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Mòdul MD2301 - Formació general; 564497 – Química orgànica i inorgànica MASTER ON DRUGS, COSMETICS AND FOOD QUALITY Dr. Antonio Delgado Universitat de Barcelona October 2009
Session 2 Addition reactions . Electrophilic adittion to alkenes. Catalytic hydrogenation. Electrophilic addition of halogens. Electrophilic addition of hydrogen halides. Hydration of alkenes. Mechanistic considerations and synthetic applications.  Nucleophilic addition and nucleophilic “addition-elimination” at the carbonyl group . Reactivity of ketones and carboxylic acid derivatives. The enolate as nucleophile: the aldol reaction. Synthetic applications.
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Catalytic hydrogenation
[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Hydrogenation is a sterospecific process (syn addition)
Electrophilic addition of halogens to alkenes The reaction with  bromine  results in a color change  from red to colorless , which is sometimes used as a  test for unsaturation
Bromination is a sterospecific process (anti addition)
A cyclic bromonium ion explains the stereochemistry
 
[object Object],[object Object]
 
Electrophilic Addition of Hydrogen Halides to alkenes
This result is known as  Markovnikov’s rule  and is based on the stability of the carbocation formed by the addition of the proton
 
Electrophilic hydration of alkenes: synthesis of alcohols by thermodynamic control
[object Object],Electrophilic hydration of alkenes
Nucleophilic addition at the carbonyl group
Nucleophilic addition at the carbonyl group
Nucleophilic addition of hydrides and Grignard reagents
[object Object],Nucleophilic addition of primary amines
 
 
 
 
 
Enolates as nucleophiles (C-C bond formation)
 
One molecule of aldehyde acts as the nucleophile and the other as the electrophile

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