TECNOLOGIE IN SINTESI ORGANICA

Degree course: 
Corso di First cycle degree in Chemical Sciences and Technologies
Academic year when starting the degree: 
2014/2015
Year: 
3
Academic year in which the course will be held: 
2016/2017
Course type: 
Supplementary compulsory subjects
Seat of the course: 
Como - Università degli Studi dell'Insubria
Credits: 
6
Period: 
Second semester
Standard lectures hours: 
60
Detail of lecture’s hours: 
Lesson (60 hours)
Requirements: 

The student has to show a good knowledge of Organic Chemistry 1 and Organic Chemistry 2

Assessment: 
Voto Finale

The student at the end of the course will have to prove
a) to know the main reactions of interconversion of the most common functional groups
b ) to know the main methods of protection of the above functional groups
c ) to Know the main retrosynthetic strategies
d ) to know how to plan the synthesis of an organic compound in all its issues ( regio- chemo- and stereoselectivity )

Converting alcohols to electrophilic agents (via halides and sulfonic esters). Conversion by substitution to give nitriles, nitro compounds, azides, amines, amides, ethers and thioethers, phosphorus-centered intermediates Conversion of carboxylic acid derivatives by acylating agents, esters, amides.
Protective groups of alcohols and phenols, vicinal diols, aldehydes and ketones, carboxylic acids, amines
Retrosynthetic analysis: definition of the target molecule, disconnection, interconversion of functional groups, reagents, synthon, synthetic equivalent, latent functionality, orthogonal protection
Strategy of retrosynthesis: disconnections of a C-X group [carboxylic acids and derivatives, alcohols, ethers, thioethers, and halides). Disconnect two C-X [1,1- groups, 1,2- and 1,3-difunctionalized. Disconnect C-X in the amine synthesis. Disconnection via a group: alcohols (Grignard, reductions, epoxides), alkenes (elimination, Mannich, Wittig, HWE, McMurry, metathesis ] aryl ketones (Friedel Crafts), α-carbonyl (formation of enolates and equivalents , enols and equivalents, alkylation of enolates and enols). Disconnections CC via disconnection of two groups: 1,3-dicarbonyls [β-dicarbonyl, αβ-unsaturated compounds, condensation of carbonyl (self-condensation, and intramolecular), Mannich, Wittig, enamines]; 1,5-dicarbonyls [Michael of enolates and enamines, Robinson].

J. Clayden, N. Greeves, S. Warren Organic Chemistry , 2nd Edition, Oxford University Press 2012 (ISBN 978-0-19-927029-3)

J. Clayden, S. Warren Solution Manual to Accompany Organic Chemistry , 2nd Edition, Oxford University Press 2013 (ISBN 978-0-19-966334-7)

S. Warren Organic Synthesis The Disconnection Approach, Wiley, 1982

S. Warren Workbook for Organic Synthesis , Wiley 1982

Professors

PALMISANO GIOVANNI