Organic Chemistry A
A.Y. 2024/2025
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.
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
Organic Chemistry A (48 hours)
Peryciclic reactions (15-18 hours): electrocyclic, sigmatropic and cycloaddition reactions. Reactions that involve atom or group transfer. Molecular orbitals of alkens and conjugated systems: frontier molecular orbitals. Conrotatory and disrotatory reactions. Nazarov cyclization, Cope and Claisen rearrangements (and similar reactions) in the frame of the sigmatropic reactions. Suprafacial and antarafacial approaches. Hydrogen and alkyl group shifts in the frame of the sigmatropic reactions. Oxy-Cope and anionic oxy-Cope rearrangements. Cycloadditions: 4+2 and 2+2. Exo and endo products. Inverse cycloadditions. Lewis acid catalyzed cycloadditions.
Stereochemistry (4-6 hours): Methods for the preparation of enantiomerically pure compounds. Methods to determine the enantiomeric excess. Methods to determine the absolute configuration. Molecular symmetry. Chirality due to non-carbon stereocenters. Other chiral systems: allenes, biaryls, stereoplanes, helical structures.
Regio- and Stereo-chemistry (4 hours): formation of heterocycles. Thorpe-Ingold effect. Balwin's rules. Exo, endo, tet and trig cyclizations. Stereochemical control in six-membered rings
Rearrangements (4-6 hours): In addition to the ones discussed in the frame of the peryciclic reactions, rearrangements induced by neighbouring group participation. Wagner-Meerwein, pinacol, Favorski, Beckmann rearrangements
Each topic is accompanied by in-dept studies (presented by students during the lessons) and problem sections. (14 hours)
Organic Chemistry Laboratory A
Some of the reactions discussed in the course will be performed in the laboratory, focusing on inert atmosphere working and other advanced techniques. Stereochemical aspects of the reactions will also be considered.
Peryciclic reactions (15-18 hours): electrocyclic, sigmatropic and cycloaddition reactions. Reactions that involve atom or group transfer. Molecular orbitals of alkens and conjugated systems: frontier molecular orbitals. Conrotatory and disrotatory reactions. Nazarov cyclization, Cope and Claisen rearrangements (and similar reactions) in the frame of the sigmatropic reactions. Suprafacial and antarafacial approaches. Hydrogen and alkyl group shifts in the frame of the sigmatropic reactions. Oxy-Cope and anionic oxy-Cope rearrangements. Cycloadditions: 4+2 and 2+2. Exo and endo products. Inverse cycloadditions. Lewis acid catalyzed cycloadditions.
Stereochemistry (4-6 hours): Methods for the preparation of enantiomerically pure compounds. Methods to determine the enantiomeric excess. Methods to determine the absolute configuration. Molecular symmetry. Chirality due to non-carbon stereocenters. Other chiral systems: allenes, biaryls, stereoplanes, helical structures.
Regio- and Stereo-chemistry (4 hours): formation of heterocycles. Thorpe-Ingold effect. Balwin's rules. Exo, endo, tet and trig cyclizations. Stereochemical control in six-membered rings
Rearrangements (4-6 hours): In addition to the ones discussed in the frame of the peryciclic reactions, rearrangements induced by neighbouring group participation. Wagner-Meerwein, pinacol, Favorski, Beckmann rearrangements
Each topic is accompanied by in-dept studies (presented by students during the lessons) and problem sections. (14 hours)
Organic Chemistry Laboratory A
Some of the reactions discussed in the course will be performed in the laboratory, focusing on inert atmosphere working and other advanced techniques. Stereochemical aspects of the reactions will also be considered.
Prerequisites for admission
Students must have knowledge of Organic Chemistry I and Organic Chemistry II. Therefore students must know the chemistry of aliphatic and aromatic compounds in order to deep understand the lesson contents.
Teaching methods
Lessons will be given in the conventional way.
For the laboratory module, the lab work will (ariound 2 weeks) take place indicatively at the end of November.
For the laboratory module, the lab work will (ariound 2 weeks) take place indicatively at the end of November.
Teaching Resources
(1) Slides presented during the lessons available through Ariel site.
(2) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reactions and Synthesis, V Edition, 2007 Springer Science;
(3) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, V Edition, 2007 Springer Science.
(4) Some recent relevant scientific papers related to the topics of the course
(2) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reactions and Synthesis, V Edition, 2007 Springer Science;
(3) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, V Edition, 2007 Springer Science.
(4) Some recent relevant scientific papers related to the topics of the course
Assessment methods and Criteria
The exam will take place in oral and written form
CHIM/06 - ORGANIC CHEMISTRY - University credits: 9
Laboratories: 48 hours
Lessons: 48 hours
Lessons: 48 hours
Professors:
Bernardi Anna, Passarella Daniele
Shifts:
Educational website(s)
Professor(s)
Reception:
Tuesady and Thursday 14.30 - 15.30
Office - Via Golgi 19 - Dept of Chemistry or Chat in Teams (book by mail)