L16 - Enols And Enolates Flashcards
1
Q
What is resonance?
A
Electrons arranged differently
2
Q
What are tautomers?
A
Atoms arranged differently
3
Q
What are keto/enol?
A
These are constitutional isomers
- different compounds
- different structures
- same formula
4
Q
How are enols formed in acid?
A
- protenated ketone
- A- attacks acidic H
- forms db to C-C, forms O-H (w/o +)
5
Q
How are enols formed in base?
A
- B- attacks acidic H
- forms db C-C, forms O-
= enolate
6
Q
What is the rank order of formation of enols/enolates?
A
Acyl chloride > ketone > ester > amide
7
Q
Why do we draw the oxyanion?
A
- O is more electronegative than C
= O- is more stabalised than C-
= C- is more reactive than O-
Enolates are nucleophiles + usually react through the C
8
Q
How does halogenation occur in basic conditions?
A
- OH- attacks acidic H
- forms C-C db, and O-
- O- reforms dn, db on C-C takes halogen
- OH- attacks C on C=O
- O- kicks out halogen with C as LG
- forms alc + CX3
- ROO’ + CHX3
9
Q
What happens in C-C bond forming reactions?
A
Electrophile + electrophile
- turn one into a nucleophile by making the C=O a C-O-
- O- kicks back in
- db in C-C attacks C=O
- C-C bond made, O-
