Chapter 22 Flashcards
What do ketones react with to have reactive alpha carbons?
Catalytic acid/base OR strong base
Enol
Carbon with OH and a double bond
Enolate
Carbon with double bond and O-
Where do enols and enolates add groups to?
Distal end of DB
Ketone plus catalytic acid/base
Enol
When will enol form be favored?
Enol being stabilized by nearby groups
Enolates are ________ stabilized _______–
resonance, anions
What parts of enolates can attack electrophiles?
O or C at db
What’s a major factor in making enolates?
Using a super strong base (Like LDA! Electophile that steals H from ketone)
What happens if strong base like LDA is used on more weakly acidic proton?
Weaker acid created
H3O+ and Br2
Adds Br to Alpha carbon
H3O+ and Br2 if ketone is asymmetrical
Major added to mark, minor meta (more stable more sub)
Removing mark halide
Base (adds DB)
- H3O+, Br2 2. py
Adds DB at extended methyl
- Br, PBr3
Adds br at alpha position of carbox acid
NaOH, Br2
Br to less sub side of ketone
- NaOH, Br2
- H3O+
Turns methyl ketone to carboxylic acid
Aldehyde plus base
Can combine 2 aldehydes
Aldehyde and base favors
aldol
Ketone and base favors
Ketone
Aldol addition vs condensation
Adds OH, adds alkyl chane with db and H2O as side
Cold NaOH
Adds OH group
Hot NaOH
Adds DB
NaOH or LDA
Can fuse things
Intramolecular Aldol
Compounds with 2 carbonyl groups that can fuse to form a ring. Uses NaOH and heat
