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Summary Organic Chemistry 2 CH19-23

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In this pdf file, a part of the course SK-BORC13 is summarized. This is done for the chapters 19 to 23. Some parts are lined with red. These parts weren't included in the course in the study year () but it may change over time. This file contains all the reactions and their mechanisms under each ot...

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Organische Chemie 2


Aldehydes and Ketones: Nucleophilic addition reactions

Naamgeving aldehydes Preparation of ketones
A) Oxidation of secondary alcohols




Naamgeving keton


Ozonlysis




Friedel-Crafts acylation

Preparing Aldehydes
A) oxidation of primary alcohols



B) diorganocopper reaction with acid chlorides
(Dress-Martin
periodinane)




B) partial reduction of esters


Oxidation of aldehydes and ketones
Ketonen zijn over het algemeen inert voor oxidatie,
terwijl aldehydes gemakkelijk oxideren tot
carboxylate acids. Dit komt doordat aldehydes een
proton bevat die kan worden verwijderd tijdens
oxidatie.

,Oxidation of aldehyde


A) addition of water: hydration
The equilibrium
is determined by
the structure
of the carbonyl




The mechanism of hydration of carbonyl compounds:
basic conditions


Nucleophilic addition reaction of aldehydes en
ketones
General mechanism of a nucleophilic addition
reaction




The mechanism of hydration of carbonyl compounds:
acidic conditions



Aldehydes zijn reactiever dan ketonen in nucleofiele
additie reacties:
- Bij de aldehyde (een substituent) vindt er minder
sterische hindering plaats dan een keton (twee
substituenten). Lower transition state.
- Electronic: aldehyde carbonyl groepen hebben een
hogere polarisatie (inductieve en resonantie effect).



B) addition of HCN to give cyanohydrins



De elektron donerende resonantie effect van de
aromatische ring zorgt ervoor dat een aromatische
aldehyde minder reactief is in nucleofiele additie
reacties door de carbonyl groep minder electrofiel
te maken.

, C) Addition of hydride to give alcohols: reduction E) addition of amines to give imine and enamine




Ea) addition of primary amines to give imines



D) addition of Grignard reagents to give alcohols Mechanism of imine formation by reaction with a
carbonyl compound


Mechanism of the Grignard reaction




Eb) addition of secondary amines to give enamines




Mechanism of enamine formation by reaction with
a carbonyl compound with a secondary amine

See imine
carbinolamine
for these
mechanism
steps

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