Organic Chemistry Advanced
A.Y. 2023/2024
Learning objectives
The aim of the course is to drive the student to develop a basic knowledge of the organic reactions in the frame of the synthesis of organic compounds. The course has to enable the student to face the understanding of the modern literature concerning the organic synthesis and to plan simple synthetic sequences. The course is accompanied by two or three seminars given by experts of chemical companies that are involved in organic synthesis
Expected learning outcomes
Students will: design of synthesis of organic molecules based on retrosynthetic analysis; use basic concepts for the understanding of the role of reagents, solvents and reaction conditions; suggest reasonable mechanisms to justify the formation of unexpected products; take into account drawbacks associated to the scale-up of particular reactions or preparations
Lesson period: Second 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
Second semester
Course syllabus
Retrosynthetic analysis and synthetic strategies (compounds 1,2 - 1,3 - 1,4 - 1,5 - 1,6 difunctionalized. (7 ore)
Functional group interconversion: a) conversion of alcohols to alkylating agents, b) introduction of functional groups by nucleophilic substitution, c) interconversion of carboxylic acids derivatives. (6 ore)
Protective groups (OH, NH2, CO, COOH): principal protective groups, revision of the mechanisms involved in the principal reactions for the introduction and removal of protective groups. (14 ore)
Oxidation reactions: oxidation of alcohols to aldehydes, ketones and carboxylic acids; addition of oxygen at carbon-carbon double bond; allylic oxidation; oxidative cleavage of carbon-carbon double bond; oxidation of ketones and aldehydes. (10 ore)
Reduction reactions: addition of hydrogen to carbon-carbon multiple bonds; catalytic hydrogenation of carbonyl group; hydrogen transfer; hydride-donors reagents (groups III and IV); dissolving-metal reductions; reductive deoxygenation of carbonyl groups. (7 ore)
Critical analysis of synthetic strategies reported in the literature with reference to the topics of the course. (4 ore)
Functional group interconversion: a) conversion of alcohols to alkylating agents, b) introduction of functional groups by nucleophilic substitution, c) interconversion of carboxylic acids derivatives. (6 ore)
Protective groups (OH, NH2, CO, COOH): principal protective groups, revision of the mechanisms involved in the principal reactions for the introduction and removal of protective groups. (14 ore)
Oxidation reactions: oxidation of alcohols to aldehydes, ketones and carboxylic acids; addition of oxygen at carbon-carbon double bond; allylic oxidation; oxidative cleavage of carbon-carbon double bond; oxidation of ketones and aldehydes. (10 ore)
Reduction reactions: addition of hydrogen to carbon-carbon multiple bonds; catalytic hydrogenation of carbonyl group; hydrogen transfer; hydride-donors reagents (groups III and IV); dissolving-metal reductions; reductive deoxygenation of carbonyl groups. (7 ore)
Critical analysis of synthetic strategies reported in the literature with reference to the topics of the course. (4 ore)
Prerequisites for admission
Basic concepts of organic chemistry. Standard techniques for purification and structure elucidation (NMR, MS, IR).
Teaching methods
Conventional teaching, use of the webpage ARIEL for the sharing of the lesson files, useful links, problems and useful documents
Teaching Resources
a) F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reactions and Synthesis, V Edition, 2007 Springer Science.
b) S. Warren, P. Wyatt - Organic Synthesis: The Disconnection approach. 2008 Wiley
c) S. Warren, P. Wyatt - Workbook for Organic Synthesis: The Disconnection approach. II Edition, 2008 Wiley
d) J. Clayden, N. Greeves, S. Warren - Organic Chemistry, II Edition, 2012 Oxford
Recent papers regarding total synthesis of natural products, convenient synthesis of API or synthetic methodologies
b) S. Warren, P. Wyatt - Organic Synthesis: The Disconnection approach. 2008 Wiley
c) S. Warren, P. Wyatt - Workbook for Organic Synthesis: The Disconnection approach. II Edition, 2008 Wiley
d) J. Clayden, N. Greeves, S. Warren - Organic Chemistry, II Edition, 2012 Oxford
Recent papers regarding total synthesis of natural products, convenient synthesis of API or synthetic methodologies
Assessment methods and Criteria
Written and Oral examination. The written exam is usually composed by 6-12 question/exercises related to guided synthesis, reaction mechanisms, synthesis of simple organic molecules and critical analysis of synthetic schemes reported in the recent literature. The oral examination is aimed to deepen the concepts of the written examination.
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)