Organic Chemistry Advanced

Goals
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

Acquired skills
Design of synthesis based on retrosynthetic analysis. Use of basic concepts for the understanding of the role of reagents, solvents and reaction conditions. Suggesting of reasonable mechanisms to justify the formation of unexpected products. Taking into account drawbacks associated to the scale-up of particular reactions or preparations

Course content
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)

Suggested prerequisites
Courses of Organic Chemistry I and II

Reference material
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

Prerequisites
Basic concepts of organic chemistry. Standard techniques for purification and structure elucidation (NMR, MS, IR).

Assessment method
Written and Oral examination. The written exam is usually composed by 6-10 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.

Language of instruction
Italian

Attendance Policy:
Recommended. The attendance is accompanied by two written tests to evaluate the level of the learning and the efficacy of the course

Mode of teaching:
traditional

Website
http://dpassarellaaco.ariel.ctu.unimi.it/v3/Home/default.aspx

Further Information
Copies of the lecture slides and other material considered useful for an in-depth study are available on Ariel web page after the end of each lesson.