cyclohexane systems.
Molecular rearrangements (8 hours)
Rearrangements in addition to those discussed within the context of pericyclic reactions. Rearrangements involving the initial participation of a neighboring group. Wagner-Meerwein, pinacol, Favorskii, and Beckmann rearrangements. Additional less common rearrangements that play key roles in recent total syntheses of structurally complex natural products and other complex organic molecules.
Laboratory activities
Advanced organic synthesis experiments involving reactions carried out under an inert atmosphere, the use of techniques for handling air- and moisture-sensitive compounds, and the purification and characterization of the products obtained. Critical analysis of the experimental results and discussion of the chemo-, regio-, and stereoselectivity of the transformations performed.
Electrocyclic reactions, sigmatropic rearrangements, cycloadditions, and group transfer reactions. Molecular orbitals of alkenes and conjugated polyenes: frontier molecular orbital (FMO) theory. Conrotatory and disrotatory reaction modes and their stereochemical consequences. The Nazarov cyclization as a representative electrocyclic reaction. Cope and Claisen rearrangements (including selected variants) as examples of sigmatropic rearrangements. Suprafacial and antarafacial processes. Hydrogen and alkyl shifts as examples of sigmatropic rearrangements. Oxy-Cope, anionic oxy-Cope, and aza-Cope rearrangements. [4+2] and [2+2] cycloadditions. Endo and exo selectivity. Inverse electron-demand cycloadditions. Lewis acid-catalyzed cycloadditions.
Stereochemistry (8 hours)
Methods for the preparation of enantiomerically pure compounds. Determination of enantiomeric excess. Methods for assigning absolute configuration. Molecular symmetry. Chirality arising from stereogenic elements other than carbon. Additional sources of chirality, including allenes, biaryls (atropisomerism), planar chirality, and helical molecules.
Regio- and stereochemistry (8 hours)
Formation of heterocyclic compounds. The Thorpe-Ingold effect. Baldwin's rules for ring closure. Exo/endo and tet/trig cyclizations. Stereochemical control in cyclohexane systems.
Molecular rearrangements (8 hours)
Rearrangements in addition to those discussed within the context of pericyclic reactions. Rearrangements involving the initial participation of a neighboring group. Wagner-Meerwein, pinacol, Favorskii, and Beckmann rearrangements. Additional less common rearrangements that play key roles in recent total syntheses of structurally complex natural products and other complex organic molecules.
Laboratory activities
Advanced organic synthesis experiments involving reactions carried out under an inert atmosphere, the use of techniques for handling air- and moisture-sensitive compounds, and the purification and characterization of the products obtained. Critical analysis of the experimental results and discussion of the chemo-, regio-, and stereoselectivity of the transformations performed.
Prerequisites for admission
A solid background in the topics covered in Organic Chemistry I and Organic Chemistry II is required to successfully follow this course. In particular, students are expected to have a thorough understanding of the structure and reactivity of organic compounds, the fundamental reaction mechanisms of organic chemistry, stereochemistry, and the basic methodologies of organic synthesis.
Teaching methods
The course is delivered through face-to-face lectures supported by the use of the blackboard and PowerPoint presentations. The lectures include opportunities for discussion and interaction with students, also through the analysis of examples drawn from the recent scientific literature.
Laboratory sessions provide students with the opportunity to apply experimentally the concepts and methodologies introduced during the lectures, reinforcing both their theoretical understanding and practical skills.
Laboratory sessions provide students with the opportunity to apply experimentally the concepts and methodologies introduced during the lectures, reinforcing both their theoretical understanding and practical skills.
Teaching Resources
1) Course lecture slides available through the Ariel online learning platform.
2) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reactions and Synthesis, 5th Edition, Springer Science, 2007.
3) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, 5th Edition, Springer Science, 2007.
4) Recent research articles selected made available through the Ariel online learning platform.
2) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reactions and Synthesis, 5th Edition, Springer Science, 2007.
3) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, 5th Edition, Springer Science, 2007.
4) Recent research articles selected made available through the Ariel online learning platform.
Assessment methods and Criteria
Students may choose one of the following assessment methods:
a) Oral examination. The final assessment is based on an oral examination designed to evaluate the student's knowledge and understanding of the topics covered in the course. The final grade will also take into account the student's performance in the laboratory activities.
b) Continuous assessment. Students will give one or more individual or pair presentations based on recent research articles selected by the student in agreement with the instructor and related to the topics covered in the course. The presentations will be assessed on the basis of the quality of the presentation, the ability to critically analyze the scientific literature, and active participation in the subsequent scientific discussion. The continuous assessment will be completed by an individual written examination covering the course content. The final grade will be determined by the overall performance in the presentations, the written examination, and the laboratory activities.
a) Oral examination. The final assessment is based on an oral examination designed to evaluate the student's knowledge and understanding of the topics covered in the course. The final grade will also take into account the student's performance in the laboratory activities.
b) Continuous assessment. Students will give one or more individual or pair presentations based on recent research articles selected by the student in agreement with the instructor and related to the topics covered in the course. The presentations will be assessed on the basis of the quality of the presentation, the ability to critically analyze the scientific literature, and active participation in the subsequent scientific discussion. The continuous assessment will be completed by an individual written examination covering the course content. The final grade will be determined by the overall performance in the presentations, the written examination, and the laboratory activities.
CHEM-05/A - Organic Chemistry - University credits: 9
Laboratories: 48 hours
Lessons: 48 hours
Lessons: 48 hours
Professors:
Bernardi Anna, Passarella Daniele
Shifts:
Professor(s)
Reception:
Tuesady and Thursday 14.30 - 15.30
Office - Via Golgi 19 - Dept of Chemistry or Chat in Teams (book by mail)