The notes from lecture 7 of the organic chemistry course. The document contains clear images. Furthermore, it is organized and clearly marked. Most of it is written in English, but it also contains a number of Dutch notes.
We krijgen periodic table, maar zonder elektronegativiteit. Dit is van F, en hoe verder van F
hoe minder elektronegatief?
Imine gemaakt van keton. Imine has a double bond between N and C.
- Acid catalyzed koolstof word nucleofiel
- Full orbital, want geeft elektronen weg: in dit geval een free electron pair. Bij pijl van
N naar C van keton
- Hemiaminal is not stable
- Deprotonated to get the imine
- Er ontstaat een nieuw reactie pad omdat N drie bindingen kan vormen in plaats van
twee (bij O)
Equilibrium
Primary amine has two H and one R
Secondary amine has one H and two R
What happens with secondary amine?
- Deprotonated and maken a single bond to double bond. De dubbele binding
verschuift als het ware.
o Ontstaat een enamine
Leg reacties naast elkaar om verschil te zien
Keton met alcohol
Keton naar amine
Keton naar enamine
Aldehyde + amine imine enamine
Enamine meest gewild of juist andersom?
- Examenvragen lijken erg op werkcollege vragen, alleen iets andere groepen bijv.
Formaldehyde gives double reductive amination
- Reageert twee keer
, Carbonyl vs carboxyl group
- De reactivity is different
Carbonyl: dubbel gebonden O en twee R
Carboxyl: dubbel gebonden O en één R en een X
- X is een OH / NHR / …
Slide 18: X is een leaving group
Cl- is a good leaving group: tetrahedral intermediate is labile
Methyl anion and ethoxide are bad leaving groups
Derivatives is always related to an ..?
How mesomeric structures do we have? Bepaald stabiliteit
If the second mesomeric structure make sense, than the delocalization is strong
- Reasonable
Very unlicky the delocalization is weak
- Positive charge on oxygen is bijv less plausible delocalization lager
- Plus lading op Cl is heel onwaarschijnlijk, dus hele lage delocalizetion
The less delocalization it has, how more reactive, how more electrophility
Which parameters influence the reaction?
- Good enough electrophile?
- Good enough nucleophile?
- Better leaving group than ..?
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