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...
Test Bank for Organic Chemistry 9th Edition By McMurry || All Verified Chapters (1 - 31) || Newest 2024 A+
Test Bank For Organic Chemistry 9th Edition by John E. McMurry, All Chapters 1-31
Organic and Biosynthesis summary ( Gigga summariezed) for second year pharmacy students RuG
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Universiteit Utrecht (UU)
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Organische Chemie (SKBORC13)
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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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